United States v. Freeman
17 F.4th 255
| 2d Cir. | 2021Background
- Freeman was indicted for conspiring to distribute ≥5 kg cocaine and ≥280 g cocaine base; a §851 information raised his recidivist mandatory minimums.
- Plea agreement and allocution correctly stated a 20‑year mandatory minimum imprisonment (life max) but misstated the mandatory minimum supervised‑release term as 5 years (the correct statutory minimum was 10).
- The PSR correctly listed a 10‑year supervised‑release minimum; Freeman did not object to the PSR and initially did not seek to withdraw his plea.
- The district court later noted the Rule 11 error, Freeman moved to withdraw his plea before sentencing (citing reliance on the plea terms, coercion re: his girlfriend, and ineffective assistance).
- The district court denied withdrawal as the Rule 11 error was harmless (noting the First Step Act reduced imprisonment minimum from 20 to 15 years, leaving the combined mandatory minimum unchanged) and Freeman’s sworn allocution and other record statements contradicted his coercion/innocence claims.
- Freeman was sentenced to 15 years’ imprisonment and 10 years’ supervised release and appealed, raising Rule 11 harmlessness, voluntariness, and ineffective assistance claims.
Issues
| Issue | Plaintiff's Argument (United States) | Defendant's Argument (Freeman) | Held |
|---|---|---|---|
| Standard/burden on appeal for preserved Rule 11 errors | Government: district denial reviewed for abuse of discretion and defendant bears burden | Freeman: harmless‑error standard should apply but he bears burden | Court: Where defendant moved to withdraw before sentencing, preserved Rule 11 error is reviewed for harmless error and the government bears the burden on appeal to show no effect on substantial rights (Vonn/Dominguez Benitez line). |
| Whether misstatement of supervised‑release mandatory minimum was harmless | Error was harmless given the overall penalties known, PSR correction, and First Step Act keeping combined mandatory minimum same | Misstatement induced plea; affected substantial rights and plea voluntariness | Held harmless: the record shows Freeman knew he faced life supervised release, PSR corrected error, and government proved beyond a reasonable doubt Freeman would have pleaded anyway. |
| Voluntariness of plea (factual basis and coercion claims) | Freeman’s sworn allocution admitted the drug quantities and denied coercion; those admissions are presumptively reliable | Freeman claims he was confused about quantities and coerced (girlfriend’s prosecution) | Court: Freeman’s sworn answers at allocution and other record statements contradict later claims; plea was knowing and voluntary. |
| Ineffective assistance of counsel (failure to catch Rule 11 error and challenge drug quantities) | Any counsel error caused no prejudice because Freeman would have pleaded regardless and his sworn admissions undermine quantity challenge | Counsel was deficient for failing to identify the Rule 11 error and challenge overcharging | Held: Even if counsel erred, Freeman cannot show prejudice under Strickland; his ineffectiveness claim fails. |
Key Cases Cited
- United States v. Vonn, 535 U.S. 55 (2002) (preserved Rule 11 errors on appeal are subject to harmless‑error review and government bears burden)
- Dominguez Benitez v. United States, 542 U.S. 74 (2004) (reiterating Vonn and harmless‑error review for Rule 11 violations)
- United States v. Andrades, 169 F.3d 131 (2d Cir. 1999) (discussing Rule 11 warnings and harmless error in plea withdrawal context)
- United States v. Saenz, 969 F.2d 294 (7th Cir. 1992) (misstatement of supervised‑release minimum held harmless where maximum life was known)
- Blackledge v. Allison, 431 U.S. 63 (1977) (sworn plea allocutions carry strong presumption of verity)
- United States v. Torres, 129 F.3d 710 (2d Cir. 1997) (defendant’s post‑allocution contradictions to sworn statements insufficient to withdraw plea)
- Strickland v. Washington, 466 U.S. 668 (1984) (two‑prong ineffective assistance standard)
- Hill v. Lockhart, 474 U.S. 52 (1985) (applying Strickland in plea context)
- United States v. Johnson, 850 F.3d 515 (2d Cir. 2017) (government must show harmlessness beyond a reasonable doubt when Rule 11 error raised below)
- United States v. Ferrara, 954 F.2d 103 (2d Cir. 1992) (Rule 11(h) permits disregarding non‑prejudicial technical violations)