United States v. David Major ( 2022 )


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  •                                In the
    United States Court of Appeals
    For the Seventh Circuit
    ____________________
    No. 20-2829
    UNITED STATES OF AMERICA,
    Plaintiff-Appellee,
    v.
    DAVID D. MAJOR,
    Defendant-Appellant.
    ____________________
    Appeal from the United States District Court for the
    Central District of Illinois.
    No. 19-cr-10014 — James E. Shadid, Judge.
    ____________________
    ARGUED NOVEMBER 2, 2021 — DECIDED APRIL 27, 2022
    ____________________
    Before SYKES, Chief Judge, and FLAUM and JACKSON-
    AKIWUMI, Circuit Judges.
    FLAUM, Circuit Judge. David Major pleaded guilty without
    the benefit of a plea agreement to three charges stemming
    from his activities dealing heroin and fentanyl. Major was
    sentenced to twenty years’ imprisonment. He now challenges
    the basis of his sentence, arguing that the district court’s fac-
    tual findings were erroneous and caused it to calculate an in-
    correct Sentencing Guidelines range. He also argues that his
    2                                                 No. 20-2829
    designation as a “career offender” overstated his past crimi-
    nal conduct, so that his sentencing under the career offender
    Guidelines range was therefore unreasonable.
    Because the district court made no clear errors in its find-
    ings of fact and did not abuse its discretion in deciding Ma-
    jor’s sentence, we affirm.
    I.   Background
    A. A.K.’s Overdose Death and the Government’s Subse-
    quent Investigation
    In December 2018, a twenty-six-year-old woman, A.K.,
    was found dead in her bedroom in Pekin, Illinois, with fresh
    needle marks on her arm consistent with heroin use. An au-
    topsy later determined that her cause of death was the “com-
    bined toxic effects of acetyl fentanyl, fentanyl, and Mitragyn-
    ine,” though officers did not find any drugs in the home.
    Officers began investigating A.K.’s death and learned that
    the night before she died, she had taken an Uber home from
    an address where a person named Dawn Bukowski lived with
    her boyfriend. When the officers interviewed Bukowski, she
    admitted that she used heroin and had provided some to A.K.
    around 6:30 PM the night before she was found dead. Bukow-
    ski explained that A.K. had reached out to Bukowski’s boy-
    friend through the “dark web,” looking for heroin because
    she was afraid she was about to start experiencing with-
    drawal symptoms. A.K. did not know where else to obtain the
    drugs since she had only recently moved to the area. Bukow-
    ski’s account was confirmed by text messages recovered from
    her phone. Bukowski’s texts also revealed that she told her
    boyfriend A.K. was “really fucked up” after she injected the
    No. 20-2829                                                  3
    drugs at Bukowski’s home immediately after purchasing
    them. Bukowski later testified that she “could tell that [A.K.]
    was really, really messed up” shortly after taking the drugs,
    though she appeared to “snap[] out of it” by the time she left
    Bukowski’s house, around 7:30 PM.
    A.K. took the rest of her unused drugs with her when she
    left Bukowski and got in her Uber. The driver later told offic-
    ers that A.K. seemed “intoxicated but not overly intoxicated”
    during the ride to her home. When A.K. arrived home, she
    greeted her parents, who said that she appeared normal, be-
    fore heading to her room for the night. Her mother discovered
    her unresponsive in her bedroom around 5:30 AM the next
    morning.
    Bukowski told the investigating officers that she had pur-
    chased the drugs she resold to A.K. from someone named
    “Don,” whom the officers soon determined to be the Defend-
    ant, David Major. In February and March 2019, police set up
    a series of controlled drug buys from Major. Often, these buys
    resulted in the source receiving drugs directly from Major,
    but sometimes, Major would direct the source to contact “the
    girls,” his associates Stephanie Lobb and Natalia Menchaca.
    After the controlled buys, police arrested Lobb and
    Menchaca as they were returning to the Peoria area from Chi-
    cago. In their possession, the women had 9.4 grams of heroin
    and fentanyl. Both provided cooperative statements to law
    enforcement. Menchaca stated that she had been acquiring
    heroin from Major for about eight months and had worked
    for him for the last three months. She further stated that she
    and Lobb traveled to Chicago about once a week to purchase
    between a half-ounce and an ounce of heroin for Major. Lobb
    provided similar information and estimated that the pair had
    4                                                   No. 20-2829
    made about fifteen trips to Chicago over the last few months
    for this purpose. Police subsequently arrested Major, who
    waived his Miranda rights and admitted that he sold drugs
    and had purchased them from a contact in Chicago. Text mes-
    sages between Major and Bukowski confirmed that he sold
    her drugs and that his heroin was laced with fentanyl. For in-
    stance, he sent her a picture of a white, rock-like substance,
    with a caption referring to “that fintnal.”
    In April 2019, a grand jury indicted Major, Menchaca, and
    Lobb with drug-trafficking and conspiracy offenses (none of
    which directly pertained to the December 2018 drug transac-
    tion that led to A.K.’s death). Major eventually pleaded guilty
    to three charges: one count of conspiring between December
    2018 and March 2019 to distribute and possess with intent to
    distribute heroin and fentanyl, see 
    21 U.S.C. § 846
    , and two
    counts of distributing heroin and fentanyl in February 2019,
    see 
    21 U.S.C. § 841
    (a)(1), (b)(1)(C). At the change-of-plea hear-
    ing, he specifically admitted under oath that he “actually dis-
    tribute[d] heroin and fentanyl.”
    B. Incident Involving Major’s Co-Defendant
    After Major entered his guilty plea, the Probation Office
    prepared a presentence investigation report (“PSR”), which,
    among other things, described the statements Lobb and
    Menchaca made to the police. Based on Menchaca’s state-
    ments, the PSR indicated that the conspiracy involved over
    100 grams of heroin and 0.4 grams of fentanyl.
    A few months after the Probation Office filed its first PSR
    and while Lobb was on bail, she called her attorney to de-
    scribe a disturbing incident, which her attorney then relayed
    to the police. Lobb stated that on the afternoon of April 28,
    No. 20-2829                                                    5
    2020, she was approached at her place of work (Burger King)
    by someone she knew as “Ray Ray.” She had met Ray Ray
    before and knew him as Major’s close friend (at the time, she
    thought they were brothers) and his “enforcer.” Ray Ray en-
    tered the drive-through lane going the opposite direction and
    pulled up to Lobb. He held up his phone and told her that
    Major wanted to talk to her. She responded that she could not
    talk to him, and Ray Ray then stated that he thought he had
    seen her walking a few days earlier. Ray Ray then drove off.
    Lobb later testified that she felt “threatened and intimi-
    dated” by the incident, specifically because she had heard sto-
    ries about Ray Ray’s violent past and knew that Major relied
    on Ray Ray to “tak[e] care of things for him.” In fact, Lobb
    testified, she had received a letter from Major from jail regard-
    ing the instant criminal conspiracy, instructing her to “stand
    tall or stay strong,” because Major “kn[ew] who set [them]
    up” and “Ray Ray’s gonna handle it.” Lobb was sufficiently
    spooked by the incident that two days later she arranged with
    Pretrial Services to move out of the area.
    To investigate this incident, officers obtained recordings
    of Major’s phone calls from jail. From these calls, officers
    learned that Major told a variety of people that it was “very
    important” that he speak with Lobb. On April 27, Major
    placed one such call to his daughter, in which he asked if she
    remembered the “girl that people was talking about that you
    was supposed to be looking for?” His daughter responded
    that she did not remember her name, and Major explained
    that it was Lobb and further advised his daughter to call the
    Burger King where Lobb worked immediately after hanging
    up with him. He told his daughter to tell Lobb that Major was
    not mad at her and that nothing was going to happen to her.
    6                                                   No. 20-2829
    Later that day, Major made a similar call to another woman.
    He told this woman to tell Lobb that Major was “not mad at
    her and ain’t nobody going do shit to her. I need to talk to her,
    it’s very important.”
    The next day, Major made a call and spoke to Ray Ray,
    whose real name is Kimmit Smith. Ray Ray told Major, “That
    bitch is scared as hell,” to which Major replied that he knew
    it and that he hoped Ray Ray did not scare her. Major then
    laughed and said, “I hope you don’t try and tell the people
    I’m trying to do anything … what they say?” Ray Ray told
    Major that the woman had asked what Major wanted her to
    say. Ray Ray then said, “Some things a mother fucker can’t
    say over these lines.” Major replied, “I know, that’s the truth
    … that’s why I needed the number.” When Ray Ray told Ma-
    jor that he didn’t ask for the woman’s phone number because
    “she got scared and I [Ray Ray] got scared,” Major began
    laughing again.
    Major then told Ray Ray that Menchaca had said that Ma-
    jor was buying an ounce of heroin per week, which he said
    was “bullshit” and was why he needed to speak to Lobb. Ray
    Ray replied that Lobb had told him that she could not talk to
    Major. Major then said that he did not want Ray Ray to scare
    her and that he needed to “clean it up.” Major told him to “get
    on it today.” A few minutes later, Major called Ray Ray back
    and told him that he didn’t need anybody saying, “These peo-
    ple came up here and blew on me[,] so you got to calm a
    mother fucker down today.” Major said that he was upset be-
    cause Menchaca had lied about the amount of drugs they had
    dealt and that he needed Lobb to tell the truth that it was a
    lesser amount than what Menchaca had claimed. Major gave
    Ray Ray the phone number for Burger King and told him he
    No. 20-2829                                                    7
    needed to go up there that day. He said it would “help him
    out a lot” if Lobb said they never went up there (presumably
    Chicago) for ounces and “that’s the truth.” He later clarified
    that Lobb’s testimony to this effect would undermine the
    credibility of Menchaca’s statements during sentencing.
    C. Major’s Sentencing
    The Probation Office filed its final, revised PSR on Septem-
    ber 10, 2020, a few days before sentencing. In addition to re-
    counting the above facts (including Major’s phone calls from
    jail), the PSR calculated a Sentencing Guidelines range based
    on Major’s offenses, related conduct, and criminal history.
    It calculated his base offense level for the conspiracy
    charge to be 24. Because he was “an organizer, leader, man-
    ager, or supervisor” in the conspiracy, two levels were added.
    See U.S.S.G. § 3B1.1(c). Two more levels were added for ob-
    struction of justice, based on Major’s phone calls from jail and
    Ray Ray’s approaching Lobb at work. See U.S.S.G. § 3C1.1.
    This brought his adjusted offense level to 28. His total offense
    level was increased to 32, however, because he qualified as a
    “career offender” under U.S.S.G. § 4B1.1 (he had a previous
    felony drug conviction and a conviction for aggravated kid-
    napping). The PSR stated that a reduction for acceptance of
    responsibility was inappropriate. Major’s criminal history
    was calculated to be category III, but based on his qualifica-
    tion as a career offender, it was increased to category VI. An
    offense level of 32 and a criminal history category of VI re-
    sulted in a Guidelines imprisonment range of 210–262 months
    for each count. The statutory maximum for each of Major’s
    offenses of conviction is 20 years, which altered the guideline
    imprisonment range to 210–240 months. The PSR stated that
    the probation officer had not identified any factors under 18
    8                                                 No. 20-
    2829 U.S.C. § 3553
    (a) that warranted a sentence outside of this
    range.
    At the sentencing hearing, Major’s counsel objected to cer-
    tain factual findings in the PSR and argued that the career of-
    fender status overstated Major’s criminal history because his
    predicate conviction for aggravated kidnapping was over
    twenty-five years old. As relevant to this appeal, the factual
    findings Major challenged were: (1) that Major was the sup-
    plier of the fentanyl-laced heroin that led to A.K.’s overdose
    death, (2) that Major had obstructed justice by attempting to
    influence Lobb’s testimony, and (3) that Major had not ac-
    cepted responsibility for his conduct. Notably, despite Ma-
    jor’s recorded phone calls disputing Menchaca’s account of
    the drug quantity at issue, Major withdrew his objection to
    the amount of heroin and fentanyl set forth in the final PSR—
    even though the Probation Office increased the calculated
    amount of fentanyl from .4 grams to 9.8 grams between the
    first and final PSR and the heroin assessment had not
    changed.
    To make its rulings on Major’s objections, the court heard
    testimony from the officer who responded to the scene after
    A.K.’s mother found her dead, Bukowski (the woman who
    bought drugs from Major and then resold some of them to
    A.K.), Lobb, and the officer who investigated Major’s phone
    calls from jail. The testimony essentially conveyed the facts
    recounted above. Based on this testimony, the district court
    rejected all of Major’s arguments.
    The district court also heard a victim impact statement
    from A.K.’s mother and a statement from Major himself.
    A.K.’s mother addressed Major and stated:
    No. 20-2829                                                    9
    This is a loss that I will never recover from, pain
    that time does not heal or even ease. Every day
    I relive the experience of finding my daughter. I
    see her unseeing eyes. I feel the unnatural cold-
    ness of her body.
    I see mothers interacting with daughters, and I
    don’t have that any longer. I see grandchildren
    that I will never have, milestones that will never
    be reached, dreams and plans unfulfilled, a life
    extinguished. And for this reason, I hope that
    the Court would see fit to give you the maxi-
    mum sentence so that the likelihood of your
    participation in this act again would not hap-
    pen.
    Major began his statement by giving his condolences to
    A.K.’s mother, but quickly clarified, “I’m not even sure who’s
    at fault, but I understand that me, being a heroin dealer, that
    you would look at me as being at fault here…. I know that my
    actions could possibly did [sic] play a role or possibly did, but
    I just want you to know that I do send my condolences to you
    and your family.” Major then expressed his remorse to the
    court and stated that he only dealt drugs to feed his own ad-
    diction and to treat a medical condition that made it difficult
    for him to eat. Major then transitioned to minimizing his con-
    duct. He described himself as “just a drug user who was get-
    ting high, to have some few friends to direct that high, and
    with their money I could get by with.” He also stated, “I never
    meant to sell nobody no fentanyl. I can’t believe that I’m hon-
    estly facing this much time when all I actually did was sell
    Dawn two dime, three dime bags of dope for $50. That’s what
    my conspiracy really consists of. Your Honor, I sold a friend
    10                                                  No. 20-2829
    a bag of dope for $50 on two different occasions.” When the
    court clarified whether it was Major’s position that he never
    knew the heroin he purchased and resold had fentanyl in it,
    Major responded, “I mean, no, I didn’t. All I knew, I was get-
    ting heroin.”
    Before handing down Major’s sentence, the court
    stated:
    I’m glad you made a statement, Mr. Major, be-
    cause it confirms for me that I made the right
    decision on acceptance of responsibility … be-
    cause clearly the evidence is otherwise…. And I
    can only say after listening to you, Mr. Major,
    that I’m more comfortable with the decision—I
    think I was right anyway, but I’m way more
    comfortable with the decision I made now about
    acceptance. And I guess the only thing I can say
    is if you spend a lifetime of being untruthful,
    that you—there comes a point where you don’t
    even know where the truth would help you,
    okay?
    Given that Major had pushed fentanyl-laced heroin onto
    the streets of the community, deposited large sums of money
    in connection with his crimes, was a leader in the conspiracy,
    had a history of violence, played a part in the overdose death
    of A.K., and attempted to obstruct justice, the court decided
    that the statutory maximum sentence of twenty years’ impris-
    onment was appropriate.
    Major now appeals this sentence.
    No. 20-2829                                                   11
    II.   Discussion
    Major challenges his sentence on four grounds. Namely,
    he argues: (1) the court erred by finding that he sold the drugs
    that caused A.K.’s death, (2) the court erred by finding that he
    had obstructed justice, (3) the court erred by finding he had
    not accepted responsibility, and (4) the court abused its dis-
    cretion by sentencing him as a career offender because that
    label overstated the seriousness of his criminal history.
    We use a two-step process to review a district court’s sen-
    tencing decisions. “First, we determine whether the district
    court committed any procedural error, such as failing to cal-
    culate (or improperly calculating) the Guidelines range, treat-
    ing the Guidelines as mandatory, failing to consider the
    § 3553(a) factors, selecting a sentence based on clearly errone-
    ous facts, or failing to adequately explain the chosen sen-
    tence—including an explanation for any deviation from the
    Guidelines range.” United States v. Faulkner, 
    885 F.3d 488
    , 498
    (7th Cir. 2018) (internal quotation marks omitted) (quoting
    United States v. Reyes-Hernandez, 
    624 F.3d 405
    , 409 (7th Cir.
    2010)). “Whether the district court followed proper sentenc-
    ing procedure is a legal question reviewed de novo.” United
    States v. Pape, 
    601 F.3d 743
    , 746 (7th Cir. 2010). Although, as
    noted, it is a procedural error to select a sentence based on
    erroneous facts, Faulkner, 885 F.3d at 498, we review the dis-
    trict court’s findings of fact underlying the selected sentence
    only for clear error, United States v. Ranjel, 
    872 F.3d 815
    , 818
    (7th Cir. 2017). Major’s first three arguments challenge the fac-
    tual findings underpinning the district court’s sentence and
    thus fall under this first step.
    12                                                    No. 20-2829
    Second, “[i]f no procedural error is found, then the sen-
    tence is reviewed for substantive reasonableness”; we review
    the substantive reasonableness of a sentence for abuse of dis-
    cretion. Faulkner, 885 F.3d at 498. “A sentence is substantively
    reasonable ‘if the district court gives meaningful considera-
    tion to the factors enumerated in 
    18 U.S.C. § 3553
    (a), includ-
    ing the advisory Sentencing Guidelines, and arrives at a sen-
    tence that is objectively reasonable in light of the statutory fac-
    tors and the individual circumstances of the case.’” United
    States v. Patel, 
    921 F.3d 663
    , 672 (7th Cir. 2019) (quoting United
    States v. Rosen, 
    726 F.3d 1017
    , 1027 (7th Cir. 2013)). “[W]e pre-
    sume that a within-Guidelines sentence is reasonable.” 
    Id.
    Major’s fourth and final argument—that the district court
    should have used its discretion to ignore Major’s “career of-
    fender” designation—amounts to a challenge to the reasona-
    bleness of the court’s sentencing decision.
    A. The District Court’s Factual Findings
    “Generally, facts considered at sentencing must be proved
    by a preponderance of the evidence.” United States v. Lucas,
    
    670 F.3d 784
    , 792 (7th Cir. 2012). Such facts must be based on
    “reliable evidence, rather than speculation or unfounded alle-
    gations.” 
    Id.
     “Evidence will satisfy this requirement if it bears
    sufficient indicia of reliability to support its probable accu-
    racy.” 
    Id.
     (quoting United States v. Santiago, 
    495 F.3d 820
    , 824
    (7th Cir. 2007)). Sentencing courts may also draw inferences
    and conclusions based on testimony given and evidence in-
    troduced at a sentencing hearing. 
    Id.
    “We will not disturb a sentencing court’s factual findings
    unless they are clearly erroneous.” Ranjel, 872 F.3d at 818. This
    standard is deferential, and “we will reverse only if ‘after re-
    viewing the entire record, we are left with the firm and
    No. 20-2829                                                                13
    definite conviction that a mistake has been made.’” Id. (quot-
    ing United States v. Marty, 
    450 F.3d 687
    , 689–90 (7th Cir. 2006)).
    “If two possible conclusions can be drawn from the evidence,
    then the choice between them cannot be clearly erroneous.”
    United States v. May, 
    748 F.3d 758
    , 760 (7th Cir. 2014).
    1. Finding Regarding A.K.’s Overdose Death
    First, Major argues that the district court clearly erred
    when it determined that he supplied the drugs that contrib-
    uted to A.K.’s death. Significantly, the government did not
    seek a statutory enhancement to Major’s sentence because he
    was not charged with the particular sale of drugs to Bukowski
    that Bukowski resold to A.K. See 
    21 U.S.C. § 841
    (b)(1)(C) (re-
    quiring a sentence of twenty years to life if “death or serious
    bodily injury results from the use of [the distributed] sub-
    stance”); U.S.S.G. § 2D1.1(a)(2) (increasing the base offense
    level if “the offense of conviction establishes that death … re-
    sulted from the use of the substance”(emphasis added)). 1 Ra-
    ther, the district court considered its finding about the rela-
    tionship between Major and A.K.’s death when it weighed the
    sentencing factors set forth in 
    18 U.S.C. § 3553
    (a).
    Major’s argument on this point boils down to a contention
    that A.K. must have acquired more drugs from a different
    source after leaving Bukowski’s home. Major seems to believe
    1 For this reason, the government did not have to prove that the heroin
    and fentanyl Major distributed was the “but-for” cause of A.K.’s death,
    under Burrage v. United States, 
    571 U.S. 204
    , 218–19 (2014). See United States
    v. Lawler, 
    818 F.3d 281
    , 285 (7th Cir. 2016) (“Nothing … prevents a sentenc-
    ing court, when determining a defendant’s ultimate sentence, from con-
    sidering the fact that death resulted,” even if the government cannot prove
    but-for causation beyond a reasonable doubt).
    14                                                No. 20-2829
    that, because A.K. did not overdose the first time she injected
    the drugs Bukowski provided, A.K. could not have subse-
    quently overdosed if she injected the remainder of the drugs
    at home. But these inferences are not supported by the evi-
    dence submitted at the sentencing hearing. Cf. Lucas, 
    670 F.3d at 792
     (noting that sentencing determinations cannot be based
    on “speculation or unfounded allegations”).
    Bukowski testified that A.K. was “really, really messed
    up” immediately after injecting the fentanyl-laced heroin that
    Bukowski had received from Major. In fact, Bukowski testi-
    fied that she had shot up heroin with a number of people but
    had “never seen nobody act like that.” A.K.’s behavior was
    strange enough that Bukowski contacted her boyfriend at the
    time to share her concern. Evidence also reflected that A.K.
    left Bukowski’s apartment in an Uber around 7:30 PM and that
    she took the remaining drugs from Major with her when she
    left. Her mother told officers that A.K. arrived home, briefly
    greeted her, and then went to her room, where the mother
    found her unresponsive the next morning. Bukowski also tes-
    tified that A.K. had asked her and her boyfriend for heroin
    because she was new in town, was concerned about soon ex-
    periencing withdrawal symptoms, and had no other means of
    acquiring the drugs. And, though A.K. left Bukowski’s apart-
    ment with leftover heroin, no drugs were found in A.K.’s
    home. Finally, the autopsy report concluded that the toxic ef-
    fects of heroin and fentanyl contributed to A.K.’s death. This
    evidence supports the district court’s finding.
    Furthermore, the district court specifically found that Bu-
    kowski was credible. “[W]here a sentencing challenge boils
    down to a credibility decision, … our review is especially def-
    erential to the district judge’s assessment of the testimony.”
    No. 20-2829                                                                15
    United States v. Etchin, 
    614 F.3d 726
    , 738 (7th Cir. 2010). And
    even though no corroboration is necessary for a court to ac-
    cept witness testimony, see 
    id. at 739
    , Bukowski’s statements,
    the testimony of the investigating officer, the Uber receipts,
    and text messages from the time all corroborate each other.
    The district court’s finding was not clearly erroneous, and this
    finding supported its weighing of the factors set forth in 
    18 U.S.C. § 3553
    (a).
    2. Obstruction of Justice Finding
    Second, Major challenges the district court’s finding that
    he obstructed justice by attempting to influence Lobb’s testi-
    mony. 2 An offense-level enhancement for obstruction of jus-
    tice is appropriate if:
    (1) the defendant willfully obstructed or im-
    peded, or attempted to obstruct or impede, the
    administration of justice with respect to the
    2 Although obstruction of justice typically increases a defendant’s offense
    level under the Guidelines by two points, U.S.S.G. § 3C1.1, which would
    have brought Major’s offense level up to a 28, Major’s qualification as a
    “career offender” independently established a higher offense level of 32,
    making this finding irrelevant for the purpose of increasing his offense
    level, U.S.S.G. § 4B1.1(b)(3). This would ordinarily moot his challenge to
    the obstruction-of-justice finding. See United States v. Collins, 352 F. App’x
    96, 98 (7th Cir. 2009) (noting that where the defendant was sentenced
    based on the higher offense level associated with a career offender desig-
    nation, any challenge to a separate offense level adjustment would be
    moot). The district court, however, also considered Major’s acts of obstruc-
    tion when it determined that he did not adequately accept responsibility
    for his conduct, and an acceptance-of-responsibility finding would have
    decreased Major’s offense level after accounting for the career offender des-
    ignation. Thus, his challenge to this factual finding is not moot.
    16                                                 No. 20-2829
    investigation, prosecution, or sentencing of the
    instant offense of conviction, and (2) the ob-
    structive conduct related to (A) the defendant’s
    offense of conviction and any relevant conduct;
    or (B) a closely related offense ….
    U.S.S.G. § 3C1.1. The commentary accompanying U.S.S.G.
    § 3C1.1 gives several examples of “the types of conduct to
    which this adjustment applies,” including “threatening, in-
    timidating, or otherwise unlawfully influencing a co-defend-
    ant, … or attempting to do so[.]” Id. cmt. 4(A). The intimida-
    tion of a co-defendant can be separate from “committing, sub-
    orning, or attempting to suborn perjury.” Id. cmt. 4(B).
    Major protests that there was no “evidence that [he] had
    ever threatened Lobb or … attempted to have her commit per-
    jury.” He contends that he was simply trying to encourage
    Lobb to tell the truth. Although he made some statements to
    that effect during some of his phone calls, Major also knew
    that those calls were being recorded—which he admitted dur-
    ing his allocution, when he told the district court, “I know the
    phones are recorded in jail.” Given this knowledge, it is un-
    surprising and less than persuasive that—in court—Major de-
    scribed his motive as merely encouraging Lobb to “tell the
    truth.” Additionally, this assertion is undermined by the fact
    that Major did not even object to the drug quantity set forth
    in the PSR—the very issue on which he hoped Lobb would
    contradict Menchaca.
    Moreover, even if Major did simply want Lobb to “tell the
    truth,” this does not mean the district court clearly erred
    when it held that Major’s attempts to pressure Lobb to “un-
    dermine the credibility of Menchaca” were a “clear example[]
    of trying to influence the testimony of a witness,” which
    No. 20-2829                                                     17
    constituted obstruction. We considered such a scenario in
    United States v. Cheek, 
    740 F.3d 440
     (7th Cir. 2014). In that case,
    the defendant wrote a letter to the daughter of a witness
    against him. 
    Id.
     at 453–54. In the letter, the defendant told the
    daughter that her mother (the witness) was lying to the gov-
    ernment, and he implied that the daughter should influence
    her mother to “tell the truth.” 
    Id. at 453
    . The defendant wrote:
    To prove [the charge] why would they need
    your Mom to lie on me if they had something?…
    She couldn’t get more than 5 if she would’ve
    just plead guilty without lying on me.… The
    most she can get is 5 and me LIFE if she doesn’t
    tell the truth.… So I am praying that she don’t
    let them keep scaring her.… If God is willing
    you know who won’t tell that lie and I will be
    there to see yall in the near future.
    
    Id. at 444
     (errors in original). We held that the “district court
    reasonably interpreted this effort as a willful attempt to per-
    suade [the witness’s] daughter to try to sway her mother’s tes-
    timony.” 
    Id. at 454
    . “And an effort to influence a witness’s tes-
    timony—albeit vicariously—is a prototypical example of ob-
    struction of justice.” 
    Id.
     (citing U.S.S.G. § 3C1.1 cmt. 4(A)).
    Following the reasoning in Cheek, even if Major was trying
    to urge Lobb to “tell the truth” from his point of view, such
    conduct may still constitute obstruction of justice if its pur-
    pose is to persuade a witness or co-defendant to alter her tes-
    timony. Here, the evidence clearly showed that Major made a
    frenzy of phone calls to various associates and family mem-
    bers in an attempt to affect Lobb’s testimony about the quan-
    tity of drugs at issue. The context around these calls—in par-
    ticular, the fact that Major asked his enforcer Ray Ray to get
    18                                                   No. 20-2829
    involved, the fact that Major was intentionally vague on the
    recorded phone line about what he wanted his associates to
    do, and the fact that Major and Ray Ray laughed about how
    Lobb was “scared as hell”—was sufficient for the court to con-
    clude that this attempt to influence Lobb’s testimony was un-
    lawful.
    Thus, the district court did not err in finding that Major
    attempted to influence his co-defendant’s testimony, and this
    factual finding supported its determination—discussed fur-
    ther below—that Major obstructed justice in a way that was
    incompatible with accepting responsibility for his conduct.
    3. Acceptance of Responsibility Finding
    Major next challenges the district court’s finding that he
    had not accepted responsibility for his conduct and therefore
    was not entitled to a reduction in his offense level under the
    Guidelines. The Guidelines state that a two-level reduction is
    appropriate if “the defendant clearly demonstrates ac-
    ceptance of responsibility for his offense.” U.S.S.G. § 3E1.1(a).
    The defendant bears the burden of proving his acceptance of
    responsibility by a preponderance of the evidence. United
    States v. Lister, 
    432 F.3d 754
    , 759 (7th Cir. 2005). “We review
    the district court’s decision on this fact-based finding for clear
    error.” 
    Id.
     In doing so, we accord “[g]reat deference” to the
    sentencing court, which is better equipped to “assess whether
    a particular defendant is motivated by genuine acceptance of
    responsibility or by a self-serving desire to minimize his own
    punishment.” United States v. Cunningham, 
    103 F.3d 596
    , 598
    (7th Cir. 1996) (citation and internal quotation marks omit-
    ted).
    No. 20-2829                                                     19
    When making this finding, “the sentencing judge is re-
    quired to look beyond formalistic expressions of culpability
    and to determine whether the defendant has manifested an
    acceptance of personal responsibility for his offense in a moral
    sense.” 
    Id.
     (citation omitted). For this reason, simply pleading
    guilty does not entitle a defendant to a reduction for ac-
    ceptance of responsibility. United States v. Sellers, 
    595 F.3d 791
    ,
    793 (7th Cir. 2010). “A defendant who falsely denies, or frivo-
    lously contests, relevant conduct that the court determines to
    be true” generally will not qualify for the reduction. See
    U.S.S.G. § 3E1.1 cmt. 1(A). “Attempt[ing] to minimize [one’s]
    level of involvement in an offense” is sufficient to deny a re-
    duction for acceptance of responsibility, even when the de-
    fendant has pleaded guilty. United States v. Munoz, 
    610 F.3d 989
    , 993 (7th Cir. 2010).
    Once again, plenty of evidence supported the district
    court’s factual finding. First, “[c]onduct resulting in an [ob-
    struction-of-justice] enhancement … ordinarily indicates that
    the defendant has not accepted responsibility for his criminal
    conduct.” U.S.S.G. § 3E1.1 cmt. 4. It is only in “extraordinary
    cases” that a defendant may receive an enhancement for ob-
    struction of justice and also receive a reduction for acceptance
    of responsibility. Id. It was not clearly erroneous for the dis-
    trict court to conclude that this was not such an extraordinary
    case.
    Moreover, Major objected to the presentence report’s con-
    clusion that he sold the drugs that led to A.K.’s death, which
    was a fact the court found to be both true and relevant. See
    U.S.S.G. § 1B1.3 (defining “relevant conduct” for sentencing
    purposes to include “harm that resulted from” acts that were
    “part of the same course of conduct … as the offense of
    20                                                   No. 20-2829
    conviction”). On appeal, Major argues that his counsel—not
    Major—contested whether heroin and fentanyl he sold con-
    tributed to A.K.’s death. In support, he cites United States v.
    Purchess, in which we held that “where the defendant remains
    … silent as to relevant conduct but his lawyer challenges cer-
    tain facts alleged in the PSR,” then the district court “should
    attempt to ensure that the defendant understands and ap-
    proves the argument before attributing the factual challenges
    in the argument to the defendant for purposes of assessing
    acceptance of responsibility.” 
    107 F.3d 1261
    , 1268 (7th Cir.
    1997); see also Munoz, 
    610 F.3d at 994
     (distinguishing between
    factual challenges, which will jeopardize an acceptance-of-re-
    sponsibility reduction, and legal arguments regarding undis-
    puted facts, which will not).
    But Purchess is not relevant here, because Major personally
    disputed whether his drugs caused A.K.’s death in his allocu-
    tion at sentencing. For example, Major told A.K.’s mother,
    “I’m not even sure who’s at fault [for A.K.’s death], but I un-
    derstand that me, being a heroin dealer, that you would look
    at me as being at fault here.” When the district court asked
    directly whether Major was admitting to selling Bukowski the
    heroin and fentanyl that she resold to A.K., Major responded,
    “Sir, by what’s being said here today, I really don’t know be-
    cause, you know, I, I—first, I really didn’t believe that I didn’t
    [sic] sell them bags to [Bukowski] because I know what took
    place that particular day…. I’m just saying I don’t know, and
    I don’t believe the State [sic] proved to know it either. But it’s
    a possibility that she did get them from me.” It is clear from
    this exchange that Major himself contested this factual find-
    ing.
    No. 20-2829                                                   21
    This, combined with the obstruction of justice finding, was
    more than sufficient for the court to conclude that Major had
    not accepted responsibility for his conduct. But any lingering
    doubt is erased by other statements Major made during his
    allocution. For instance, Major attempted to minimize his con-
    duct, telling the district court, “I never meant to sell nobody
    no fentanyl. I can’t believe that I’m honestly facing this much
    time when all I actually did was sell [Bukowski] two dime,
    three dime bags of dope for $50. That’s what my conspiracy
    really consists of. Your Honor, I sold a friend a bag of dope
    for $50 on two different occasions.” He also doubled down on
    his claim that he did not know that the heroin he sold con-
    tained fentanyl—despite his admissions to the contrary in text
    messages (referring to “that fintnal”) and under oath at his
    change-of-plea hearing. When directly asked by the district
    court at sentencing, “So, you had no idea fentanyl was in
    them?” Major replied, “I mean, no, I didn’t.” Immediately af-
    ter this exchange, the district court concluded, “I’m glad you
    made a statement, Mr. Major, because it confirms for me that
    I made the right decision on acceptance of responsibility….”
    Ample evidence supported the district court’s conclusion
    that Major had not accepted responsibility for his conduct by
    the time he was sentenced; this finding was not clearly erro-
    neous.
    B. The Substantive Reasonableness of Major’s Sentence
    Finally, Major argues that his sentence was substantively
    unreasonable because—even though he technically qualifies
    as a career offender under the Sentencing Guidelines—that
    label overstates his criminal history. In essence, Major argues
    that the district court abused its discretion when it did not ig-
    nore the career offender enhancement when it sentenced him.
    22                                                        No. 20-2829
    A defendant is classified as a career offender if:
    (1) the defendant was at least eighteen years old
    at the time the defendant committed the instant
    offense of conviction; (2) the instant offense of
    conviction is a felony that is either a crime of vi-
    olence or a controlled substance offense; and (3)
    the defendant has at least two prior felony con-
    victions of either a crime of violence or a con-
    trolled substance offense.
    U.S.S.G. § 4B1.1(a). Such a designation sets the defendant’s
    criminal history category to Category VI, and when the of-
    fense of conviction’s statutory maximum sentence is between
    twenty and twenty-five years (as is the case for Major), the
    designation sets the offense level to 32. See id. § 4B1.1(b)(3).
    For Major, this resulted in a Guidelines range of 210–262
    months’ imprisonment, which was adjusted to 210–240 due to
    the statutory maximum of twenty years’ imprisonment for his
    convictions. 3 The district court sentenced Major to 240
    months’ incarceration.
    As we have noted, Major was convicted of two prior of-
    fenses that qualify him for the career offender designation: a
    previous felony drug conviction and a conviction for aggra-
    vated kidnapping. Major does not challenge these facts. But,
    he complains, he was convicted of aggravated kidnapping in
    1993, over twenty-five years prior to his sentencing in this
    case. He also argues that the nature of that crime is unrelated
    3Without the career offender designation, Major’s offense level would
    have been 28, his criminal history would have been Category III, and his
    Guidelines range would have been 97–121 months’ imprisonment. See
    U.S.S.G. Ch. 5, Pt. A.
    No. 20-2829                                                   23
    to the instant conviction and that the aggravated kidnapping
    conviction has “no bearing” on his propensity to commit
    other offenses similar to the drug distribution charges at issue
    in this case.
    For support, Major points to a Sentencing Guidelines pol-
    icy statement, which says that “[i]f reliable information indi-
    cates that the defendant’s criminal history category substan-
    tially over-represents the seriousness of the defendant’s crim-
    inal history or the likelihood that the defendant will commit
    other crimes, a downward departure may be warranted.”
    U.S.S.G. § 4A1.3(b)(1). Although the Supreme Court’s deci-
    sion in United States v. Booker, 
    543 U.S. 220
     (2005), rendered
    the departure provisions “obsolete,” “district courts can still
    take guidance from the departure provisions” and consider
    them “when assessing the § 3553(a) factors.” United States v.
    Bell, 
    887 F.3d 795
    , 798 (7th Cir. 2018) (citation and internal
    quotation marks omitted).
    Notwithstanding Major’s arguments, the district court
    handed down a sentence squarely within the concededly ap-
    plicable career-offender Guidelines range. Such sentences are
    presumed to be reasonable on appeal. See Rita v. United States,
    
    551 U.S. 338
    , 347 (2007). Moreover, in “reviewing sentences
    for substantive reasonableness, we do not substitute our judg-
    ment for that of a district judge, who is better situated to make
    individualized sentencing decisions.” United States v. Porraz,
    
    943 F.3d 1099
    , 1104 (7th Cir. 2019). In fact, we will “uphold a
    sentence so long as the judge offers an adequate statement of
    his reasons consistent with the sentencing factors enumerated
    in 
    18 U.S.C. § 3553
    (a).” 
    Id.
    Here, the district court did just that. It thoroughly ex-
    plained the reasons for its sentence, citing in particular the
    24                                                  No. 20-2829
    following facts: Major’s prior conviction for aggravated kid-
    napping, his previous drug distribution conviction, the fact
    that he “went right back to dealing drugs” after serving a
    fourteen-year sentence for his drug conviction, his decision to
    deal in the particularly dangerous combination of heroin
    laced with fentanyl, his leadership role in the conspiracy, the
    need to protect others from him, his attempt to obstruct jus-
    tice, his minimization of his own wrongdoing, and his role in
    the unfortunate death of A.K. Given these facts, the court did
    not abuse its discretion by sentencing Major as a career of-
    fender and imposing a Guidelines sentence of 240 months in
    prison.
    III.    Conclusion
    For the foregoing reasons, the decision of the district court
    is AFFIRMED.