Denzil Earl McKathan v. United States ( 2020 )


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  •                Case: 17-13358   Date Filed: 08/12/2020   Page: 1 of 50
    [PUBLISH]
    IN THE UNITED STATES COURT OF APPEALS
    FOR THE ELEVENTH CIRCUIT
    ________________________
    No. 17-13358
    ________________________
    D.C. Docket Nos. 1:15-cv-00611-KD,
    1:14-cr-00290-KD-C-1
    DENZIL EARL MCKATHAN,
    Petitioner - Appellant,
    versus
    UNITED STATES OF AMERICA,
    Respondent - Appellee.
    ________________________
    Appeal from the United States District Court
    for the Southern District of Alabama
    ________________________
    (August 12, 2020)
    Before ROSENBAUM, BRANCH, and DUBINA, Circuit Judges.
    ROSENBAUM, Circuit Judge:
    Darned if you do and darned if you don’t. That dilemma is nothing new.
    Indeed, around 800 B.C.E., Homer wrote of the problem in his epic poem The
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    Odyssey. There, the conundrum appeared when Odysseus found himself “caught
    between the Scylla and Charybdis,” a phrase we continue to use today to refer to the
    darned-if-you-and-darned-if-you-don’t scenario.1
    The Supreme Court has also coined a catchphrase for a particular version of
    this dilemma: “classic penalty situation.” Minnesota v. Murphy, 
    465 U.S. 420
    , 435
    (1984). A “classic penalty situation” arises when a person must choose between
    incriminating himself, on the one hand, or suffering government-threatened
    punishment for invoking his Fifth Amendment privilege to remain silent, on the
    other. See
    id. But the Supreme
    Court has also identified a solution to this problem: when a
    “classic penalty situation” occurs, the Fifth Amendment privilege is self-executing,
    and the government is deemed to have compelled the speaker’s statements in
    1
    The phrase refers to two extremely perilous (mythical) hazards that Odysseus, on his way
    home from the Trojan War, encountered when he had to navigate the narrow Strait of Messina
    (separating what are now known as the island of Sicily and the so-called “toe” of the Italian
    peninsula). The Strait was sandwiched between the Scylla and Charybdis. The Scylla was a six-
    headed monster who, from a cliff on one side of the Strait, reached out into the Strait and snatched
    up and devoured sailors. And the Charybdis was a whirlpool that sank ships that sailed too close
    on the other side of the Strait, trying to avoid the Scylla. Odysseus knew he was darned if he sailed
    closer to the Scylla and darned if he didn’t and instead passed through the Strait closer to the
    Charybdis. In the end, Odysseus gambled on sailing closer to the Scylla, betting she would eat
    only a few of his sailors, since he feared the Charybdis’s vortex might take his whole ship. Though
    Odysseus survived the Strait, he lost some sailors to the Scylla. Homer, The Odyssey (Robert
    Fitzgerald trans., Farrar, Strauss and Giroux 1998) (1961). The expression “caught between the
    Scylla and Charybdis,” has such force that thousands of years later, we continue to employ it to
    refer to the dilemma of being darned if you do and darned if you don’t. See, e.g., The Police,
    Wrapped Around Your Finger, on SYNCHRONICITY (A&M Records 1983) (“You consider me
    a young apprentice, caught between the Scylla and Charybdis: hypnotized by you if I should
    linger, staring at the ring around your finger”).
    2
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    violation of the Fifth Amendment. See
    id. As a result,
    the statements are rendered
    inadmissible in a criminal prosecution. See
    id. Petitioner-Appellant Denzil McKathan’s
    habeas petition raises the question
    of whether, while on supervised release, McKathan faced a “classic penalty
    situation” when his probation officer asked him to answer questions that would
    reveal he had committed new crimes. For reasons we explain below, we conclude
    that he did.
    McKathan’s attorneys never raised this argument during his criminal
    proceedings on the newly revealed crimes. Had they done so and on that basis filed
    a motion to suppress the statements McKathan made and the evidence the
    government derived from those statements, the government would have had to
    establish that it nonetheless would have obtained the incriminating evidence against
    McKathan through other, lawful means. If the government had been unable to do
    so, it is reasonably likely that McKathan would have prevailed on his suppression
    motion, and the outcome of McKathan’s case would have been different. As a result,
    McKathan would be entitled to habeas relief upon a showing that his counsel’s
    performance was deficient in failing to raise this argument. But because the current
    record lacks information concerning whether the evidence derived from McKathan’s
    statements otherwise would have been admissible, we vacate the district court’s
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    denial of McKathan’s 28 U.S.C. § 2255 motion and remand for further proceedings
    consistent with this opinion.
    I.
    To understand the issue in this case, we must review the facts of four events:
    (1) McKathan’s 2005 conviction for possession of child pornography; (2)
    McKathan’s 2014 violation of his supervised-release term that was imposed as a
    result of his 2005 conviction; (3) McKathan’s 2014 conviction for receipt of child
    pornography; and (4) McKathan’s 28 U.S.C. § 2255 motion to set aside his 2014
    conviction for receipt of child pornography. Below, we review the facts of each of
    these events.
    A. McKathan’s 2005 Conviction for Possession of Child Pornography
    In 2005, McKathan pled guilty to possessing child pornography, in violation
    of 18 U.S.C § 2252A(a). United States v. McKathan, Case No. 1:05-cr-00094-CG
    (S.D. Ala. 2005) (“McKathan I” or “2005 Case”). The district court sentenced him
    to 27 months’ imprisonment, plus a lifetime term of supervised release.
    Once McKathan completed his prison term in 2007, he began living under the
    terms of his supervised release. One of those terms required McKathan “to answer
    truthfully all inquiries by the probation officer and follow the instructions of the
    probation officer.” Another allowed his probation officer to conduct reasonable
    searches of McKathan’s residence—including of his electronic devices, since
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    McKathan had also agreed to forgo using a computer with internet access.
    McKathan’s terms of release informed him that if he violated his supervised release,
    the court could revoke his supervised release and send him back to prison.
    B. McKathan’s 2014 Violation of his Supervised Release
    In September 2014, McKathan’s probation officer, Rafael Goodwin, Jr.,
    became concerned with McKathan. Goodwin had conducted a Facebook search on
    all sex offenders under his supervision and learned that someone had opened a
    Facebook account in McKathan’s name, in September 2014, using an Android
    mobile device. Because McKathan’s terms prohibited him from using a computer
    with access to the internet without Goodwin’s permission, on September 19, 2014,
    Goodwin paid McKathan a surprise visit at his apartment to investigate.
    When Goodwin walked into McKathan’s apartment, he spotted an Android
    phone on the bed. Upon seeing it, Goodwin asked McKathan if he recently obtained
    a new phone. McKathan responded that he had had the same phone for some time.
    Then Goodwin wanted to know whether the phone could access the internet.
    McKathan conceded that it could. Goodwin examined the phone. Discovering its
    contents to be protected by a personal identification number (“PIN”), Goodwin
    instructed McKathan to enter his PIN to unlock the phone, and McKathan complied.
    Once Goodwin had access, he explored McKathan’s phone. He found that
    McKathan was using a mobile application for Facebook. Goodwin asked about
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    McKathan’s Facebook use, and McKathan admitted the account Goodwin had found
    was his. When Goodwin examined the account, he found no inappropriate content
    on it.
    But then Goodwin reviewed McKathan’s phone’s internet browser history.
    The browsing history reflected that somebody had visited sites with terms such as
    “preteen” and “sexy lil girls.” Upon seeing this, Goodwin asked McKathan whether
    he had been viewing child pornography. McKathan conceded he had. So Goodwin
    confiscated the phone and instructed McKathan to report to Goodwin on September
    22, 2014. At Goodwin’s request, McKathan also provided him with the PIN itself.
    Goodwin took McKathan’s phone back to the Probation Office, where he
    “more thorough[ly] inspect[ed]” it.     He found downloaded images of child
    pornography.
    When McKathan checked in with Goodwin on September 22, Goodwin gave
    McKathan a blank affidavit form and instructed him to write, consistent with
    McKathan’s admissions to Goodwin on September 19, that he had been using his
    phone to access the internet for a year, and it was the only means he had used to
    access child pornography. McKathan did as instructed.
    The district court then held a hearing to determine whether McKathan’s
    supervised release should be revoked.        At this hearing, Christopher Knight
    represented McKathan. Goodwin testified, describing his Facebook search, the
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    evidence he obtained from accessing McKathan’s phone, and McKathan’s
    subsequent admissions. After hearing Goodwin’s testimony, the court revoked
    McKathan’s supervised release and sent him back to prison, to be followed by a
    reimposed term of supervised release for life, with the same conditions that had been
    imposed in McKathan’s 2005 Case. We refer in this opinion to the events leading
    to and resulting in the revocation of McKathan’s supervised release as the
    “Supervised-release Proceedings.”
    C. McKathan’s 2014 Conviction for Receipt of Child Pornography
    That, however, was not the end of the story. Goodwin had provided the U.S.
    Attorney’s Office with a copy of images he had found on McKathan’s phone. He
    had also turned McKathan’s phone over to the Department of Homeland Security,
    so its agents could seek a search warrant, relying on Goodwin’s investigation. Based
    entirely on what Goodwin told the Homeland Security agents, they procured a
    warrant for the phone. The agents used the PIN McKathan provided to Goodwin to
    access the phone and then imaged and searched it. The search revealed that
    McKathan had downloaded images of child pornography.
    In November 2014, a federal grand jury charged McKathan with three counts
    of knowingly receiving child pornography, in violation of 18 U.S.C.
    § 2252A(a)(2)(A) (Counts One to Three), and one count of knowingly possessing
    material containing an image of child pornography, in violation of 18 U.S.C.
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    § 2252A(a)(5)(B) (Count Four). United States v. McKathan, Case No. 1:14-cr-
    00290 (S.D. Ala. 2014) (“McKathan II” or “2014 Case”). Since Knight was familiar
    with the case from the revocation hearing, the court appointed him to represent
    McKathan on the new charges.
    But McKathan soon filed a pro se motion requesting that the court appoint
    him new counsel. Contrary to McKathan’s desire, Knight did not want to file a
    motion to suppress challenging whether Goodwin’s search was lawful under the
    Fourth Amendment. The district court granted McKathan’s motion and appointed
    Cindy Powell.
    Soon after Powell was appointed, McKathan filed a pro se motion to suppress
    “(1) any and all evidence seized as a result of any search and/or seizure and the fruits
    of any search and/or seizure, [and] (2) any and all written and/or oral statements
    taken from me and the fruits of any such statements.” Three days later, Powell filed
    an amended motion to suppress on behalf of McKathan. Although the amended
    motion stated that McKathan sought suppression “pursuant to the 4th, 5th, and 6th
    Amendments of the U.S. Constitution,” it set forth only a Fourth Amendment
    argument, asserting that the government had obtained McKathan’s statements and
    the fruits of the browser-history search through an illegal search that violated the
    Fourth Amendment.
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    During the hearing on the suppression motion, defense counsel argued only
    that McKathan’s cell phone does not qualify as a “computer device” that is
    prohibited by the terms of his supervised release.       The district court denied
    McKathan’s amended suppression motion because it found no Fourth Amendment
    violation. It noted that since McKathan was a supervised releasee, his probation
    officer needed only reasonable suspicion to conduct a valid search under the Fourth
    Amendment. And McKathan had supplied that reasonable suspicion when he
    admitted his phone had access to the internet and implicitly conceded the phone was
    his.
    Since the district court had already found no Fourth Amendment violation,
    nothing required it to continue its analysis to determine whether some exception for
    a Fourth Amendment violation rendered the evidence admissible, anyway.
    Nevertheless, the district court added that, “unless the Government want[ed] to argue
    otherwise,” “there’s no inevitable discovery here,” and “there was no voluntary
    consent to the search of his phone.” The government did not argue otherwise.
    Having lost his suppression motion, McKathan asked Powell about the
    possibility of entering a conditional plea that would allow him to preserve his right
    to appeal on the suppression issue. But Powell dismissed the idea and said to
    McKathan, “Did you not hear [the judge] the other day? You don’t have any
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    meritorious arguments. There’s nothing . . . to preserve.” So Powell advised him
    that he should consider pleading guilty.
    McKathan followed that advice and entered into a plea agreement with the
    government.     Under that agreement, McKathan pled guilty to one count of
    knowingly receiving child pornography in violation of 18 U.S.C. § 2252A(a)(2)(A).
    He also agreed to waive his right to appeal and to file a collateral attack, with limited
    exceptions. As relevant here, the waiver did not preclude McKathan from claiming
    ineffective assistance of counsel in a motion filed under 28 U.S.C. § 2255. For its
    part, the government agreed to dismiss the three remaining counts of the indictment.
    At sentencing, the district court imposed a term of 188 months in prison.
    McKathan did not directly appeal his conviction.
    D. McKathan’s 28 U.S.C. § 2255 Petition
    In November 2015, McKathan filed a pro se habeas petition to vacate, set
    aside, or correct his conviction in the 2014 Case under 28 U.S.C. § 2255. McKathan
    v. United States, Case No. 1:15-cv-00611-KD (S.D. Ala. 2015) (“McKathan III” or
    “§ 2255 Case”). He asserted that his counsel had been ineffective, in violation of
    the Sixth Amendment, because they did not challenge the admission of his
    statements and the fruits of those statements, all of which, McKathan alleged, had
    been obtained in violation of the Fifth Amendment.
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    McKathan eventually enlisted counsel to assist him and filed an amended
    habeas petition, raising the same Sixth Amendment claim (based on counsel’s failure
    to seek suppression for an alleged Fifth Amendment violation) McKathan had made
    in his earlier pro se filing. 2 More specifically, McKathan contended that his counsel
    (both Knight and Powell) were constitutionally deficient for failing to use the Fifth
    Amendment—rather than the Fourth Amendment—to seek to suppress his
    statements to Goodwin about his phone and his PIN, as well as the evidence
    Goodwin derived from those disclosures.
    A magistrate judge held an evidentiary hearing on McKathan’s habeas
    petition. During that hearing, as relevant here, McKathan presented testimony from
    Knight and Powell. In addition, McKathan himself testified.
    Knight, who had represented McKathan throughout the Supervised-release
    Proceedings and during the initial stages of the 2014 Case, testified that he
    considered filing a motion to suppress based upon the Fourth Amendment. After
    reviewing the relevant law, though, Knight concluded that a motion filed on that
    basis would fail, and he so advised McKathan.
    Though Knight looked into a motion based on the Fourth Amendment, he
    conceded that it never occurred to him to proceed under the Fifth Amendment. As
    2
    In his counseled § 2255 motion, McKathan also argued that Powell was ineffective for
    neglecting to challenge a sentencing enhancement. The district court ultimately granted this aspect
    of McKathan’s petition and reduced his prison term from 188 months to 180 months.
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    a result, Knight never researched filing a suppression motion premised upon that
    Amendment.
    Cindy Powell, who took over McKathan’s defense from Knight in the 2014
    Case, testified that she filed the amended motion to suppress based on the Fourth
    Amendment, even though she advised McKathan it was unlikely to succeed. Powell
    could not recall whether she discussed with Knight a potential Fifth Amendment
    challenge to McKathan’s statements and their resulting fruits, though she did recall
    discussing with Knight the futility of filing a motion to suppress. But in any case,
    like Knight, Powell did not research whether McKathan might have a viable Fifth
    Amendment suppression claim.
    McKathan then took the stand on his own behalf. He stated that his probation
    officer instructed him that “if [he] did not follow the conditions [of his supervised
    release,] [he]’d be revoked and go back to prison.” So when Goodwin showed up at
    McKathan’s house in September 2014, McKathan understood he had to truthfully
    answer Goodwin’s questions about whether the phone was his, whether it had
    internet access, and whether he had been using it to view child pornography. He
    also believed he had to comply with Goodwin’s request for the phone’s PIN.
    McKathan had understood that if he had refused to enter his phone’s PIN or answer
    any of Goodwin’s questions, then his supervised release “would certainly have been
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    revoked.” To avoid that outcome, he answered Goodwin’s questions about the
    phone and its internet connection, and he provided his PIN.
    After considering McKathan’s motion and the evidence adduced at the
    hearing the magistrate judge issued a report and recommendation (“R&R”). As
    relevant here, the R&R recommended that the district court deny McKathan’s
    § 2255 claim that he received ineffective assistance of counsel when his attorneys
    did not seek under the Fifth Amendment to suppress his statements and their fruit.
    The R&R ruled based solely on its finding that McKathan had failed to show
    prejudice, even assuming his counsel had performed deficiently. 3
    McKathan objected to the R&R, but the district court agreed with it. So
    addressing only whether McKathan had demonstrated prejudice, the court denied
    McKathan’s § 2255 motion as it pertained to his ineffective-assistance claim based
    on counsel’s failure to file a Fifth Amendment challenge.
    Dissatisfied with the court’s ruling, McKathan moved under Rule 59(e), Fed.
    R. Civ. P., for the district court to vacate its judgment and grant his denied
    ineffective-assistance claim. Alternatively, McKathan asked the district court to
    issue a Certificate of Appealability (“COA”) on the question of “whether the district
    3
    The R&R nonetheless did opine in a footnote that Powell did not perform deficiently in
    failing to research or make a Fifth Amendment suppression argument because Knight, who was a
    “seasoned criminal defense attorney who has litigated numerous Fifth Amendment motions to
    suppress[,] did not see or raise the issue either.”
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    court erred in finding that [he] failed to prove Strickland’s[ 4] prejudice prong of his
    second § 2255 claim,” so he could appeal the district court’s denial of his claim.
    The district court rejected McKathan’s request to vacate its prior judgment.
    But it granted McKathan’s other request and issued a COA on “the issues presented.”
    In light of the fact that the district court denied the habeas claim on Strickland’s
    prejudice prong, we understand the district court to have granted the COA solely on
    the question of prejudice.
    McKathan now appeals.
    II.
    On an appeal of a § 2255 motion to vacate, we review legal issues de novo
    and factual findings for clear error. Rhode v. United States, 
    583 F.3d 1289
    , 1290
    (11th Cir. 2009) (per curiam).          In a § 2255 proceeding, we “allot substantial
    deference to the factfinder in reaching credibility determinations with respect to
    witness testimony.” Devine v. United States, 
    520 F.3d 1286
    , 1287 (11th Cir. 2008)
    (per curiam) (alteration adopted and citation and quotation marks omitted).
    III.
    We begin our analysis with a review of the standard that applies to claims of
    ineffective assistance of counsel.         The Sixth Amendment guarantees criminal
    defendants the right to counsel. U.S. Const. amend. VI; Gideon v. Wainwright, 372
    4
    Strickland v. Washington, 
    466 U.S. 668
    (1984).
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    50 U.S. 335
    , 344–45 (1963). As the Supreme Court has explained, “the right to counsel
    is the right to the effective assistance of counsel.” Strickland v. Washington, 
    466 U.S. 668
    , 684–86 (1984) (citation and quotation marks omitted). And that right
    applies not only at a criminal trial but also when a criminal defendant is deciding
    whether to plead guilty. See Lafler v. Cooper, 
    566 U.S. 156
    , 162 (2012); Hill v.
    Lockhart, 
    474 U.S. 52
    , 58 (1985).
    To succeed on a claim of ineffective assistance of counsel, the defendant must
    establish both that (1) his counsel’s “performance was deficient” and (2) his
    counsel’s “deficient performance prejudiced the defense.” 
    Strickland, 466 U.S. at 687
    .
    Because the district court denied McKathan’s petition without considering
    counsel’s performance under Strickland, we likewise limit our analysis to
    considering only Strickland’s prejudice requirement. Under this second prong,
    McKathan must show “a reasonable probability that, but for counsel’s
    unprofessional errors, the result of the proceeding would have been different.”
    Id. at 694.
    A reasonable probability means “a probability sufficient to undermine
    confidence in the outcome.”
    Id. In the context
    of pleas, the prejudice prong “focuses on whether counsel’s
    constitutionally ineffective performance affected the outcome of the plea process.”
    
    Lockhart, 474 U.S. at 59
    . We must ask whether a reasonable probability exists that
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    “but for counsel’s errors, [the defendant] would not have pleaded guilty and would
    have insisted on going to trial.”
    Id. And when the
    defendant’s sole complaint with
    his counsel’s performance stems from her actions in pursuing a plea instead of
    litigating a suppression issue, the defendant can demonstrate prejudice only if a
    reasonable likelihood exists that the suppression issue the attorney did not advance
    would have affected the outcome of the case. Lee v. United States, 
    137 S. Ct. 1958
    ,
    1965 (2017).
    In assessing the likelihood of success of a suppression motion based on the
    Fifth Amendment, we must first evaluate the underlying Fifth Amendment legal
    issue. If that has merit, we must then consider whether, despite the legal virtue of a
    Fifth Amendment argument, McKathan’s statements and their fruits would have
    nonetheless been admissible for an independent reason. Only if the answer to this
    second question is “no” can McKathan demonstrate that a motion to suppress based
    on the Fifth Amendment would have been reasonably likely to affect the outcome of
    his case. Therefore, in Section III.A., we evaluate the Fifth Amendment issue. Since
    we find that it has merit, in Section III.B., we consider whether the government had
    any independent basis for admission of McKathan’s statements and their fruits.
    A.
    We begin by reviewing the right at issue in the forfeited Fifth Amendment
    suppression motion. The Fifth Amendment guarantees that “[n]o person . . . shall
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    be compelled in any criminal case to be a witness against himself . . . .” U.S. Const.
    amend. V. As the Supreme Court has explained, “[t]he essence of this basic
    constitutional principle is the requirement that the State which proposes to convict
    and punish an individual produce the evidence against him by the independent labor
    of its officers, not by the simple, cruel expedient of forcing it from his own lips.”
    Estelle v. Smith, 
    451 U.S. 454
    , 462 (1981) (cleaned up). A violation of the Fifth
    Amendment occurs when “the accused is compelled to make a Testimonial
    Communication that is incriminating.” Fisher v. United States, 
    425 U.S. 391
    , 408
    (1976).
    If an individual is compelled to answer an incriminating question, “his
    answers are inadmissible against him in a later criminal prosecution.’” 
    Murphy, 465 U.S. at 426
    (citation and quotation marks omitted). The Fifth Amendment not only
    protects the individual’s compelled statements, but also bars the “evidence derived
    directly and indirectly therefrom” and “prohibits the prosecutorial authorities from
    using the compelled testimony in any respect.” Kastigar v. United States, 
    406 U.S. 441
    , 453 (1972).
    To succeed under a Fifth Amendment challenge on a motion seeking to
    suppress his statements to Goodwin and the entry of his PIN (and all fruits stemming
    from these revelations), McKathan would have had to show three things: (1) that
    the government compelled him to make a (2) testimonial communication or act and
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    (3) that the testimonial communication or act incriminated him. In re Grand Jury
    Subpoena Duces Tecum Dated Mar. 25, 2011, 
    670 F.3d 1335
    , 1341 (11th Cir. 2012);
    United States v. Ghidoni, 
    732 F.2d 814
    , 816 (11th Cir. 1984).
    The parties do not dispute that McKathan could have succeeded on the last
    two elements—that is, he engaged in testimonial communications of his PIN and
    statements to Goodwin, and those communications incriminated him. We agree.
    See In re Grand Jury 
    Subpoena, 670 F.3d at 1346
    –49 (holding that compelling a
    defendant to produce data protected by his password without providing
    constitutionally sufficient immunity violates the Fifth Amendment); see also United
    States v. Blake, 
    868 F.3d 960
    , 971 (11th Cir. 2017) (holding that a bypass order was
    necessary or appropriate because there was no other way for the FBI to execute the
    district court’s order to search the contents of an iPad, since they were passcode
    protected, and the government could not compel the user to provide the passcode,
    since that would violate the Fifth Amendment). That leaves us to consider whether
    McKathan was compelled to make these statements.
    1. The Fifth Amendment privilege can be self-executing
    Ordinarily, to claim the protections of the Fifth Amendment, an individual
    must actually invoke the right not to make statements, or his answers will not qualify
    as “‘compelled’ within the meaning of the Amendment.” 
    Murphy, 465 U.S. at 427
    (citation omitted). Yet the Supreme Court has held that if the government subjects
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    an individual to a practice that denies him “a ‘free choice to admit, to deny, or to
    refuse to answer,’” then any statement he makes to the government is considered
    compelled. Garner v. United States, 
    424 U.S. 648
    , 657 (1976) (quoting Lisenba v.
    California, 
    314 U.S. 219
    , 241 (1941)). And that statement, along with any evidence
    to which it leads, cannot be used in a criminal proceeding. Lefkowitz v. Turley, 
    414 U.S. 70
    , 78 (1973). Put more simply, when the government denies an individual a
    “free choice” to either speak or remain silent, the Fifth Amendment is considered
    “self-executing,” and an individual need not expressly invoke the right for his
    statements to be suppressed in a later criminal proceeding. 
    Murphy, 465 U.S. at 434
    –35.
    To date, the Supreme Court has identified only three “self-executing”
    circumstances. See, e.g., 
    Garner, 424 U.S. at 657
    –64. These include custodial
    settings, unless the speaker has knowingly and intelligently waived his privilege to
    remain silent, see Miranda v. Arizona, 
    384 U.S. 436
    , 467–69 (1966), extremely
    limited tax-return-filing circumstances, see Marchetti v. United States, 
    390 U.S. 39
    ,
    48–49 (1968), and situations where the government imposes a penalty if the speaker
    invokes the privilege to remain silent, see Garrity v. New Jersey, 
    385 U.S. 493
    , 500
    (1967). Only the last exception is relevant here.
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    2. The Fifth Amendment privilege is self-executing when the government
    creates a “classic penalty situation”
    In Murphy, the Supreme Court examined this last exception in the context of
    a probationer’s statements to his probation officer. Because Murphy guides our
    analysis here, where we consider whether a supervised-releasee’s statements to his
    probation officer occurred in the context of a penalty situation, we examine it in
    closer detail.
    Murphy was sentenced to a suspended prison term and three years of
    probation. 
    Murphy, 465 U.S. at 422
    . Among other conditions, his probation
    required him to report to his probation officer as directed and be truthful with the
    probation officer “in all matters.”
    Id. During one of
    the probation officer’s required meetings with Murphy, the
    officer informed him that she had received information that Murphy had admitted
    committing a rape and murder several years earlier.
    Id. at 423–24.
    Over the course
    of the meeting, Murphy confessed that he had in fact committed these crimes.
    Id. at 424.
    A couple of days later, the probation officer obtained an arrest and detention
    order from the judge who had earlier sentenced Murphy to the term of probation he
    was serving.
    Id. Not long after
    that, a grand jury indicted Murphy for first-degree
    murder.
    Id. at 425.
    In that new case, Murphy sought suppression of his confession
    on the basis that the state had procured it in violation of the Fifth and Fourteenth
    Amendments.
    Id. 20
                 Case: 17-13358     Date Filed: 08/12/2020   Page: 21 of 50
    In evaluating Murphy’s claim, the Supreme Court first observed that a
    defendant does not lose his Fifth Amendment privilege simply because he is
    imprisoned or on probation.
    Id. at 426.
    So if the government compels incriminating
    statements of a prisoner or probationer, those statements are inadmissible in a later
    trial for a crime other than the one for which the speaker has been convicted.
    Id. Nevertheless, the Court
    observed that “the general obligation to appear and
    answer questions truthfully did not in itself” change any of Murphy’s otherwise
    voluntary statements into compelled confessions.
    Id. at 427.
    Rather, to compel a
    statement in the penalty situation, the government must threaten to impose a
    “substantial” penalty if the speaker chooses to invoke his Fifth Amendment right not
    to incriminate himself.
    Id. at 434
    (citation and quotation marks omitted).
    In particular, the Court reasoned, if the government expressly or implicitly
    suggested that claiming the privilege would lead to revocation of probation, “it
    would have created the classic penalty situation, the failure to assert the privilege
    would be excused, and the probationer’s answers would be deemed compelled and
    inadmissible in a criminal prosecution.”
    Id. at 435
    . 
    So the Court homed in on
    whether the government expressly or implicitly indicated to Murphy that his
    invocation of the Fifth Amendment would result in revocation of his probation.
    Despite this rule concerning the “classic penalty situation,” the Court
    recognized that the government can “validly insist on answers to even incriminating
    21
    Case: 17-13358     Date Filed: 08/12/2020   Page: 22 of 50
    questions” in the course of probation supervision, provided it understands it may not
    use the required answers in a separate criminal proceeding, as opposed to a
    revocation-of-probation proceeding.
    Id. at 435
    n.7. Indeed, the Court explained, the
    government can revoke probation if a probationer refuses to answer a question, in
    violation of an express condition of probation.
    Id. But the government
    cannot both
    require answers to incriminating questions in the course of probation supervision,
    upon pain of revocation if the probationer invokes his Fifth Amendment privilege,
    and then also use the answers to those incriminating questions in an independent
    criminal prosecution.
    Id. at 435
    & n.7.
    In light of these concerns, the Supreme Court evaluated whether the
    government had, in fact, required Murphy to answer the probation officer’s
    questions or else have his probation revoked. See
    id. at 437–39.
    It found that the
    government had not.
    Id. at 439.
    In support of this conclusion, the Court noted that
    (1) Murphy’s probation condition precluded only false statements but did not
    suggest that “his probation was conditional on his waiving his Fifth Amendment
    privilege with respect to further criminal prosecution”; and (2) no reasonable basis
    existed for concluding that the state tried to tether an impermissible penalty to a
    probationer’s exercise of the Fifth Amendment privilege.
    Id. at 437–38.
    As the
    Court explained, it was aware of no case in which the state had attempted to revoke
    probation simply because a probationer declined to answer questions about his own
    22
    Case: 17-13358      Date Filed: 08/12/2020     Page: 23 of 50
    criminal conduct, and so against the background of the Supreme Court’s
    jurisprudence prohibiting threats of penalties upon invocation of the Fifth
    Amendment privilege, “Murphy could not reasonably have feared” that his
    probation would be revoked merely because he remained silent.
    Id. at 439.
    3. Robinson created a “classic penalty situation” when it permitted probation
    to be revoked because the probationer there invoked his Fifth Amendment
    privilege and thereby refused to comply with the condition of his probation
    requiring him to completely and truthfully answer his probation officer’s
    questions
    Unlike the probationer in Murphy, McKathan was under federal supervised
    release, not state probation. So to apply Murphy’s guidance, we must determine
    whether the conditions of McKathan’s federal supervised release threatened to
    penalize him with revocation of his supervised release if he invoked his Fifth
    Amendment privilege. We do that by looking to the factors the Supreme Court
    evaluated in Murphy.
    First, we examine the precise terms of McKathan’s supervised-release
    condition that he answer his probation officer’s questions. McKathan’s supervised-
    release terms required him to “answer truthfully all inquiries by the probation officer
    and follow the instructions of the probation officer.” They further informed him
    that, “[u]pon a finding of a violation of . . . supervised release, . . . the court may . .
    . revoke supervision,” sending him back to prison. Like the probation terms at issue
    in Murphy, these supervised-release provisions, on their face, prohibit only false
    23
    Case: 17-13358    Date Filed: 08/12/2020   Page: 24 of 50
    statements and do not indicate that McKathan’s supervised release “was conditional
    on his waiving his Fifth Amendment privilege with respect to further criminal
    prosecution.”
    Id. at 437.
      So if the inquiry ended here, we would find that
    McKathan’s supervised-release terms did not create a penalty situation and therefore
    did not compel him to incriminate himself.
    But the analysis does not end with this step. Rather, we must also consider
    the second Murphy factor, which is whether there was any reasonable basis for
    McKathan to have thought that his invocation of his Fifth Amendment privilege
    would result in revocation of his supervised release. See
    id. Relatedly, we also
    consider whether, in the Eleventh Circuit, the government has successfully
    attempted to revoke supervised release in any case, merely because the supervised
    releasee invoked his Fifth Amendment privilege. See
    id. at 439.
    McKathan points to United States v. Robinson, 
    893 F.2d 1244
    (11th Cir. 1990)
    (per curiam), as an example of such a case. Robinson was serving a term of
    probation following his conviction for currency smuggling.
    Id. at 1244.
    Under his
    probation agreement, Robinson was required to report to his probation officer and
    to “give an account of himself and to respond completely and truthfully to questions
    asked by the probation officer.”
    Id. at 1244–45
    (alteration adopted and internal
    quotation marks omitted). Robinson had previously reported $25,000 in income on
    his tax return but had asserted the Fifth Amendment as to the income’s source.
    Id. 24
                 Case: 17-13358     Date Filed: 08/12/2020   Page: 25 of 50
    at 1244 & n.1. The probation officer asked Robinson about the source of that
    income.
    Id. at 1244.
    In response, Robinson again claimed his Fifth Amendment
    privilege to remain silent.
    Id. Based on Robinson’s
    refusal to answer the probation
    officer’s question, the court later revoked Robinson’s probation. See
    id. This Court affirmed.
    Id. at 1245
    . 
    Quoting Murphy, we first noted that a
    probationer’s reliance on his Fifth Amendment privilege to avoid self-incrimination
    does not preclude the government from, as relevant in Robinson’s case, “revoking
    probation for a refusal to answer that violated an express condition of
    probation . . . .”
    Id. (emphasis added) (quoting
    Murphy, 465 U.S. at 435 
    n.7). In
    applying this rule, we determined that Robinson’s failure to “completely and
    truthfully” report his “continuing . . . unlawful money smuggling activities” as the
    terms of his probation required was a violation of his probation.
    Id. (emphasis omitted). Though
    we reasoned that “[t]he issue is not invocation of the privilege,
    but the failure to report,” we nonetheless concluded that the failure to report—
    regardless of why—“alone can justify revocation of probation.”
    Id. (citation and quotation
    marks omitted). Because unlike McKathan, Robinson did not challenge
    the use of his silence in separate criminal charges, our decision was not inconsistent
    with the Supreme Court’s distinction between use of a probationer’s statements in
    revocation proceedings following a prior conviction and their use in a “pending or
    later criminal prosecution.” See 
    Murphy, 465 U.S. at 435
    & n.7.
    25
    Case: 17-13358         Date Filed: 08/12/2020         Page: 26 of 50
    Nevertheless, as the government conceded during oral argument, Robinson
    does “take the extra, impermissible step” Murphy warned against, of requiring a
    supervised releasee “to choose between making incriminating statements and
    jeopardizing his conditional liberty by remaining silent.”5
    Id. at 436;
    see Oral
    5
    The Dissent contends that it is “not entirely accurate” to state that the government
    conceded that “Robinson took “the extra, impermissible step’ Murphy warned against” because
    “[i]nstead, the government merely conceded that there may be a conflict between Murphy and
    Robinson, but that Robinson could be factually distinguished.” Dissent at 49 n.4. We respectfully
    disagree with our colleague. First, while the government did not use the words “extra,
    impermissible step,” it is clear that it agreed with that proposition. In particular, the following
    exchange occurred at oral argument:
    Court: [W]e’ve said in Robinson, if you don’t comply with the conditions of your
    supervised release, you go to jail. I mean, isn’t that what we’ve said?
    Government: That is what you said in that case for Robinson. I do know . . . while
    Minnesota v. Murphy, at least in certain portions disagree with Robinson of the fact
    that . . . a petitioner cannot be forced to give a statement and then go to jail on that,
    but that is of course what you say in terms of Robinson, that they can be revoked.
    Court: . . . Since we’re bound by Robinson, don’t we have to accept that when
    we’re reviewing this?
    Government: I think yes, unless we tailor Robinson to the specific language that
    was used in that particular [probation condition requiring the probationer to respond
    “completely and truthfully” to inquiries from the probation officer].
    Oral Argument, at 21:24–22:11. And second, the government did not suggest that Robinson was
    somehow consistent with Murphy or that it could be factually distinguished from Murphy; rather,
    it argued that the probation condition at issue in Robinson could be factually distinguished from
    that at issue in McKathan’s case, so Robinson’s authorization of punishment for invocation of the
    Fifth Amendment right not to incriminate oneself did not reasonably suggest that McKathan would
    be punished for invoking his Fifth Amendment right. See
    id. at 19:44–20:50.
    Later in the oral
    argument, though, the government effectively conceded that the probation condition at issue in
    Robinson could not be meaningfully distinguished from that at issue here:
    Court: [I]f we’re holding that the reason that . . . revocation was appropriate was
    because [Robinson] failed to report [answer] in response to inquiries, which . . .
    would you agree that’s what Robinson holds?
    Government: Yes.
    (cont’d.)
    26
    Case: 17-13358      Date Filed: 08/12/2020       Page: 27 of 50
    Argument at 20:20–23:10, Denzil McKathan v. United States. (No. 17-13358),
    http://www.ca11.uscourts.gov/oral-argument-recordings?title=17-13358&field_oar
    _case_name_value=&field_oral_argument_date_value%5Bvalue%5D%5Byear%
    5D=&field_oral_argument_date_value%5Bvalue%5D%5Bmonth%5D=                                 (“Oral
    Argument”). Indeed, it is a case where the government successfully “attempted to
    revoke probation merely because a probationer refused to make nonimmunized
    disclosures concerning his own criminal conduct.” 
    Murphy, 465 U.S. at 439
    .
    The Dissent asserts that Robinson did not “take the extra, impermissible step”
    that 
    Murphy, 465 U.S. at 436
    , prohibits. Dissent at 51 n.4. It bases this argument
    solely on the premise that in Robinson, the government revoked Robinson’s
    probation because Robinson “invo[ked] the privilege” and “was found to be in
    violation of the reporting condition of his probation, but it was the reporting violation
    that was the issue, not the defendant’s invocation of the privilege.”
    Id. at 50
    (emphasis omitted).
    Most respectfully, that is a distinction without a difference. Invoking the
    privilege and not reporting (meaning not answering questions) after the privilege has
    Court: . . . Then how could [McKathan] not fail to report so [he] would avoid the
    Robinson problem and still not respond to the question about the PIN? Is there a
    way to do that? Maybe there is.
    Government: . . . There may be a way. At this very moment, I can’t think of a
    way . . . .
    Oral Argument, at 26:37–27:30.
    27
    Case: 17-13358     Date Filed: 08/12/2020    Page: 28 of 50
    been invoked are one and the same thing—like six of one, half dozen of the other.
    And it is not possible to both invoke the Fifth Amendment privilege and “completely
    and truthfully” answer the probation officer’s incriminating question. See United
    States v. Saechao, 
    418 F.3d 1073
    , 1080–81 (9th Cir. 2005). Robinson necessarily
    approves of a “classic penalty situation.” And a reasonable person in McKathan’s
    position would understand Robinson to authorize punishment for a supervised
    releasee’s refusal to answer his probation officer’s questions.
    Moreover, unlike with the probationer in Murphy, the record contains direct
    evidence that McKathan incriminated himself because he feared that his supervised
    release would be revoked if he remained silent. See
    id. at 437.
    McKathan testified
    that his probation officer instructed him that “if [he] did not follow the conditions
    [of his supervised release,] [he]’d be revoked and go back to prison.” McKathan
    explained that he understood as a result of this instruction that his supervised release
    “would certainly have been revoked” if he had refused to enter his phone’s PIN or
    answer any of Goodwin’s questions. Operating in a post-Robinson world, we cannot
    say that McKathan’s understanding that he was in a “classic penalty situation” was
    unreasonable.
    For that reason, under Murphy, the government was well within its rights to
    revoke McKathan’s supervised release, based on the incriminating statements
    McKathan made in response to Goodwin’s questions. But it could not also use those
    28
    Case: 17-13358     Date Filed: 08/12/2020    Page: 29 of 50
    same statements, which McKathan made under the “classic penalty situation,” to
    prosecute McKathan for a new crime.
    We are not the first Circuit to reach this conclusion. In Saechao, 
    418 F.3d 1073
    , the Ninth Circuit considered the same issue we face today. See
    id. at 1075.
    Saechao’s state probation conditions required him to “promptly and truthfully
    answer all reasonable inquiries by the Department of Correction or County
    Community Correction Agencies.”
    Id. His probation terms
    also stated that failure
    to comply with any of the conditions “was grounds for arrest, revocation of
    probation, or modification of conditions.”
    Id. Saechao’s probation officer
    questioned him about whether he possessed a firearm, which would be a violation
    of his probation and a violation of the felon-in-possession statute.
    Id. at 1075–76.
    Saechao acknowledged that a hunting rifle was in the apartment that he shared with
    his parents.
    Id. The probation officer
    and a colleague then confiscated the rifle and
    left Saechao’s residence.
    Id. at 1076
    . 
    Soon after, Saechao was arrested and charged
    with being a felon in possession of a firearm, in violation of federal law.
    Id. In that separate
    case, Saechao moved to suppress his statements to the probation officer.
    Id. The district court
    granted the motion, concluding that the statements had been
    “compelled” within the meaning of the Fifth Amendment.
    Id. The Ninth Circuit
    affirmed.
    Id. at 1081
    . 
    It determined that the state had taken
    the “impermissible step of requiring Saechao to choose between making
    29
    Case: 17-13358    Date Filed: 08/12/2020   Page: 30 of 50
    incriminating statements and jeopardizing his conditional liberty by remaining
    silent.”
    Id. at 1076
    (quoting 
    Murphy, 465 U.S. at 436
    ) (alterations adopted and
    quotation marks omitted).     And it found further that “there [was] certainly a
    reasonable basis under Murphy for a probationer to conclude that, although the
    invocation of the Fifth Amendment [was] not explicitly prohibited, an exercise of
    that right by invoking the privilege or simply by remaining silent would constitute
    grounds for revocation of probation.”
    Id. at 1079
    (emphasis in original).
    In reaching these conclusions, the Ninth Circuit explained that the condition
    requiring Saechao to “promptly and truthfully answer all reasonable inquiries”
    required Saechao to actually provide an answer to the question asked, and invoking
    the Fifth Amendment privilege to remain silent would not be an “answer” to the
    question.
    Id. at 1080
    (emphasis in original). In support of this determination, the
    Ninth Circuit pointed to Robinson.
    Id. at 1080
    –81. It said, “[t]he Eleventh Circuit,
    confronted with a nearly identical probation condition, explicitly rejected the
    argument that by ‘answering’ a probation officer’s inquiry with an invocation of the
    Fifth Amendment, the probationer would comply with an obligation to answer or
    respond to his probation officer’s inquiries and thereby avoid a revocation of his
    probation.”
    Id. at 1080
    . Rather, the Ninth Circuit explained, “the Eleventh Circuit
    held that invoking the Fifth Amendment did not constitute a response to a question,
    but rather was a refusal to answer that violated an express condition of probation.”
    30
    Case: 17-13358     Date Filed: 08/12/2020    Page: 31 of 50
    Id. at 1081
    (citation and quotation marks omitted). As a result, the Ninth Circuit
    observed, Robinson’s invocation of his Fifth Amendment privilege “promptly led
    the government to seek the revocation of Robinson’s probation, which the district
    court granted and the Eleventh Circuit affirmed.”
    Id. (citing Robinson,
    893 F.2d at
    1244–45).
    The U.S. Sentencing Commission has also felt a need in the wake of post-
    Murphy opinions like Robinson to clarify that defendants should not be punished for
    failing to truthfully answer their probation officer’s questions if the failure resulted
    from an invocation of the Fifth Amendment privilege. In 2016, the Commission, in
    Amendment 803, added Application Notes to the Commentary to Sections 5B1.3
    and 5D1.3 of the U.S. Sentencing Guidelines Manual that effectively abrogate
    Robinson. See U.S. Sentencing Guidelines Manual amend. 803 (U.S. Sentencing
    Comm’n 2016). They state, “[a]lthough the condition in subsection (c)(4) requires
    the defendant to ‘answer truthfully’ the questions asked by the probation officer, a
    defendant’s legitimate invocation of the Fifth Amendment privilege against self-
    incrimination in response to a probation officer’s question shall not be considered a
    violation of this condition.” U.S.S.G. § 5B1.4, cmt. n.1 (2016); U.S.S.G. § 5D1.3,
    cmt. n.1 (2016). Since these application notes were made effective November 1,
    2016, no supervised-releasee who chose or chooses to answer questions after that
    31
    Case: 17-13358        Date Filed: 08/12/2020   Page: 32 of 50
    date could demonstrate that he reasonably believed or believes he was or is faced
    with the “classic penalty situation” Murphy prohibits.
    But McKathan answered his probation officer’s questions in 2014, before the
    Sentencing Commission promulgated Amendment 803. So Amendment 803 cannot
    control our analysis in his case.
    Nevertheless, the changes to the Commentary further demonstrate that we
    held in Robinson that the government may revoke supervised release simply because
    a probationer invokes his Fifth Amendment privilege in response to a question from
    his probation officer. Having so held in that case, we may not now find that
    McKathan’s supervised-release provision requiring him to answer all inquiries from
    his probation officer did not place him in the “classic penalty situation” Murphy
    warns against.
    4. Robinson’s existence requires us to conclude that McKathan’s view that
    he was subjected to a “classic penalty situation” was objectively
    reasonable
    As we have noted, in Robinson, the government did not seek to use
    Robinson’s silence in a separate criminal prosecution, and Robinson did not
    complain in a separate criminal proceeding that he had been coerced to answer his
    probation officer’s questions on penalty of revocation of his probation. Rather, the
    government used Robinson’s silence—and Robinson objected that the government
    used his silence—only to punish him for violating his probation conditions. But that
    32
    Case: 17-13358     Date Filed: 08/12/2020    Page: 33 of 50
    is permissible under Murphy. What is not permissible is giving a probationer a
    reasonable belief that if he refuses to answer his probation officer’s incriminating
    questions, his probation will be revoked and then using statements derived as a
    result of that “classic penalty situation” in a criminal prosecution. Because of
    Robinson’s existence, though, that is what happened here, in McKathan’s case.
    We suggested in 2003 that a case like McKathan’s might well require
    suppression, in a criminal prosecution, of statements elicited by a probation officer
    in the course of supervising supervised release:
    There is thus a substantial basis in our cases for concluding that if the
    State, either expressly or by implication, asserts that invocation of the
    privilege would lead to revocation of probation, it would have created
    the classic penalty situation, the failure to assert the privilege would be
    excused, and the probationer’s answers would be deemed compelled
    and inadmissible in a criminal prosecution.
    See United States v. Zinn, 
    321 F.3d 1084
    , 1091 (11th Cir. 2003) (quoting 
    Murphy, 465 U.S. at 435
    ).     Here, because of Robinson and the government’s use of
    McKathan’s coerced statements in his separate criminal prosecution, McKathan’s
    counsel could have argued that suppression was required on exactly this “substantial
    basis.”
    Finally, the laundry list of cases the Dissent sets forth for the proposition that
    a penalty may not be imposed on someone for exercising his Fifth Amendment right
    not to incriminate himself, see Dissent at 49-50, does not change the analysis or
    somehow allow us to ignore Robinson. The cited cases speak in general principles;
    33
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    none of them other than Murphy and Robinson themselves deals with the ways in
    which the government coerced or made use of compelled testimony that are at issue
    here.6 And we have already explained why, under Murphy, Robinson creates the
    “classic penalty situation” here, where the supervised-releasee’s statements, coerced
    on pain of revocation for invocation of the Fifth Amendment privilege, were used
    against him in a separate criminal case.
    In short, we conclude that there is a reasonable likelihood that a Fifth
    Amendment suppression motion would have been successful.
    B.
    That brings us to whether the fruits of McKathan’s statements would have
    nonetheless been admissible for an independent reason. The government argues that
    they would have been, so any Fifth Amendment legal win would have been a purely
    Pyrrhic victory. 7
    6
    For example, besides predating both Murphy and Robinson, Baxter v. Palmigiano, 
    425 U.S. 308
    , 316 (1976), and Lefkowitz v. Turley, 
    414 U.S. 70
    , 85 (1973), deal with the use of
    compelled statements in civil, rather than criminal, proceedings. Chavez v. Martinez, 
    538 U.S. 760
    (2003), also does not involve use of compelled statements in criminal proceedings.
    Id. at 769– 70.
    United States v. Vangates, 
    287 F.3d 1315
    (11th Cir. 2002), while a little closer in that the
    criminal defendant claimed she had been subjected to a “classic penalty situation,” is similarly
    irrelevant here. There, Vangates, a police officer, incriminated herself during her testimony in a
    civil trial for which she was subpoenaed to testify by a private attorney. The government
    prosecuted her, using her statements. We concluded the statements had not been coerced because
    no state action compelled her to forgo her Fifth Amendment rights.
    Id. at 1324. 7
               The term “Pyrrhic victory,” where the battle is won but the war is lost, finds its origins in
    the ultimately ill-fated war pursuits of King Pyrrhus of Epirus. ThoughtCo., What’s the Origin of
    the Term Pyrrhic Victory?, https://www.thoughtco.com/pyrrhic-victory-120452 (last visited Aug.
    11, 2020). Pyrrhus is said to have suffered the first Pyrrhic victory around 280 B.C.E.
    Id. Though 34 Case:
    17-13358       Date Filed: 08/12/2020      Page: 35 of 50
    In particular, the government suggests that it would have inevitably
    discovered the evidence of child pornography on McKathan’s phone, since
    McKathan’s supervised release required him to consent to reasonable searches, and
    Goodwin had reason to suspect he was violating the terms of his release. Goodwin’s
    beliefs were based on the following: McKathan had a Facebook account and opened
    it with an Android phone, and he had an Android phone on his bed.
    The “inevitable discovery” doctrine applies when the government can show
    by a preponderance of the evidence that it would have discovered the evidence by
    some other lawful means. See Utah v. Strieff, 
    136 S. Ct. 2056
    , 2061 (2016) (“[T]he
    inevitable discovery doctrine allows for the admission of evidence that would have
    been discovered even without the unconstitutional source.”); Nix v. Williams, 
    467 U.S. 431
    , 444 (1984). For that doctrine to apply in this Circuit, the government must
    also demonstrate that before the unlawful activity occurred, it was actively pursuing
    the lawful means that would have rendered discovery inevitable. United States v.
    Virden, 
    488 F.3d 1317
    , 1322 (11th Cir. 2007). The inevitable-discovery doctrine
    can apply when a Fifth Amendment violation occurs. United States v. Martinez-
    Gallegos, 
    807 F.2d 868
    , 870 (9th Cir. 1987) (per curiam).
    he defeated the Romans in two battles, he endured an extremely high number of casualties.
    Id. As a result,
    he wound up eventually losing the war.
    Id. 35
                    Case: 17-13358         Date Filed: 08/12/2020        Page: 36 of 50
    Here, in the context of McKathan’s § 2255 Case, the district court had no
    reason to analyze—and the government had no reason to argue—whether the
    inevitable-discovery doctrine could apply, since the district court determined that
    McKathan could not prevail on his Fifth Amendment argument. 8 For these reasons,
    the record lacks information that would allow us to assess the viability of an
    inevitable-discovery argument. Therefore, we cannot determine whether, as a legal
    matter, the government would have been permitted to search McKathan’s phone.
    Nor can we assess the government’s proffer at oral argument that it would have been
    able to view the contents without compelling McKathan to provide his PIN to unlock
    it, since it “has tools and has methods, and has used them in many cases to get in[to]
    [phones] before.” Oral Argument at 24:17–24:23.
    As a result, we cannot evaluate, in the final analysis, whether there was a
    reasonable likelihood that the outcome of McKathan’s case would have been
    different, had his counsel filed a suppression motion based on the Fifth Amendment.
    But because McKathan would have prevailed on the Fifth Amendment suppression
    8
    When it ruled on McKathan’s Fourth Amendment suppression motion in McKathan II,
    the district court did say that it saw no basis for inevitable discovery on the record before it at that
    time, and the government did not object. But that did not occur in McKathan’s § 2255 Case. And
    at the time the district court remarked on the inevitable-discovery doctrine, it had just ruled on a
    clearly unmeritorious Fourth Amendment suppression motion (and the Fifth Amendment
    argument had not been made at that time). So neither the court nor the government had any reason
    to actually evaluate any alternative bases for admission of the evidence from McKathan’s phone.
    Under these circumstances, we cannot say that the government waived its right to pursue an
    inevitable-discovery argument.
    36
    Case: 17-13358    Date Filed: 08/12/2020   Page: 37 of 50
    issue, it now becomes necessary to consider whether the evidence would have
    otherwise been admissible.
    Therefore, we must vacate the denial of McKathan’s § 2255 motion and
    remand for further proceedings. In those proceedings, the government must receive
    the opportunity to present any evidence and arguments to show that the evidence
    from McKathan’s phone would have otherwise been admissible, and the district
    court shall rule on any such arguments. Should the district court conclude that the
    evidence would have been otherwise admissible, it shall deny the § 2255 motion,
    since filing the Fifth Amendment suppression motion would not have been
    reasonably likely to change the outcome in McKathan II. But should the district
    court determine that the evidence would not have been otherwise admissible, it shall
    address whether McKathan’s counsel performed deficiently by failing to raise the
    Fifth Amendment issue in McKathan II. See 
    Strickland, 466 U.S. at 687
    .
    IV.
    For these reasons, we vacate the district court’s denial of McKathan’s § 2255
    motion and remand for further proceedings consistent with this opinion.
    VACATED AND REMANDED.
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    Case: 17-13358     Date Filed: 08/12/2020    Page: 38 of 50
    BRANCH, Circuit Judge, dissenting:
    In this case, McKathan, while on supervised release as a result of his 2005
    conviction for possession of child pornography, failed to invoke his Fifth
    Amendment privilege in response to his probation officer’s questions and made
    testimonial statements (including revealing his PIN which was used to unlock his
    phone) that both revealed he had violated the terms of his release and implicated
    himself in a new crime. His supervised release was thereafter revoked based upon
    a finding that he had violated the terms of his release. The government then used
    the incriminating statements he made to his probation officer against him in a
    subsequent criminal prosecution for receipt of child pornography. After pleading
    guilty to the new charge, McKathan filed a 28 U.S.C. § 2255 motion to vacate
    sentence arguing that his counsel was ineffective for failing to file a Fifth
    Amendment-based motion to suppress the testimonial communications he made to
    his probation officer. The district court denied the claim, concluding that he failed
    to establish prejudice. This appeal followed. To address McKathan’s ineffective-
    assistance claim, we must consider the underlying merits of his Fifth Amendment
    challenge. Because I disagree with the majority that McKathan’s failure to invoke
    the Fifth Amendment privilege should be excused, I respectfully dissent.
    The ultimate question in this case is whether McKathan established that he
    38
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    was prejudiced by his counsel’s failure to file a Fifth Amendment based motion to
    suppress the testimonial communications he made to his probation officer pursuant
    to the two-prong deficient performance and prejudice test set forth in Strickland v.
    Washington, 
    466 U.S. 668
    , 687 (1984). To establish prejudice, McKathan must
    show “a reasonable probability that, but for counsel’s errors, he would not have
    pleaded guilty and would have insisted on going to trial.” Premo v. Moore, 
    562 U.S. 115
    , 129 (2011) (quoting Hill v. Lockhart, 
    474 U.S. 52
    , 59 (1985)). This
    inquiry in turn requires an evaluation of the merit of the underlying Fifth
    Amendment challenge. See Kimmelman v. Morrison, 
    477 U.S. 365
    , 375 (1986)
    (explaining that when defense counsel’s failure to litigate a suppression issue is the
    basis of the ineffectiveness claim, in order to demonstrate prejudice, the defendant
    must prove that his suppression claim is meritorious, and that there is a “reasonable
    probability” that the suppression issue the attorney did not advance would have
    affected the outcome of the case); see also Lee v. United States, 
    137 S. Ct. 1958
    ,
    1965 (2017) (explaining ineffectiveness claim premised on counsel’s failure to
    litigate a suppression issue in the context of a plea).
    The Fifth Amendment guarantees that “[n]o person . . . shall be compelled in
    any criminal case to be a witness against himself . . . .” U.S. Const. amend. V. To
    succeed on a motion seeking to suppress his statements to the probation officer and
    the entry of his PIN (and all fruits stemming from these revelations), based on a
    39
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    Fifth Amendment challenge McKathan would have had to show three things:
    “(1) compulsion, (2) a testimonial communication or act, and (3) incrimination.”
    In re Grand Jury Subpoena Duces Tecum Dated Mar. 25, 2011, 
    670 F.3d 1335
    ,
    1341 (11th Cir. 2012). As the majority notes, the parties do not dispute that the
    communications at issue satisfy the last two elements. Therefore, the only
    question we must answer is whether McKathan has satisfied the first element—was
    he compelled to provide the incriminating communications in question? The
    majority says the answer to this inquiry is yes because McKathan was in a “classic
    penalty situation.” A “classic penalty situation” arises when a person must choose
    between incriminating himself, on the one hand, or suffering government-
    threatened punishment for invoking his Fifth Amendment privilege to remain
    silent, on the other. Minnesota v. Murphy, 
    465 U.S. 420
    , 435 (1984).
    As previously noted, at the time of the statements in question, McKathan
    was serving a lifetime term of supervised release after pleading guilty and serving
    a term of imprisonment for possession of child pornography. In relevant part, the
    terms of his supervised release: (1) required McKathan “to answer truthfully all
    inquiries by the probation officer and follow the instructions of the probation
    officer”; (2) prohibited him from possessing and using a computer with internet
    access without the permission of his probation officer; (3) authorized his consent
    “to periodic, unannounced examinations of his computer equipment, which may
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    Case: 17-13358         Date Filed: 08/12/2020         Page: 41 of 50
    include retrieval and copying of all data from his computer and any internal or
    external peripherals to ensure compliance with this condition, and/or removal of
    such equipment for the purpose of conducting a more through [sic] inspection”;
    and (4) authorized his consent to reasonable searches of his person and residence
    based upon reasonable suspicion that he had violated a condition of his release.1
    Finally, McKathan’s terms of release informed him that “[u]pon a finding of a
    violation of probation of supervised release, . . . the [c]ourt may (1) revoke
    supervision or (2) extend the term of supervision, and/or (3) modify the conditions
    of supervision.”
    I now turn to McKathan’s Fifth Amendment challenge. Ordinarily, to claim
    the protections of the Fifth Amendment, an individual must expressly invoke the
    right, or his answers will not qualify as “‘compelled’ within the meaning of the
    Amendment.” 
    Murphy, 465 U.S. at 427
    . It is undisputed that McKathan provided
    incriminating testimonial statements to his probation officer and did not invoke his
    1
    While the supervised release conditions imposed are not at issue, I note that “[a]
    probation condition is not necessarily invalid simply because it affects a probationer’s ability to
    exercise constitutionally protected rights.” Owens v. Kelley, 
    681 F.2d 1362
    , 1366 (11th Cir.
    1982) (quoting United States v. Tonry, 
    605 F.2d 144
    , 150 (5th Cir. 1979)). Rather,
    “[p]robationers . . . are subject to limitations to which ordinary citizens are free. Such limitations
    are permitted because probationers have been convicted of crimes and have thereby given the
    state a compelling interest in limiting their liberty in order to effectuate their rehabilitation and to
    protect society. Probationers also have a diminished expectation of privacy. Because they have
    been convicted of crimes for which they could be incarcerated, probationers reasonably expect
    infringements on their privacy which law-abiding citizens neither expect nor receive.”
    Id. at 1367–68
    (internal citations and quotations omitted).
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    Fifth Amendment privilege. Yet, as relevant here, where an individual is faced
    with a classic penalty situation, the privilege becomes self-executing.
    Id. at 434
    –
    35 (citing Garrity v. New Jersey, 
    385 U.S. 493
    (1967)).
    As in this case, the issue before the Murphy Court was whether the Fifth
    Amendment prohibited the admission of incriminating statements the defendant
    made to his probation officer in a subsequent criminal prosecution for another
    crime, notwithstanding the fact that the defendant failed to claim the 
    privilege. 465 U.S. at 422
    . Specifically, Murphy was on probation after pleading guilty to false
    imprisonment.
    Id. The terms of
    his probation included that he participate in a
    treatment program for sexual offenders, “report to his probation officer as directed,
    and be truthful with the probation officer ‘in all matters.’”
    Id. Murphy was informed
    that if he failed to comply with these conditions, he could be “return[ed]
    to the sentencing court for a probation revocation hearing.”
    Id. His probation officer
    later learned that during treatment in the sexual offender program, Murphy
    admitted to an earlier rape and murder.
    Id. at 423.
    The probation officer called
    Murphy in for a meeting, and, during the course of the meeting, Murphy denied the
    false imprisonment charge to which he had pled guilty, but admitted that he had
    committed the rape and murder.
    Id. at 423–24.
    An arrest warrant was issued, and
    the State later returned an indictment charging Murphy with first-degree murder.
    Id. at 424–25.
    Seeking to suppress the use of his incriminating statements in the
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    new criminal proceeding, Murphy argued that his failure to assert the Fifth
    Amendment privilege should have been excused because “he was compelled to
    make incriminating disclosures instead of claiming the privilege” as his probation
    could be revoked “if he was untruthful to his probation officer.”
    Id. at 434
    . The
    Supreme Court ultimately found this contention “unpersuasive on close
    examination.”
    Id. Specifically, the Court
    found that the terms of Murphy’s
    probation “proscribed only false statements; it said nothing about his freedom to
    decline to answer particular questions and certainly contained no suggestion that
    his probation was conditional on his waiving his Fifth Amendment privilege with
    respect to further criminal prosecution.”
    Id. at 437.
    Thus, like Murphy, this case
    requires a determination of whether McKathan’s failure to assert the privilege
    should be excused (i.e., did the circumstances give rise to self-executing privilege
    against self-incrimination). 2
    The relevant factors we must consider in making this determination are:
    (1) whether the government in fact required McKathan via the terms of his
    supervised release to answer the probation officer’s question or else have his
    probation revoked; or (2) whether there was any reasonable basis for McKathan to
    have thought that his invocation of his Fifth Amendment privilege would in and of
    2
    Similar to Murphy, McKathan asserts that he believed that his supervised release would
    be revoked if he was not truthful with his probation officer, and, therefore he was “compelled” to
    make the incriminating statements instead of claiming the privilege.
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    Case: 17-13358     Date Filed: 08/12/2020    Page: 44 of 50
    itself result in revocation of his supervised release. See
    id. at 434–39. I
    agree with
    the majority that, just as in Murphy, the answer to the first inquiry in McKathan’s
    case is a resounding no. The terms of McKathan’s supervised release, on their
    face, merely proscribe only false statements, and do not indicate, explicitly or
    implicitly, that his release was in any way “conditional on his waiving his Fifth
    Amendment privilege with respect to further criminal prosecution.”
    Id. at 437.
    This conclusion leads us to the second inquiry—whether it was reasonable
    for McKathan to conclude that he faced a “classic penalty situation.” How do we
    tell if McKathan’s belief was reasonable? The Supreme Court’s opinion in
    Murphy provides guidance. In Murphy, without deciding whether the
    reasonableness inquiry is subjective or objective, the Court held that Murphy’s
    belief that he was in a classic penalty situation was unreasonable because: (1) there
    was “no direct evidence Murphy confessed because he feared that his probation
    would be revoked if he remained silent,” (2) Supreme Court case law made it clear
    that such a revocation is constitutionally impermissible, and (3) no case had been
    identified where the state “attempted to revoke probation merely because a
    probationer refused to make nonimmunized disclosures concerning his own
    criminal conduct.”
    Id. at 438−39
    (emphasis added). Applying a similar analysis to
    this case, the majority holds that McKathan’s belief that his supervised release
    would have been revoked if he did not answer the probation officer’s questions
    44
    Case: 17-13358        Date Filed: 08/12/2020       Page: 45 of 50
    was reasonable because there is direct evidence that he feared as much and there is
    caselaw in this Circuit where the government attempted to revoke probation merely
    because the probationer asserted his Fifth Amendment privilege. I disagree.
    The majority points to McKathan’s testimony during the § 2255 evidentiary
    hearing that he was instructed that “if [he] did not follow the conditions that [he
    would] be revoked and go back to prison” as direct evidence that McKathan
    reasonably feared that his supervised release would be revoked if he did not answer
    the probation officer’s questions. But that instruction in and of itself does not
    render McKathan’s alleged belief that he was in a classic penalty situation
    reasonable. If it did, then the Supreme Court would have determined that there
    was a reasonable basis for Murphy—who was likewise informed that if he failed to
    comply with the conditions of his probation then his probation could be revoked—
    to believe he was in a classic penalty situation, which was not the Court’s holding.
    Id. at 422, 437–39.
    Indeed, like Murphy, McKathan was not expressly advised that
    an assertion of the privilege would result in the imposition of a penalty—a factor
    the Supreme Court cited in distinguishing Murphy’s case from the classic penalty
    situation it found existed in Garrity.3
    Id. at 438. 3
              In Garrity, two New Jersey police officers were subjected to questioning as part of an
    investigation by the state attorney general concerning alleged fixing of traffic 
    tickets. 385 U.S. at 494
    . Prior to being questioned, each officer was warned that: “(1) that anything he said might
    be used against him in any state criminal proceeding; (2) that he had the privilege to refuse to
    answer if the disclosure would tend to incriminate him; but (3) that if he refused to answer he
    45
    Case: 17-13358        Date Filed: 08/12/2020       Page: 46 of 50
    Likewise, McKathan’s asserted understanding that, because of this
    instruction, his supervised release “would certainly have been revoked” if he
    refused to answer the probation officer’s questions was simply not reasonable
    under the circumstances. As in Murphy, the terms and conditions of McKathan’s
    supervised release were “accurately summarized” in the notices provided to
    McKathan detailing both the standard and special conditions of his release. See
    id. at 438.
    Both notices provided that “[u]pon a finding of a violation of probation or
    supervised release, I understand that the court may (1) revoke supervision,
    (2) extend the term of supervision, and/or (3) modify the conditions of
    supervision.” (emphasis added). And, McKathan, a high school graduate with
    “some college” education, signed the documents detailing the terms and conditions
    of his release, attesting that they were read to him, that he had been provided with
    copies of the notices, and that he understood the conditions. Regardless, even
    accepting McKathan’s contentions that he believed his supervised release would be
    revoked for exercising his Fifth Amendment privilege, as the Supreme Court
    concluded in Murphy, “that belief would not have been reasonable” in light of
    would be subject to removal from office.”
    Id. The officers answered
    the questions posed to
    them, and some of those answers were used in subsequent criminal proceedings against them for
    conspiracy to obstruct the administration of traffic laws.
    Id. at 495.
    The Supreme Court
    determined that those officers were in a classic penalty situation—“[t]he choice imposed . . . was
    one between self-incrimination or job forfeiture.”
    Id. at 496.
    Therefore, the Court held that the
    officers had not waived the Fifth Amendment privilege even though they failed to assert it, and
    the statements were coerced and could not be used against the officers in subsequent criminal
    proceedings.
    Id. at 498–500. 46
                 Case: 17-13358     Date Filed: 08/12/2020    Page: 47 of 50
    Supreme Court decisions that “have made clear that the [government] could not
    constitutionally carry out a threat to revoke [a term of supervised release] for the
    legitimate exercise of the Fifth Amendment privilege.”
    Id. McKathan and the
    majority point to this Circuit’s decision in United States
    v. Robinson, 
    893 F.2d 1244
    (11th Cir. 1990) (per curiam), as supporting the
    reasonableness of McKathan’s classic penalty situation belief. They contend that
    Robinson is purportedly an example of a case in which the government attempted
    to revoke a term of probation merely because a defendant invoked his Fifth
    Amendment privilege, and we then sanctioned such an attempt by affirming on
    appeal. Thus, according to the majority, “[o]perating in a post-Robinson world, we
    cannot say that McKathan’s understanding that he was in a ‘classic penalty
    situation’ was unreasonable.”
    But Robinson was not a classic penalty situation case where the government
    attempted to revoke a defendant’s probation simply because he invoked his Fifth
    Amendment privilege. To the contrary, consistent with Murphy and countless
    other Supreme Court cases, Robinson expressly acknowledged that “a probationer
    has a fifth amendment right to avoid 
    self-incrimination.” 893 F.2d at 1245
    .
    Rather, the issue before us in Robinson was “whether the United States may revoke
    probation where the probation agreement explicitly requires a probationer to report
    [his sources of income] and to ‘give an account of’ [himself] and to respond
    47
    Case: 17-13358     Date Filed: 08/12/2020     Page: 48 of 50
    completely and truthfully to questions asked by the probation officer” about that
    report but the probationer does not do so.
    Id. at 1244–45
    . Indeed, when
    questioned about the source of income reported on his tax return, Robinson, a
    convicted currency smuggler, invoked the privilege, suffered no penalty upon
    invocation of the privilege, and was not compelled to give any statements over his
    claim of privilege.
    Id. True, Robinson’s probation
    was later revoked because he
    was found to be in violation of the reporting condition of his probation, but it was
    the reporting violation that was the issue, not the defendant’s invocation of the
    privilege.
    Id. at 1245
    (“When Robinson failed to report these activities completely
    and truthfully as per the terms of his probation, he committed a probation violation.
    The issue was not invocation of the privilege, but the failure to report. ‘[T]here is
    no question that failure to comply with reporting requirements is a serious
    violation of probationary conditions, and that such failure alone can justify
    revocation of probation.’” (second emphasis added) (quoting United States v.
    Morin (Roger), a/k/a Video (Paris), 
    889 F.2d 328
    , 332 (1st Cir. 1989))). That his
    probation was thereafter revoked, at least in part, for his failure to fulfill the terms
    of his probation by responding “completely and truthfully” to questions asked by
    the probation officer is not inconsistent with Murphy. As the Murphy Court
    acknowledged, while the government cannot revoke a defendant’s probation as a
    penalty for the defendant invoking the Fifth Amendment privilege, “nothing in the
    48
    Case: 17-13358       Date Filed: 08/12/2020     Page: 49 of 50
    Federal Constitution would prevent [the government] from revoking probation for
    a refusal to answer that violated an express condition of probation or from using
    the probationer’s silence as ‘one of a number of factors to be considered by a
    finder of fact’ in deciding whether other conditions of probation have been
    violated.” See 
    Murphy, 465 U.S. at 435
    n.7 (quoting Lefkowitz v. Cunningham,
    
    431 U.S. 801
    , 808 n.5 (1977)). 4
    Accordingly, contrary to the majority’s conclusion, “McKathan’s
    understanding that he was in a ‘classic penalty situation’” was not reasonable
    simply because he was “in a post-Robinson world.” In fact, such a belief is
    directly contradicted by Robinson’s express acknowledgement that “a probationer
    has a fifth amendment right to avoid self-incrimination,” 
    Robinson, 893 F.2d at 1245
    , as well as a plethora of well-established precedent from both the Supreme
    Court and this Court. See, e.g., Chavez v. Martinez, 
    538 U.S. 760
    , 768–69 (2003)
    (“[N]o ‘penalty’ may ever be imposed on someone who exercises his core Fifth
    4
    Thus, contrary to the majority’s position, Robinson does not “take the extra,
    impermissible step” Murphy warned against, of requiring a supervised releasee “to choose
    between making incriminating statements and jeopardizing his conditional liberty by remaining
    silent.” Indeed, the majority goes as far as to say that the government also concedes that
    Robinson took “the extra, impermissible step” Murphy warned against, but that is not entirely
    accurate. Instead, the government merely conceded that there may be a conflict between Murphy
    and Robinson, but that Robinson could be factually distinguished. Oral Argument at 21:25–
    22:05, Denzil McKathan v. United States. (No. 17-13358), http://www.ca11.uscourts.gov/oral-
    argument-recordings?title=17-13358&field_oar_case_name_value=&field_oral_
    argument_date_value%5Bvalue%5D%5Byear%5D=&field_oral_argument_date_value%5Bvalu
    e%5D%5Bmonth%5D= (“Oral Argument”)
    49
    Case: 17-13358     Date Filed: 08/12/2020   Page: 50 of 50
    Amendment right not to be a ‘witness’ against himself in a ‘criminal case.’”);
    
    Murphy, 465 U.S. at 426
    ; Baxter v. Palmigiano, 
    425 U.S. 308
    , 316 (1976)
    (explaining that prisoners have Fifth Amendment rights, and, therefore, if they are
    compelled to furnish incriminating testimonial evidence during prison disciplinary
    proceedings, “they must be offered ‘whatever immunity is required to supplant the
    privilege’” (quoting Lefkowitz v. Turley, 
    414 U.S. 70
    , 85 (1973))); United States v.
    Vangates, 
    287 F.3d 1315
    , 1320 (11th Cir. 2002) (noting that a person cannot be
    penalized for asserting the Fifth Amendment privilege). In light of well-
    established precedent “proscribing threats of penalties for the exercise of Fifth
    Amendment rights, [McKathan] could not reasonably have feared that the assertion
    of the privilege would have led to revocation.”
    Id. at 439.
    Consequently, for the above reasons, McKathan did not face a classic penalty
    situation, and, therefore, he cannot benefit from this exception to the general rule
    that the Fifth Amendment privilege must be claimed and is not self-executing. As
    in Murphy, McKathan’s Fifth Amendment challenge is without merit and the
    statements he made to his probation officer could be used in a subsequent criminal
    proceeding.
    Id. at 440.
    Thus, McKathan cannot demonstrate that he was prejudiced
    by counsel’s failure to file a Fifth Amendment motion to suppress the testimonial,
    incriminating statements at issue, 
    Hill, 474 U.S. at 59
    , and I would affirm the denial
    of his § 2255 petition. I respectfully dissent.
    50