Eleventh Circuit Adopts a Time‑of‑Conviction Analysis for § 851 “Felony Drug Offense” Predicates

Introduction

This unpublished Eleventh Circuit decision, United States v. Charles Brown, Jr. (No. 22-10485, Apr. 4, 2025), affirms a 262-month sentence imposed after the defendant pleaded guilty to possession with intent to distribute heroin and fentanyl, in violation of 21 U.S.C. § 841(a)(1), (b)(1)(C). The appeal raised two principal issues:

Whether the district court erred procedurally and substantively in imposing an enhancement under 21 U.S.C. § 851 based on prior state drug convictions—specifically, whether those convictions qualified as “felony drug offenses” and whether the court complied with the procedural safeguards in § 851(b)–(c).
Whether the district court erred in applying the Sentencing Guidelines’ career-offender enhancement under U.S.S.G. § 4B1.1.

The panel (Jordan, Newsom, and Anderson, JJ., per curiam) held there was no plain error in applying either enhancement. Most notably, the court expressly extended the Supreme Court’s and this Circuit’s time-of-conviction (backward-looking) approach—developed in the Armed Career Criminal Act (ACCA) context—to § 851’s predicate inquiry, concluding that a state drug conviction remains a qualifying “felony drug offense” even if federal or state drug definitions later narrow (e.g., by removing a substance like ioflupane from the cocaine definition).

Summary of the Opinion

The Eleventh Circuit affirmed Brown’s sentence in full. On the § 851 issue, the court held:

Substantively, Brown’s prior Florida cocaine convictions from 2005 and 2012 qualified as “felony drug offenses” under 21 U.S.C. § 802(44) because, applying a backward-looking analysis, they qualified at the time of the convictions—even if the drug schedules later changed. The court relied on United States v. Jackson (11th Cir. 2022) and the Supreme Court’s subsequent affirmation of the backward-looking approach in Brown v. United States (2024).
Procedurally, any failure to conduct the colloquy required by § 851(b) was harmless because Brown’s valid predicate convictions were more than five years old, and § 851(e) would have barred any validity challenge anyway.
The § 851 information listing multiple prior convictions adequately notified Brown of the government’s intent; no separate, standalone § 851(c) hearing was required so long as the court addressed the objections at sentencing.

On the career-offender enhancement, the court held that Florida aggravated assault with a firearm is a “crime of violence” under U.S.S.G. § 4B1.2 in light of this Circuit’s precedent and the Florida Supreme Court’s clarification of mens rea; together with Brown’s 2019 cocaine conviction, that provided the two required predicates under § 4B1.1. The panel emphasized that the issue was foreclosed by binding Eleventh Circuit precedent (Somers).

Analysis

Precedents Cited and Their Influence

United States v. Jackson, 55 F.4th 846 (11th Cir. 2022) and Brown v. United States, 602 U.S. 101 (2024):
Jackson held that ACCA’s “serious drug offense” predicate inquiry is backward-looking: courts assess whether the state offense was a qualifying predicate under then-current law at the time of the state conviction, not under later, narrowed schedules. The Supreme Court affirmed this approach in Brown. Although § 851 uses “felony drug offense” (§ 802(44)) rather than ACCA’s “serious drug offense,” the Eleventh Circuit found no reason not to apply the same logic to § 851 predicates. That extension is the principal doctrinal development in this opinion.
Taylor v. United States, 495 U.S. 575 (1990):
The panel invoked the categorical approach—examining statutory elements, not case-specific facts—when evaluating whether the prior convictions qualified. This frames the analysis of overbreadth arguments about Florida’s drug statutes.
United States v. Laines, 69 F.4th 1221 (11th Cir. 2023), United States v. Candelario, 240 F.3d 1300 (11th Cir. 2001), and Chamu v. U.S. Att’y Gen., 23 F.4th 1325 (11th Cir. 2022):
These cases informed the court’s rejection—under plain-error review—of Florida “cocaine” overbreadth arguments based on stereoisomer coverage. The court noted an absence of binding precedent clearly establishing that Florida’s definition is broader in a way that matters, and observed prior doubt about the existence of nongeometric diastereomers of cocaine.
United States v. Weaver, 905 F.2d 1466 (11th Cir. 1990) and United States v. James, 642 F.3d 1333 (11th Cir. 2011):
These cases support the holding that a district court’s failure to conduct the § 851(b) colloquy is harmless when the predicate convictions are older than five years and thus immune from collateral attack by virtue of § 851(e).
United States v. Woodyard, 349 F. App’x 518 (11th Cir. 2009), United States v. Rodriguez, 851 F.3d 931 (9th Cir. 2017), and United States v. Arreola-Castillo, 539 F.3d 700 (7th Cir. 2008):
These authorities support the proposition that the § 851(c) “hearing” may occur as part of the sentencing proceeding; no separate standalone hearing is required.
Somers v. United States, 66 F.4th 890 (11th Cir. 2023); Somers v. United States, 355 So. 3d 890 (Fla. 2022); Turner v. Warden Coleman FCI (Medium), 709 F.3d 1328 (11th Cir. 2013) (abrogated on other grounds by Johnson v. United States, 576 U.S. 591 (2015)); and United States v. Golden, 854 F.3d 1256 (11th Cir. 2017):
Together, these decisions anchor the conclusion that Florida aggravated assault is a qualifying “crime of violence” under the Guidelines’ elements clause, given the Florida Supreme Court’s mens rea clarification (at least knowing conduct, not mere recklessness).
Standards and burden cases: United States v. DiFalco, 837 F.3d 1207 (11th Cir. 2016) (plain-error review), United States v. Bennett, 472 F.3d 825 (11th Cir. 2006) (plain error), United States v. Lee, 586 F.3d 859 (11th Cir. 2009) (government bears burden to prove § 851 predicates), Perez v. United States, 249 F.3d 1261 (11th Cir. 2001) (clarity of § 851 information), United States v. Cevallos, 538 F.2d 1122 (5th Cir. 1976) (§ 851(b) colloquy purpose), and Smith v. GTE Corp., 236 F.3d 1292 (11th Cir. 2001) (prior-precedent rule).

Legal Reasoning

1) The § 851 enhancement: backward-looking predicate analysis and procedural compliance

Brown argued his Florida cocaine convictions (2005, 2012) could not be “felony drug offenses” because today both federal and Florida definitions exclude ioflupane (a radiopharmaceutical once captured within the “cocaine” definitional umbrella). The court applied the categorical approach and, crucially, adopted a backward-looking lens: the inquiry is whether the convictions qualified at the time they were entered. Because the schedules changed only after Brown’s convictions, they remain qualifying predicates. The panel drew a direct analogy to ACCA precedent (Jackson) and the Supreme Court’s subsequent endorsement (Brown v. United States), concluding the same temporal rule should govern § 851’s predicate analysis under § 802(44).

Brown also argued Florida’s “narcotic drug” definition (via Schedule II: cocaine and ecgonine “including any of their stereoisomers”) is broader than the federal definition (“optical and geometric isomers”). On plain-error review, the court refused to find obvious error for several reasons:

No controlling precedent clearly deems Florida’s definition overbroad for this purpose.
The Eleventh Circuit has expressed doubt that cocaine has nongeometric diastereomers in a way that would create a realistic mismatch.
Given that any single prior cocaine conviction sufficed to trigger § 851, resolving the stereoisomer debate was unnecessary once the backward-looking rule secured at least one valid predicate.

Procedurally, the panel addressed three § 851 points:

Information listing multiple convictions (§ 851(a)): The government’s notice identified multiple Florida convictions and case details. The court held that listing multiple qualifying priors still “unambiguously” signals intent to seek an enhancement, satisfying § 851(a).
Omitted § 851(b) colloquy: Although the district court did not conduct the statutory colloquy (ask the defendant to affirm/deny the convictions and warn that unraised challenges are forfeited), the panel found harmless error. Because at least two predicate convictions were more than five years old, § 851(e) time-barred any validity challenge, so the omission did not prejudice Brown.
No separate § 851(c) hearing: The sentencing hearing sufficed; § 851(c) does not require a standalone proceeding where the court considers the written objections and confirms whether they are being pursued.

Finally—and critically—the § 851 enhancement mattered: without it, § 841(b)(1)(C)’s default statutory maximum is 20 years. With § 851, the maximum increases to 30 years. Brown’s 262-month sentence exceeds 240 months; thus, affirming the § 851 enhancement was necessary to preserve the lawfulness of the sentence’s length.

2) The career-offender enhancement: Florida aggravated assault is a “crime of violence”

To qualify as a career offender under U.S.S.G. § 4B1.1, a defendant must have at least two prior felony convictions of either a “crime of violence” or a “controlled substance offense.” The PSR identified, among others, Brown’s:

2019 conviction for possession of cocaine with intent to sell (uncontested as a “controlled substance offense”).
2005 convictions for aggravated assault with a firearm.

Relying on Somers and related Eleventh Circuit authority, the panel held Florida aggravated assault categorically qualifies as a “crime of violence” under the Guidelines’ elements clause because Florida assault requires at least knowing conduct (not mere recklessness). Brown conceded Somers foreclosed his argument; the panel emphasized it is bound by Circuit precedent. Those two predicates sufficed to trigger career-offender status, making it unnecessary to reach the 2012 drug convictions.

3) Standards of review shaped the outcome

Because Brown did not raise the substance of his § 851 predicate objections below and withdrew objections at sentencing, the Eleventh Circuit reviewed for plain error. Likewise, he did not preserve a challenge to career-offender status. Plain error requires a clear or obvious error that affects substantial rights and seriously affects the fairness, integrity, or public reputation of judicial proceedings. That demanding standard drove much of the court’s restraint, especially on the Florida “cocaine” overbreadth arguments.

Impact

Doctrinal extension to § 851 predicates: The opinion formally imports the ACCA’s time-of-conviction principle into § 851’s “felony drug offense” inquiry. In the Eleventh Circuit, practitioners should expect courts to assess § 851 predicates based on the law at the time of the prior conviction, rejecting arguments predicated on later descheduling or definitional narrowing. This matters for substances like ioflupane whose regulatory status has evolved.
Florida “cocaine” overbreadth: The panel again signals skepticism—especially on plain-error review—toward stereoisomer-based overbreadth attacks on Florida cocaine statutes. Absent binding authority proving overbreadth and a realistic probability of prosecution for a non-federal isomer, such arguments are unlikely to succeed without preservation and a developed record.
§ 851 procedure and harmless error: While district courts should conduct § 851(b) colloquies, the failure to do so will often be deemed harmless if the predicates are more than five years old (and thus time-barred from validity challenges). Defendants must preserve timely, specific objections to avoid this outcome.
Career offender and Florida aggravated assault: Somers continues to control: Florida aggravated assault counts as a “crime of violence” under the Guidelines’ elements clause. That holding will routinely supply one predicate for career-offender status when paired with a qualifying drug offense.
Sentencing ceilings: Where the Guidelines range exceeds § 841(b)(1)(C)’s default 20-year cap, the § 851 enhancement (if valid) becomes outcome-determinative, as it raises the maximum to 30 years. Defense counsel who can defeat § 851 can force the statutory cap to govern, even when the Guidelines are higher.
Publication status: The opinion is unpublished and thus non-precedential in the Eleventh Circuit. Nevertheless, it is a strong indicator of how panels will apply Brown and Jackson in the § 851 context.

Complex Concepts Simplified

Categorical approach: Courts compare elements of the prior statute of conviction to the federal definition; they generally do not look at the specific facts of the defendant’s prior conduct.
Backward-looking (time-of-conviction) rule: Whether a prior offense qualifies as a predicate is assessed based on the law in force when the defendant was convicted of that prior offense. Later changes to drug schedules or definitions do not retroactively strip the conviction of its predicate status.
“Felony drug offense” (§ 802(44)): An offense punishable by more than one year that prohibits conduct related to narcotic drugs, marijuana, anabolic steroids, or depressant/stimulant substances. The opinion treats this § 802(44) definition as controlling for § 851 in this case.
§ 851 procedure:
- Government must file an information specifying the prior convictions to be used for enhancement (§ 851(a)).
- Court should ask the defendant to affirm/deny those convictions and warn that failure to challenge before sentencing bars later attacks (§ 851(b)).
- If disputed, the court must hold a hearing to resolve the challenge (§ 851(c)). The hearing may be conducted as part of sentencing.
- Validity challenges to convictions older than five years are barred (§ 851(e)).
Plain error vs. harmless error:
- Plain error applies when the defendant failed to preserve an objection; reversal requires an obvious legal error affecting substantial rights and the fairness of proceedings.
- Harmless error applies when error occurred but did not affect the outcome (e.g., a missing § 851(b) colloquy where § 851(e) would bar the challenge anyway).
Isomers and overbreadth: Federal law includes optical and geometric isomers of cocaine; Florida law references “stereoisomers.” Overbreadth arguments assert the state law covers more substances. The Eleventh Circuit has been skeptical that any real-world prosecutions hinge on nongeometric diastereomers of cocaine.
Career offender (U.S.S.G. § 4B1.1): Applies if the instant offense is a qualifying felony and the defendant has at least two prior felony convictions for a “crime of violence” or a “controlled substance offense.” Florida aggravated assault—requiring at least knowing conduct—qualifies as a “crime of violence” under binding Circuit precedent.

Practice Notes

Defense counsel should preserve specific § 851 predicate challenges and request the § 851(b) colloquy. Absent preservation, the odds of reversal on plain-error review are low.
When the Guideline range exceeds 20 years for § 841(b)(1)(C) offenses, defeating the § 851 enhancement can cap the sentence at 240 months—potentially game-changing.
Government § 851 informations can list multiple convictions; to limit exposure, defendants should move to strike legally ineligible priors early.
Florida aggravated assault remains a potent predicate for career-offender status. Unless and until Somers is overruled, challenges in this Circuit will be foreclosed.
Overbreadth arguments based on Florida’s cocaine definition require careful scientific and legal development to show a realistic probability of prosecution for conduct outside the federal definition. On a cold record and plain-error review, they will almost certainly fail.

Conclusion

The Eleventh Circuit’s unpublished opinion in United States v. Brown, Jr. significantly clarifies that the Supreme Court’s backward-looking predicate analysis, forged in ACCA jurisprudence, governs § 851’s “felony drug offense” inquiry as well. That holding sustains the use of older state drug convictions as § 851 predicates even when the controlled-substances landscape later shifts (as with ioflupane). The court also reaffirms that omissions in the § 851(b) colloquy can be harmless where § 851(e) bars validity challenges due to age, and that a § 851(c) “hearing” may be conducted within the sentencing proceeding. On the Guidelines side, Somers continues to cement Florida aggravated assault as a “crime of violence,” enabling career-offender designations when paired with a qualifying drug offense.

Although non-precedential, this decision is a strong signal of how Eleventh Circuit panels will handle § 851 predicate questions post–Brown v. United States. Practically, it underscores the importance of timely, specific objections, the limited utility of isomer-based overbreadth arguments on plain-error review, and the determinative effect a valid § 851 enhancement can have on sentences under § 841(b)(1)(C).