Whiteside v. United States

• Decision Date: 08 April 2014
• Docket Number: No. 13–7152.,13–7152.
• Citation: 748 F.3d 541
• Parties: Deangelo Marquis WHITESIDE, Petitioner–Appellant, v. UNITED STATES of America, Respondent–Appellee.
• Court: U.S. Court of Appeals — Fourth Circuit

748 F.3d 541

Deangelo Marquis WHITESIDE, Petitioner–Appellant,

v.UNITED STATES of America, Respondent–Appellee.

No. 13–7152.

United States Court of Appeals, Fourth Circuit.

Argued: Jan. 29, 2014.

Decided: April 8, 2014.

ARGUED:Ann Loraine Hester, Federal Defenders of Western North Carolina, Inc., Charlotte, North Carolina, for Appellant. Amy Elizabeth Ray, Office of the United States Attorney, Asheville, North Carolina, for Appellee. ON BRIEF: Henderson Hill, Executive Director, Federal Defenders of Western North Carolina, Inc., Charlotte, North Carolina, for Appellant. Anne M. Tompkins, United States Attorney, Office of the United States Attorney, Charlotte, North Carolina, for Appellee.

Before WILKINSON and GREGORY, Circuit Judges, and DAVIS, Senior Circuit Judge.

Vacated and remanded for resentencing by published opinion. Judge GREGORY wrote the majority opinion, in which Senior Judge DAVIS joined. Senior Judge DAVIS wrote a separate concurring opinion, and Judge WILKINSON wrote a dissenting opinion.

GREGORY, Circuit Judge:

This case presents the question of whether a federal inmate may use a 28 U.S.C. § 2255 motion to challenge a sentence that was based on the career offender enhancement under the United States Sentencing Guidelines when subsequent case law reveals the enhancement to be inapplicable to him. We find that he may, and in doing so hold that the mistake results in a fundamental miscarriage of justice that is cognizable on collateral review. For the reasons stated below, we grant a certificate of appealability, vacate the petitioner's sentence, and remand the case for resentencing.

I.

The facts relevant to this appeal are brief and largely undisputed. In July 2009, the petitioner-appellant, Deangelo Whiteside, was indicted on charges of possession with intent to distribute at least 50 grams of crack cocaine, in violation of 21 U.S.C. § 841(a)(1). Shortly thereafter, the government filed an Information pursuant to 21 U.S.C. § 851 notifying Whiteside that it intended to seek an enhanced penalty based on a 2002 North Carolina felony drug conviction.

Whiteside then entered into a plea agreement with the government. The agreement acknowledged the possibility that Whiteside might be designated a career offender under U.S.S.G. § 4B1.1. It also contained several waivers of Whiteside's rights to challenge his conviction and sentence in an appeal or collateral proceeding. As discussed in more detail below, the parties dispute whether these provisions bar Whiteside's current claim.

Whiteside pled guilty to the offense in October 2009 and the probation office began preparing a presentence report. The probation officer concluded that Whiteside was responsible for 1,951.9 grams of powder cocaine and 468.3 grams of crack cocaine, generating a base offense level of 32.¹ The probation officer also determined that a 1999 North Carolina conviction for felony possession with intent to sell and deliver cocaine, along with the 2002 drug conviction, qualified Whiteside for the career offender enhancement under § 4B1.1.² The enhancement raised Whiteside's base offense level to 37 and his criminal history category from V to VI. After a three-level reduction for acceptance of responsibility, Whiteside's Sentencing Guidelines range was 262 to 327 months in prison. In light of the government's § 851 Information, the prior felony drug convictions also subjected Whiteside to a mandatory minimum term of imprisonment of twenty years.

Prior to Whiteside's sentencing hearing, the government filed a § 5K1.1 motion seeking a downward departure based on the petitioner's substantial assistance. The government recommended that Whiteside receive a sentence based on a total offense level of 32 and a criminal history category VI, which yielded a 210 to 262 month Guidelines range. The district court granted the government's motion and, on July 9, 2010, sentenced Whiteside to 210 months' imprisonment, a sentence below both his Guidelines range and the twenty-year mandatory minimum.

On August 17, 2011, this Court issued its en banc decision in United States v. Simmons, 649 F.3d 237 (4th Cir.2011). In Simmons, we overruled circuit precedent and held that a North Carolina conviction is a crime punishable by a term of imprisonment exceeding one year only when the defendant's particular criminal history and the nature of his offense so warrant. See id. at 247 & n. 9. It is undisputed that under Simmons, Whiteside's predicate convictions were not punishable by more than a year in prison, and were he sentenced today he would not be subject to either the career offender enhancement or the twenty-year statutory minimum penalty.

Whiteside argues that without those enhancements he would have faced a Guidelines range of 140 to 175 months and a statutory term of ten years to life. Assuming the same downward departure based on substantial assistance—eighty percent of the low end of the Guidelines—Whiteside contends that his sentence would have been 112 months, roughly eight years shorter than the sentence he received.

On May 18, 2012, Whiteside filed a 28 U.S.C. § 2255 motion to vacate his sentence. He argued that, in light of Simmons, he did not qualify as a career offenderand that he should be resentenced without the enhancement.³ The district court dismissed Whiteside's motion to vacate, concluding that it was untimely, that Whiteside waived his right to collaterally attack his sentence in his plea agreement, and that he was not eligible for post-conviction relief because he received a sentence beneath the statutory maximum. The district court also declined to issue a certificate of appealability. This appeal followed.

II.

A.

We must first address whether Whiteside's motion to vacate is procedurally barred. The first question on this point is whether Whiteside in his plea agreement waived his right to collaterally attack his sentence. We review this issue de novo. See United States v. Copeland, 707 F.3d 522, 528 (4th Cir.2013).

The relevant portions of Whiteside's plea agreement are as follows:

20. Defendant, in exchange for the concessions made by the United States in this plea agreement, waives all such rights to contest the conviction except for: (1) claims of ineffective assistance of counsel or (2) prosecutorial misconduct. Defendant also ... knowingly and expressly waives all rights conferred by 18 U.S.C. § 3742 or otherwise to appeal whatever sentence is imposed with the two exceptions set forth above. Defendant also reserves right to appeal ruling as to career offender pursuant to USSG § 4B1.1.

21. Also, in exchange for the concessions made by the United States, defendant agrees that the United States preserves all its rights and duties with respect to appeal as set forth in 18 U.S.C. § 3742(b), while the defendant waives all rights to appeal or collaterally attack the sentence of conviction with the two exceptions set forth above.

The government contends that under these terms, Whiteside waived his right to collaterally attack his sentence on all grounds except that of ineffective assistance of counsel or prosecutorial misconduct. We disagree, finding that the language of the plea agreement is ambiguous and does not clearly specify which rights were waived.

In short, the paragraphs quoted above contradict one another. Paragraph 20 states that the defendant may challenge his conviction only on the two grounds just mentioned. It goes on to state that the defendant retains his right to appeal his sentence with respect to the career offender enhancement. However, paragraph 21 then states that he may only challenge his sentence (through either a direct appeal or § 2255 motion) on ineffective assistance or prosecutorial misconduct grounds. This simply does not make sense. Either the parties intended to limit the defendant's right to challenge his sentence to two grounds, a result which would render the career offender reference at the end of paragraph 20 superfluous, or the statement in paragraph 21 limiting Whiteside's rights to challenge his sentence to two grounds was a mistake and should instead have cited three possible bases for a challenge. Either reading is problematic, leaving it impossible to say exactly which rights Whiteside waived. When a plea agreement is unclear, it must be construed against the government. See United States v. Jordan, 509 F.3d 191, 199–200 (4th Cir.2007). As such, we hold that Whiteside did not waive his right to challenge the career offender enhancement in a collateral proceeding.

B.

We next consider whether Whiteside's motion to vacate was timely. A § 2255 petitioner ordinarily has one year from the date on which his conviction becomes final in order to file a motion to vacate. 28 U.S.C. § 2255(f)(1). Whiteside's conviction became final on August 17, 2010, but he did not file his motion until May 18, 2012, well beyond the one-year period. However, the statute of limitations in § 2255(f)(1) may be equitably tolled in certain circumstances. Specifically, equitable tolling applies if the petitioner can show “ ‘(1) that he has been pursuing his rights diligently, and (2) that some extraordinary circumstance stood in his way’ and prevented timely filing.” Holland v. Florida, 560 U.S. 631, 649, 130 S.Ct. 2549, 177 L.Ed.2d 130 (2010) (quoting Pace v. DiGuglielmo, 544 U.S. 408, 418, 125 S.Ct. 1807, 161 L.Ed.2d 669 (2005)). Relief is limited to cases “where—due to circumstances external to the party's own conduct—it would be unconscionable to enforce the limitation period against the party and gross injustice would result.” United States v. Sosa, 364 F.3d 507, 512 (4th Cir.2004).

As explained below, we find that the erroneous application of the career offender enhancement worked a gross miscarriage of justice. We also hold that Whiteside pursued his rights diligently by filing his motion within a year of our decision in Simmons and that extraordinary circumstances prevented him from filing the motion...