Deangelo Whiteside v. United States
2014 U.S. App. LEXIS 6425
4th Cir.2014Background
- Deangelo Whiteside pleaded guilty in 2009 to possession with intent to distribute crack and was sentenced in 2010 after the district court applied the U.S.S.G. § 4B1.1 career-offender enhancement and a § 851 information—producing a Guidelines range of 262–327 months; the court granted a § 5K1.1 downward departure and imposed 210 months.
- In 2011 this Court (en banc) decided United States v. Simmons, narrowing which North Carolina convictions qualify as predicate offenses; under Simmons Whiteside’s prior convictions would not qualify.
- Whiteside filed a § 2255 motion in May 2012 arguing his career-offender enhancement (and the related statutory minimum) were improperly applied in light of Simmons.
- The district court dismissed the § 2255 motion as untimely, finding waiver and procedural bars, and declined a certificate of appealability; Whiteside appealed.
- The Fourth Circuit (majority) held: (1) the plea waiver was ambiguous and did not bar collateral review; (2) equitable tolling applied because pre-Simmons precedent made relief futile; and (3) an erroneous career-offender designation can amount to a fundamental miscarriage of justice cognizable on collateral review — vacating and remanding for resentencing.
Issues
| Issue | Plaintiff's Argument | Defendant's Argument | Held |
|---|---|---|---|
| Whether plea agreement waived § 2255 challenge to career-offender designation | Whiteside: waiver ambiguous and reserved right to appeal career-offender ruling | Government: plea-waiver plainly forfeited collateral attack except ineffective assistance or prosecutorial misconduct | Waiver ambiguous (contradictory paragraphs) and construed against government; Whiteside did not waive collateral challenge to career-offender status |
| Whether § 2255 one-year statute of limitations bars Whiteside’s motion | Whiteside: equitable tolling applies because Simmons made earlier petitions futile; he filed promptly after Simmons | Government: Whiteside could have filed earlier; futility is not an extraordinary circumstance | Equitable tolling applied: prior circuit precedent made success impossible before Simmons, so filing within a year of Simmons was diligent and timely |
| Whether an erroneous career-offender enhancement is cognizable on collateral review | Whiteside: enhancement is so consequential it causes a fundamental miscarriage of justice; he would have received a substantially lower sentence | Government: post-Booker advisory Guidelines errors are ordinary sentencing errors not remedyable under § 2255 absent extra factors; finality favors denial | Erroneous application of career-offender enhancement can constitute a fundamental miscarriage of justice cognizable on § 2255 collateral review; vacated and remanded for resentencing |
| Whether the sentence being below the statutory maximum bars relief | Whiteside: being below maximum does not cure the fundamental unfairness of a misapplied career-offender status | Government: sentence under statutory maximum is lawful and non-reviewable via § 2255 for Guidelines errors | Court: being below statutory maximum does not preclude relief; career-offender status materially anchors sentencing and its misapplication can be fundamentally unjust |
Key Cases Cited
- United States v. Simmons, 649 F.3d 237 (4th Cir. en banc 2011) (narrowed what state convictions qualify as predicates for career-offender status)
- Holland v. Florida, 560 U.S. 631 (2010) (equitable tolling standard for habeas petitions; courts must apply equitable principles flexibly)
- Davis v. United States, 417 U.S. 333 (1974) (post-conviction change that renders conduct noncriminal is a miscarriage of justice cognizable on collateral review)
- Booker v. United States, 543 U.S. 220 (2005) (rendered Guidelines advisory; effect on collateral-review analysis discussed)
- United States v. Mikalajunas, 186 F.3d 490 (4th Cir. 1999) (ordinary Guidelines misapplications typically not a miscarriage of justice)
- Narvaez v. United States, 674 F.3d 621 (7th Cir. 2012) (initially held career-offender misclassification could be a miscarriage of justice; post-Booker limitation later articulated)
- Sun Bear v. United States, 644 F.3d 700 (8th Cir. 2011) (en banc) (held career-offender misapplication is ordinary Guidelines error not cognizable on § 2255)
- Spencer v. United States, 727 F.3d 1076 (11th Cir. 2013) (panel held erroneous career-offender designation can be a fundamental defect cognizable on collateral review)