United States v. Daniel A. Rodriguez ( 2021 )


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  •        USCA11 Case: 19-12451    Date Filed: 08/25/2021   Page: 1 of 21
    [DO NOT PUBLISH]
    IN THE UNITED STATES COURT OF APPEALS
    FOR THE ELEVENTH CIRCUIT
    ________________________
    No. 19-12451
    Non-Argument Calendar
    ________________________
    D.C. Docket No. 1:17-cr-20904-UU-1
    UNITED STATES OF AMERICA,
    Plaintiff-Appellee,
    versus
    DANIEL A. RODRIGUEZ,
    Defendant-Appellant.
    ________________________
    Appeal from the United States District Court
    for the Southern District of Florida
    ________________________
    (August 25, 2021)
    Before JORDAN, GRANT, and LAGOA, Circuit Judges.
    PER CURIAM:
    USCA11 Case: 19-12451        Date Filed: 08/25/2021    Page: 2 of 21
    Daniel Rodriguez (“Rodriguez”) appeals his conviction and his 400-month
    sentence for conspiracy to possess with intent to distribute a controlled substance
    and controlled substance analogues, in violation of 
    21 U.S.C. § 846
    , conspiracy to
    commit money laundering, in violation of 
    18 U.S.C. § 1956
    (h), possession with
    intent to distribute a controlled substance analogue, in violation of 
    21 U.S.C. §§ 802
    (32)(A), 841(a)(1), 841(b)(1)(C), and 813, possession with intent to distribute
    a controlled substance, in violation of 
    21 U.S.C. §§ 841
    (a)(1) and (b)(1)(C), and 
    18 U.S.C. § 2
    , and money laundering, in violation of 
    18 U.S.C. § 1957
    . Rodriguez
    raises eleven issues on appeal, which we will address in turn.
    I.
    Rodriguez argues that the district court erred when it accepted his guilty plea
    because there was an insufficient factual basis for his plea. Specifically, he argues
    that the proffer merely mirrored the indictment and did not contain the essential
    elements of the charges against Rodriguez.
    Normally, we review a district’s court’s decision to accept a guilty plea for
    abuse of discretion and review for clear error the district court’s factual findings that
    the requirements of Federal Rule of Criminal Procedure 11 were satisfied. United
    States v. Houser, 
    70 F.3d 87
    , 89 (11th Cir. 1995). Under Rule 11(b), the district
    court “must determine that there is a factual basis for the plea” before entering a
    judgment of guilt. Fed. R. Crim. P. 11(b)(3). The standard for evaluating a challenge
    2
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    to the factual basis for a guilty plea is simply whether the trial court was presented
    with evidence such that “a court could reasonably find that the defendant was
    guilty.” United States v. Rodriguez, 
    751 F.3d 1244
    , 1255 (11th Cir. 2014) (quoting
    United States v. Owen, 
    858 F.2d 1514
    , 1516–17 (11th Cir.1988)). However, when
    a defendant does not object to a Rule 11 violation in the district court, we will review
    for plain error only. 
    Id. at 1251
    . In order to demonstrate this plain error, the
    defendant must demonstrate that: (1) there was error; (2) the error was plain; and (3)
    the error affected his substantial rights. United States v. Puentes-Hurtado, 
    794 F.3d 1278
    , 1285-86 (11th Cir. 2015) If these elements are satisfied, we may reverse the
    error only if it “seriously affect[s] the fairness, integrity, or public reputation of
    judicial proceedings.” 
    Id.
    Here, we conclude that the district court did not commit either clear error or
    plain error when it determined that there was a sufficient factual basis for
    Rodriguez’s guilty plea because the factual proffer provided sufficient evidence for
    the district court to reasonably find that Rodriguez was guilty of the charges in the
    superseding indictment.      See Rodriguez, 751 F.3d at 1255; see also Puentes-
    Hurtado, 794 F.3d at 1287 (holding that knowing participation in a conspiracy can
    be shown through proof of surrounding circumstances, such as acts committed by
    the defendant that furthered the purpose of the conspiracy). Accordingly, we affirm
    the district court’s acceptance of the guilty plea.
    3
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    II.
    Rodriguez argues that the district court erred when it denied his motion to
    withdraw his guilty plea because he had alleged sufficient facts to justify such a
    withdrawal.        Rodriguez argues that his change of plea was unknowing and
    involuntary because the government had used information in violation of Kastigar 1
    and his attorney had provided ineffective assistance of counsel.
    We review a district court’s denial of a request to withdraw a guilty plea for
    abuse of discretion. United States v. Freixas, 
    332 F.3d 1314
    , 1316 (11th Cir. 2003).
    “It is well settled, however, that there is no absolute right to withdraw a guilty plea
    prior to imposition of a sentence.” United States v. Buckles, 
    843 F.2d 469
    , 471 (11th
    Cir. 1988). The decision to grant a withdrawal is left to the sound discretion of the
    district court and we may only reverse if a denial was arbitrary or unreasonable. 
    Id.
    Under Rule 11, a defendant may withdraw his guilty plea if he can show a “fair and
    just reason” for requesting the withdrawal. Fed. R. Crim. P. 11(d)(2)(B).
    In determining whether a defendant has met his burden of showing a “fair and
    just reason” to withdraw his guilty plea, the district court may consider the totality
    of circumstances surrounding the plea, including: “(1) whether close assistance of
    counsel was available; (2) whether the plea was knowing and voluntary; (3) whether
    judicial resources would be conserved; and (4) whether the government would be
    1
    Kastigar v. United States, 
    406 U.S. 441
     (1972).
    4
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    prejudiced if the defendant were allowed to withdraw his plea.” Buckles, 
    843 F.2d at 471-72
     (internal citation omitted). If the first two factors weigh against a
    defendant, the district court need not give “considerable weight” or “particular
    attention” to the remaining factors. See United States v. Gonzalez-Mercado, 
    808 F.2d 796
    , 801 (11th Cir. 1987).
    When analyzing a challenge under Rule 11, there is a strong presumption that
    statements made during the plea colloquy are true. See United States v. Medlock, 
    12 F.3d 185
    , 187 (11th Cir. 1994). A defendant may not withdraw his guilty plea based
    on dissatisfaction with an anticipated sentence and we may consider the timing of a
    defendant’s motion to withdraw his guilty plea to determine the true motive for
    withdrawal. See Gonzalez-Mercado, 
    808 F.2d at 801
    .
    We will “not generally consider claims of ineffective assistance of counsel
    raised on direct appeal where the district court did not entertain the claim nor develop
    a factual record.” United States v. Bender, 
    290 F.3d 1279
    , 1284 (11th Cir. 2002);
    see also United States v. Souder, 
    782 F.2d 1534
    , 1539-40 (11th Cir. 1986) (stating
    that this issue must be raised by a collateral attack in district court, such as an action
    under 
    28 U.S.C. § 2255
    ). An exception exists in rare instances where the record is
    sufficiently developed to allow review on direct appeal. United States v. Tyndale,
    
    209 F.3d 1292
    , 1294 (11th Cir. 2000).
    5
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    As an initial matter, we will not consider any of Rodriguez’s claims of
    ineffective assistance of counsel because the record is not sufficiently developed to
    address this issue on direct appeal. See Bender, 
    290 F.3d at 1284
    . Here, the district
    court did not abuse its discretion when it denied Rodriguez’s motion to withdraw his
    guilty plea because Rodriguez failed to present a “fair and just reason” for the
    withdrawal of his guilty plea. See Buckles, 
    843 F.2d at 471-72
    . Moreover, the
    district court’s decision to deny the withdrawal of the guilty plea is neither arbitrary
    nor unreasonable. See 
    id.
     During the plea colloquy, Rodriguez swore under oath
    that he was satisfied with the representation and advice of his attorneys, that he had
    a full opportunity to discuss the charges, that it was his intention to plead guilty to
    all the charges, that he knew his sentence might be more severe than anticipated, and
    that he had reviewed and signed the factual proffer. Rodriguez’s claim that ADB-
    FUBINACA was not a controlled substance or controlled substance analogue is not
    supported by the record, as he conceded these facts in the factual proffer and the
    record evidence demonstrates that ADB-FUBINACA was added to the list of
    schedule I controlled substances on April 10, 2017, and before then, it was
    substantially similar to AB-FUBINACA, a controlled substance. Accordingly, we
    affirm the district court’s denial of the motion to withdraw the guilty plea.
    6
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    III.
    Rodriguez argues that the district court erred when it did not grant his motions
    for recusal because the recusal order from 1994 was still applicable and,
    alternatively, the same reasons for recusal in 1994 still exist in this case because
    Judge Ungaro served on the Southern District of Florida at the same time as Judge
    Highsmith.
    “Generally, a voluntary, unconditional guilty plea waives all nonjurisdictional
    defects in the proceedings.” United States v. Patti, 
    337 F.3d 1317
    , 1320 (11th Cir.
    2003). The denial of a motion for recusal pursuant to 
    28 U.S.C. § 455
    (a) is a “pretrial
    defect which is sublimated within a guilty plea” such that a defendant waives the
    right to appeal the denial when he has entered an unconditional guilty plea. 
    Id.
     at
    1322 Section 455(a) provides that: “Any justice, judge, or magistrate judge of the
    United States shall disqualify himself in any proceeding in which his impartiality
    might reasonably be questioned.” 
    28 U.S.C. § 455
    (a). When we review a § 455(a)
    motion, the standard “is whether an objective, disinterested, lay observer fully
    informed of the facts underlying the grounds on which recusal was sought would
    entertain a significant doubt about the judge’s impartiality . . . and any doubts must
    be resolved in favor of recusal.” Patti, 
    337 F.3d at 1322
     (internal quotation marks
    and citations omitted).
    7
    USCA11 Case: 19-12451       Date Filed: 08/25/2021   Page: 8 of 21
    Here, we conclude that the plain wording of the 1994 recusal order which
    Rodriguez seeks to enforce demonstrates that the order applied only to the
    proceeding for which it was issued. Moreover, Rodriguez waived any argument
    concerning his § 455(a) motion when he entered a voluntary and unconditional
    guilty plea in the district court. See Patti, 
    337 F.3d at 1320
    . Accordingly, we affirm
    the district court’s denial of the motions to recuse.
    IV.
    Rodriguez argues that the district court erred when it denied his motion to
    suppress evidence because the government learned of the location of the storage
    unit through a breach of attorney-client privilege and the government engaged in
    coercive behavior to procure consent from his attorney to search the storage unit.
    He also argues that the government lacked probable cause to search the storage
    unit and no exigent circumstances existed at the time of the search and seizure.
    Generally, the “district court’s denial of a motion to suppress is a mixed
    question of law and fact.” United States v. Barsoum, 
    763 F.3d 1321
    , 1328 (11th
    Cir. 2014). Accordingly, “we review a district court’s factual findings for clear
    error and review its application of law to the facts de novo.” 
    Id.
     However, a
    defendant waives the right to challenge a district court’s ruling on a motion to
    suppress after he enters an unconditional guilty plea. United States v. McCoy, 477
    8
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    21 F.2d 550
    , 551 (5th Cir. 1973); see also United States v. Charles, 
    757 F.3d 1222
    ,
    1227 n.4 (11th Cir. 2014).
    Here, Rodriguez waived the right to appeal the district court’s denial of his
    motion to suppress evidence when he entered a voluntary and unconditional guilty
    plea. See McCoy, 477 F.2d at 551. Accordingly, we affirm the district court’s
    denial of the motion to suppress.
    V.
    Rodriguez argues that the district court erred in applying the two-level
    enhancement under U.S.S.G. § 2D1.1(b)(15)(A) because the record clearly
    demonstrates that he did not maintain the storage facility for the purpose of
    manufacturing or distributing a controlled substance.
    We review for clear error a district court’s findings of fact which underlie its
    determination that a sentencing enhancement applies. United States v. Duperval,
    
    777 F.3d 1324
    , 1331 (11th Cir. 2015). Thus, we will review a district court’s
    determination of whether a defendant maintained a premises for the manufacture or
    distribution of drugs for clear error. United States v. George, 
    872 F.3d 1197
    , 1205
    (11th Cir. 2017). A district court’s factual finding is clearly erroneous when, after a
    review of the evidence, we are left with “a definite and firm conviction a mistake
    has been made.” United States v. Dimitrovski, 
    782 F.3d 622
    , 628 (11th Cir. 2015).
    9
    USCA11 Case: 19-12451      Date Filed: 08/25/2021   Page: 10 of 21
    Section 2D1.1(b)(12) of the 2016 Sentencing Guidelines provides that: “If the
    defendant maintained a premises for the purpose of manufacturing or distributing a
    controlled substance, increase by 2 levels.” U.S.S.G. § 2D1.1(b)(12) (2016). This
    two-level increase applies to a defendant “who knowingly maintains a premises . . .
    for the purpose of manufacturing or distributing a controlled substance, including
    storage of a controlled substance for the purpose of distribution.” Id. 2D1.1, cmt.
    n.17. When determining whether the defendant “maintained” the premises, courts
    should consider: (1) “whether the defendant held a possessory interest in (e.g.,
    owned or rented) the premises;” and (2) “the extent to which the defendant controlled
    access to, or activities at, the premises.” Id. The Sentencing Guidelines further
    provide that:
    Manufacturing or distributing a controlled substance need not be the
    sole purpose for which the premises was maintained, but must be one
    of the defendant’s primary or principal uses for the premises, rather
    than one of the defendant’s incidental or collateral uses for the
    premises. In making this determination, the court should consider
    how frequently the premises was used by the defendant for
    manufacturing or distributing a controlled substance and how
    frequently the premises was used by the defendant for lawful
    purposes.
    Id.
    Here, the district court did not clearly err when it determined that Rodriguez
    maintained the storage unit for the purpose of manufacturing or distributing a
    controlled substance because the government provided sufficient evidence to
    support a finding that one of the primary purposes of the storage unit was to store
    10
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    ADB-FUBINACA before distribution in the drug trafficking scheme. See U.S.S.G.
    § 2D1.1, cmt. n.17. Reviewing the evidence on the record, one is not left with a
    “definite and firm conviction a mistake has been made.” See Dimitrovski, 782 F.3d
    at 628.    Accordingly, we affirm the district court’s determination that the
    enhancement was applicable.
    VI.
    Rodriguez argues that the two-level enhancement under U.S.S.G. §
    2D1.1(b)(15)(A), for using friendship and affection to involve another individual in
    the illegal conspiracy, is inapplicable because the mere existence of a romantic
    relationship is insufficient to support the enhancement and there was no evidence
    that he actively played on Lucia Mendez’s (“Mendez”) affection or emotions to get
    her to participate in the drug scheme.
    We review for clear error a district court’s findings of fact which underlie its
    determination that a sentencing enhancement applies. Duperval, 777 F.3d at 1331.
    A district court’s factual finding is clearly erroneous when, after a review of the
    evidence, we are left with “a definite and firm conviction a mistake has been made.”
    Dimitrovski, 782 F.3d at 628. “The government bears the burden of establishing the
    facts necessary to support a sentencing enhancement by a preponderance of the
    evidence.” Id. The preponderance-of-the-evidence standard “simply requires the
    11
    USCA11 Case: 19-12451       Date Filed: 08/25/2021    Page: 12 of 21
    trier of fact to believe that the existence of a fact is more probable than its
    nonexistence.” United States v. Trainor, 
    376 F.3d 1325
    , 1331 (11th Cir. 2004).
    The 2016 Sentencing Guidelines provide for a two-level sentencing
    enhancement if a defendant received an adjustment under § 3B1.1 and:
    (A) (i) the defendant used fear, impulse, friendship, affection, or
    some combination thereof to involve another individual in the illegal
    purchase, sale, transport, or storage of controlled substances, (ii) the
    individual received little or no compensation from the illegal
    purchase, sale, transport, or storage of controlled substances, and (iii)
    the individual had minimal knowledge of the scope and structure of
    the enterprise[.]
    U.S.S.G. § 2D1.1(b)(15)(A).
    We afford substantial deference to the factfinder’s credibility determinations.
    United States v. Lewis, 
    674 F.3d 1298
    , 1303 (11th Cir. 2012). We will accept a
    district court’s credibility determination “unless it is contrary to the laws of nature,
    or is so inconsistent or improbable on its face that no reasonable factfinder could
    accept it.” United States v. Ramirez-Chilel, 
    289 F.3d 744
    , 749 (11th Cir. 2002).
    Here, the district court did not commit a clear error when it determined that
    Rodriguez used friendship and affection to involve Mendez in the drug trafficking
    conspiracy because there was sufficient evidence on the record to support the district
    court’s finding. Mendez testified that she had never been involved in any criminal
    activities before entering her relationship with Rodriguez and that she believed
    Rodriguez used their relationship and psychological manipulation to involve her in
    12
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    the conspiracy. Importantly, the district court also found Mendez’s testimony to be
    credible and without contradiction, and we will not overturn that determination
    because there is no evidence that this finding was so improbable that no reasonable
    factfinder could accept it. See Ramirez-Chilel, 
    289 F.3d at 749
    . Accordingly, we
    affirm the district court’s determination that the enhancement was applicable.
    VII.
    Rodriguez argues that the district court erred when it included the weight of
    the carrier medium in its calculation of the weight of the controlled substance
    because it leads to the absurd result of disproportionate sentences. He also argues
    that the district court failed to consider treating the carrier medium in this case in the
    same manner that the sentencing guidelines treat blotter paper when calculating the
    weight of LSD. Moreover, he argues that the carrier medium shouldn’t be included
    in the weight calculation because the heavy cardstock paper is inert, not a cutting
    agent, its weight can consistently be determined and separated from the drug, and it
    does not expand the amount of drug sold nor exasperate the actual substance.
    Unless otherwise specified, the weight of a controlled substance set forth in
    U.S.S.G. § 2D1.1(c) refers to the weight of any “mixture or substance” containing a
    detectable amount of the controlled substance. U.S.S.G. § 2D1.1(c)(A). Generally,
    the weight of a “mixture” or “substance” includes the carrier medium that contains
    the relevant controlled substance. United States v. Camacho, 
    261 F.3d 1071
    , 1073
    13
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    (11th Cir. 2001) (citing Chapman v. United States, 
    500 U.S. 453
    , 461-68 (1991)).
    The 2016 Sentencing Guidelines provide that a “[m]ixture or substance does not
    include materials that must be separated from the drug itself before the drug can be
    used.” U.S.S.G. § 2D1.1, cmt. n.1 (2016).
    Our precedent provides that, when calculating the weight of a “mixture or
    substance” containing a detectable amount of a controlled substance, we follow the
    market-oriented approach set forth in Chapman. Griffith v. United States, 
    871 F.3d 1321
    , 1335 (11th Cir. 2017) (citing Chapman, 
    500 U.S. at 461
    ). Thus, while
    unusable portions or waste products are not considered, “[t]he entire weight of drug
    mixtures which are usable in the chain of distribution should be considered in
    determining a defendant’s sentence.” 
    Id.
    Here, the district court did not commit a clear error by including the weight
    of the carrier medium when it calculated the weight of the controlled substance. The
    government provided evidence that the paper impregnated with ADB-FUBINACA,
    which was utilized in the drug trafficking operation, was either smoked or ingested
    by inmates to take the drug. Rodriguez provided no evidence that inmates or non-
    inmates could separate out the ADB-FUBINACA from the impregnated paper in
    order to take the drug. Following the market-oriented approach we have adopted,
    because the carrier paper was neither a waste product nor unusable and was used in
    the chain of distribution, the weight of the carrier paper should be included in the
    14
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    calculation of the weight of the ADB-FUBINACA in this case. See Griffith, 871
    F.3d at 1335. Accordingly, we affirm the district court’s inclusion of the carrier
    medium in the calculation of the drug weight.
    VIII.
    Rodriguez argues that the district court erred when it denied his Kastigar
    claims because the district court improperly credited the government agent’s
    testimony that he had discovered the allegedly defective evidence through
    independent means. We review a Kastigar claim deferentially and will affirm the
    district court’s decision unless it is clearly erroneous. United States v. Nyhuis, 
    8 F.3d 731
    , 741 (11th Cir. 1993). Under clear error review, we will affirm the district
    court’s decision “so long as it is plausible in light of the record reviewed in its
    entirety.” United States v. Ladson, 
    643 F.3d 1335
    , 1341 (11th Cir. 2011) (citation
    omitted). In Kastigar, the Supreme Court held that when the government wishes to
    prosecute a defendant who has given self-incriminating testimony under a grant of
    immunity, to avoid a Fifth Amendment violation, the prosecution is prohibited from
    “using the compelled testimony in any respect” that would “lead to the infliction of
    criminal penalties on the witness.” Kastigar v. United States, 
    406 U.S. 441
    , 453
    (1972). When we are presented with a Kastigar claim, we must “determine whether
    any of the evidence used against the defendant was in any way derived from his
    compelled immunized testimony.” United States v. Hill, 
    643 F.3d 807
    , 877 (11th
    15
    USCA11 Case: 19-12451       Date Filed: 08/25/2021    Page: 16 of 21
    Cir. 2011) Moreover, the government bears the burden of demonstrating that all of
    the evidence it obtained and used against the defendant was untainted by immunized
    testimony. 
    Id.
    Here, we conclude that the district court’s decision that there was no Kastigar
    violation was not clearly erroneous because the government provided sufficient
    evidence that it obtained the allegedly tainted evidence through independent means.
    See Hill, 
    643 F.3d at 877
    . Because the district court’s decision is plausible in light
    of the record, we will not reverse. See Ladson, 
    643 F.3d at 1341
    . Accordingly, we
    affirm the district court’s determination that there was no Kastigar violation.
    IX.
    Rodriguez argues that the district court committed a clear and plain error
    because it randomly decided what to include in the drug amount and engaged in
    gross speculation and improper guess work when it determined that he was
    responsible for more than 1,000 kilograms of marijuana.
    We review a district court’s calculation of drug quantity for clear error.
    United States v. Rodriguez, 
    398 F.3d 1291
    , 1296 (11th Cir. 2005). Thus, we will
    only disturb the district court’s quantity approximation if we are left with a “definite
    and firm conviction that a mistake has been committed.” United States v. Almedina,
    
    686 F.3d 1312
    , 1315 (11th Cir. 2012). We have held that if the amount of drugs
    seized does not reflect the scale of the offense, the district court must approximate
    16
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    the drug quantity attributable to the defendant. United States v. Dixon, 
    901 F.3d 1322
    , 1349 (11th Cir. 2018). “In estimating the quantity, the trial court may rely on
    evidence demonstrating the average frequency and amount of a defendant’s drug
    sales over a given period of time.” United States v. Reeves, 
    742 F.3d 487
    , 506 (11th
    Cir. 2014). “This determination may be based on fair, accurate, and conservative
    estimates of the drug quantity attributable to a defendant, but it cannot be based on
    calculations of drug quantities that are merely speculative.” 
    Id.
     (alteration adopted)
    (quoting Almedina, 686 F.3d at 1316).
    Here, the district court did not clearly err when it calculated the amount of
    drugs that were attributable to Rodriguez for purposes of sentencing. Because the
    government had only seized a portion of the mailed packages that constituted the
    drug trafficking operation, the district court had to approximate the drug quantity
    attributable to Rodriguez. See Dixon, 901 F.3d at 1349. Moreover, the district court
    was permitted to rely on evidence that demonstrated the average frequency and
    amount of packages and drugs that Rodriguez distributed from October 2016 to
    February 9, 2018. See Reeves, 742 F.3d at 506.
    Reviewing the district court’s calculation determination, we are not left with
    a definite and firm conviction that a mistake was committed. See Almedina, 686
    F.3d at 1315. The calculation was based on using the average weight of intercepted
    packages and extrapolating that average to unseized packages that were verified.
    17
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    Additionally, the district court’s assumption that less than 15% of the unseized
    Barnes & Noble packages contained ADB-FUBINACA appears to be a fair and
    conservative estimate of the drug quantity.          See Reeves, 742 F.3d at 506.
    Accordingly, we affirm the district court’s calculation of the drug amount
    attributable to Rodriquez.
    X.
    Rodriguez argues that the district court abused its discretion when it issued an
    order which prohibited both parties from filing motions because that blanket
    prohibition kept him from being able to present a full defense. Moreover, the
    prohibition undermined the fairness and integrity of the proceedings.
    When a defendant fails to object to an error before the district court, we review
    the argument for plain error. United States v. Hall, 
    314 F.3d 565
    , 566 (11th Cir.
    2002). Under this standard of review, the appellant must prove: (1) an error
    occurred; (2) the error was plain; and (3) the error affected substantial rights. United
    States v. DiFalco, 
    837 F.3d 1207
    , 1221 (11th Cir. 2016) (“An error is plain where it
    is ‘clear’ or ‘obvious.’”). If these three conditions are satisfied, we can only notice
    the forfeited error if “the error seriously affects the fairness, integrity, or public
    reputation of judicial proceedings.” 
    Id. at 1221
     (citation omitted). “The plain error
    test is ‘difficult to meet’ and places ‘a daunting obstacle before the appellant,’” such
    that we should only notice a forfeited error “in those circumstances in which a
    18
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    miscarriage of justice would otherwise result.”        
    Id.
     (citations omitted).   The
    defendant bears the burden of establishing that the plain error prejudiced him by
    affecting his substantial rights. United States v. Brown, 
    586 F.3d 1342
    , 1345 (11th
    Cir. 2009). To establish prejudice on plain error review, the defendant must show
    there is a reasonable probability that, but for the error, a different outcome would
    have occurred; and a reasonable probability is a probability “sufficient to undermine
    confidence in the outcome.” United States v. Garcia, 
    906 F.3d 1255
    , 1267 (11th
    Cir. 2018)
    District courts possess broad discretion to manage their dockets. United
    States v. McCutcheon, 
    86 F.3d 187
    , 190 (11th Cir. 1996). A defendant must show
    prejudice to establish that the district court abused this discretion. See 
    id.
     However,
    this Court will not reverse an alleged constitutional error which is ultimately
    harmless. United States v. Roy, 
    855 F.3d 1133
    , 1167-68 (11th Cir. 2017).
    Here, the district court did not commit a plain error by issuing the order which
    limited the filing of motions by both parties because, even if we were to assume that
    the district court committed a plain error, Rodriguez cannot demonstrate that the
    error affected a substantial right or that the error seriously affected the fairness,
    integrity, or public reputation of judicial proceedings. See DiFalco, 837 F.3d at
    1221-22. Rodriguez filed over 30 motions between the issuance of the order and the
    imposition of his sentence and the district court granted or denied many of these
    19
    USCA11 Case: 19-12451     Date Filed: 08/25/2021    Page: 20 of 21
    motions on the merits.      Furthermore, only four of Rodriguez’s motions were
    stricken, based on filing defects. Thus, Rodriguez cannot demonstrate that he
    suffered any harm or prejudice from the district court’s order, nor can he show that
    there was a reasonable possibility that if the order had not been issued that the
    outcome of this proceeding would have been altered. See Garcia, 906 F.3d at 1267.
    Accordingly, we find that the district court did not commit a reversible error.
    XI.
    Rodriguez argues that the district court clearly erred when it adopted the 1:167
    ratio for tetrahydrocannabinol (“THC”) to convert the weight of ADB-FUBINACA
    to an equivalent weight of marijuana because ADB-FUBINACA is not substantially
    similar to THC.
    Because the identification of the “most closely related substance” is a finding
    of fact, we review the district court’s determination for clear error. See Duperval,
    
    777 F.3d 1331
    . When determining the most closely related substance under the
    Guidelines, the district court must consider “to the extent practicable,” the following
    factors:
    (A) Whether the controlled substance not referenced in this guideline
    has a chemical structure that is substantially similar to a controlled
    substance referenced in this guideline.
    (B) Whether the controlled substance not referenced in this guideline
    has a stimulant, depressant, or hallucinogenic effect on the central
    nervous system that is substantially similar to the stimulant,
    20
    USCA11 Case: 19-12451      Date Filed: 08/25/2021   Page: 21 of 21
    depressant, or hallucinogenic effect on the central nervous system of a
    controlled substance referenced in this guideline.
    (C) Whether a lesser or greater quantity of the controlled substance
    not referenced in this guideline is needed to produce a substantially
    similar effect on the central nervous system as a controlled substance
    referenced in this guideline.
    U.S.S.G. § 2D1.1, cmt. n.6 (2016). Under U.S.S.G § 2D1.1, THC is converted to an
    equivalent weight of marijuana using a 1:167 ratio. Id. cmt. n.8(D).
    Here, we conclude that the district court did not commit clear error by
    determining that ADB-FUBINACA was most closely related to THC and that the
    corresponding 1:167 ratio should be utilized. The district court’s determination is
    sufficiently supported by expert testimony and evidence. Furthermore, the evidence
    provided by Rodriguez does not establish that the district court committed a clear
    error but merely provides a plausible alternate finding.        See United States v.
    Saingerard, 
    621 F.3d 1341
    , 1343 (11th Cir. 2010) (“Where there are two permissible
    views of the evidence, the factfinder’s choice between them cannot be clearly
    erroneous.”). Accordingly, we affirm the district court’s determination that ADB-
    FUBINACA is most closely related to THC and its adoption of the 1:167 conversion
    ratio.
    AFFIRMED.
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