United States v. Oral Roger Russell, 994 F.3d 1230

Background

Russell pled guilty to possessing with intent to distribute 50 grams or more of crack cocaine; plea Factual Basis and PSR attributed ~441.2 grams; he was sentenced as a career offender to 262 months’ imprisonment and did not appeal.
Fair Sentencing Act (2010) raised crack quantity thresholds; First Step Act §404 (2018) authorized district courts to retroactively reduce sentences for "covered offenses."
Russell sent a pro se one-page letter asking the district court to appoint counsel to help him file a First Step Act motion; the court sua sponte treated the letter as a First Step Act motion, ordered a government response, and denied relief without giving Russell an opportunity to be heard.
Russell filed a pro se motion for reconsideration, submitting rehabilitative evidence and arguing eligibility; the district court again denied relief, stating either that Russell was ineligible (due to the drug quantity) or that it would decline to exercise discretion.
On appeal the government conceded, post-Jones, that Russell is eligible; the Eleventh Circuit vacated and remanded because the district court’s orders were ambiguous about whether it thought Russell ineligible or merely declined to exercise discretion and because the record lacked an adequate explanation for denial.
A concurring judge would additionally require remand because the court recharacterized Russell’s letter as a substantive First Step Act motion without notice or opportunity to withdraw, invoking Castro concerns about prejudice from recharacterization.

Issues

Issue	Russell's Argument	Government's Argument	Held
1) Is Russell eligible for relief under First Step Act §404?	Conviction for an offense with the §841 element (50 g+) makes him a "covered offense" and he did not receive the lowest Fair Sentencing Act penalty.	Initially argued ineligibility (pointing to higher factual drug quantity); later conceded eligibility post-Jones.	Russell is eligible under Jones framework.
2) May the district court look to sentencing findings of drug quantity to deny relief?	Use the statutory element (the offense of conviction) to determine coverage; prior sentencing findings do not automatically preclude relief.	Court relied on PSR/plea factual quantity to say penalty unchanged by Fair Sentencing Act.	Court must follow Jones: consider charging/plea/sentencing record, but eligibility turns on statutory element and whether sentence already equals the Fair Act minimum; here eligibility exists.
3) Did the district court abuse its discretion in denying a reduction without adequate explanation?	District court provided no reasoned basis showing consideration of §3553(a) arguments; appellate review therefore impossible.	Government contends remand is unnecessary because district court would have denied relief on the merits.	Vacated and remanded: record and orders lack sufficient explanation to know whether denial was for ineligibility or discretionary denial; meaningful appellate review is not possible.
4) Was recharacterization of Russell’s letter as a First Step Act motion without notice permissible?	Recharacterization deprived Russell of notice and his one opportunity to seek First Step Act relief; Castro requires warning/opportunity to withdraw.	District court may recharacterize pro se filings to match substance; no prejudice argued.	Majority reserves the point but concurrence holds recharacterization without warning was error and warrants remand; the majority vacated and remanded on the explanation/ambiguity ground.

Key Cases Cited

United States v. Jones, 962 F.3d 1290 (11th Cir. 2020) (sets framework for First Step Act §404 eligibility and review)
Castro v. United States, 540 U.S. 375 (2003) (district court must warn pro se litigant before recharacterizing filings that carry adverse consequences)
Apprendi v. New Jersey, 530 U.S. 466 (2000) (drug-quantity findings that increase punishment must be made by a jury beyond a reasonable doubt)
Johnson v. United States, 877 F.3d 993 (11th Cir. 2017) (courts must adequately explain sentencing decisions to permit meaningful appellate review)
Chavez-Mesa v. United States, 138 S. Ct. 1959 (2018) (district courts must provide enough explanation to allow appellate review of sentencing choices)
Dorsey v. United States, 567 U.S. 260 (2012) (addressed Fair Sentencing Act temporal application)
Gall v. United States, 552 U.S. 38 (2007) (sentencing explanations requirement and reasonableness review)
Harris v. United States, 989 F.3d 908 (11th Cir. 2021) (standard of review for First Step Act discretionary denials)