United States v. Segundo Dominguez-Caicedo ( 2022 )


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  •                 FOR PUBLICATION
    UNITED STATES COURT OF APPEALS
    FOR THE NINTH CIRCUIT
    UNITED STATES OF AMERICA,              No. 19-50268
    Plaintiff-Appellee,
    D.C. No.
    v.                    3:18-cr-00421-
    BEN-2
    SEGUNDO MARCIAL DOMINGUEZ-
    CAICEDO,
    Defendant-Appellant.
    UNITED STATES OF AMERICA,              No. 19-50271
    Plaintiff-Appellee,
    D.C. No.
    v.                    3:18-cr-00421-
    BEN-3
    VICTOR GASPAR CHICHANDE,
    Defendant-Appellant.
    UNITED STATES OF AMERICA,              No. 19-50274
    Plaintiff-Appellee,
    D.C. No.
    v.                    3:18-cr-00421-
    BEN-1
    ANDRIAN ANDRES CORTEZ-
    QUINONEZ, AKA Andrian Andres
    Quinonez-Cortez,                         OPINION
    Defendant-Appellant.
    2         UNITED STATES V. DOMINGUEZ-CAICEDO
    Appeal from the United States District Court
    for the Southern District of California
    Roger T. Benitez, District Judge, Presiding
    Argued and Submitted July 29, 2021
    Pasadena, California
    Filed July 18, 2022
    Before: MILAN D. SMITH, JR. and KENNETH K. LEE,
    Circuit Judges, and EDUARDO C. ROBRENO, *
    District Judge.
    Opinion by Judge Milan D. Smith, Jr.
    *
    The Honorable Eduardo C. Robreno, United States District Judge
    for the Eastern District of Pennsylvania, sitting by designation.
    UNITED STATES V. DOMINGUEZ-CAICEDO                        3
    SUMMARY **
    Criminal Law
    The panel affirmed Adrian Andres Cortez-Quinonez’s,
    Segundo Marcial Domingez-Caicedo’s, and Victor Gaspar
    Chichande’s convictions for conspiring to distribute cocaine
    on board a vessel, possession of cocaine with intent to
    distribute on board a vessel, and aiding and abetting;
    affirmed Dominguez-Caicedo’s and Cortez-Quinonez’s
    sentences; vacated Chichande’s sentence; and remanded for
    Chichande’s resentencing.
    Coast Guard officers boarded a suspicious panga boat
    carrying the defendants near the Galapagos Islands after the
    boat ignored warnings to stop. Officers then detained the
    defendants, and the Coast Guard transferred them to a series
    of Coast Guard cutters, eventually transferring them to DEA
    custody in Long Beach, where a DEA agent had each
    defendant sign a Rule 5 waiver that allowed them to be
    transferred to San Diego instead of going before a magistrate
    judge in Long Beach.
    The defendants moved to dismiss the indictment for
    outrageous government conduct based on their treatment
    aboard the Coast Guard cutters. In order to secure dismissal
    of an indictment due to outrageous government conduct, a
    defendant must show a nexus between the conduct and either
    securing the indictment or procuring the conviction. The
    defendants claimed that the nexus between the
    Government’s conduct and securing the indictment is
    **
    This summary constitutes no part of the opinion of the court. It
    has been prepared by court staff for the convenience of the reader.
    4        UNITED STATES V. DOMINGUEZ-CAICEDO
    satisfied because if the Coast Guard had chosen to treat the
    defendants and other detainees humanely, they couldn’t have
    conducted their Pacific operations. The panel wrote that this
    is not the type of nexus this court generally considers
    sufficient to establish outrageous government conduct
    requiring dismissal of an indictment, noting that nearly all
    police actions are broadly connected to securing indictments.
    The panel wrote that the Ninth Circuit appears to have
    assumed without deciding that outrageous government
    conduct could apply to conditions of confinement, so long as
    there is a nexus between the conduct and securing the
    indictment or conviction. Because there is no nexus here,
    the panel did not revisit that conclusion. The defendants
    argued that even if outrageous government conduct does not
    require dismissal of the indictment, the district court should
    have used its supervisory powers to provide the same
    remedy, asserting that the government should tread lightly in
    international waters, and the court should not condone
    mistreatment of foreigners with no connection to the United
    States. The panel wrote that pursuant to United States v.
    Matta-Ballesteros, 
    71 F.3d 754
     (9th Cir. 1995), that is not a
    sufficient reason to hold that the district court abused its
    discretion by not dismissing the indictment. The panel
    therefore affirmed the district court’s denial of the
    defendants’ motions to dismiss the indictment.
    The defendants also sought to dismiss the indictment for
    violation of Fed. R. Crim. P. 5, which requires that the
    Government bring defendants before a magistrate judge
    without unnecessary delay. The panel held that a court has
    the power to dismiss an indictment for egregious violations
    of Rule 5, and that the proper inquiry is whether
    transportation to the United States as a whole was
    unnecessarily delayed, rather than whether there was some
    other district in the United States in which the defendant
    UNITED STATES V. DOMINGUEZ-CAICEDO                  5
    could have been brought before a magistrate judge more
    quickly. The panel held that the district court did not clearly
    err in its determination that 23 days was not an unreasonable
    delay, given that the Coast Guard needed to transport the
    defendants from near the Galapagos Islands to San Diego.
    The panel therefore concluded that the Coast Guard’s
    decision to take the defendants to California, rather than
    Florida, did not violate Rule 5. The panel also held that the
    district court did not clearly err in finding that the delays
    between arrival in Long Beach and presentment before a
    magistrate judge in San Diego were reasonable. Because the
    panel held that the Government did not violate Rule 5, it did
    not need to examine whether the defendants voluntarily
    signed their Rule 5 waivers, or whether the facts of this case
    present a Rule 5 violation that warrants dismissal of the
    indictment.
    Cortez-Quinonez argued that even if there was no Rule
    5 violation, his statement still should have been suppressed
    because it was involuntary. The panel held that the district
    court did not err by finding that the statement was voluntary
    under the Due Process Clause, where, at the time he gave his
    statement, Cortez-Quinonez was no longer experiencing the
    coercive government misconduct he alleged is the treatment
    he received on the Coast Guard cutter.
    The panel next addressed the defendants’ prosecutorial
    misconduct claims. The panel held that the prosecutor’s use
    of a “drug trafficker’s playbook” analogy during closing
    argument did not constitute prosecutorial misconduct
    because the prosecutor’s references to a “playbook” were not
    meant to imply that there was an actual playbook in
    evidence; instead, the prosecutor used the analogy to explain
    why the defendants did what they did. Rejecting the
    contention that the prosecutor committed misconduct by
    6        UNITED STATES V. DOMINGUEZ-CAICEDO
    arguing in closing that Dominguez-Caicedo was in charge
    but arguing at sentencing that Cortez-Quinonez was the
    leader, the panel wrote that the prosecutor did not argue facts
    that he knew were untrue, and that it was not inconsistent for
    him to point out all of these facts about Dominguez-Caicedo
    and Cortez-Quinonez both in closing argument and at
    sentencing. For the same reasons, the panel rejected Cortez-
    Quinonez’s argument that the prosecutor’s alleged
    misconduct resulted in depriving him of a minor role
    reduction, violating his right to due process. The panel held
    that the prosecutor’s statement that “throwing cocaine
    overboard on a vessel is knowing possession of cocaine” was
    harmless error in the context of the entire trial.
    In order to corroborate his duress defense, Dominguez-
    Caicedo attempted to call as an expert witness an attorney
    who grew up near where Dominguez-Caicedo lived in
    Colombia, and who would have testified that he is aware that
    armed criminal paramilitary groups in the area kidnap,
    intimidate, and use violence to further their criminal
    enterprises.      Dominguez-Caicedo contended that, in
    excluding the testimony, the district court’s focus on the
    Daubert factors of reliable principles and methods was
    misplaced, where the subject of the testimony was to be his
    knowledge and experience, rather than his scientific
    analyses. The panel held that, given the extremely broad
    latitude the Supreme Court has said district courts have in
    conducting this inquiry, the district court did not abuse its
    discretion by looking at these particular factors and finding
    the proposed witness’s testimony wanting.
    All three defendants challenged the district court’s denial
    of their requests for minor role reductions at sentencing. The
    panel clarified how district courts should conduct the minor
    role analysis. To be eligible for either a “minimal” role
    UNITED STATES V. DOMINGUEZ-CAICEDO                  7
    adjustment, which comes with a guidelines reduction of at
    least four levels, U.S.S.G. § 3B1.2(a), cmt. 4, or a “minor’
    role adjustment, which provides a reduction of at least two
    levels, id. at cmt 5, the defendant must be substantially less
    culpable than the average participant in the criminal activity.
    The relevant comparison is to the other participants in the
    defendant’s crime, not to typical defendants who commit
    similar crimes. To determine whether a defendant is
    substantially less culpable than the average participant in the
    offense, a district court must (1) identify all of the
    individuals for whom there is sufficient evidence of their
    existence and participation in the overall scheme;
    (2) calculate a rough average level of culpability for these
    individuals, taking into consideration the five factors in
    comment 3(C) to the Mitigating Role Guideline; and
    (3) compare the defendant’s culpability to that average.
    The panel agreed with Chichande that the district court’s
    exclusion of his recruiter from the analysis was erroneous
    because the proper comparison is the average of all of the
    individuals who participated in Chichande’s offense,
    including those that the district court believed were leaders
    or organizers or who were otherwise highly culpable.
    Because the district court misunderstood the appropriate
    legal standard, the panel vacated Chichande’s sentence and
    remanded for the district court to conduct the minor role
    analysis applying the correct legal standard. The panel
    concluded that the Government did not meet its burden of
    establishing that any error was harmless.
    The panel held that the district court did not abuse its
    discretion in denying Cortez-Quinonez a minor role
    adjustment. The panel wrote that the fact that illicit drugs
    are often traceable to larger drug trafficking organizations
    does not mean that district courts must compare the conduct
    8        UNITED STATES V. DOMINGUEZ-CAICEDO
    of each defendant convicted of a drug crime to that of every
    hypothetical member of a drug trafficking organization; the
    relevant comparators are the actual participants in the
    defendant’s crime, and the district court is not required to
    compare the defendant’s culpability with that of the
    unidentified person.
    The panel held that the district court likewise did not err
    in denying Dominguez-Caicedo a minor role reduction. The
    panel wrote that the district court did not determine that the
    “guys with guns” and the “man who commandeered Mr.
    Dominguez” were “likely participants,” and therefore did
    not err by excluding them from the comparison. Because
    Dominguez-Caicedo did not properly object to the
    Presentence Report at all, the district court was not required
    to address his argument raised for the first time in his
    sentencing memorandum—and never mentioned during the
    sentencing hearing—that there was sufficient evidence that
    the individuals identified were involved in the crime.
    UNITED STATES V. DOMINGUEZ-CAICEDO               9
    COUNSEL
    Robert H. Rexrode III, Law Offices of Robert Rexrode, San
    Diego, California, for Defendant-Appellant Segundo
    Marcial Dominguez-Caicedo.
    Michael Marks (argued), Federal Defenders of San Diego
    Inc., San Diego, California, for Defendant-Appellant
    Andrian Andres Cortez-Quinonez.
    Mark F. Adams, Law Offices of Mark F. Adams, San Diego,
    California, for Defendant-Appellant Victor Gaspar
    Chichande.
    D. Benjamin Holley (argued), Assistant United States
    Attorney; Daniel E. Zipp, Chief, Appellate Section, Criminal
    Division; Robert S. Brewer, Jr., United States Attorney;
    United States Attorney’s Office, San Diego, California; for
    Plaintiff-Appellee.
    10        UNITED STATES V. DOMINGUEZ-CAICEDO
    OPINION
    M. SMITH, Circuit Judge:
    The defendants in these three consolidated cases—
    Adrian Andres Cortez-Quinonez, Segundo Marcial
    Dominguez-Caicedo, and Victor Gaspar Chichande—were
    convicted of conspiring to distribute cocaine on board a
    vessel, possession of cocaine with intent to distribute on
    board a vessel, and aiding and abetting. In this appeal, they
    challenge the district court’s denial of their pre-trial motions
    to dismiss the indictment. Defendants also argue that the
    prosecutor committed misconduct in his closing argument.
    Individually, Dominguez-Caicedo contends that the district
    court improperly excluded expert testimony that supported
    his duress defense. Cortez-Quinonez individually appeals
    the district court’s decision not to suppress his post-arrest
    statements. He also argues that the prosecutor committed
    misconduct by arguing at his sentencing that Cortez-
    Quinonez was the ringleader, after arguing at trial that
    Dominguez-Caicedo was in charge. Finally, all three
    defendants argue that the district court erred by not granting
    them minor role reductions at sentencing. We have
    jurisdiction pursuant to 
    28 U.S.C. § 1291
    , and we affirm the
    defendants’ convictions and Dominguez-Caicedo’s and
    Cortez-Quinonez’s sentences. We vacate Chichande’s
    sentence and remand for resentencing.
    FACTUAL AND PROCEDURAL BACKGROUND
    On December 31, 2017, the Coast Guard cutter Stratton
    spotted a suspicious vessel—a 30- to 40-foot “panga” boat—
    carrying the three defendants near the Galapagos Islands.
    The Coast Guard observed the vessel and determined that it
    had no indicia of nationality. From a Coast Guard
    helicopter, Officer Charles Arena activated the helicopter’s
    UNITED STATES V. DOMINGUEZ-CAICEDO               11
    blue law-enforcement lights and broadcast a message to the
    boat via maritime radio in English and Spanish, informing
    the vessel that the United States Coast Guard was ordering
    them to halt. When the panga did not stop, Arena ordered
    the “precision marksman” onboard the helicopter to fire
    warning shots into the water in front of the panga, some of
    which contained an orange tracer that makes the shots more
    visible. After discharging the warning shots, Arena
    observed “the occupants onboard start to throw items
    overboard,” including “packages that were tied together.”
    The Coast Guard later determined that the packages were
    attached to a “GPS buoy” that was also thrown overboard.
    When the panga still did not stop, the marksman fired two
    more warning shots into the water aft of the panga’s engine,
    apparently to signal that those on board should move away
    from the engine, and then shot out the engine. Dominguez-
    Caicedo testified that by the time he saw the helicopter, it
    was shooting at the panga. He did not know that it was a
    U.S. Coast Guard helicopter. Cortez-Quinonez stated that
    he thought the shots from the helicopter were going to kill
    them.
    Three officers from the Coast Guard then boarded the
    panga. Dominguez-Caicedo told the officers who boarded
    the panga that they had been out fishing. Cortez-Quinonez
    identified himself as the “master” of the vessel through an
    interpreter, to one of the Coast Guard officers. Cortez-
    Quinonez gave the officers his Ecuadorian identification
    card. The other two defendants said that they did not have
    any identification with them. The Coast Guard then detained
    the three defendants and transferred them to the Stratton.
    Several days later, on January 2, 2018, they were transferred
    to the Northland, another Coast Guard vessel, where they
    were detained until January 3.
    12       UNITED STATES V. DOMINGUEZ-CAICEDO
    On board the Stratton, according to Officer Welzant of
    the Coast Guard, the standard protocol dictates that each
    detainee is given an initial medical screening by the medical
    corpsman—essentially a nurse. They are not told where they
    are headed, they do not get an opportunity to contact their
    families, and they do not know how long they will be on
    board. Detainees are chained to a cable that runs the length
    of the deck inside the helicopter hangar (emptied of
    helicopters). Each detainee is chained to the cable using an
    eighteen-inch ankle shackle. The detainees remain chained
    at all times of the day and night, except for trips to the
    bathroom and approximately one hour per day of exercise
    time, during which the detainees are permitted to walk freely
    on the deck. Detainees can shower periodically. Cortez-
    Quinonez testified that he was forced to shower with the
    other two defendants while officers laughed at their “private
    parts and how [they] were naked,” though it was not clear on
    which cutter this allegedly occurred. Welzant stated that
    there were no group showers on the Stratton. Welzant
    testified that detainees are escorted to use the restroom upon
    request, unless the crew is launching a helicopter or a small
    boat, which would take approximately ten minutes.
    However, the Stratton’s detainee logbook showed that the
    three defendants were rarely taken to the restroom between
    6:30 p.m. and 7:00 a.m. the next morning. When the three
    defendants in this case were detained, there were thirty-
    seven total detainees on board the Stratton.
    Welzant testified that Defendants were provided with
    mats approximately half an inch thick on which to sleep.
    The Coast Guard confiscated the clothes that the defendants
    were wearing and gave them disposable Tyvek painters’
    coveralls to wear instead. These coveralls often ripped and
    exposed detainees. Each person also routinely receives a
    blanket. Detainees are fed three meals per day, primarily
    UNITED STATES V. DOMINGUEZ-CAICEDO                 13
    consisting of rice and beans, supplemented with fruit
    approximately every other day. A jug of water is accessible
    to detainees at all times. Welzant stated that the detainees
    are also provided with dominoes, cards, and Spanish-
    language Bibles. Officer Jordan Groff testified to the
    conditions aboard the Northland, which were substantially
    similar to those on board the Stratton, except that the
    detainees ate eggs, potatoes, toast, enchiladas, spaghetti, and
    chicken, rather than rice and beans.
    On January 3, 2018, the defendants were transferred to
    another Coast Guard cutter, the Mohawk. The defendants
    were transferred to the Mohawk—which was heading for
    Florida—because the Coast Guard suspected that the
    Department of Justice would prosecute the case in Florida.
    On the Mohawk, the detainees were kept on the top deck,
    exposed to the elements. According to Coast Guard officer
    Kristopher Meyer, the crew erects a tent on that deck while
    detainees are on-board to provide some shelter from the
    elements. The Mohawk crew does not provide any sleeping
    mats, though they do give each detainee a blanket and a
    towel.
    While the defendants were on the Mohawk, there were
    numerous rain squalls, which caused the deck to become
    wet. When it rained during the night, the detainees would
    either have to stand up or try to sleep while laying on the wet
    deck. On the Mohawk, detainees were served rice and beans
    for every meal. The defendants testified that the rice and
    beans were very undercooked, and that these meals resulted
    in them suffering gastrointestinal distress. The Mohawk’s
    detainee log shows that Gaspar Chichande refused five
    meals in a row, and that Cortez-Quinonez and Dominguez-
    Caicedo refused three meals in a row. Cortez-Quinonez
    14       UNITED STATES V. DOMINGUEZ-CAICEDO
    testified that he was denied medical care on board the
    Mohawk, despite complaining of pain.
    The defendants were aboard the Mohawk for five days.
    On January 8, 2018, they were transferred back to the
    Stratton—which was heading to California—because the
    Department of Justice had designated the Southern District
    of California as the prosecuting district. If the defendants
    had remained on the Mohawk, they would have arrived in
    Florida on January 17, 2018. However, the Coast Guard
    determined that there was no aircraft available to fly the
    defendants from Florida to California to prosecute them in
    the designated district.
    On January 16, 2018, the defendants were transferred
    from the Stratton to their final cutter, the Active. The
    conditions of confinement on the Active were similar to
    those on the Stratton, except that the area where the
    defendants were shackled was protected from the elements
    only by a canvas tarp, and the sleeping mats provided were
    an inch-and-a-half thick. In addition, the temperature
    dropped as low as 50 degrees during the time the defendants
    were onboard the Active. Dominguez-Caicedo testified that
    he was extremely cold on the Active.
    Dominguez-Caicedo and Cortez-Quinonez testified that
    the shackles and living conditions onboard the cutters caused
    them significant physical pain. A psychologist, Dr. Julia
    Kuck, testified as an expert witness at the defendants’
    motion to dismiss hearing. Dr. Kuck had interviewed
    Gaspar Chichande and diagnosed him with post-traumatic
    stress disorder (PTSD) with dissociative symptoms and
    panic attacks. This diagnosis was based on antecedent
    traumatic events such as childhood neglect, abandonment,
    and trauma. Dr. Kuck testified that the “primary triggering
    event” for Gaspar Chichande’s PTSD was the Coast Guard
    UNITED STATES V. DOMINGUEZ-CAICEDO                 15
    helicopter firing its gun at the panga. She also referred to the
    treatment aboard the Coast Guard cutters as psychological
    torture due to “unrelenting cold,” “wet conditions on deck,”
    “feral treatment of individuals,” and “induced desperation.”
    The Coast Guard had intended to land the Active in San
    Diego, but due to bad weather, it was prevented from doing
    so. Instead, the Active landed in Long Beach on January 22,
    2018, where DEA Agent Brandon Pullen met the ship and
    took custody of the defendants. Pullen testified that none of
    the three defendants appeared to be ill or under the influence
    of drugs or alcohol. Pullen had each defendant sign a Rule
    5 waiver that allowed them to be transferred to San Diego
    instead of going before a magistrate judge in Long Beach.
    The waivers also advised Defendants that they were entitled
    to remain silent and to have an attorney appointed to
    represent them.
    Pullen then advised each defendant of his Miranda rights
    in Spanish through another DEA agent, who served as an
    interpreter. Each defendant signed a Miranda waiver. After
    signing the waiver, Cortez-Quinonez made incriminating
    statements that suggested he knew that he was transporting
    drugs. At a pre-trial hearing, Cortez-Quinonez testified that
    at the time he signed the Miranda form, he did not
    understand that a lawyer could be appointed for him free of
    charge; the form does not specify that the appointed attorney
    would be free of charge. The statements were nonetheless
    introduced at trial. The jury convicted the defendants on all
    charges.
    STANDARDS OF REVIEW
    We review de novo the district court’s decision on the
    motion to dismiss for outrageous government conduct, and
    we review for abuse of discretion the district court’s decision
    16        UNITED STATES V. DOMINGUEZ-CAICEDO
    not to use its supervisory powers to dismiss the indictment.
    United States v. Restrepo, 
    930 F.2d 705
    , 712 (9th Cir. 1991).
    We review “a district court’s finding that a pre-arraignment
    delay was reasonable for clear error.” United States v. Liera,
    
    585 F.3d 1237
    , 1242 (9th Cir. 2009) (citation omitted).
    In reviewing alleged prosecutorial misconduct to which
    a defendant objected at trial, we review under the harmless
    error standard. United States v. Alcantara-Castillo, 
    788 F.3d 1186
    , 1190 (9th Cir. 2015). Under the harmless error
    standard, we must view “the challenged conduct in the entire
    context of the trial, and reverse only if it appears more
    probable than not that prosecutorial misconduct materially
    affected the fairness of the trial.” 
    Id.
     (citation and internal
    quotation marks omitted). If the defendant does not
    contemporaneously object, we review the alleged
    misconduct for plain error. 
    Id.
     Under plain error, “[w]e may
    reverse if (1) there was error; (2) it was plain; (3) it affected
    the defendant’s substantial rights; and (4) viewed in the
    context of the entire trial, the impropriety seriously affected
    the fairness, integrity, or public reputation of judicial
    proceedings.” 
    Id.
     at 1190–91 (citation and internal quotation
    marks omitted). Furthermore, where a defendant alleges
    multiple instances of misconduct, we must consider the
    combined prejudicial effect of the misconduct. Berger v.
    United States, 
    295 U.S. 78
    , 89 (1935). In considering the
    cumulative effect of alleged misconduct, where the
    defendant objected to some—but not all—of the alleged
    misconduct, we review for plain error. Alcantara-Castillo,
    788 F.3d at 1191.
    UNITED STATES V. DOMINGUEZ-CAICEDO               17
    ANALYSIS
    A
    Prior to trial, the defendants moved to dismiss the
    indictment for outrageous government conduct based on
    their treatment aboard the Coast Guard cutters. They also
    sought to dismiss the indictment for violation of Federal
    Rule of Criminal Procedure 5, which requires that the
    Government bring defendants before a magistrate judge
    without unnecessary delay.
    “The argument that an indictment must be dismissed
    because of outrageous government conduct is derived from
    a comment by the Supreme Court in United States v. Russell,
    
    411 U.S. 423
     (1973),” in which the Court distinguished a
    claim of outrageous government conduct from a claim of
    entrapment. Restrepo, 
    930 F.2d at 712
    . While entrapment
    depends on the defendant’s criminal predisposition, “[a]n
    indictment may be set aside because of outrageous
    government conduct whether or not the defendant was
    predisposed to engage in criminal activity.” 
    Id.
     (citation
    omitted).
    “In order to show outrageous government conduct,
    defendants must show conduct that violates due process in
    such a way that it is ‘so grossly shocking and so outrageous
    as to violate the universal sense of justice.’” United States
    v. Stinson, 
    647 F.3d 1196
    , 1209 (9th Cir. 2011) (quoting
    Restrepo, 
    930 F.2d at 712
    ). A claim of outrageous
    government conduct is “a claim that government conduct in
    securing an indictment was so shocking to due process
    values that the indictment must be dismissed.” United States
    v. Nickerson, 
    731 F.3d 1009
    , 1015 (9th Cir. 2013) (citation
    omitted). Therefore, in order to secure dismissal of an
    indictment due to outrageous government conduct, a
    18       UNITED STATES V. DOMINGUEZ-CAICEDO
    defendant must show a nexus between the conduct and either
    “securing the indictment or [ ] procuring the conviction.” 
    Id.
    Defendants claim that the nexus between the
    Government’s conduct and securing the indictment is
    satisfied because “if the Coast Guard had chosen to treat
    Appellants and other detainees humanely, they simply
    couldn’t have conducted their Pacific operations.”
    Specifically,
    [o]ne officer testified that feeding rice and
    beans [to the detainees] was the only
    affordable way for the Coast Guard to
    accomplish its mission. Another testified that
    the excessive restraint of defendants resulted
    from too few watchmen and too many
    detainees. Coast Guard testified that it
    couldn’t get detainees to shore because its
    helicopters were old and didn’t have long
    range. They claimed they couldn’t wait for
    diplomatic clearance to get people off the
    cutters because it would upset the ability to
    patrol the ocean.
    This is not the type of nexus that we generally consider
    sufficient to establish outrageous government conduct
    requiring dismissal of an indictment. For example, in
    Nickerson, the defendant argued that her indictment should
    have been dismissed based on “outrageous government
    conduct of videotaping her while she was using the toilet in
    a holding cell at the police station.” 731 F.3d at 1014. The
    video camera that captured the defendant in Nickerson
    served a variety of purposes, including “medical and security
    concerns, such as if a detainee attempts suicide, if a physical
    altercation occurs between detainees, or if a detainee
    UNITED STATES V. DOMINGUEZ-CAICEDO               19
    becomes progressively more intoxicated or sick in the
    holding cell and needs medical attention.” Id. at 1011.
    Furthermore, the cameras “deter abusive police conduct[.]”
    Id. We held that “there was no nexus between that conduct
    and the criminal proceeding at issue.” Id. at 1015.
    Accepting Dominguez-Caicedo’s logic would have
    compelled the opposite conclusion. After all, if a medical or
    security concern resulted in the death of an arrested person,
    that would preclude the prosecutor from securing an
    indictment against that person. In other words, nearly all
    police actions are broadly connected to securing indictments.
    That cannot mean that all police actions have a nexus within
    the meaning of the outrageous government conduct doctrine.
    We have dismissed an indictment due to outrageous
    government conduct in a published opinion only once, in
    Greene v. United States, 
    454 F.2d 783
     (9th Cir. 1971). In
    Greene, “the government supplied the equipment and raw
    material for a bootlegging operation and was the defendant’s
    sole customer.” United States v. Mayer, 
    503 F.3d 740
    , 754
    (9th Cir. 2007). We held that the government could not
    “involve itself so directly and continuously over such a long
    period of time in the creation and maintenance of criminal
    operations, and yet prosecute its collaborators.” Greene,
    454 F.2d at 787. The type of nexus in Greene between the
    allegedly outrageous conduct and securing an indictment or
    conviction is not present in this case.
    Indeed, the development of the outrageous government
    conduct concept suggests that it does not even apply to
    conditions of pre-trial detention. For that reason, the
    Eleventh Circuit has rejected claims similar to those
    Defendants raise here. See United States v. Jayyousi,
    
    657 F.3d 1085
    , 1112 (11th Cir. 2011) (holding that the
    outrageous government conduct doctrine “does not apply” to
    20        UNITED STATES V. DOMINGUEZ-CAICEDO
    alleged mistreatment between arrest and indictment). Unlike
    the Eleventh Circuit, our circuit appears to have assumed
    without deciding that outrageous government conduct could
    apply to conditions of confinement, so long as there is a
    nexus between the conduct and securing the indictment or
    conviction. E.g., Nickerson, 731 F.3d at 1015. Because
    there is no nexus here, it is unnecessary to revisit that
    conclusion.
    Separate from the outrageous government conduct
    claim, federal courts also “have inherent supervisory powers
    to order dismissal of prosecutions” for three reasons: (1) to
    remedy “the violation of a recognized statutory or
    constitutional right”; (2) to ensure “that a conviction rests on
    appropriate considerations validly before a jury”; and (3) “to
    deter future illegal conduct.” United States v. Matta-
    Ballesteros, 
    71 F.3d 754
    , 763 (9th Cir. 1995) (citation
    omitted). Defendants argue that even if outrageous
    government conduct does not require dismissal of the
    indictment, the district court should have used its
    supervisory powers to provide the same remedy. Their
    reasoning rests on the assertion that the “government should
    tread lightly in international waters, and the court should not
    condone mistreatment of foreigners with no connection to
    the United States.” Pursuant to Matta-Ballesteros, that is not
    a sufficient reason to hold that the district court abused its
    discretion by not dismissing the indictment. Therefore, we
    affirm the district court’s denial of Defendants’ motions to
    dismiss for outrageous government conduct.
    B
    Defendants’ joint Rule 5 claim requires us to determine
    (1) whether dismissal of an indictment is a remedy available
    for violation of Rule 5; and (2) if so, whether Defendants
    have shown that they are entitled to this remedy. We hold
    UNITED STATES V. DOMINGUEZ-CAICEDO               21
    that a court has the power to dismiss an indictment for
    egregious violations of Rule 5, but that the Government did
    not violate Rule 5 in this case.
    1
    “A person making an arrest outside the United States
    must take the defendant without unnecessary delay before a
    magistrate judge[.]” Fed. R. Crim. P. 5(a)(1)(B). This is
    termed the “‘presentment’ requirement,” and it is meant “to
    prevent secret detention” and “inform a suspect of the
    charges against him[.]” Corley v. United States, 
    556 U.S. 303
    , 306 (2009). The predecessor to Rule 5(a) was McNabb
    v. United States, 
    318 U.S. 332
     (1943), in which the Supreme
    Court held that “unwarranted detention” between arrest and
    presentment “led to tempting utilization of intensive
    interrogation.” Mallory v. United States, 
    354 U.S. 449
    , 453
    (1957). “[I]t was deemed necessary to render inadmissible
    incriminating statements elicited from defendants during a
    period of unlawful detention.” 
    Id.
     Thus, the normal remedy
    for violation of Rule 5 is suppression of statements made
    during the unnecessary delay. 
    Id.
     When an individual does
    not make any incriminating statements during the delay in
    presentment, we have previously suggested that vacating the
    conviction and dismissing the indictment is a “drastic
    remedy” that the court can “invoke.” United States v.
    Jernigan, 
    582 F.2d 1211
    , 1214 (9th Cir. 1978). However,
    we appear never to have granted that remedy in any prior
    case.
    In Bayless v. United States, 
    381 F.2d 67
    , 70–71 (9th Cir.
    1967), we affirmed the district court’s denial of a motion to
    dismiss based on violation of Rule 5(a). We held that
    because the Government did not obtain any incriminating
    evidence between arrest and presentment, the defendant was
    not prejudiced by the Government’s violation of Rule 5(a).
    22       UNITED STATES V. DOMINGUEZ-CAICEDO
    
    Id. at 71
    . Consequently, the motion to dismiss the
    indictment “was correctly denied.” Id.; see United States v.
    Mejia, 39 F. App’x 568, 569–70 (9th Cir. Apr. 29, 2002)
    (finding that a thirteen-day delay in presentment, while
    “reprehensible,” did not warrant dismissal of the
    indictment). Conversely, in United States v. Osunde, 
    638 F. Supp. 171
    , 176 (N.D. Cal. 1986), the Northern District of
    California reasoned that a 106-day delay between arrest and
    presentment was a “flagrant” violation of Rule 5(a). And
    “[a]lthough the Court [could not] point to case law
    supporting dismissal, rather than suppression of evidence,
    for flagrant violations of Rule 5(a),” it held that Osunde’s
    lengthy delay—with no incriminating evidence to
    suppress—made dismissal of the indictment appropriate. 
    Id.
    at 176–77.
    The Second and Eighth Circuits have outright rejected
    dismissal of the indictment as a remedy for violation of Rule
    5, with holdings that appear to foreclose dismissal even in
    egregious circumstances. United States v. Peeples, 
    962 F.3d 677
    , 687–88 (2d Cir. 2020); United States v. Cooke,
    
    853 F.3d 464
    , 471 (8th Cir. 2017) (holding that because the
    purpose of Rule 5 is to deter purposeful delay in presentment
    in order to extract a confession, “the appropriate remedy for
    a violation of Rule 5(a)(1)(A) is not dismissal of an
    indictment, but suppression of evidence illegally obtained as
    a result of the violation.”). However, we are bound by
    Bayless and Jernigan, both of which determined that
    dismissal could be a remedy for particularly egregious
    violations of Rule 5 where no other relief is available. Thus,
    we examine whether the Government violated Rule 5.
    Because we conclude that it did not, we need not reach the
    question of whether the district court should have dismissed
    the indictment on that basis.
    UNITED STATES V. DOMINGUEZ-CAICEDO               23
    2
    Defendants argue that the Government violated Rule
    5(a) by (1) having Defendants travel to California instead of
    Florida; and (2) having Defendants sign Rule 5 waivers that
    then allowed the Government to interrogate them before
    presentment, which took place the day after they arrived in
    the United States.
    “Whether or not undue delay occurred . . . must be
    determined upon the individual facts of each case.” Gray v.
    United States, 
    394 F.2d 96
    , 100 (9th Cir. 1967). The district
    court found that “the 23-day delay [between interdiction and
    arraignment] was reasonable” because “[o]n average, it takes
    20 days to transport a detained individual from the Eastern
    Pacific to the U.S.” Further, the district court stated, “the
    coast guard needed to determine which district in the United
    States would be responsible for the prosecution of the case
    and, therefore[,] where the defendants would be
    transported.” According to the district court, the officer in
    charge of “figuring out how to transport the defendants to
    this district as quickly as possible” considered several
    options, including taking the defendants by ship to Florida,
    with a connecting flight to San Diego. However, because
    “[e]ach of these options had drawbacks,” the officer
    “determined that transporting via coast guard cutter [to San
    Diego] was the most expeditious way of transporting [the
    defendants].” Finally, the district court stated that the
    timeline of transportation to San Diego and presentment the
    next morning constituted “bringing the defendants before a
    magistrate judge without unnecessary delay.”
    i
    First, Defendants contend that the district court engaged
    in the wrong inquiry when examining their transportation to
    24         UNITED STATES V. DOMINGUEZ-CAICEDO
    California. Instead of asking whether the Government
    transported Defendants to the prosecuting district without
    unnecessary delay, Defendants claim that the district court
    should have asked whether the Government transported
    Defendants to a magistrate judge without unnecessary
    delay. 1 It is undisputed that Defendants could have arrived
    in Florida five days earlier than they arrived in California.
    The issue is whether delay caused by the choice to transport
    Defendants directly to the prosecuting district (California, in
    this case) is an “unnecessary” delay for Rule 5 purposes.
    The district court implicitly held that it was not, and we
    agree.
    Until now, we have not addressed whether a delay in
    arraignment caused by the Government’s choice to send a
    defendant interdicted on the high seas directly to the
    prosecuting district (rather than the closest magistrate judge)
    is “unnecessary delay.”         In the Fourth Amendment
    unreasonable seizure context, the Supreme Court has stated
    that “[e]xamples of unreasonable delay [in presentment] are
    delays for the purpose of gathering additional evidence to
    justify the arrest, a delay motivated by ill will against the
    arrested individual, or delay for delay’s sake.” Cnty. of
    Riverside v. McLaughlin, 
    500 U.S. 44
    , 56 (1991). In
    McLaughlin, the Court specifically cited the “often
    unavoidable delays in transporting arrested persons from one
    facility to another” as a “practical realit[y]” that would not
    qualify as unreasonable. 
    Id. at 57
    .
    1
    Defendants’ joint brief incorrectly states that Rule 5(a) requires
    transportation to “the nearest available magistrate.” This was the
    language in an outdated version of Rule 5. The current language does
    not require that Defendants be transported to the nearest magistrate, only
    that they are transported to one without unnecessary delay.
    UNITED STATES V. DOMINGUEZ-CAICEDO               25
    Other courts that have addressed delays in presentment
    of defendants arrested on the high seas have uniformly held
    that such delays are reasonable. See, e.g., United States v.
    Savchenko, 
    201 F.R.D. 503
    , 506 (S.D. Cal. 2001) (holding
    that sixteen days to transport defendants apprehended
    500 nautical miles from Mexico to the Southern District of
    California was reasonable); United States v. Barahona-
    Estupinan, 
    2004 WL 7333779
    , at *5 (S.D. Cal. Mar. 19.
    2004) (six days to transport Defendants from near the
    Mexico-Guatemala border to San Diego was not
    unreasonable); United States v. Torres-Iturre, 
    2016 WL 2757283
    , at *3–4 (S.D. Cal. May 12, 2016) (twenty-one days
    to transport Defendants 2439 nautical miles to San Diego
    was reasonable); United States v. Aragon, 
    2017 WL 2889499
    , at *14 (S.D.N.Y. Jul. 5, 2017) (sixteen-day delay
    caused by transporting Defendants from the Pacific Ocean
    to New York for prosecution was not unreasonable).
    Importantly, none of these cases compare the time it took
    the Government to bring the defendants to the prosecuting
    district to the time it would have taken to bring the
    defendants to the closest district. The Eleventh Circuit
    addressed this distinction, writing that “the MDLEA does
    not prohibit the government from taking offenders to Florida
    rather than California” because “[a] person violating the
    MDLEA may be tried in any district, if the offense was
    begun or committed upon the high seas.” United States v.
    Cabezas-Montano, 
    949 F.3d 567
    , 591 (11th Cir. 2020)
    (citation and internal quotation marks omitted). Therefore,
    the Eleventh Circuit said, “the issue here is not where the
    defendant was taken, but why it took the government 49 days
    to present the defendant arrested outside the United States
    before a magistrate judge in the United States for a probable
    cause hearing.” 
    Id.
     The court then applied the Eleventh
    Circuit’s test for determining whether a particular delay was
    26       UNITED STATES V. DOMINGUEZ-CAICEDO
    unnecessary. 
    Id.
     at 591–92. Like the Eleventh Circuit, we
    hold that the proper inquiry is whether transportation to the
    United States as a whole was unnecessarily delayed, rather
    than whether there was some other district in the United
    States in which the defendant could have been brought
    before a magistrate judge more quickly.
    The district court did not clearly err in its determination
    that twenty-three days was not an unnecessary delay, given
    that the Coast Guard needed to transport Defendants from
    near the Galapagos Islands to San Diego. In fact, Defendants
    do not contend that twenty-three days was an unreasonable
    amount of time to reach California. We therefore conclude
    that the Coast Guard’s decision to take Defendants to
    California, rather than Florida, did not violate Rule 5.
    ii
    There was a second period of delay between Defendants
    arriving in Long Beach and their presentment in San Diego.
    Defendants argue that this period of delay also violated Rule
    5. Although they signed Rule 5 waivers in Long Beach,
    Defendants say that this was involuntary. Defendants also
    contend that the waiver only excused the Government from
    presenting them to a magistrate judge in Long Beach; it did
    not allow delay of presentment once Defendants arrived in
    San Diego.
    Defendants arrived in Long Beach on January 22 at
    approximately 11:30 a.m., and cleared customs at 11:50 a.m.
    Agent Pullen took Defendants to the San Diego DEA office,
    arriving about 3:00 p.m. (with a stop for food at In-N-Out).
    That morning or the day before, Pullen had made an
    appointment for the 5:30 p.m. booking window for the
    defendants at the prison in San Diego. After Mirandizing
    Defendants, Pullen conducted brief interviews with each (ten
    UNITED STATES V. DOMINGUEZ-CAICEDO                 27
    to twenty minutes), and then took them to the prison for
    booking. They went before a magistrate judge the next
    morning, January 23.
    We have never addressed whether the standard
    procedures for booking arrestees in the Southern District of
    California violate Rule 5. However, numerous district courts
    have concluded that they do not. In United States v. Lauina,
    
    2016 WL 1573195
    , at *1 (S.D. Cal. Apr. 18, 2016), the
    district court found “it necessary to revisit the current
    presentment procedures” because “certain detainees are still
    not presented on either the day of their arrest or the day
    following their arrest.” The court explained, “In this district,
    rather than transporting detainees directly to a Magistrate
    Judge, arresting agents take detainees to the Metropolitan
    Correctional Center (“MCC”) for initial processing.” 
    Id.
    This is because “the MCC provides the necessary function
    of organizing detainees prior to their initial appearance.” 
    Id.
    The court wrote that “bringing detainees directly to the Court
    would likely be disorganized, cause unsafe conditions, and
    be an inefficient use of the Court’s time.” 
    Id.
     At the time of
    Lauina, “[t]he MCC maintain[ed] three booking windows
    each day at approximately 9:00 a.m., 12:30 p.m., and
    5:00 p.m.” 
    Id. at *2
    .
    Following Lauina, in United States v. Portocarrero-
    Angulo, 
    2017 WL 3283856
    , at *8 (S.D. Cal. Aug. 1, 2017),
    the district court rejected an international-waters defendant’s
    argument that a Friday-to-Monday delay between arrival in
    San Diego and presentment was unnecessary. The court
    wrote, “General Order No. 605 of this Court requires the
    Department of Justice, through the Bureau of Prisons and the
    U.S. Marshal Service, to ensure that every detainee being
    brought before the Court has been screened for and
    determined not to have transmittable tuberculosis.” 
    Id.
     The
    28       UNITED STATES V. DOMINGUEZ-CAICEDO
    court went on to state that “[t]he need to complete this
    screening makes the delay between Defendant’s arrival in
    San Diego on Friday afternoon and his presentment the next
    Monday reasonable.” 
    Id.
    Defendants arrived in Long Beach around 11:50 a.m., so
    the 5:30 p.m. booking window was the earliest available.
    Although Cortez-Quinonez states that the Magistrate Judge
    was arraigning defendants until “at least 5 p.m.,” that does
    not support the contention that Defendants could have been
    arraigned after their tuberculosis screening at 5:30 p.m.
    Furthermore, there is no evidence that Pullen purposely
    delayed the booking and presentment to interrogate the
    defendants. Under these circumstances, the district court’s
    finding that the delays in presentment were reasonable was
    not clearly erroneous. Because we hold that the Government
    did not violate Rule 5, we need not examine whether
    Defendants voluntarily signed their Rule 5 waivers, or
    whether the facts of this case present a Rule 5 violation that
    warrants dismissal of the indictment.
    C
    Cortez-Quinonez also argues that in the event we find
    that there was no Rule 5 violation, his statement still should
    have been suppressed because it was involuntary.
    Upon arrival at the DEA office in San Diego, Cortez-
    Quinonez and the Spanish-language interpreter had the
    following exchange in Spanish, which has been translated
    into English. Per the court translator, “Non-standard
    spelling, word choice and grammar in English reflect the
    manner of the Spanish spoken, and have been underlined.
    Ambiguous utterances have been rendered with different
    UNITED STATES V. DOMINGUEZ-CAICEDO                       29
    possibilities (or inferred meaning) in brackets.” 2
    Additionally, words the agent spoke in English are italicized.
    Agent: Okay. Before doing it any questions,
    you have to understand your rights. You
    have… right to… remeintz silent. Anything
    that you say can be useds against you. Before
    of a kert. Before doing it any questions, you
    have the right to consult an attorney. You
    have the right to have an attorney present
    during the… inter-egation. In the event of
    not being able to pay for the services of a
    attorney, and if you so wish, an [would/were
    to] be… appointed… before doing it any
    questions.         Have you understood
    [his/her/its/your] rights?
    Cortez-Quinonez: Yes.
    Agent: Okay. Are you availab-, wel-, willing
    to answer somes questions, or do you want an
    attorney?
    Cortez-Quinonez: Yes, I am willing to… to
    the questions, because… now, being here—
    you do understand me?—one, one’s family
    members—you understand me?—things,
    how they are in [one’s] country… when one
    suffers from hardship…
    2
    We have reproduced the translation of the transcript exactly as it
    appears in the record. The translation appears to be a literal word-for-
    word substitution of English for Spanish.
    30    UNITED STATES V. DOMINGUEZ-CAICEDO
    Agent: Yes, but, are you sure, or, or… do you
    want an attorney?
    Cortez-Quinonez: [Okay…/What?] There,
    there isn’t, there isn’t any money to pay an…
    Agent: That’s fine. The, uh, here, in this
    country, they give you an… attorney. You
    don’t have to pay.
    [pause]
    Agent: So, so, do you want to talk, or [does
    he/does she/do you] want to wait? Until
    speaking with your attorney.
    Cortez-Quinonez: But, the attorney, [until
    when/for how long]? This morning?
    Agent: Yes, but… [that’s that/nothing can be
    done].    You can’t… leave.         You do
    understand me?
    [pause]
    Agent: So, do you want to wai’ for, for… an
    attorney?
    Cortez-Quinonez: No, well, my buddy
    doesn’t have [enough] for… an attorney
    neither, just the… the questions—you do
    understand me?
    Agent: Okay, so, you want to talk?
    UNITED STATES V. DOMINGUEZ-CAICEDO            31
    [pause]
    Agent: Okay. so put yours… initials here, at
    each point. And then, “have you… uh,
    understood [his/her/its/their/your] rights?”
    put “yes.” And then “are you are willid to
    asnwer somes questions”, “yes.” Okay? So,
    initials, at each point…
    Cortez-Quinonez: [UI] the, of my first name,
    or—
    Agent: —Mm-hmm—
    Cortez-Quinonez: —of my last name?
    Agent: Yes. Your, uh, first name.
    Cortez-Quinonez: My first name. Like that,
    like it is here, written down?
    Agent: Yes. Mm-hmm.
    ....
    Agent: And then, here, uh… that “yes,” you
    have understood.
    [pause]
    Agent: And then, here, that “yes,” you want
    to talk.
    [pause]
    32        UNITED STATES V. DOMINGUEZ-CAICEDO
    Agent: Initials, at each point.
    Cortez-Quinonez: Just of my name?—
    Agent: —Yes.
    [pause]
    Agent: Okay, and the [Ø] goes; put your
    signature, here.
    [pause]
    Agent: Thank you.
    Cortez-Quinonez then gave an incriminating statement that
    was used against him at trial.
    Pursuant to the Due Process Clause, a statement is
    voluntary only if it is “the product of a rational intellect and
    a free will.” Blackburn v. Alabama, 
    361 U.S. 199
    , 208
    (1960). “[T]he characteristics of the accused and the details
    of the interrogation” are relevant considerations. United
    States v. Kelley, 
    953 F.2d 562
    , 564–65 (9th Cir. 1992).
    However, introduction of a statement at trial that was given
    without “coercive government misconduct” does not violate
    the Due Process Clause. Colorado v. Connelly, 
    479 U.S. 157
    , 163 (1986). It appears that the only coercive
    government misconduct Cortez-Quinonez has alleged is his
    treatment on board the Coast Guard cutter. However, at the
    time Cortez-Quinonez gave his statement, he was no longer
    experiencing this treatment. Cortez-Quinonez was advised
    of his rights, indicated he understood them, asked a
    clarifying question about his right to counsel, and then gave
    an inculpatory statement. The district court did not err by
    UNITED STATES V. DOMINGUEZ-CAICEDO               33
    finding that the statement was voluntary under the Due
    Process Clause.
    D
    1
    We turn next to Defendants’ prosecutorial misconduct
    claims. In closing argument, the prosecutor stated, “when
    the coast guard showed up, [Defendants] had to pull from the
    drug trafficker’s playbook. Play number one. You saw it on
    the video. Don’t move. They might not spot you.” After
    defense counsel objected, and the court overruled the
    objection, the prosecutor clarified, “I’m not talking about a
    playbook somewhere. I’m talking about what they did and
    what the facts in evidence show. Okay? Just so we’re clear.”
    The prosecutor went on to discuss “Plan B. Act normal.
    Nothing to see here,” “Plan C, speed away,” and “Plan D,”
    which “was throw the drugs overboard.” After Plan D,
    “there’s more in the playbook,” because “Plan E” is to
    “deceive.” Finally, “Plan F” was “[t]hings that they have
    said” at trial—namely, that they were forced to transport the
    narcotics. The prosecutor returned to the playbook analogy
    several times.
    Defense counsel objected to the prosecutor’s use of the
    playbook analogy, so we review under the harmless error
    standard. First, we must determine whether the reference to
    a playbook was error. Alcantara-Castillo, 788 F.3d at 1190.
    Defendants characterize the prosecutor’s alleged misconduct
    as stating facts that were not in evidence—namely, that there
    was a drug trafficker’s playbook that Defendants were
    following.
    The prosecutor’s reference to the playbook analogy is
    distinct from statements of facts not in evidence that this
    34         UNITED STATES V. DOMINGUEZ-CAICEDO
    court has held to be misconduct requiring reversal. See, e.g.,
    United States v. Toomey, 
    764 F.2d 678
    , 681 (9th Cir. 1985)
    (holding that a prosecutor’s statement that “[w]e know that
    the delivery of heroin base . . . occurred on April 28” when
    there was no evidence that the package contained heroin
    base was harmless); United States v. Wilkes, 
    662 F.3d 524
    ,
    540 (9th Cir. 2011) (holding that a prosecutor’s statement
    that a defense witness lied because he “has an ax to grind”
    was not improper reference to facts not in evidence).
    In this case, the prosecutor’s references to a “playbook”
    clearly were not meant to imply that there was an actual
    playbook in evidence that listed Plans A–F. 3 Instead, the
    prosecutor was using the playbook analogy to provide a
    framework to consider Defendants’ different actions during
    the Coast Guard’s interdiction.
    Defendants also argue that the prosecutor’s use of the
    playbook analogy constituted improper vouching and
    implied extra-record knowledge not available to the jury.
    The transcript of the prosecutor’s closing argument simply
    does not bear this out. As stated above, the playbook
    analogy was used to explain why the defendants did what
    they did, creating an overarching narrative for the video
    showing the interdiction. The prosecutor’s argument was
    based on the facts in evidence. We hold that this argument
    did not constitute prosecutorial misconduct, and so we do
    not address whether the referenced misconduct was harmless
    error.
    3
    This contrasts with the case Defendants cite, United States v.
    McGill, 
    815 F.3d 846
     (D.C. Cir. 2016), in which the court held that a
    prosecutor committed misconduct by arguing that the defendant’s letters
    from jail constituted a “playbook” that the defense attorney and
    witnesses all consulted in order to put on a false defense.
    UNITED STATES V. DOMINGUEZ-CAICEDO               35
    2
    Defendants also contend that the prosecutor committed
    misconduct by arguing in closing that Dominguez-Caicedo
    was in charge but arguing at sentencing that Cortez-
    Quinonez was the leader.
    In closing, the prosecutor said:
    Here is [Gaspar Chichande’s] testimony from
    this trial. “In fact, you indicated Mr. Cortez
    was the captain, he was in charge, didn’t
    you?” And he said, “Well, because he had a
    device with him, and that’s why I said he was
    the captain.” “But he had a device, and he
    would tell you to drive such and such route?”
    “Yes, sir.” “And in fact, you specifically
    called him the captain?”           “Yes, sir.”
    “Because he was in charge?” And he says, “I
    think so.” Right? He thinks he’s in charge
    because he’s manning the engines, but you
    know from watching the video that
    Mr. Dominguez is the one calling the shots.
    You see it. He’s this one that turns around
    and gives the order.
    The prosecutor also stated “Mr. Dominguez [is] the man
    giving the order for the boat to take off[.]” In other words,
    Gaspar Chichande testified that he believed Cortez-
    Quinonez was the captain of the boat, but the video of the
    interdiction showed that Dominguez-Caicedo gave the order
    for the boat to take off.
    At Cortez-Quinonez’s sentencing, the district court
    began by giving counsel his tentative on the sentence—
    240 months. Cortez-Quinonez’s attorney “strongly urge[d]”
    36        UNITED STATES V. DOMINGUEZ-CAICEDO
    the court to “come off [its] tentative” based on the argument
    that Cortez-Quinonez was more similar to Gaspar Chichande
    (who got 180 months) in terms of relative culpability than he
    was to Dominguez-Caicedo (who got 216 months). The
    court stated, “I haven’t disregarded your arguments yet, but
    so far, it kind of has struck me that it’s Mr. Cortez that really
    was the one that was most culpable and most in charge.” The
    prosecutor then argued:
    In terms of the suggestion that [Cortez-
    Quinonez] wasn’t in charge, our trial strategy
    is not what is necessarily 100 percent what
    actually is—who’s in charge, right?
    The fact that we may highlight a particular
    person in closing argument is a trial strategy
    in light of how the trial played out and the
    evidence, but what we do know—so I
    wouldn’t take too much from that.
    But what we do know is that Mr. Gaspar
    Chichande testified, and he said that it was
    Mr. Cortez who had the GPS communication
    device. . . . Mr. Cortez says in his post-arrest
    statement that, in fact, [the bosses] were
    telling him—giving instructions, that sort of
    stuff [through the device].
    He’s also the one who instructs Mr. Gaspar
    Chichande to activate the GPS device. That’s
    testimony that’s uncontroverted in the
    trial. . . . When the coast guard comes
    onboard, who is it that says he’s the captain?
    It’s Mr. Cortez.
    UNITED STATES V. DOMINGUEZ-CAICEDO                 37
    In context, it is clear that the prosecutor did not argue
    facts in closing that he knew were untrue. The trial evidence
    showed both that Dominguez-Caicedo gave the order for the
    boat to take off, attempting to outrun the Coast Guard, and
    that Cortez-Quinonez was driving the boat, communicating
    with the bosses back in South America, and gave the order
    for Gaspar Chichande to activate the GPS buoy before
    throwing the narcotics overboard. It was not inconsistent for
    the prosecutor to point out all of these facts, both in closing
    argument and at sentencing. We hold that this alleged
    misconduct also does not constitute error.
    3
    Cortez-Quinonez argues that the prosecutor’s alleged
    misconduct resulted in depriving him of a minor role
    reduction, violating his right to due process. However, for
    the same reasons that the prosecutorial misconduct claim
    fails, Cortez-Quinonez’s due process claim also fails—the
    prosecutor highlighted different facts that were not
    inconsistent with each other at different stages of the
    proceeding.
    4
    In closing argument, the prosecutor said, “Ladies and
    gentlemen, throwing cocaine overboard on a vessel is
    knowing possession of cocaine. All right? Just watch this
    [video] clip. That’s the element in a heartbeat.” Defense
    counsel objected, and the district court overruled the
    objection. The prosecutor then immediately clarified:
    The evidence shows that what they’re doing
    is knowing possession of the cocaine. They
    know that it’s there, they have control of it,
    and they’re throwing it overboard, and you
    38       UNITED STATES V. DOMINGUEZ-CAICEDO
    infer from their actions that they know it’s
    cocaine or some other drug . . . and clearly
    when the coast guard comes, they don’t
    throw the fuel barrels and all that overboard.
    They’re throwing the cocaine overboard.
    Defendants argue that although “the prosecutor softened the
    categorical nature of this incorrect statement of the law,”
    “that softening came too late,” resulting in the jury being
    “most likely left with the incorrect view of the law that
    simply possessing something that turned out to be cocaine is
    sufficient to prove knowing possession under the law.”
    The jury was instructed that “an act is done knowingly if
    the defendant is aware of the act and does not act through
    ignorance, mistake, or accident. . . . You may consider
    evidence of the defendant’s words, acts, or omissions along
    with all the other evidence in deciding whether the defendant
    acted knowingly.” Although it is true that throwing wrapped
    bales overboard without knowing that there is cocaine inside
    is not in itself enough to establish knowing possession, the
    prosecutor immediately clarified that he meant the jury could
    infer knowledge of the contents of the packages based on
    their throwing them overboard. This error was harmless in
    the context of the entire trial.
    E
    Dominguez-Caicedo attempted to call an expert witness,
    Diego Alexander Marinez, an attorney in Colombia.
    Mr. Marinez grew up approximately 40 miles from the area
    where Dominguez-Caicedo lived (Barbacoas). He travels to
    Barbacoas at least once per month for work. According to
    the offer of proof submitted to the district court, Mr. Marinez
    was prepared to testify that he is familiar with armed
    criminal paramilitary groups in that area. He also would
    UNITED STATES V. DOMINGUEZ-CAICEDO                 39
    have testified that he “is aware” that these groups kidnap,
    intimidate, and use violence to further their criminal
    enterprises, including drug trafficking. Mr. Marinez also
    stated that he “is aware” that these groups dress in military
    garb and carry assault rifles in broad daylight in the area.
    Mr. Marinez’s testimony would have been offered to
    corroborate Dominguez-Caicedo’s duress defense. At trial,
    Dominguez-Caicedo testified that five paramilitary
    members carrying machine guns kidnapped him and forced
    him to transport narcotics. However, the district court
    excluded Mr. Marinez’s expert testimony on the grounds
    that it was not “based on sufficient facts or data which is the
    product of reliable principles and methods” and that the
    witness had not “applied the principles and methods reliably
    to the facts in the case.” The district court continued:
    I can’t find what principles and methods the
    supposed expert would use. I don’t even
    know what he’s an expert in. There’s no
    indicia that any other experts would accept
    the principles or the opinions or conclusions
    that this so-called expert would proffer. I
    don’t know what his educational background
    is on the subject. I don’t know of any
    publications or other certifications or
    professional memberships that he belongs to
    that would allow him to express an opinion
    on any of the things that he has proffered. I
    don’t know what materials he may have
    received or reviewed. I don’t know his prior
    experience as an expert in the area. I don’t
    know what records he may have reviewed,
    what procedures, and what methodology did
    he use once in arriving at this so-called
    40       UNITED STATES V. DOMINGUEZ-CAICEDO
    opinion, what examinations, what research,
    what testing, what surveys, or what
    verifications were used. I don’t know what,
    if anything, he did to, for example, try to
    disprove any hypothetical or ultimate
    conclusion that he has reached. I don’t know,
    in fact, looking at this, any of this, whether he
    really has any knowledge whatsoever of any
    of the things that [he] has testified or
    proposes to testify to.
    In all, the district court found “absolutely no indicia
    whatsoever of reliability,” and that the testimony would not
    be helpful.
    Dominguez-Caicedo contends that the district court’s
    focus on the Daubert factors of reliable principles and
    methods was misplaced. Instead, Dominguez-Caicedo
    argues that the district court’s focus should have been on the
    “knowledge and experience” of the expert, since the subject
    of the expert’s testimony was to be his knowledge and
    experience, rather than his scientific analyses.
    In Daubert v. Merrell Dow Pharmaceuticals, Inc.,
    
    509 U.S. 579
     (1993), the Supreme Court listed several
    relevant factors for assessing the reliability of scientific
    expert testimony under Federal Rule of Evidence 702.
    Among these were whether the expert’s theory or technique
    has been tested; whether it “has been subjected to peer
    review and publication”; the “error rate” of “a particular
    scientific technique”; and the general acceptance of a theory
    or technique within the scientific community. 
    509 U.S. at
    593–94. Then, in Kumho Tire, the Supreme Court
    discussed how to apply Daubert to expert testimony that was
    not scientific in nature:
    UNITED STATES V. DOMINGUEZ-CAICEDO                  41
    We conclude that Daubert’s general
    holding—setting forth the trial judge’s
    general “gatekeeping” obligation—applies
    not only to testimony based on “scientific”
    knowledge, but also to testimony based on
    “technical”      and     “other      specialized”
    knowledge. We also conclude that a trial
    court may consider one or more of the more
    specific factors that Daubert mentioned when
    doing so will help determine that testimony’s
    reliability. But, as the Court stated in
    Daubert, the test of reliability is “flexible,”
    and Daubert’s list of specific factors neither
    necessarily nor exclusively applies to all
    experts or in every case. Rather, the law
    grants a district court the same broad latitude
    when it decides how to determine reliability
    as it enjoys in respect to its ultimate reliability
    determination.
    Kumho Tire Co. v. Carmichael, 
    526 U.S. 137
    , 141–42
    (1999) (internal citations omitted).
    Although some of the factors the district court listed are
    not obviously relevant to Mr. Marinez, some are. For
    example, Mr. Marinez’s offer of proof omits how
    Mr. Marinez “is aware” of the activities of FARC. As the
    district court stated, then, there is no indicia that other
    experts on FARC would agree with Mr. Marinez’s opinion
    that FARC uses “intimidation and violence in the town of
    Barabaoas [sic] and its surrounding area to further their
    criminal enterprises” and that “these armed groups do little
    to hide their existence in the town of Barbacoas.” It was also
    unclear “what, if anything,” Mr. Marinez did to try to
    disprove his opinion that these individuals are part of FARC.
    42         UNITED STATES V. DOMINGUEZ-CAICEDO
    In short, the offer of proof fell short of showing the basis for
    Mr. Marinez’s expert opinion that Dominguez-Caicedo’s
    testimony about FARC kidnapping him was plausible.
    Dominguez-Caicedo is correct in that the factors the
    district court listed apply more directly to testimony of a
    scientific nature, which Mr. Marinez’s was not. However,
    given the extremely broad latitude the Supreme Court has
    said district courts have in conducting this inquiry, we hold
    the district court did not abuse its discretion by looking at
    these particular factors and finding Mr. Marinez’s testimony
    wanting. See Kumho Tire, 
    526 U.S. at 142
    .
    F
    All three defendants challenge the district court’s denial
    of their requests for minor role reductions at sentencing.
    When reviewing sentencing decisions, we review the district
    court’s identification of the relevant legal standard de novo,
    its factual findings for clear error, and its application of the
    legal standard to the facts for abuse of discretion. United
    States v. Gasca-Ruiz, 
    852 F.3d 1167
    , 1170 (9th Cir. 2017)
    (en banc). We begin by clarifying how district courts should
    conduct the minor role analysis before turning to each
    defendant’s specific arguments.
    1
    A defendant who is “plainly among the least culpable of
    those involved in the conduct of a group” may receive a
    “minimal” role adjustment, which comes with a Sentencing
    Guidelines reduction of at least four levels. 4 U.S.S.G.
    4
    We say “at least” because a mitigating role adjustment can interact
    with other provisions of the Sentencing Guidelines to trigger additional
    adjustments. See, e.g., U.S.S.G. § 2D1.1(a)(5).
    UNITED STATES V. DOMINGUEZ-CAICEDO                       43
    § 3B1.2(a), cmt. 4. A defendant “who is less culpable than
    most other participants in the criminal activity, but whose
    role could not be described as minimal” may receive a
    “minor” role adjustment, which provides a reduction of at
    least two levels. Id. at cmt. 5. To be eligible for either
    adjustment, the defendant must also be “substantially less
    culpable than the average participant in the criminal
    activity.” Id. at cmt. 3(A).
    The relevant comparison is to the other participants in
    the defendant’s crime, not to typical defendants who commit
    similar crimes. 5 See United States v. Diaz, 
    884 F.3d 911
    ,
    916 (9th Cir. 2018). Thus, in this case, the district court was
    required to compare the defendants to the other participants
    in their crimes, not to typical defendants occupying their
    roles, such as typical drug transporters. Further, when the
    mitigating role commentary instructs courts to compare the
    defendant’s culpability to that of “the average participant in
    the criminal activity,” it is not referring to the actual level of
    culpability of any single participant. It is instead referring to
    the mathematical average, i.e., a “single value that represents
    the midpoint of a broad sample of subjects.” Average,
    Black’s Law Dictionary (11th ed. 2019). Thus, “all likely
    participants in the criminal scheme” must be included in
    calculating the average. Diaz, 884 F.3d at 916–17 (emphasis
    added); United States v. Rojas-Millan, 
    234 F.3d 464
    , 472
    (9th Cir. 2000).
    To determine whether a defendant is substantially less
    culpable than the average participant in the offense, a district
    5
    In the past we have referred to these typical defendants as
    “hypothetical average participants,” but we use the term “typical
    defendant” here because it is more precise, and it avoids confusion with
    our discussion of the “average participant” referred to in comment 3(A).
    44       UNITED STATES V. DOMINGUEZ-CAICEDO
    court must proceed in three steps. First, the court must
    identify all of the individuals for whom there is “sufficient
    evidence of their existence and participation in the overall
    scheme.” Rojas-Millan, 
    234 F.3d at 474
    . Second, the court
    must calculate a rough average level of culpability for these
    individuals, taking into consideration the five factors in
    comment 3(C) to the Mitigating Role Guideline. See Diaz,
    884 F.3d at 916. Third, the court must compare the
    defendant’s culpability to that average. If the defendant is
    substantially less culpable than that average and meets the
    other criteria, he should be granted a mitigating role
    adjustment. If the defendant is not substantially less
    culpable than that average, he is not eligible for the
    adjustment.
    The Government and some district courts appear to have
    interpreted United States v. Hurtado, 
    760 F.3d 1065
    , 1069
    (9th Cir. 2014), overruled on other grounds by Gasca-Ruiz,
    852 F.3d at 1174, to suggest that a court must first identify
    all participants in the crime and then disregard participants
    of above-average culpability (and, presumably, those of
    below-average culpability) and compare the defendant’s
    culpability only to the remaining individuals whom the
    district court deems to be of average culpability. A court
    following this approach compares the defendant’s
    culpability to only the median participants’ actual level of
    culpability instead of comparing the defendant’s culpability
    to the average level of culpability of all the participants in
    the offense.
    This understanding of Hurtado is incorrect. At the
    outset, we note that much of Hurtado has been overruled or
    UNITED STATES V. DOMINGUEZ-CAICEDO                          45
    abrogated. 6 But to the extent anything remains of Hurtado,
    it simply stands for the proposition that comparing a
    defendant to only the most culpable subset of the participants
    in the offense does not demonstrate that the defendant is
    entitled to a minor role reduction. Instead, the district court
    must compare the defendant’s culpability with the average
    level of culpability of all of the participants in the crime.
    Hurtado did not set forth an entirely different method of
    performing the minor role analysis.
    Nor could it have. Fourteen years earlier, we held that
    courts should compare a defendant’s culpability to “all
    participants in the criminal scheme for which he was
    charged” even if those co-participants are not charged.
    Rojas-Millan, 
    234 F.3d at 472
    . There, the Nevada Highway
    Patrol stopped Rojas-Millan as he was couriering drugs east
    from Los Angeles to Nevada. 
    Id.
     at 467–68. In the car with
    6
    For instance, Hurtado states that the district court “did not clearly
    err when it found that Hurtado was a typical commercial drug
    smuggler—no better, no worse,—and not entitled to a minor role
    reduction” and that “[t]he district court was not clearly erroneous in
    finding that although Hurtado may have been a cog in some larger wheel,
    he was an essential cog who . . . knowingly smuggled a large quantity of
    narcotics into the United States . . . .” 760 F.3d at 1067. But the 2015
    amendments to the mitigating role commentary made clear that the
    relevant comparison is to other participants in the defendant’s crime, not
    to “typical” defendants committing similar crimes, and that “[t]he fact
    that a defendant performs an essential or indispensable role in the
    criminal activity is not determinative.” U.S.S.G § 3B1.2 cmt. n.3(C).
    Similarly, Hurtado suggested that various factors “alone” could “justify
    denial of minor role” but we have since held that “the assessment of a
    defendant’s eligibility for a minor-role adjustment must include
    consideration of the factors identified by the Amendment, not merely the
    benchmarks established by our caselaw that pre-dates Amendment 794’s
    effective date.” Diaz, 884 F.3d at 916. We have also since held that
    Hurtado applied the wrong standard of review. See Gasca-Ruiz,
    852 F.3d at 1174.
    46       UNITED STATES V. DOMINGUEZ-CAICEDO
    him was Jorge Adame-Farias. Id. After being convicted of
    various drug crimes, Rojas-Millan sought a minor role
    reduction, which the district court denied. Id. at 472. The
    district court concluded that Rojas-Millan was not
    substantially less culpable than Adame-Farias, who was
    charged alongside Rojas-Millan, and that it could not
    compare Rojas-Millan’s conduct against the drug supplier in
    Los Angeles and the recipient in Nevada because they were
    not charged. Id.
    We vacated the sentence and remanded, holding that “the
    district court should have evaluated [Rojas-Millan’s] role
    relative to all participants in the criminal scheme for which
    he was charged.” Id. We explained that “ignoring the
    actions of other participants . . . subjects less culpable
    defendants to longer sentences simply because their more
    involved co-conspirators managed to escape arrest or were
    tried separately. We see no reason why the Guidelines
    would sanction such a regime, and we find confirmation in
    the language of § 3B1.2 that the intent was not to do so.” Id.
    at 473. We thus vacated Rojas-Millan’s sentence and
    remanded for the district court to compare Rojas-Millan’s
    culpability “relative to the involvement of other likely
    actors, such as the alleged Los Angeles supplier and the
    Reno distributor . . . if the district court found sufficient
    evidence of their existence and participation.” Id. at 473–
    74. The only limit on the comparison group we recognized
    in Rojas-Millan was that the district court was required to
    find “sufficient evidence of [the comparators’] existence and
    participation” in the crime. Id. at 474. If the district court
    found on remand that the Los Angeles supplier and Reno
    distributor participated, it was required to compare Rojas-
    Millan’s culpability to theirs. Id. at 473–74. We did not hold
    that the district court could decline to consider the Los
    Angeles and Reno participants’ culpability if it determined
    UNITED STATES V. DOMINGUEZ-CAICEDO               47
    that they were leaders or organizers or were otherwise of
    “above-average” culpability. Indeed, to do so would be
    inconsistent with our observation that “ignoring the actions
    of other participants” undermines the purpose of the minor
    role reduction because doing so “subjects less culpable
    defendants to longer sentences simply because their more
    involved co-conspirators managed to escape arrest or were
    tried separately.” Id. at 473.
    Since we already held in Rojas-Millan that “all
    participants in the criminal scheme” must be included in the
    comparison, we could not have departed from that rule in
    Hurtado to require district courts to exclude the most highly
    culpable participants. See Miller v. Gammie, 
    335 F.3d 889
    ,
    900 (9th Cir. 2003) (en banc). Further, while the “median”
    approach does not turn on who is charged, it is even less
    consistent with the purposes of the minor role reduction than
    the approach we disapproved of in Rojas-Millan because it
    would exclude the most culpable participants in every case,
    even if they were charged, simply because they are highly
    culpable. This approach grossly distorts the court’s
    assessment of the defendant’s relative role. Finally, in the
    eight years since it was decided, we have never cited
    Hurtado in a published opinion for the proposition that
    district courts may exclude highly culpable participants from
    the comparison.
    In sum, Hurtado did not change our longstanding
    approach to the mitigating role analysis, which requires
    district courts to include “all participants in the criminal
    scheme” in the comparison. Rojas-Millan, 
    234 F.3d at 472
    ;
    see also Diaz, 884 F.3d at 916–17. With these clarifications
    in mind, we turn to each defendant’s arguments.
    48       UNITED STATES V. DOMINGUEZ-CAICEDO
    2
    Chichande argues that the district court erred by
    excluding his recruiter from the comparison. We agree. The
    district court concluded that Chichande’s recruiter existed
    and participated, yet it excluded him from the comparison
    group. The court stated at sentencing:
    So the defendant has to show me well, who’s
    the average participant so that I can then
    make a determination as to whether or not the
    defendant is, in fact, substantially less
    culpable than the average participant . . . . So
    what do we know? Well, we know this
    gentleman was recruited by someone who, in
    my opinion, if that individual were before
    me, would receive an aggravated role for
    being a leader/organizer. We have the people
    with the guns . . . . So taking a look at the
    people that are involved, there are three
    people on the boat. I believe, frankly, that
    probably one of them is somewhat more
    culpable than the other two. And I do believe
    that this defendant, given the fact that he was
    more candid and forthright, probably
    deserves a break in that regard. It doesn’t
    really affect my assessment of minor role
    . . . . So what do I know? I know that there
    were men with guns. I know that there was a
    recruiter or someone that got this fellow into
    this venture. But I don’t know who the
    average participant would be. And I don’t
    know that this defendant would be
    substantially less culpable than whoever that
    average participant is.
    UNITED STATES V. DOMINGUEZ-CAICEDO                49
    This discussion shows that the district court attempted to
    identify a single “average participant” with whom to
    compare Chichande. When the district court could not
    identify such an individual, it denied the minor role
    adjustment, apparently without comparing Chichande’s
    culpability with anyone’s. At a minimum, the court
    excluded the recruiter. This analysis was erroneous. As we
    have explained, the proper comparison is to the average of
    all of the individuals who participated in Chichande’s
    offense, including those that the district court believed were
    leaders or organizers or who were otherwise highly culpable.
    Because the district court misunderstood the appropriate
    legal standard, we vacate Chichande’s sentence and remand
    for the district court to conduct the minor role analysis
    applying the correct legal standard.
    The Government argues that any error in the district
    court’s minor role analysis was harmless because the district
    court made an alternative Guidelines calculation assuming it
    granted Chichande a minor role reduction and stated that it
    would impose the same “sentence regardless of whether [it]
    gave him minor role.” We disagree.
    “A mistake in calculating the recommended Guidelines
    sentencing range is a significant procedural error that
    requires us to remand for resentencing.” United States v.
    Munoz-Camarena, 
    631 F.3d 1028
    , 1030 (9th Cir. 2011).
    “When a defendant is sentenced under an incorrect
    Guidelines range—whether or not the defendant’s ultimate
    sentence falls within the correct range—the error itself can,
    and most often will, be sufficient to show a reasonable
    probability of a different outcome absent the error.” Molina-
    Martinez v. United States, 
    136 S. Ct. 1338
    , 1345 (2016).
    Accordingly, we have vacated sentences and remanded for
    resentencing when district courts have misunderstood the
    50       UNITED STATES V. DOMINGUEZ-CAICEDO
    law governing the minor role reduction. See, e.g., Diaz,
    884 F.3d at 918; Rojas-Millan, 
    234 F.3d at 475
    . At the same
    time, a sentencing error can be harmless. See Munoz-
    Camarena, 631 F.3d at 1030 n.5. To establish harmlessness,
    the Government must show that “it is more probable than
    not” that the error did not affect the sentence. United States
    v. Morales, 
    108 F.3d 1031
    , 1040 (9th Cir. 1997) (en banc);
    see also United States v. Olano, 
    507 U.S. 725
    , 734 (1993).
    A “district court’s mere statement that it would impose
    the same . . . sentence no matter what the correct calculation
    cannot, without more, insulate the sentence from remand.”
    Munoz-Camarena, 631 F.3d at 1031; see also United States
    v. Williams, 
    5 F.4th 973
    , 978 (9th Cir. 2021). This is because
    a district court’s analysis must “flow from an initial
    determination of the correct Guidelines range,” 
    id. at 1031
    ,
    and the district court must keep that range “in mind
    throughout the process,” 
    id. at 1030
     (quoting United States
    v. Carty, 
    520 F.3d 984
    , 991 (9th Cir. 2008)). At the same
    time, a sentencing error may be harmless if the district court
    “acknowledges that the correct Guidelines range is in dispute
    and performs [its] sentencing analysis twice, beginning with
    both the correct and incorrect range.” 
    Id.
     at 1030 n.5.
    The Government argues that that is what the district
    court did here. We disagree. When it came time to impose
    the sentence, the district court started by determining that
    Chichande’s criminal history category was I, his base
    offense level was 38, and a two-level upward adjustment was
    warranted because he co-piloted the boat, for a total offense
    level of 40. This yielded a Guidelines range of 292 to
    365 months. See U.S.S.G. Manual Ch. 5 Pt. A (U.S. Sent’g
    Comm’n 2018). The district court then concluded that a
    292-month sentence “would be excessive” because
    Chichande was a first-time offender, discussed the 18 U.S.C.
    UNITED STATES V. DOMINGUEZ-CAICEDO              51
    § 3553(a) factors, and ultimately imposed a sentence of
    180 months. After imposing the sentence, the district court
    provided Chichande with a copy of the supervised release
    conditions and informed him that he could appeal.
    Immediately afterward the following exchange occurred:
    Counsel for Chichande: Yes, I’ve told him
    that I will file that Notice of Appeal this
    morning.
    The Court: All right. Is there anything else I
    need to address? Is there anything – well, I
    guess for purposes of making sure we all
    understand – by the way, I did do a guideline
    calculation assuming that I gave him minor
    role. I think that would have resulted in, if
    I’m not mistaken, a range of 121 to
    151 months. I think I did a calculation giving
    him acceptance. That would result in 97 to
    121 months.
    But as I said, my sentence was based on [the]
    3553(a) factors. Given the seriousness of the
    offense and the nature of the offense, the
    circumstances of the offense, the amount of
    the drugs, the fact that a shooting was
    required, I think 180 months is a reasonable
    sentence, and I would impose that sentence
    regardless of whether I gave him minor role.
    In that case, I would be varying up. In this
    case, I’m varying down. Anything else I’ve
    missed?
    The district court’s discussion of the alternative ranges
    at the very end of the sentencing hearing does not
    52        UNITED STATES V. DOMINGUEZ-CAICEDO
    demonstrate that the district court conducted the sentencing
    a second time starting with the correct range and keeping it
    in mind throughout the process. The conclusory nature of
    this discussion, and the fact that it occurred after the district
    court had already imposed Chichande’s sentence and only in
    response to Chichande’s declaration that he would appeal
    suggest that the district court did not meaningfully consider
    this range in arriving at its sentence. Since the Government
    has not met its burden of establishing that any error was
    harmless, we vacate Chichande’s sentence and remand for
    resentencing so that the district court may apply the correct
    legal standard.
    3
    Cortez-Quinonez argues that the district court erred
    because it “expressly acknowledged the existence of a
    Pablo-Escobar-type drug lord” and “a giant, complex drug-
    trafficking organization” but nevertheless refused to include
    members of that organization in the comparison. In the
    district court, Cortez-Quinonez cited a report that the
    Sentencing Commission sent to Congress listing roles of
    individuals often involved in drug trafficking organizations
    in order of their typical culpability and argued that the court
    was required to compare his conduct to individuals
    occupying those roles who “likely” were involved in his
    crime.
    The fact that illicit drugs are often traceable to larger
    drug trafficking organizations does not mean that district
    courts must compare the conduct of each defendant
    convicted of a drug crime to that of every hypothetical
    member of a typical drug trafficking organization. See
    United States v. Rosas, 
    615 F.3d 1058
    , 1068 (9th Cir. 2010)
    (“Every drug trafficking defendant could point to an
    unknown network preceding them in the drug trade. Such an
    UNITED STATES V. DOMINGUEZ-CAICEDO                 53
    argument will normally be ineffective when considering
    whether the defendant is entitled to a mitigating role
    reduction.”). We have repeatedly held that the relevant
    comparators are the actual participants in the defendant’s
    crime. See, e.g., Diaz, 884 F.3d at 916–18; United States v.
    Benitez, 
    34 F.3d 1489
    , 1498 (9th Cir. 1994); United States v.
    Petti, 
    973 F.2d 1441
    , 1447 (9th Cir. 1992). The 2015
    Amendments to the mitigating role commentary confirmed
    that interpretation. See United States v. Quintero-Leyva,
    
    823 F.3d 519
    , 522–23 (9th Cir. 2016). By “actual
    participants,” we mean only participants for whom there is
    “sufficient evidence of their existence and participation.”
    Rojas-Millan, 
    234 F.3d at 474
    . Even if one can assume
    based on how drug trafficking organizations typically
    operate that it is likely that another unidentified person
    participated in the crime, the district court is not required to
    compare the defendant’s culpability with that of the
    unidentified person. Indeed, without evidence of the
    proposed comparator’s existence or participation the district
    court has nothing against which to compare the defendant’s
    conduct. In this case, for example, Cortez-Quinonez invited
    the district court to speculate about what roles hypothetical
    participants in drug trafficking organizations typically
    occupy and to compare those hypothetical participants’
    imagined conduct to his own. We have repeatedly rejected
    these kinds of comparisons in the past, and we do so again
    today. See Diaz, 884 F.3d at 913–18 (holding that district
    court properly limited the comparison group to Diaz’s
    recruiter and co-participant and properly declined to
    compare Diaz’s culpability to that of “‘unknown’
    individuals who ‘have to exist in order for a drug trafficking
    organization to function’”); Rosas, 
    615 F.3d at 1068
    (holding that district court properly limited the comparison
    group to Rosas’ two co-participants and properly declined
    to compare him to “unknown participants in the drug chain,
    54       UNITED STATES V. DOMINGUEZ-CAICEDO
    including ‘the source of the marijuana, distributors,
    packagers, sellers, etc.’”).
    In arguing to the contrary, Cortez-Quinonez relies
    heavily on our statements in Diaz and Rojas-Millan
    instructing district courts to consider “likely” participants.
    But Cortez-Quinonez takes the word “likely” out of context.
    We have referred to likely participants to make clear that the
    defendant does not necessarily need to know the
    participant’s name or see the participant for there to be
    sufficient evidence of that person’s participation in the
    offense. See Diaz, 884 F.3d at 917; Rojas-Millan, 
    234 F.3d at
    473–74. But we have never required a comparison to
    unknown persons one might assume participated but about
    whom there is no evidence of their actual participation.
    Therefore, the district court did not err by declining to
    compare Cortez-Quinonez’s culpability to the unknown
    “Pablo-Escobar-type drug lord” and unknown members of
    “a giant, complex drug-trafficking organization” that may
    have been involved in the manufacture and distribution of
    the drugs Cortez-Quinonez was transporting.
    Cortez-Quinonez next argues that the district court erred
    by “ignor[ing] [his] lack of ownership in the drugs and his
    relatively low compensation.” But the district court heard
    argument regarding this factor, stated that it considered all
    “five nonexhaustive factors,” and ultimately adopted the
    Government’s analysis of them. And even if the district
    court erroneously weighed that factor against Cortez-
    Quinonez, that one of the five factors in comment 3(C)
    weighed in favor of Cortez-Quinonez does not mean that the
    district court abused its discretion in denying the minor role
    adjustment. See Quintero-Leyva, 823 F.3d at 523.
    UNITED STATES V. DOMINGUEZ-CAICEDO                 55
    4
    Dominguez-Caicedo’s arguments are similar. He claims
    that the district court identified “the man who
    commandeered Mr. Dominguez into participating in this
    offense” and “the ‘guys with the guns’ who approached
    Dominguez” as “potential likely participants” but
    nevertheless improperly refused to compare his culpability
    to theirs. He also argues that the district court improperly
    “overlooked” “all the persons” the Government identified in
    its pre-trial expert disclosure, “those who actually own the
    cocaine at the heart of this case,” and “those who recruited
    and tricked Mr. Dominguez’s co-defendants.” Once again,
    we disagree.
    With respect to the “guys with guns” and “man who
    commandeered Mr. Dominguez into participating in this
    offense” Dominguez-Caicedo’s characterization is not
    consistent with the record. Dominguez-Caicedo testified at
    trial that while he was harvesting bananas in rural Colombia,
    he was kidnapped by five armed men wearing hoodies and
    masks who told him they needed him for a mission. He
    testified that these men eventually placed him on the boat
    carrying the drugs at issue here. At sentencing, the district
    court made clear that it did not believe Dominguez-
    Caicedo’s account and did not find these individuals to be
    likely participants in the offense. The court explained: “I
    mean, Mr. Dominguez-Caicedo was hoping that by telling
    his story, he was going to [be] able to convince the jury that
    he was acting under duress. The jury didn’t believe it. It’s
    a self-serving statement that I frankly – I don’t buy, either. I
    don’t accept it.” Therefore, contrary to Dominguez-
    Caicedo’s argument, the district court did not determine that
    the “guys with guns” and the “man who commandeered
    56       UNITED STATES V. DOMINGUEZ-CAICEDO
    Mr. Dominguez” were “likely participants,” and therefore
    did not err by excluding them from the comparison.
    Next, the district court was not required to address the
    people the Government identified in its pre-trial expert
    disclosure, the people who allegedly owned the cocaine, and
    the people who allegedly recruited Dominguez-Caicedo’s
    co-defendants because Dominguez-Caicedo failed to object
    to the Presentence Report’s (PSR) conclusion that he did not
    provide evidence of their existence and participation in the
    offense.
    The PSR concludes that “the defendant has presented no
    information supporting the fact that he was substantially less
    culpable than the other identified participants in this offense
    as he appears to have held the same role as CORTEZ and
    GASPAR.” It also says that “Defense counsel . . . believes
    a minor role adjustment is appropriate, but did not provide
    any basis for it.” Federal Rule of Criminal Procedure
    32(f)(1) requires parties to “state in writing any objections,
    including objections to material information . . . contained in
    or omitted from the [PSR].” If a party objects to a material
    factual assertion in or omission from the PSR, the district
    court must rule on the objection. Fed. R. Crim. P.
    32(i)(3)(B); see also United States v. Petri, 
    731 F.3d 833
    ,
    837–39 (9th Cir. 2013). But if a party does not object, the
    district court is not required to address factual assertions
    raised for the first time in a sentencing memorandum or at
    the sentencing hearing. Petri, 731 F.3d at 841.
    Petri is illustrative. There, Petri objected to the PSR’s
    recommendation that the district court deny Petri’s request
    for a minor role reduction because, among other things, he
    alleged that he was “used by the more sophisticated
    individuals in the scheme, including a man named ‘Sorin,’
    whom Petri identified as the ringleader.” Id. at 836. But
    UNITED STATES V. DOMINGUEZ-CAICEDO                           57
    while Petri cited Sorin’s alleged involvement in support of
    his objection to the PSR’s recommendation to deny him a
    minor role reduction, he did not specifically object to the
    omission of factual information about Sorin in the PSR. Id.
    at 836, 841. In other words, Petri objected to the probation
    officer’s ultimate recommendation that the court deny the
    minor role reduction but did not specifically object to the
    probation officer’s decision not to include “any factual
    assertion regarding whether ‘Sorin’ manipulated or coerced
    Petri into complicity.” Id. at 841. In his sentencing
    memorandum and during the sentencing hearing, Petri’s
    attorney attempted to supplement the record with details
    about Sorin’s alleged coercion and argued that recently
    discovered documents showed Sorin was involved. Id.
    at 836–37. The district court ultimately denied the minor
    role reduction without addressing whether Sorin coerced
    Petri. Id. at 837. On appeal, we held that the district court
    “had no responsibility to rule on . . . if ‘Sorin’ coerced” Petri
    because Petri’s objection to the PSR was not specifically
    directed at the alleged factual omissions in the PSR. Id.
    at 841.
    Dominguez-Caicedo did not properly object to his
    presentence report at all. 7 Therefore, the district court was
    7
    Dominguez-Caicedo included a footnote in his sentencing
    memorandum citing to Cortez-Quinonez’s objections to his PSR and
    stated that “Mr. Dominguez joins in his co-defendant’s analysis
    regarding the applicability of a mitigating role adjustment in this case.”
    Dominguez-Caicedo’s footnote is not a proper objection to the PSR.
    First, it does not dispute any of the factual assertions or alleged omissions
    in his own PSR. Second, we held in Petri that an argument in a
    sentencing memorandum does not constitute an objection to a PSR.
    Third, Dominguez-Caicedo filed his sentencing memorandum after the
    deadline for objecting to the PSR. The deadline for objecting to the PSR
    is “14 days after receiving” it, Fed. R. Crim. P. 32(f)(1), and Dominguez-
    58         UNITED STATES V. DOMINGUEZ-CAICEDO
    not required to address his argument raised for the first time
    in his sentencing memorandum—and never mentioned
    during the sentencing hearing—that there was sufficient
    evidence that the individuals he identified were involved in
    the crime.
    CONCLUSION
    We affirm all three defendants’ convictions, and
    Dominguez-Caicedo’s and Cortez-Quinonez’s sentences.
    We vacate Chichande’s sentence and remand for
    resentencing consistent with this opinion.
    AFFIRMED in part,                      and      VACATED            and
    REMANDED in part.
    Caicedo filed his sentencing memorandum 28 days after the PSR was
    filed. For each of these reasons, Dominguez-Caicedo’s footnote was not
    a proper objection to the PSR, and it did not require the district court to
    address whether these individuals participated in the crime.