“Time-of-State-Conviction” Reaffirmed: Career-Offender Predicates and United States v. Alacaliph Woodard

1. Introduction

The Eleventh Circuit’s unpublished decision in United States v. Alacaliph Woodard, No. 23-10687 (11th Cir. July 7, 2025), provides yet another data-point in the evolving doctrine governing “career offender” status under the U.S. Sentencing Guidelines.

Mr. Alacaliph Woodard was convicted by a jury of three counts: (i) conspiracy to possess methamphetamine with intent to distribute, (ii) possession of methamphetamine with intent to distribute, and (iii) possession of a firearm in furtherance of a drug-trafficking crime. He received a 240-month sentence—already a 120-month downward variance from the 360-month low end of his advisory Guidelines range.

On appeal Woodard pressed two principal arguments:

1. He was improperly designated a “career offender,” because one of his 2007 Alabama drug convictions involved ioflupane, a substance removed from both the federal and Alabama controlled-substance schedules in 2015; and
2. His sentence was procedurally and substantively unreasonable, chiefly because of alleged unwarranted disparities between his sentence and those of his codefendants.

The Eleventh Circuit, per curiam, rejected both arguments and affirmed. Central to the ruling is the Court’s express reliance on (and explanation of) the “time-of-state-conviction” rule that emerged in United States v. Dubois. Although Dubois itself endured an intervening Supreme Court “grant-vacate-remand” (GVR) order, the Eleventh Circuit panel emphasized that the rule remains binding after Dubois III (2025).

2. Summary of the Judgment

The Court held:

• Career-Offender Designation: Valid. The 2007 Alabama conviction qualified as a “controlled substance offense” because ioflupane was a controlled substance at the time Woodard was convicted. Under the “time-of-state-conviction” rule, later descheduling is irrelevant.
• Procedural Reasonableness: No error. The district court correctly calculated the Guidelines range, acknowledged the § 3553(a) factors, and explained its variance.
• Substantive Reasonableness: No abuse of discretion. Woodard was not “similarly situated” to his codefendants: he had an additional firearm conviction, went to trial, and had a more serious criminal history.
• Disposition: Sentence AFFIRMED.

3. Analysis

3.1 Precedents Cited and Their Influence

• United States v. Dubois, 94 F.4th 1284 (11th Cir. 2024) (Dubois I), vacated and remanded, 145 S. Ct. 1041 (2025) (Dubois II), reinstated, 2025 WL 1553843 (11th Cir. June 2, 2025) (Dubois III).
  • Adopted the “time-of-state-conviction” approach to determine whether a state drug offense is a “controlled substance offense” for Guidelines purposes.
  • Woodard relies on Dubois as binding circuit precedent; the panel expressly treats it as controlling.
• United States v. Rahimi, 602 U.S. 680 (2024).
  • The Supreme Court’s Second-Amendment decision prompted the GVR in Dubois II. Rahimi concerned firearm restrictions, not drug predicates, but underscored that the GVR did not undermine Dubois’s drug-law holding.
• Gall v. United States, 552 U.S. 38 (2007).
  • Established the two-step procedural/substantive reasonableness framework. The panel uses Gall’s abuse-of-discretion standard.
• United States v. Dixon, 874 F.3d 678 (11th Cir. 2017).
  • Reaffirmed de novo review for whether a predicate is a “controlled substance offense.”
• United States v. Cavallo, 790 F.3d 1202 (11th Cir. 2015) and companion cases (Duperval, Jayyousi, Azmat).
  • Provide the analytical framework for evaluating alleged sentencing disparities among codefendants.
• Additional authority: Irey (weight of § 3553 factors), Goldman (downward variances), Wayerski, Turner, Amedeo, Baldwin, Steiger, etc.

3.2 Court’s Legal Reasoning

1. Controlled-Substance Predicate:
   The Eleventh Circuit applied a categorical approach: it compared the Alabama statute as it existed in 2007 with the federal definition of a “controlled substance” at that time. Because ioflupane was scheduled then, the conviction categorically qualified.
   Key holding: subsequent descheduling in 2015 does not retroactively strip the conviction of its career-offender status.
2. Procedural Review:
   Using Gall, the panel verified (i) correct Guidelines calculation (360 months–life); (ii) acknowledgment that Guidelines are advisory; (iii) consideration of § 3553(a) factors; (iv) absence of clearly erroneous facts; and (v) an adequate sentencing explanation.
3. Substantive Review:
   The 240-month sentence fell 120 months below the Guidelines floor and far below statutory maxima (life on § 924(c); 20 years on meth counts). The court found no “unwarranted” disparity because:
• Woodard’s firearm conviction and criminal history distinguished him from codefendants.
• He opted for trial while others pleaded guilty—cooperating plea discounts are established and permissible.
• Guidelines calculation inherently addresses disparity concerns.

3.3 Impact of the Judgment

This decision, though unpublished, has practical and doctrinal significance:

• Stabilizes the “Time-of-State-Conviction” Rule: The panel’s express reaffirmation, post-Rahimi, reduces uncertainty created by the GVR saga in Dubois. District courts in the Eleventh Circuit are now on firm footing to use older state drug convictions as career-offender predicates, even if the substance has since been descheduled.
• Guidance for Counsel: Defendants cannot successfully challenge predicate validity merely by pointing to subsequent legislative or regulatory changes unless they can distinguish Dubois (e.g., if the substance was never federally scheduled at any time, or if the state statute is non-divisible and overbroad at the predicate date).
• Sentencing Disparities Claims: The decision reiterates that disparities among codefendants seldom yield relief on appeal unless defendants are “apples-to-apples” comparable. Going to trial, having different counts, or possessing a distinct criminal history will typically defeat such claims.
• Future Litigation:
  • Petitions seeking en banc review of Dubois-based holdings may rise, but this case signals strong panel adherence.
  • Possible Supreme Court interest remains, as descheduling arguments intersect with evolving federal drug policy (e.g., cannabis reclassification debates). Yet Woodard shows the inertia of precedent until the Supreme Court—or Congress—speaks.

4. Complex Concepts Simplified

Career Offender (U.S.S.G. § 4B1.1)

If a defendant is at least 18 and has two prior “crime of violence” or “controlled substance” felonies, his offense level and criminal-history category are automatically enhanced, often vastly increasing the advisory range.

Controlled Substance Offense (U.S.S.G. § 4B1.2(b))

A felony involving manufacture, distribution, or possession with intent to distribute a controlled substance.

Time-of-State-Conviction Rule

For Guidelines purposes, courts look to whether the substance was controlled when the defendant was convicted under state law—not at federal sentencing.

Procedural vs. Substantive Reasonableness (Gall)

Procedural review ensures the sentencing process was correct; substantive review asks whether the final sentence is “too harsh or too lenient” in light of § 3553(a).

Plain Error Review

A stringent standard when an objection was not preserved below; the appellant must show (1) error, (2) that is “plain,” (3) affecting substantial rights, and (4) seriously affecting the fairness or integrity of the proceedings.

5. Conclusion

United States v. Alacaliph Woodard may be unpublished, but it carries weight. It cements the Eleventh Circuit’s allegiance to the “time-of-state-conviction” yardstick for identifying controlled-substance predicates under the Sentencing Guidelines, even after Supreme Court vacatur turbulence. Moreover, it illustrates the high bar for overturning a within- or below-Guidelines sentence on reasonableness grounds, particularly where defendant-specific factors justify differential treatment among codefendants. Practitioners should therefore (a) scrutinize the historical status of substances at the time of prior convictions, and (b) prepare robust, individualized arguments when asserting sentencing disparities. For district courts, the decision validates reliance on accurate Guidelines calculations and careful § 3553(a) explanations to withstand appellate scrutiny.