Court Opinion

ID: 9399932
Source: CourtListenerOpinion
Date Created: 2023-06-06 19:01:10.57776+00
Date Added: 2024-06-11T17:19:40.921562
License: Public Domain

USCA11 Case: 20-12907     Document: 77-1      Date Filed: 06/06/2023   Page: 1 of 40

                                                              [PUBLISH]
                                     In the
                 United States Court of Appeals
                          For the Eleventh Circuit

                           ____________________

                                  No. 20-12907
                           ____________________

        UNITED STATES OF AMERICA,
                                                        Plaintiﬀ-Appellee,
        versus
        CLIFFORD LAINES, JR.,

                                                     Defendant-Appellant.

                           ____________________

                  Appeals from the United States District Court
                      for the Southern District of Florida
                     D.C. Docket No. 1:18-cr-20980-CMA-1
                            ____________________

                           ____________________
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        2                     Opinion of the Court                 20-12907

                                   No. 21-11535
                            ____________________

        UNITED STATES OF AMERICA,
                                                         Plaintiﬀ-Appellee,
        versus
        CLIFFORD LAINES, JR.,

                                                     Defendant-Appellant.

                            ____________________

                  Appeals from the United States District Court
                      for the Southern District of Florida
                     D.C. Docket No. 1:18-cr-20980-CMA-1
                            ____________________

        Before WILLIAM PRYOR, Chief Judge, and ROSENBAUM and MARCUS,
        Circuit Judges.
        WILLIAM PRYOR, Chief Judge:
               In this appeal, Cliﬀord Laines challenges his drug- and ﬁre-
        arm-related convictions as well as his sentence under the Armed
        Career Criminal Act. Laines argues that insuﬃcient evidence sup-
        ports two of his convictions and that he is entitled to a new trial
        based on Brady v. Maryland, 373 U.S. 83 (1963), and Giglio v. United
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        20-12907               Opinion of the Court                         3

        States, 405 U.S. 150 (1972). But suﬃcient evidence supports Laines’s
        convictions. He has also not established that it is reasonably proba-
        ble that a new trial would result in a diﬀerent outcome as required
        by Brady, nor has he provided any evidence of perjured testimony
        as required by Giglio. Finally, Laines argues for the ﬁrst time on ap-
        peal that the district court erroneously sentenced him because his
        earlier cocaine conviction under Florida law does not constitute a
        serious drug oﬀense under the Armed Career Criminal Act. But the
        district court did not plainly err in sentencing him. We aﬃrm
        Laines’s convictions and sentence.

                                I. BACKGROUND
               Cliﬀord Laines was released from prison in September 2018
        after serving more than 25 years as punishment for second-degree
        murder. He was later arrested on October 7, 2018, and November
        4, 2019. This appeal concerns convictions that arose from these ar-
        rests.
               On October 7, 2018, police oﬃcers conducted a traﬃc stop
        on a vehicle in which Laines was a passenger. When the vehicle
        came to a stop, Laines exited and began walking away. One of the
        police oﬃcers noticed a bulge in Laines’s waistband and ordered
        him to stop walking. The oﬃcer caught up with Laines, patted him
        down, and removed a loaded gun with an extended magazine from
        his waistband. Laines was arrested, indicted for being a felon in pos-
        session of a ﬁrearm, and released on bond.
              On November 4, 2019, three police oﬃcers—Jordy Yanes-
        Martel, Carlos Romero, and Bryan Blanco—were at a gas station.
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        4                      Opinion of the Court                 20-12907

        Oﬃcer Yanes-Martel noticed Laines riding a purple bicycle and car-
        rying a bag. Oﬃcer Yanes-Martel recalled a “be on the lookout”
        order recently issued for a person matching Laines’s description, so
        he alerted his fellow oﬃcers. When Oﬃcer Romero ordered Laines
        to stop, Laines ﬂed.
                The oﬃcers gave chase, two on foot and one in a patrol car.
        Oﬃcer Blanco, who pursued by car, caught up with Laines ﬁrst and
        tased him to prevent him from jumping over a residential fence.
        When the oﬃcers searched Laines, they found a gun and a “sub-
        stantial amount of drugs” in his backpack. The drugs included ma-
        rijuana, heroin, and cocaine, as well as substances that could be
        used to dilute or counterfeit those drugs. The drugs were primarily
        contained in small plastic bags or plastic wrap inside of a mason jar.
        Laines was carrying $244 in cash in varying denominations. He also
        carried a two-dollar bill in the mason jar, which drug dealers some-
        times carry for good luck. A grand jury charged Laines with ﬁve
        counts arising from his possession of a ﬁrearm and possession of
        illegal drugs with the intent to distribute them.
               At trial, Laines objected that a prosecution witness imper-
        missibly testiﬁed to the ultimate issue of whether he intended the
        drugs he possessed for personal use or distribution. See FED. R.
        EVID. 704(b). While examining expert witness Shaun Perry, an
        agent for the federal Drug Enforcement Administration, the pros-
        ecutor referred to a photograph of the packages of drugs found in
        Laines’s bag. The prosecutor asked the witness “whether or not
        [the drugs] would be for personal use or for distribution, based on
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        20-12907               Opinion of the Court                         5

        [his] training and experience[.]” Agent Perry replied, “This is deﬁ-
        nitely for distribution. This wouldn’t be consistent with someone
        just using it for personal use.”
               After the defense moved to strike the testimony, the district
        court instructed the jury to disregard it. Later, Laines moved under
        Rule 29 for a judgment of acquittal as to counts four and ﬁve on
        the ground that, without Agent Perry’s stricken testimony, there
        was no evidence that Laines had the intention to distribute the
        drugs. The prosecution responded by describing other evidence
        that could support a ﬁnding of intent. The district court denied the
        motion.
               After cross-examining Oﬃcer Blanco, Laines’s attorneys
        stated that they learned for the ﬁrst time that he had searched
        Laines’s cell phone at the police station after Laines was arrested in
        November 2019. Blanco testiﬁed that after Laines had refused to
        identify himself to the police and the oﬃcers found no identiﬁca-
        tion on his person, Blanco searched the phone for evidence of
        Laines’s identity. Oﬃcer Blanco further explained that the cell
        phone was unlocked but that he did not have permission from
        Laines or a warrant to conduct a search. Blanco testiﬁed that he
        looked at the phone for “[j]ust a few seconds.” He opened the
        photo gallery application in search of “[a]nything that might have
        [Laines’s] name on it” and found a photo of Laines’s Florida iden-
        tiﬁcation card. Oﬃcer Blanco testiﬁed that he did not remember if
        he had searched texts, email, call history, or social media. He testi-
        ﬁed that he did not look for any information about individuals
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        6                      Opinion of the Court                20-12907

        relevant to the investigation or “[a]nything related to” guns or drug
        sales. He did not recall whether he had seen any photographs of
        drugs or guns. Contrary to Blanco’s testimony that he was alone,
        Oﬃcer Romero testiﬁed that he had been present during the phone
        search, but he did not recall whether any application other than the
        photo gallery was searched.
                Defense counsel moved for a mistrial. She argued that the
        search of a cell phone “needs to be disclosed to the defense,” espe-
        cially because the defense had “asked the Government, at the[] dis-
        covery conference . . . if the cell phone had been searched or
        viewed and was told no.” Initially, the prosecutors responded that
        they had no previous knowledge of the search, but two days later
        they admitted that the prosecutor ﬁrst assigned to the case had
        been aware. The prosecution did not deny that the search was “im-
        proper” but maintained that “there ha[d] been no evidence that
        ha[d] come out at trial that was as a result of [Oﬃcer Blanco] look-
        ing into the phone.” The district court denied the motion for a mis-
        trial.
               The jury convicted Laines of being a felon in possession of
        a ﬁrearm and ammunition on October 7, 2018, 18 U.S.C.
        § 922(g)(1); being a felon in possession of a ﬁrearm and ammuni-
        tion on November 4, 2019, id.; knowingly possessing cocaine or
        heroin with intent to distribute on November 4, 2019, 21 U.S.C.
        § 841(a)(1); and knowingly possessing a ﬁrearm in furtherance of a
        drug traﬃcking oﬀense on November 4, 2019, 18 U.S.C.
        § 924(c)(1)(A)(i). Laines was acquitted of a charge for being a felon
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        20-12907               Opinion of the Court                        7

        in possession of a ﬁrearm and ammunition on a separate occasion.
        The probation oﬃce recommended that Laines be sentenced as an
        armed career criminal based on his prior convictions for possession
        of cocaine with intent to sell, resisting arrest with violence, and
        second-degree murder. See 18 U.S.C. § 924(e)(1). Laines did not ob-
        ject to either the facts of his prior convictions or his status as an
        armed career criminal. The district court sentenced Laines to 300
        months of imprisonment followed by ﬁve years of supervised re-
        lease.
                Before he was sentenced, Laines moved for a new trial on
        the counts arising from his November 2019 arrest on the ground
        that the police had unconstitutionally searched his phone. Laines
        further argued that the government was obligated to disclose the
        illegal search and disclose that the search did not reveal any evi-
        dence of drug traﬃcking because this information could be used
        for exculpatory and impeachment purposes. The district court de-
        nied the motion.
               Laines later moved again for a new trial on the counts that
        arose from the November 2019 arrest because Oﬃcer Yanes-Mar-
        tel—one of the oﬃcers who arrested Laines and served as a witness
        for the prosecution—had allegedly committed misconduct and was
        the subject of internal investigations. Laines listed three incidents
        of misconduct by Oﬃcer Yanes-Martel, occurring on January 14,
        February 3, and March 22, 2020. In January, Yanes-Martel allegedly
        “used excessive force while making an illegal arrest and subse-
        quently falsiﬁed information in police reports.” In February, Yanes-
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        8                      Opinion of the Court                  20-12907

        Martel allegedly “failed to follow procedure regarding body worn
        cameras and pat-downs of an arrestee.” In March, Yanes-Martel al-
        legedly used excessive force when he “str[uck] an arrestee twice in
        the head with his elbow.” Two of these incidents took place before
        Laines’s trial, and the third took place between his trial and sentenc-
        ing. An investigation into one of these incidents also began before
        trial, and two other investigations were opened between trial and
        sentencing.
                The government contends that it was unaware of the allega-
        tions before trial and that it had been informed of only one investi-
        gation before sentencing. Prosecutors initially interviewed Oﬃcer
        Yanes-Martel in November 2019, shortly before the trial was origi-
        nally scheduled to take place and before any of the incidents had
        occurred. According to the prosecution, in February 2020, the trial
        team requested information about any charges or investigations
        concerning Yanes-Martel from his police department, which did
        not respond until March 17, 2020—after trial. And that response,
        the government tells us, “indicated only a pending disciplinary mat-
        ter related to” the February incident. The government further con-
        tends that the trial team was not even aware of the police depart-
        ment’s response until Laines requested information respecting the
        alleged misconduct.
               Laines asserts that he learned about these investigations only
        after he had ﬁled his appeal. For this reason, he styled his second
        motion for a new trial as a request for an indicative ruling that
        would inform this Court that the district court “would grant Mr.
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        20-12907                Opinion of the Court                          9

        Laines’ Second Motion for a New Trial if the Court of Appeals
        were to remand . . . for that purpose.” (Citing FED. R. CRIM. P. 37.)
        The district court denied the motion. It found that “the Govern-
        ment’s case against [Laines] rested on overwhelming evidence—in-
        cluding recordings from oﬃcers’ body worn cameras—independ-
        ent of ” Yanes-Martel’s testimony.

                          II. STANDARDS OF REVIEW

               Three standards govern our review. “We review both a chal-
        lenge to the suﬃciency of the evidence and the denial of a Rule 29
        motion for judgment of acquittal de novo.” United States v. Gamory,
        635 F.3d 480, 497 (11th Cir. 2011). “We view the evidence in the
        light most favorable to the government, making all reasonable in-
        ferences and credibility choices in the government’s favor, and then
        determine whether a reasonable jury could have found the defend-
        ant guilty beyond a reasonable doubt.” Id. (alteration adopted) (ci-
        tation and internal quotation marks omitted). “A jury’s verdict can-
        not be overturned if any reasonable construction of the evidence
        would have allowed the jury to ﬁnd the defendant guilty beyond a
        reasonable doubt.” United States v. Capers, 708 F.3d 1286, 1297 (11th
        Cir. 2013) (quoting United States v. Herrera, 931 F.2d 761, 762 (11th
        Cir. 1991)). “[W]e review an alleged Brady-Giglio violation de novo
        and the denial of a motion for a new trial for an abuse of discre-
        tion.” United States v. Gallardo, 977 F.3d 1126, 1142 n.12 (11th Cir.
        2020). Finally, although we review de novo “whether a conviction
        qualiﬁes as a serious drug oﬀense under the [Armed Career Crimi-
        nal Act],” United States v. White, 837 F.3d 1225, 1228 (11th Cir. 2016),
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        10                      Opinion of the Court                   20-12907

        we review issues raised for the ﬁrst time on appeal for plain error,
        United States v. Bennett, 472 F.3d 825, 831 (11th Cir. 2006). “This
        standard requires that there be error, that the error be plain, and
        that the error aﬀect a substantial right.” Id. An error is “plain” if “it
        is ‘obvious’ or ‘clear under current law.’” United States v. Candelario,
        240 F.3d 1300, 1309 (11th Cir. 2001) (citation omitted). Only then
        may we “exercise our discretion to notice the forfeited error if the
        error seriously aﬀects the fairness, integrity, or public reputation of
        judicial proceedings.” Bennett, 472 F.3d at 832.
                                  III. DISCUSSION
                We divide our discussion into four parts. First, we explain
        that the record contains suﬃcient evidence to support Laines’s
        drug-related convictions. Second, we explain that Laines is not en-
        titled to a new trial based on an alleged Brady or Giglio violation.
        Third, we explain that the district court did not plainly err in ruling
        that Laines’s prior cocaine conviction qualiﬁed as a “serious drug
        oﬀense.” Finally, we explain that Laines’s advisory sentencing
        guideline range was not erroneously enhanced.
               A. Suﬃcient Evidence Supports Laines’s Drug Convictions.
               Laines appeals the denial of his motion for acquittal on the
        drug-related charges due to insuﬃciency of the evidence. See FED.
        R. CRIM. P. 29(a). Laines’s drug-related convictions required proof
        beyond a reasonable doubt that Laines intended to distribute the
        drugs he possessed. See 21 U.S.C. § 841(a)(1) (providing that it is
        “unlawful for any person knowingly or intentionally . . . to . . . pos-
        sess with intent to manufacture, distribute, or dispense, a controlled
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        20-12907                Opinion of the Court                          11

        substance” (emphasis added)); 18 U.S.C. § 924(c)(l)(A) (providing
        that “any person who, during and in relation to any . . . drug traf-
        ﬁcking crime . . . uses or carries a ﬁrearm, or who, in furtherance of
        any such crime, possesses a ﬁrearm, shall” be punished (emphasis
        added)); see also Cintron v. U.S. Att’y Gen., 882 F.3d 1380, 1383 (11th
        Cir. 2018) (explaining that, in general, “simple possession is not
        punishable as a felony under the [Controlled Substances Act], so it
        is not a drug trafficking crime” within the meaning of section 924).
        Laines argues that the only evidence of intent to distribute or en-
        gage in drug traﬃcking was the “inadmissible testimony of Agent
        Perry,” which the district court instructed the jury to disregard. We
        disagree.
               Suﬃcient evidence supports Laines’s drug-related convic-
        tions. We have explained that “[i]ntent to distribute can be proven
        circumstantially.” United States v. Poole, 878 F.2d 1389, 1392 (11th Cir.
        1989). For example, “the quantity” of the drug and “the existence
        of implements such as scales commonly used in . . . distribution”
        may constitute circumstantial evidence of such intent. Id.; see also
        United States v. Mercer, 541 F.3d 1070, 1076 (11th Cir. 2008) (explain-
        ing that “the jury could infer intent to distribute” from “a large
        number of plastic jeweler’s bags, [a] ‘drug ledger,’ the amount of
        [the drug], the lack of paraphernalia used to consume the drug,
        and testimony about [the] Defendant’s purchase of [drugs]” (foot-
        notes omitted)). The jury heard evidence that Laines’s possession
        of substances that could be used to dilute or “counterfeit” drugs,
        the division of drugs into small bags, the large quantity of small-
        denomination cash, the backpack as a method of conveyance, the
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        12                      Opinion of the Court                  20-12907

        type of gun Laines possessed, and the two-dollar bill he carried
        with the drugs were all consistent with drug sales. On this record,
        we cannot say that “there is no reasonable construction of the evi-
        dence from which the jury could have found the defendant guilty
        beyond a reasonable doubt.” United States v. Ifediba, 46 F.4th 1225,
        1242 (11th Cir. 2022) (citation and internal quotation marks omit-
        ted).
                Ordinarily, when the district court instructs the jury to dis-
        regard inadmissible testimony as it did here, “the error is cured.”
        United States v. Benz, 740 F.2d 903, 916 (11th Cir. 1984). In his reply
        brief, Laines also argues that Agent Perry’s testimony was not only
        inadmissible but was also so prejudicial that it rendered the error
        incurable. See id. Because Laines failed to argue in his initial brief
        that the error was incurable, that issue is forfeited. Miccosukee Tribe
        of Indians of Fla. v. Cypress, 814 F.3d 1202, 1210 (11th Cir. 2015).
             B. Laines Is Not Entitled to a New Trial Under Brady or Giglio.
                Laines twice moved for a new trial, but the district court de-
        nied both motions. First, he moved for a new trial under Brady
        based on the revelation at trial that the police unconstitutionally
        searched Laines’s phone after his 2019 arrest. Second, Laines
        moved for a new trial under Brady and Giglio based on his discovery,
        after this appeal was noticed, that an arresting oﬃcer and prosecu-
        tion witness was the subject of internal investigations. Laines ap-
        peals the denial of those motions.
              Under Brady v. Maryland, a court should grant a new trial if
        the prosecution suppresses favorable evidence that is material to
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        20-12907                Opinion of the Court                         13

        the defendant’s guilt or punishment and that creates a “reasonable
        probability” of a diﬀerent trial outcome. United States v. Vallejo, 297
        F.3d 1154, 1164 (11th Cir. 2002); see Brady, 373 U.S. at 87. The de-
        fendant must also establish that he did “not possess the evidence
        and could not obtain the evidence with any reasonable diligence.”
        Vallejo, 297 F.3d at 1164. And the Supreme Court explained in Giglio
        v. United States that the due process rights articulated in Brady are
        also violated when “undisclosed evidence” establishes that the
        prosecution knowingly relied on perjured and material testimony.
        Davis v. Terry, 465 F.3d 1249, 1253 (11th Cir. 2006) (citation omitted);
        see Giglio, 405 U.S. at 154–55.
        1. No Brady Violation Occurred Regarding the Cell Phone Search.
               Laines asserts that he is entitled to a new trial on the charges
        that arose from his November 2019 arrest under Brady because the
        prosecution failed to disclose in advance of trial that his cell phone
        had been searched by the police after that arrest. He argues that,
        had the search been revealed before trial, his trial strategy would
        have changed in two ways: he would have argued that a lack of ev-
        idence of drug traﬃcking on his phone weighed against a ﬁnding
        of guilt, and he would have used the evidence of the illegal search
        to impeach Oﬃcer Blanco. But Laines’s arguments fail to establish
        that he is entitled to a new trial.
               Laines cannot establish that the evidence from his phone
        was suﬃciently favorable to create a reasonable probability of a dif-
        ferent result. Laines argues that “[t]he evidence is favorable . . . be-
        cause the absence of evidence of drug traﬃcking in the phone is
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        14                     Opinion of the Court                 20-12907

        exculpatory.” He asserts that “if the defense had known about the
        search of the cell phone prior to trial, Mr. Laines would have called
        his own expert to testify about the absence of the evidence in the
        cell phone.” But Laines oﬀers no support for the proposition that
        the phone contained no evidence of drug traﬃcking. As the district
        court explained, “no one testiﬁed regarding the absence of evidence
        of drug traﬃcking on [Laines’s] phone.” (Emphasis added.) Testi-
        mony that one or two police oﬃcers brieﬂy glanced at the phone
        and did not happen to notice any evidence of drug traﬃcking
        proves little. So Laines cannot establish that “there is a reasonable
        probability” that a diﬀerent outcome would have resulted as re-
        quired under Brady. See Vallejo, 297 F.3d at 1164.
               Even if the evidence were exculpatory, Laines also cannot
        establish that he could not have obtained the evidence with reason-
        able diligence. Laines asserts that he took the only reasonably dili-
        gent step he could when defense counsel asked the prosecution
        “whether law enforcement searched the phone.” But, as the district
        court explained, we “can presume that [Laines] knows the contents
        of his own cell phone.” Laines could have examined the phone dur-
        ing discovery and made this argument at trial even though he was
        unaware beforehand that the police had brieﬂy searched the phone
        after his arrest. So, he could have learned of the evidence with “rea-
        sonable diligence,” id., before trial.
               Finally, Laines cannot establish that he lacked an oppor-
        tunity to impeach Oﬃcer Blanco based on the illegal search of his
        phone. Laines contends that, because he learned of the search at
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        20-12907               Opinion of the Court                         15

        trial, he did not have “the time to fully prepare to use the impeach-
        ment evidence.” But we have recognized that a defendant can “re-
        ceive[] . . . information during the trial” and still “fail[] to demon-
        strate that the disclosure came so late that it could not be eﬀectively
        used.” United States v. Knight, 867 F.2d 1285, 1289 (11th Cir. 1989).
        In an extensive line of questioning before the jury, defense counsel
        impeached Oﬃcer Blanco for conducting a search that violated the
        police department’s policy—a policy “based on” the Constitution.
        And Laines’s conviction does not hinge on Oﬃcer Blanco’s credi-
        bility because Blanco’s testimony was corroborated by that of the
        other oﬃcers and by body camera footage, as we explain later in
        this opinion. So Laines has not established “a reasonable probabil-
        ity that the outcome would have been diﬀerent” had the evidence
        been disclosed. See Vallejo, 297 F.3d at 1164.

         2. No Brady or Giglio Violation Occurred Regarding the Witness
                        Subject to Internal Investigations.

                Laines argues that he is entitled to a new trial under Brady
        and Giglio because Oﬃcer Yanes-Martel—one of the oﬃcers who
        arrested him in 2019 and served as a witness for the government—
        was the subject of three internal investigations for misconduct. The
        district court denied Laines’s motion for a new trial on this basis. It
        found that “the Government’s case against [Laines] rested on over-
        whelming evidence,” independent of Yanes-Martel’s testimony.

             We agree that Laines’s argument fails. Under Giglio, Laines
        would have to prove “that the prosecution’s case included perjured
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        16                      Opinion of the Court                  20-12907

        testimony.” Davis, 465 F.3d at 1253 (citation omitted). He has not
        done so. He also cannot satisfy Brady’s materiality requirement in
        this circumstance.

                Laines contends that the misconduct undermines Oﬃcer Ya-
        nes-Martel’s credibility and, by extension, “undermines the legal
        basis for the stop” in November 2019. Laines suggests that he
        would have argued that the initial stop was illegal, so the resulting
        arrest and search were constitutionally inﬁrm. See United States v.
        Jones, 619 F.2d 494, 498 (5th Cir. 1980); Wong Sun v. United States, 371
        U.S. 471, 484 (1963). But even if Laines could have proved that the
        stop was illegal—which we have no reason to believe he could have
        done—such evidence is not “material either to guilt or to punish-
        ment” as required under Brady. Brady, 373 U.S. at 87; see also Smith
        v. Sec’y, Dep’t of Corr., 572 F.3d 1327, 1342 n.9 (11th Cir. 2009) (ex-
        pressing doubt “that Brady applies outside the realm of exculpatory
        evidence and extends to evidence useful to the defense in a fruit-of-
        the-poisonous-tree quest”).

               Laines also argues that the misconduct undermines Yanes-
        Martel’s testimony across the board, but the corroborating evi-
        dence would be suﬃcient to support the jury’s guilty verdict even
        if Oﬃcer Yanes-Martel had been totally discredited. The other of-
        ﬁcers’ testimony tracked that of Oﬃcer Yanes-Martel. Oﬃcers
        Blanco and Romero testiﬁed that Laines was riding a purple bicy-
        cle, that Oﬃcer Yanes-Martel identiﬁed him based on the descrip-
        tion in an alert, and that Laines ﬂed when ordered to stop. Oﬃcer
        Blanco further testiﬁed that he pursued Laines and that he found a
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        20-12907                Opinion of the Court                         17

        gun and drugs on Laines’s person. Forensic analysis, expert testi-
        mony, and body camera footage provide further support. So Laines
        has not established “a reasonable probability that the outcome [of
        his trial] would have been diﬀerent” had the information about Of-
        ﬁcer Yanes-Martel’s misconduct been revealed before trial. Vallejo,
        297 F.3d at 1164.
         C. The District Court Did Not Commit Plain Error When It Classiﬁed
         Laines’s Prior Conviction Under Section 893.13(1)(a)(1) of the Florida
                         Statutes as a “Serious Drug Oﬀense.”
               Under the Armed Career Criminal Act, if a defendant con-
        victed of being a felon in possession of a ﬁrearm under section
        922(g) “has three previous convictions . . . for a violent felony or a
        serious drug oﬀense,” a mandatory minimum sentence of 15 years
        applies. 18 U.S.C. § 924(e)(1). A “serious drug oﬀense” includes “an
        oﬀense under State law, involving manufacturing, distributing, or
        possessing with intent to manufacture or distribute, a controlled
        substance . . . [as deﬁned in 21 U.S.C. section 802], for which a max-
        imum term of imprisonment of ten years or more is prescribed by
        law.” Id. § 924(e)(2)(A)(ii). “To determine whether a defendant’s
        prior conviction qualiﬁes as a predicate oﬀense for a sentencing en-
        hancement, federal courts generally apply the ‘categorical ap-
        proach,’ meaning we look only to the elements of the statute under
        which the defendant was convicted and not at the facts underlying
        the prior conviction.” United States v. Kushmaul, 984 F.3d 1359, 1364
        (11th Cir. 2021). “[W]e presume that the prior conviction rested
        upon nothing more than the least of the acts criminalized or the
        least culpable conduct.” Id. (citation and internal quotation marks
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        18                      Opinion of the Court                  20-12907

        omitted). That is, the least culpable conduct prohibited under the
        state law must qualify as a predicate oﬀense, and all the controlled
        substances covered by the state law must also be controlled sub-
        stances under federal law.
                Laines’s status as an armed career criminal is based on three
        earlier convictions, but—for the ﬁrst time on appeal—he contests
        whether only one of them constitutes “a violent felony or a serious
        drug oﬀense,” see 18 U.S.C. § 924(e)(1), his conviction for a drug
        crime under a Florida statute. That statute prohibited the sale, pur-
        chase, manufacture, delivery, or possession with intent to distribute
        of “a controlled substance.” FLA. STAT. § 893.13(1)(a)(1) (1991); see
        id. § 893.03 (controlled substance schedule). Laines argues that his
        prior conviction does not qualify as a “serious drug oﬀense” be-
        cause, under the categorical approach, the Florida statute is not di-
        visible by drug type and is thus overbroad. He also argues that, even
        if it were divisible, the Florida statute is still overbroad because its
        deﬁnition of cocaine is more expansive than the federal deﬁnition.
        And he argues that his conviction cannot be a serious drug oﬀense
        because he was not subject to at least a ten-year maximum sentence
        under the Florida sentencing guidelines. These arguments fail.
               Because Laines did not contest at sentencing whether his
        prior conviction is a “serious drug oﬀense,” we review only for
        plain error, Bennett, 472 F.3d at 831, and Laines cannot satisfy that
        standard. We have held that a conviction under section 893.13(1)
        qualiﬁes as a “serious drug oﬀense” under the Armed Career Crim-
        inal Act. See United States v. Travis Smith, 775 F.3d 1262, 1268 (11th
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        20-12907               Opinion of the Court                       19

        Cir. 2014); United States v. Xavier Smith, 983 F.3d 1213, 1223 (11th
        Cir. 2020). Laines has identiﬁed no decision overruling or abrogat-
        ing these precedents, so he cannot establish that it is “‘obvious’ or
        ‘clear under current law’” that the district court erred. Candelario,
        240 F.3d at 1309 (citation omitted). And we have expressly rejected
        Laines’s argument that, in the light of the decision in Carachuri-
        Rosendo v. Holder, 560 U.S. 563 (2010), we must look to the sentence
        that the particular defendant could have received under the sen-
        tencing guidelines instead of the statutory maximum. See United
        States v. Gardner, 34 F. 4th 1283, 1288, 1289 & n.3 (11th Cir. 2022).
               Our dissenting colleague credits Laines’s argument that the
        prosecution failed to carry its burden of proving that the Florida
        deﬁnition of cocaine is coextensive with or narrower than the fed-
        eral deﬁnition. Dissenting Op. at 1. When Laines was convicted of
        possessing cocaine with intent to sell, Florida law encompassed, as
        it still does, “any” stereoisomer of cocaine, FLA. STAT.
        § 893.03(2)(a)(4) (1991), but federal law covered only “optical and
        geometric isomers,” 21 U.S.C. § 812(c), Sched. II(a)(4) (1988 &
        Supp. 1991). Isomers are “molecules that have the same numbers
        of the same kinds of atoms . . . but diﬀer in chemical and physical
        properties,” and “stereoisomers are isomers that have the same
        composition . . . but that diﬀer in the orientation of those parts in
        space.” Maitland Jones, Isomerism, ENCYCLOPEDIA BRITANNICA (up-
        dated Apr. 6, 2023), https://www.britannica.com/science/isomer-
        ism. Laines argues that the Florida statute’s inclusion of “any” ste-
        reoisomer of cocaine makes it broader than the federal prohibition.
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        20                      Opinion of the Court                   20-12907

                The dissenting opinion contends that our recent decision in
        Chamu v. U.S. Attorney General, 23 F.4th 1325 (11th Cir. 2022), makes
        it “clear that the government has not yet met its burden to show
        that Laines’s prior conviction for cocaine distribution . . . qualiﬁes
        as a predicate oﬀense.” Dissenting Op. at 1. In that case, an alien
        facing deportation similarly argued that Florida’s deﬁnition of co-
        caine was broader than the federal deﬁnition. Chamu, 23 F.4th at
        1327, 1329. We disagree.
                Chamu is distinguishable. Chamu addressed whether a con-
        viction under Florida Statutes section 893.13(6)(a) is “relat[ed] to a
        controlled substance” for the purpose of the Immigration and Na-
        tionality Act, id. at 1329 (quoting 8 U.S.C. § 1182(a)(2)(A)(i)(II)), not
        whether a conviction under Florida Statutes section 893.13(1)(a)(1)
        is a “serious drug oﬀense” within the meaning of the Armed Ca-
        reer Criminal Act, 18 U.S.C. § 924(e)(1). We held that Chamu failed
        to establish that cocaine has stereoisomers other than those cov-
        ered by federal law. Chamu, 23 F.4th at 1331. Indeed, we stated that
        we “seriously doubt[ed]” that Chamu’s “assertions ha[d] any scien-
        tiﬁc basis.” Id. at 1332. So “[w]e decline[d] to hold that Florida’s
        statute is broader than its federal counterpart based only on the
        possibility that it might be so.” Id. at 1331. Chamu did not abrogate
        our precedents about a prior conviction under Florida Statutes sec-
        tion 893.13(1) qualifying as a “serious drug oﬀense” under the
        Armed Career Criminal Act.
               Laines has not satisﬁed his burden on appeal of establishing
        that his sentencing classiﬁcation was plainly erroneous. Under our
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        20-12907               Opinion of the Court                         21

        precedents, the burden lies with Laines, as the appellant, to establish
        that the district court plainly erred. See, e.g., Kushmaul, 984 F.3d at
        1363 (holding that “the defendant bears the burden” to establish
        plain error). At sentencing, Laines never objected to his classiﬁca-
        tion as an armed career criminal, so the government satisﬁed its
        burden in the district court. See United States v. Lopez-Garcia, 565
        F.3d 1306, 1323 (11th Cir. 2009) (explaining that a defendant’s fail-
        ure to object to facts alleged in a presentence investigation report
        “admits those facts for sentencing purposes”). And Laines has iden-
        tiﬁed no precedent that would make it “‘obvious’ or ‘clear under
        current law’” that the Florida deﬁnition of cocaine is overbroad.
        See Candelario, 240 F.3d at 1309 (citation omitted).

        D. No Plain Error Occurred in Calculating Laines’s Advisory Sentencing
                                 Guidelines Range.

               Laines argues for the ﬁrst time on appeal that his “advisory
        sentencing guideline range was erroneously calculated.” He con-
        tends that because his “prior conviction is not a serious drug of-
        fense, he no longer qualiﬁes for either the statutory sentencing en-
        hancement under [the Armed Career Criminal Act] or the corre-
        sponding guideline enhancement.” See United States Sentencing
        Guidelines Manual § 4B1.4 (Nov. 2021). Because the district court
        did not plainly err in determining that Laines previously commit-
        ted a serious drug oﬀense under the Act, it also did not plainly err
        in applying the corresponding guideline enhancement.
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        22                  Opinion of the Court             20-12907

                             IV. CONCLUSION

              We AFFIRM Laines’s convictions and sentence.
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        20-12907             ROSENBAUM, J., Dissenting in Part                       1

        ROSENBAUM, Circuit Judge, Dissenting in Part:
               Napoleon Bonaparte said, “Respect the burden.” 1 Of
        course, he was not talking about collateral eﬀects of prior convic-
        tions. But as it turns out, that quotation is apt when we are.
               Who bears the burden of proving that a prior conviction
        qualiﬁes as a predicate conviction or doesn’t under the Armed Ca-
        reer Criminal Act (“ACCA”) is the deciding factor in this case. And
        that factor requires us to vacate Laines’s ACCA-enhanced sentence
        because the government bore the burden in the district court of
        proving that ACCA applies, but it failed to do so.
               So while I agree with the Majority Opinion that Laines’s con-
        victions should be aﬃrmed,2 I disagree with its conclusion that

        1Ralph Waldo Emerson, Napoleon; Or, the Man of the World from Representative
        Men,       https://www.napoleon.org/en/history-of-the-two-empires/arti-
        cles/napoleon-or-the-man-of-the-world-from-representative-men-1850/.
        2 For the reasons the Majority Opinion discusses, Laines received a fair trial.
        And while we can’t expect anyone—including prosecutors—to be perfect, the
        government’s several errors here are troubling. These errors include, among
        other things, Agent Perry’s improper testimony, Officer Blanco’s warrantless
        search, the government’s failure to disclose the warrantless search, and the
        government’s failure to disclose Officer Yanes-Martel’s misconduct investiga-
        tions. Indeed, even the government (rightly) concedes it erred in several ways,
        stating, “[i]n retrospect,” it would have done some things differently. While
        the government’s candor is admirable, we have often said that the govern-
        ment “owes a heavy obligation to the accused” to ensure a fair trial. United
        States v. Wilson, 149 F.3d 1298, 1303 (11th Cir. 1998) (quoting Dunn v. United
        States, 307 F.2d 883, 885 (5th Cir. 1962)). The government must do better to
        avoid these types of errors, and the U.S. Attorney’s Office should study this
        case to ascertain areas where its prosecutors need some more training.
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        2                 ROSENBAUM, J., Dissenting in Part        20-12907

        Laines’s enhanced sentence was proper. After our decision in
        Chamu v. U.S. Attorney General, 23 F.4th 1325 (11th Cir. 2022), it’s
        clear that the government has not yet met its burden to show that
        Laines’s prior conviction for cocaine distribution under Fla. Stat.
        § 893.13(1)(a)(1) qualiﬁes as a predicate oﬀense for a sentence en-
        hancement under ACCA. In light of Chamu, I would “respect the
        [government’s] burden” here, vacate Laines’s sentence, and re-
        mand to the district court to allow the government an opportunity
        to meet its burden.
                I divide my discussion into two substantive parts. In Section
        I, I explain why the government bore the burden to establish that
        Laines’s Florida cocaine-traﬃcking conviction qualiﬁes as a predi-
        cate crime under ACCA and how it failed to do so. And Section II
        shows that the government’s failure to establish that Laines’s con-
        viction serves as a predicate crime under ACCA caused plain error
        requiring remand for a new sentencing.
                                        I.

               Laines asserts that his conviction under Fla. Stat.
        § 893.13(1)(a)(1) cannot serve as a predicate oﬀense because Flor-
        ida’s deﬁnition of “cocaine” is broader than the federal deﬁnition
        of “cocaine,” so a conviction under Florida law cannot categori-
        cally qualify as a “serious drug oﬀense” under ACCA.
               To understand Laines’s argument, we must consider the
        Florida and federal deﬁnitions of “cocaine” for purposes of con-
        trolled-substance oﬀenses. Florida law deﬁnes “cocaine” as
        “[c]ocaine or ecgonine, including any of their stereoisomers, and
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        20-12907           ROSENBAUM, J., Dissenting in Part                 3

        any salt, compound, derivative, or preparation of cocaine or ecgon-
        ine.” Fla. Stat. § 893.03(2)(a)(4) (emphasis added). Meanwhile, fed-
        eral law controls “cocaine, its salts, optical and geometric isomers,
        and salts of isomers.” 21 U.S.C. § 812, Sched. II(a)(4). As we have
        explained, optical and geometric isomers “are kinds of stereoiso-
        mers.” United States v. Phifer, 909 F.3d 372, 377 n.5 (11th Cir. 2018).
        But they are not the only kinds of stereoisomers. In Chamu, we
        recognized that nongeometric diastereomers are another type of
        stereoisomer. See Chamu, 23 F.4th at 1331. So, Laines reasons, if
        nongeometric diastereomers of cocaine exist, the Florida deﬁnition
        of “cocaine” is broader than the federal deﬁnition (which includes
        only optical and geometric isomers), and a Florida conviction for
        traﬃcking cocaine cannot categorically qualify as a “serious drug
        oﬀense” under ACCA. See Mathis v. United States, 579 U.S. 500, 505
        (2016).
               No one disputes Laines’s conclusion that if nongeometric di-
        astereomers of cocaine exist, his Florida cocaine-trafficking convic-
        tion cannot be an ACCA predicate offense because then the Florida
        law criminalizes conduct that the federal law does not. And in fact,
        because of that possible mismatch between the Florida and federal
        definitions of “cocaine,” in Chamu, we explained that we could not
        “hold that Florida’s definition of cocaine is completely consistent
        with the federal definition.” Chamu, 23 F.4th at 1332. But unlike
        Laines’s criminal case, Chamu was an immigration case. So in
        Chamu, the burden fell on the migrant petitioner there to prove
        that his conviction did not qualify as a removal crime. As a result,
        we concluded we could “hold that [the petitioner] ha[d] failed to
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        4                 ROSENBAUM, J., Dissenting in Part         20-12907

        prove that [Florida law] covers more substances [than federal
        law],” id., even though it was not clear that the Florida law did not
        include more substances than the federal law.
                We can’t say the same thing here, though. Unlike in the im-
        migration context, in the criminal-sentencing environment, the
        government bears the burden of proving any sentencing enhance-
        ment—including an ACCA enhancement—applies. The Supreme
        Court has recently emphasized this point, contrasting the burden
        of proving whether a prior conviction aﬀects removability under
        the Immigration and Nationality Act (“INA”) and whether a prior
        conviction can yield an enhanced sentence under ACCA. Pereida v.
        Wilkinson, 141 S. Ct. 754 (2021). In Pereida, the Court explained that
        both ACCA and the INA “may call for the application of the cate-
        gorical approach. But while the ACCA’s categorical approach demands
        certainty from the government, the INA’s demands it from the alien.”
        Id. at 766 n.7 (emphasis added). In other words, who bears the bur-
        den to prove a given crime categorically qualiﬁes or not—the gov-
        ernment or the individual—depends on the type of case involved—
        an immigration matter or a criminal sentencing. And we must re-
        spect the diﬀerence in the burdens.
                Pereida’s recognition that the government must carry the
        burden to prove a prior conviction qualiﬁes as an ACCA predicate
        is nothing new. Our case law has long held the same thing. United
        States v. Hernandez, 145 F.3d 1433, 1440 (11th Cir. 1998) (“The bur-
        den of proof for establishing that a sentencing enhancement is war-
        ranted lies with the prosecution, and it is the duty of the district
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        20-12907           ROSENBAUM, J., Dissenting in Part                  5

        court to insure that the prosecution carries its burden of proof.”).
        See also, e.g., United States v. Lee, 586 F.3d 859, 866 (11th Cir. 2009)
        (“The prosecution bears the burden of proving that a sentencing
        enhancement under the ACCA is warranted.”); United States v.
        Young, 527 F.3d 1274, 1277 (11th Cir. 2008) (quoting Hernandez, 145
        F.3d at 1440). And as recently as 2019, we again repeated this sen-
        timent: “[t]he government bears the burden of establishing that an
        ACCA sentencing enhancement is warranted.” United States v. Har-
        ris, 941 F.3d 1048, 1051 (11th Cir. 2019).
               So after Chamu recognized that, by its terms, the Florida def-
        inition of “cocaine” may be broader than the federal deﬁnition, it’s
        clear that the government bore the burden at Laines’s sentencing
        to show that no stereoisomers other than optical and geometric
        isomers of cocaine exist.
               The government can satisfy its burden in a couple of ways.
               First, in the ordinary case, the government is often able to
        discharge its burden by comparing the text of the underlying state
        statute to the text of the federal statute and proving that the lan-
        guage of the state statute does not sweep more broadly than the
        language of the federal statute does. See, e.g., United States v. Vail-
        Bailon, 868 F.3d 1293, 1303 (11th Cir. 2017) (en banc) (holding that
        “[b]y its plain terms, felony battery in violation of Florida Statute
        § 784.041 requires the use of physical force” and therefore consti-
        tutes a “crime of violence” for ACCA purposes); United States v.
        Harrison, 56 F.4th 1325, 1336 (11th Cir. 2023) (comparing plain
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        6                  ROSENBAUM, J., Dissenting in Part         20-12907

        language of Georgia offense for robbery by intimidation to federal
        generic definition of robbery).
               But crucially, after Chamu, the government cannot make
        that showing in this case because we have acknowledged that “we
        cannot hold that Florida’s definition of cocaine is completely con-
        sistent with the federal definition.” Chamu, 23 F.4th at 1332. That
        conclusion followed from our observation that “stereoisomers in-
        clude at least one chemical subset that is not listed in federal law—
        nongeometric diastereomers.” Id. at 1331.
                Along the same lines, the government can also meet its bur-
        den to establish an ACCA predicate by pointing to controlling prec-
        edent that already answers the question of whether a defendant’s
        prior conviction qualifies as a predicate offense. See United States v.
        Fritts, 841 F.3d 937, 940 (11th Cir. 2016); United States v. White, 837
        F.3d 1225, 1231, 1235 (11th Cir. 2016). The government seeks to
        do so here, arguing that it is “settled law” that convictions under
        Fla. Stat. § 893.13(1) are categorically “serious drug offenses” under
        our decisions in United States v. Travis Smith, 775 F.3d 1262, 1267
        (11th Cir. 2014), and United States v. Xavier Smith, 983 F.3d 1213,
        1223 (11th Cir. 2020).
               But we have recently explained that the Smith decisions
        “construed the part of ACCA’s ‘serious drug offense’ definition that
        requires the state offense to involve the conduct of ‘manufacturing,
        distributing, or possessing with intent to manufacture or distrib-
        ute.’” United States v. Jackson, 55 F.4th 846, 853 (11th Cir. 2022)
        (emphasis in original), cert. granted, 2023 WL 3440568 (U.S. May 15,
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        20-12907            ROSENBAUM, J., Dissenting in Part                    7

        2023). They did not involve the part of ACCA’s definition that
        Laines challenges here—the definition of a “controlled substance.”
        Id. at 853–54. As we explained in Jackson, the most that can be said
        about the Smith decisions is that they “assumed that [ACCA’s] ‘se-
        rious drug offense’ definition and section 893.13(1) encompass the
        same universe of substances.” Id. at 854. But those decisions’ as-
        sumptions do not address the aspect of ACCA that is germane to
        Laines’s arguments, so they do not resolve Laines’s challenge.
                The Majority Opinion appears to credit the government’s
        argument that the Smith decisions resolve Laines’s challenge. It
        cites those decisions for the contention that “[w]e have held that a
        conviction under section 893.13(1) qualifies as a ‘serious drug of-
        fense’ under [ACCA],” and then says that “Laines has identified no
        decision overruling or abrogating these precedents.” Maj. Op. at
        20. But in relying on the Smith decisions, the Majority Opinion ig-
        nores Jackson and its explanation that the Smith decisions are not
        controlling in cases like this one that “ask[] us to construe the part
        of ACCA’s ‘serious drug offense’ definition that requires the state
        offense to involve ‘a controlled substance (as defined in section 102
        of the Controlled Substances Act, 21 U.S.C. § 802)).’” Jackson, 55
        F.4th at 853 (quoting 18 U.S.C. § 924(e)(2)(A)(ii)) (alteration
        adopted). 3
               To be sure, Jackson did not purport to abrogate the Smith
        decisions. But it clarified that the government cannot rely on the

        3 Because we issued Jackson after Laines filed his briefs, Laines cannot be
        faulted for not identifying Jackson.
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        8                      ROSENBAUM, J., Dissenting in Part             20-12907

        Smith decisions to conclude that § 893.13(1) is a “serious drug of-
        fense” in every circumstance. Those decisions did not sweep so
        broadly. Rather, they answered only the question of whether con-
        victions under § 893.13(1) can qualify as an ACCA predicate despite
        that statute’s lack of a mens rea element with respect to the illicit
        nature of the controlled substance. Travis Smith, 775 F.3d at 1267–
        68; Xavier Smith, 983 F.3d at 1223. The Smith decisions’ conclusion
        on that front is binding—but not any broader conclusion that pur-
        ports to foreclose all potential challenges to § 893.13(1)’s status as
        an ACCA predicate. As we’ve said many times, “regardless of what
        a court says in its opinion, the decision can hold nothing beyond
        the facts of that case.” Edwards v. Prime, Inc., 602 F.3d 1276, 1298
        (11th Cir. 2010).
               So here, the government cannot rely on either the plain text
        of the statutes or controlling precedent to meet its burden. Rather,
        it must find a different path. In its only effort to do so here, the
        government argues that “[g]eometric and optical isomers are the
        two types of stereoisomers,” 4 suggesting that no other types of ste-
        reoisomers exist. In support of this contention, the government
        cites our decision in Phifer. There, we said “[o]ptical and geometric
        isomers . . . are sub-types of stereoisomers.” 909 F.3d at 377.
               But critically, we did not say those are the only sub-types of
        stereoisomers. For good reason. Phifer was primarily concerned

        4   The government filed its brief in this case before Chamu was decided.
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        20-12907          ROSENBAUM, J., Dissenting in Part                 9

        with positional isomers—a different type of isomer than stereoiso-
        mers. Id.
               But returning to Chamu, we must conclude that the govern-
        ment’s mistake is clear, and we must reject its argument. Chamu
        expressly explains that there are three categories of stereoisomers:
        optical isomers, geometric isomers, and nongeometric diastere-
        omers. 23 F.4th at 1330 & n.2. So if nongeometric diastereomers
        of cocaine exist, then Florida’s definition of the substance is cate-
        gorically overbroad in comparison to the federal definition.
                Our sister circuits have also recognized the principle that a
        state statute whose definition covers more than the federal defini-
        tion is categorically overbroad, so convictions under that state stat-
        ute cannot categorically qualify as predicates for sentence enhance-
        ments. See United States v. Myers, 56 F.4th 595, 598–99 (8th Cir.
        2022) (holding Missouri’s definition of “cocaine” is categorically
        broader than federal definition); United States v. Owen, 51 F.4th 292,
        295–96 (8th Cir. 2022) (same for Minnesota’s definition of “co-
        caine”); United States v. Ruth, 966 F.3d 642, 647–48 (7th Cir. 2020)
        (same for Illinois’s).
                And a state law that controls more isomers of a controlled
        substance than federal law does has also led a court to hold that the
        state law is categorically overbroad to serve as a predicate offense
        for an enhanced sentence. United States v. De La Torre, 940 F.3d 938,
        951–52 (7th Cir. 2019) (holding Indiana law criminalizing distribu-
        tion of methamphetamine is categorically overbroad because state
        law controls more isomers than federal law does).
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        10                 ROSENBAUM, J., Dissenting in Part          20-12907

                 Second, the government can meet its burden by showing that
        it is factually impossible for the state statute to be broader than the
        federal statute because the chemical compound in question does
        not exist. As Chamu explains, “[i]f cocaine does not have a nonge-
        ometric diastereomer, then the two statutes cover exactly the same
        ground.” 23 F.4th at 1331. To support ACCA enhancements in
        other cases, the government has introduced expert testimony to
        show there is no mismatch between a state’s definition of a con-
        trolled substance and the equivalent federal definition. Cf. United
        States v. Rodriguez-Gamboa, 972 F.3d 1148, 1151–52 (9th Cir. 2020)
        (affirming sentence after government presented testimony from
        three experts in organic chemistry that “geometric isomers of
        methamphetamine are impossible” (internal quotation marks
        omitted)); United States v. Turner, 47 F.4th 509, 515, 523–24 (7th Cir.
        2022) (affirming sentence based on government’s expert declara-
        tions that it is “impossible to create an ester or a salt of an ester of
        cocaine”).
                But the government made no such showing here. To be
        sure, Chamu issued after Laines’s sentencing. But even before
        Chamu, the government could have anticipated this problem by
        comparing the text of the Florida deﬁnition to the text of the fed-
        eral deﬁnition and recognizing the disparity. And Chamu resolved
        any uncertainty about the scopes of those deﬁnitions. After sur-
        veying the organic-chemistry landscape, we observed there that
        Florida law’s proscription of “any stereoisomers” of cocaine is fa-
        cially broader than federal law’s ban on only “optical and geometric
        isomers” of cocaine. 23 F.4th at 1330–31 & n.2.
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        20-12907          ROSENBAUM, J., Dissenting in Part                11

               It’s true that the Chamu court “seriously doubt[ed]” that
        nongeometric diastereomers of cocaine exist. 23 F.4th at 1332. But
        even if I share those doubts, they cannot carry the day for the gov-
        ernment here. Because Laines’s case involves a criminal sentenc-
        ing, the government bears the burden to show that the enhance-
        ment applies. And as the Supreme Court has explained, “the
        ACCA’s categorical approach demands certainty from the govern-
        ment.” Pereida, 141 S. Ct. at 766 n.7 (emphasis added).
               But as in Chamu, we are left with the question of whether
        nongeometric diastereomers of cocaine exist in the real world. Just
        as the “dearth of evidence” about their existence was “fatal for
        Chamu, who b[ore] the burden of proof” there, 23 F.4th at 1332,
        that same dearth of evidence is now fatal for the government,
        which bears the burden here. To discharge its burden to show that
        convictions for cocaine distribution under Fla. Stat.
        § 893.13(1)(a)(1) can serve as a “serious drug offense” under ACCA,
        the government must show that there are no nongeometric dia-
        stereomers of cocaine.
              For its part, the Majority Opinion tries a couple of different
        paths to (incorrectly) conclude that the government satisfied its
        burden.
                First, it says that the government satisfied its burden in the
        district court when Laines did not object to the armed-career-crim-
        inal classification. Maj. Op. at 22. But the Majority Opinion’s at-
        tempt to rescue the government is inconsistent with how we’ve
        expressed the government’s burden. Indeed, as I noted, we’ve
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        12                 ROSENBAUM, J., Dissenting in Part          20-12907

        explained that “[t]he burden of proof for establishing that a sen-
        tence enhancement is warranted lies with the prosecution and it is
        the duty of the district court to insure that the prosecution carries
        its burden of proof.” Hernandez, 145 F.3d at 1440. Under Hernan-
        dez, then, even if a defendant does not object to the sentencing en-
        hancement, the district court has an obligation to ensure that the
        enhancement is proper.
                So a defendant’s failure to object is not relevant to the in-
        quiry and cannot relieve the government of its burden to establish
        the enhancement. Nor, contrary to the Majority Opinion’s conten-
        tion, can the fact that a defendant’s “failure to object to allegations
        of fact in a PSI admits those facts for sentencing purposes.” United
        States v. Lopez-Garcia, 565 F.3d 1306, 1323 (11th Cir. 2009).
        Whether a cocaine-related conviction under section 893.13(a)(1)
        qualifies as a “serious drug offense” is a legal question, the answer
        to which is the same in every case for every defendant with such a
        conviction. It is quite a stretch to characterize it as the type of “al-
        legation[] of fact” that we deem admitted in a PSI if a defendant
        fails to object.
               Rather, the way we deal with such a legal challenge when
        the defendant fails to raise it in the district court is to apply plain-
        error review. See infra Part II. Because the government sought to
        apply an enhancement, it had the burden in the district court to
        establish that the enhancement applies. And given Chamu’s recog-
        nition that the plain language of section 893.03(2)(a)(4) on its face
        encompasses nongeometric diastereomers, it has not done so.
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        20-12907           ROSENBAUM, J., Dissenting in Part                 13

               Second, the Majority Opinion confuses Laines’s burden on
        appeal to establish that his sentencing classification was plainly er-
        roneous with the government’s burden in the district court to show
        that the career-offender enhancement applied to Laines. See Maj.
        Op. at 22 (“Laines has not satisfied his burden on appeal of estab-
        lishing that his sentencing classification was plainly erroneous. Un-
        der our precedents, the burden lies with Laines, as the appellant, to
        establish that the district court plainly erred.”). Laines satisfied his
        burden on appeal to establish that his sentencing classification was
        plainly erroneous because the government failed in the district court
        to make any showing that Florida’s definition of “cocaine” is not
        categorically broader than the federal definition of “cocaine.”
                                          II.

               The government’s failure to establish that Laines’s Florida
        cocaine-trafficking conviction qualifies as an ACCA predicate
        amounts to plain error here. Because Laines did not raise this issue
        in the district court, to prevail on appeal, Laines must not only es-
        tablish that his challenge to his sentence is correct as a legal matter,
        but he must also satisfy the plain-error standard. Fed. R. Crim. P.
        52(b).
               Plain error occurs when there is (1) an error; (2) that is plain;
        (3) that affects the defendant’s substantial rights; and (4) that seri-
        ously affects the fairness, integrity, or public reputation of judicial
        proceedings. United States v. Lewis, 40 F.4th 1229, 1246 (11th Cir.
        2022). Laines satisfies all four requirements.
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        14                 ROSENBAUM, J., Dissenting in Part         20-12907

               I begin with error. As I’ve noted, it was error to conclude
        that Laines’s prior conviction can serve as a predicate offense with-
        out requiring the government to show that nongeometric diastere-
        omers of cocaine don’t exist. As Section I of this dissent explains,
        the text of Florida’s definition of “cocaine” is facially broader than
        the equivalent federal definition. See Chamu, 23 F.4th at 1331. So
        the government has not yet met its burden to prove that Laines’s
        conviction can serve as a predicate offense. See Hernandez, 145 F.3d
        at 1440 (“The burden of proof for establishing that a sentence en-
        hancement is warranted lies with the prosecution and it is the duty
        of the district court to insure that the prosecution carries its burden
        of proof.”).
               Turning to the second requirement—the plainness of that
        error—that error is plain here as the result of two lines of cases.
        One, our Hernandez line of cases, along with the Supreme Court’s
        recent affirmation in Pereida, plainly establish that in a sentencing,
        the government bears the burden of showing that a sentencing en-
        hancement applies. And two, Chamu is directly on point in con-
        cluding that, under the wording of the Florida and federal defini-
        tions of “cocaine,” uncertainty exists as to whether the Florida def-
        inition of “cocaine” is broader than the federal definition. So be-
        cause uncertainty remains, the Hernandez and Pereida line of cases
        dictates that the burden for removing that uncertainty lies squarely
        on the government’s shoulders.
               It doesn’t matter to the plain-error analysis that Chamu is-
        sued after Laines’s sentencing. Rather, “an intervening decision by
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        20-12907          ROSENBAUM, J., Dissenting in Part                15

        this Court or the Supreme Court squarely on point may make an
        error plain.” United States v. Jones, 743 F.3d 826, 829–30 (11th Cir.
        2014) (citation and internal quotation marks omitted). Here,
        Chamu fills that requirement because, as I’ve explained, it makes
        clear that the government has not yet met its burden to show that
        a Florida cocaine-distribution conviction can serve as a predicate
        offense for an enhanced sentence.
               To be sure, Chamu does not definitively establish that the
        Florida definition of “cocaine” is broader than the federal definition
        or that more than two categories of stereoisomers of cocaine exist.
        But that makes no difference because as I’ve noted, in the sentenc-
        ing context, the burden of resolving that open question is one the
        government must bear. Without proof that nongeometric dia-
        stereomers of cocaine don’t exist, we are left with a state statute
        that purports to sweep more broadly than federal law does. And
        in such circumstances, the government cannot use convictions un-
        der the state offense to support ACCA enhancements. See Mathis,
        579 U.S. at 505.
               Because Chamu makes it “plain” and “obvious” that there is
        potential daylight between the Florida definition of “cocaine” and
        the federal definition, and because the government has not met its
        burden to eliminate that daylight, Chamu establishes the plainness
        of the error with Laines’s sentence. On the record here, we have
        no reasonable basis upon which to conclude that the government
        has satisfied its burden.
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        16                 ROSENBAUM, J., Dissenting in Part           20-12907

                 This conclusion aligns with those of our sister circuits in sim-
        ilar situations. For instance, in De La Torre, the Seventh Circuit held
        that it was plain error for the district court to conclude an Indiana
        methamphetamine conviction could serve as a predicate offense
        under ACCA because the state definition of the drug was broader
        than federal definition, as the state definition captured additional
        isomers of methamphetamine. 940 F.3d at 951–53 & n.7; see also
        United States v. Garcia, 948 F.3d 789, 794 (7th Cir. 2020) (holding
        sentencing enhancement was plain error after concluding Indiana
        “marijuana” definition was broader than federal definition); United
        States v. Navarro, 54 F.4th 268, 281 (5th Cir. 2022) (finding plain er-
        ror after concluding that Colorado sex-offense law was categori-
        cally overbroad to serve as predicate offense under the Sex Of-
        fender Registration and Notification Act).
               Of course, Laines cannot prove that Chamu alone demands
        his sentence be vacated. Nor can he represent that he will ulti-
        mately receive a sentence without an ACCA enhancement. But at
        this stage, following Chamu, he can prove that the government
        hasn’t satisfied its burden and that the ACCA enhancement, as it
        currently stands, is improper.
                And even though it may seem unusual to find plain error
        and require the government to prove a negative based on a factual
        question—whether nongeometric diastereomers of cocaine exist—
        the Supreme Court has explained that “there is no legal basis for
        the . . . practice of declining to review certain unpreserved factual
        arguments for plain error.” Davis v. United States, 140 S. Ct. 1060,
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        20-12907           ROSENBAUM, J., Dissenting in Part                 17

        1062 (2020) (per curiam). So I would remand for a hearing to allow
        the government to introduce evidence about whether nongeomet-
        ric diastereomers of cocaine exist. Cf. United States v. Rodriguez-
        Gamboa, 946 F.3d 548, 552–53 (9th Cir. 2019) (remanding for evi-
        dentiary hearing to determine whether geometric isomers of meth-
        amphetamine exist).
                Although the error is plain here, I echo the Supreme Court’s
        acknowledgment that “plain-error review is not a grading system
        for trial judges.” Henderson v. United States, 568 U.S. 266, 278 (2013).
        Without an objection from Laines or the benefit of Chamu, the dis-
        trict court had little reason to question the government’s proposed
        ACCA enhancement. But the plain-error standard “has broader
        purposes, including in part allowing courts of appeals to better to
        identify those instances in which the application of a new rule of
        law to cases on appeal will meet the demands of fairness and judi-
        cial integrity.” Id. So now that we are equipped with Chamu and
        the knowledge that the Florida definition of “cocaine” is facially
        broader than the federal definition, the government must carry its
        burden to establish an enhanced sentence.
                The third and fourth prongs of the plain-error standard ask
        whether the error affected Laines’s substantial rights and whether
        the error has seriously affected the fairness, integrity, or public rep-
        utation of the judicial proceedings in this case, respectively. United
        States v. Olano, 507 U.S. 725, 732 (1993). Laines satisfies both.
              To make the “substantial rights” showing, a defendant
        “must show a reasonable probability that, but for the error, the
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        18                ROSENBAUM, J., Dissenting in Part        20-12907

        outcome of the proceeding would have been different.” Molina-
        Martinez v. United States, 578 U.S. 189, 194 (2016). Most defendants
        can do so when “the district court mistakenly deemed applicable
        an incorrect, higher [Sentencing] Guidelines range.” Id. at 200.
        Here, because of the ACCA enhancement, Laines’s Guidelines
        range was deemed to be 270–322 months, and he was sentenced to
        300 months’ imprisonment. Without the enhancement, the top
        end of his Guidelines range would be 131 months. Under Molina-
        Martinez, that difference is sufficient.
                In my view, allowing Laines’s 300-month sentence to stand
        when the government has not met its burden to show that the en-
        hanced sentence is warranted seriously affects the fairness, integ-
        rity, and public reputation of the proceedings here. Rosales-Mireles
        v. United States, 138 S. Ct. 1897, 1907–08 (2018) (explaining that
        “[t]he risk of unnecessary deprivation of liberty particularly under-
        mines the fairness, integrity, or public reputation of judicial pro-
        ceedings”).
                                        III.

               The government has not yet met its burden to show that
        Laines’s conviction for cocaine distribution can serve as a predicate
        offense for an enhanced sentence. To respect that burden, I would
        vacate Laines’s sentence and remand to the district court for a hear-
        ing to allow the government to make the requisite showing.
              I respectfully dissent.