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Whiteside v. United States

United States Court of Appeals, Fourth Circuit

April 8, 2014

UNITED STATES OF AMERICA, Respondent - Appellee

Argued January 29, 2014.

Page 542

Appeal from the United States District Court for the Western District of North Carolina, at Asheville. (1:09-cr-00069-MR-1; 1:12-cv-00118-MR). Martin K. Reidinger, District Judge.


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.


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. 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.


Page 543

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.


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.

Page 544

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 offender

Page 545

and 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.



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

Page 546

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.


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 earlier. Our decision is based on the simple fact that our case law prior to Simmons absolutely foreclosed Whiteside's current argument. In United States v. Jones, 195 F.3d 205 (4th Cir. 1999), and then again in United States v. Harp, 406 F.3d 242 (4th Cir. 2005), we rejected the arguments that we later accepted in Simmons. Had Whiteside filed a habeas petition prior to Simmons it would have been summarily denied on the basis of these decisions, as was the case for numerous other petitioners. See, e.g., Robinson v. United States, No. 5:07-cv-140, 2011 WL 676184 (E.D.N.C. Feb. 18, 2011); Jordan v. United States, No. 1:09-cv-816, 2010 WL 2347076 (M.D.N.C. June 3, 2010). We think this condition -- the complete lack of any chance at success -- constitutes an " extraordinary circumstance" that warrants equitable considerations. The obstacle was clearly external to Whiteside -- indeed, it was our incorrect interpretation of which North Carolina convictions support the career offender enhancement that prevented him from seeking relief. Once this was corrected and Whiteside had an opportunity for meaningful review, he filed his motion in a timely manner. This is not a case of a petitioner who has slept on his rights and later seeks relief from his indolence; instead, once Whiteside's right to review obtained any real significance, he acted.

The government nevertheless contends that Whiteside should have filed his petition prior to Simmons in spite of its sure defeat. In addition to simply having an air of absurdity about it, this argument would lead to the perverse result of reading the AEDPA's time limitations to encourage inmates to flood the courts with baseless petitions on the off chance that the law might one day change. Further, if Whiteside had filed his petition prior to Simmons and it had been denied, his current claim would possibly be barred as a successive

Page 547

petition. See § 2255(h).[4] Given the timing of Whiteside's conviction and our decision in Simmons, the result of the government's position is that at no point would Whiteside have been entitled to relief from an error that we consider to be a fundamental miscarriage of justice. We cannot accept such an outcome.

Nor are we bound to. We recognize that we previously held that the futility of a petitioner's claim does not constitute a circumstance external to his control. Minter v. Beck, 230 F.3d 663, 666 (4th Cir. 2000). However, our decision in Minter preceded the recent Supreme Court decision in Holland, which adopted an expansive reading of the role of equity in habeas cases. In Holland, the Supreme Court reviewed an Eleventh Circuit rule holding that attorney negligence in failing to meet a filing deadline may never serve as a basis for equitable tolling absent a showing of bad faith or dishonesty on the part of the attorney. 560 U.S. at 644. The Court rejected this rule as overly rigid. Noting equity's longstanding role in habeas relief, the Court stated that principles of equitable tolling are consistent with the " AEDPA's basic purpose of eliminating delays . . . without undermining basic habeas corpus principles and by harmonizing the statute with prior law, under which a petition's timeliness was always determined under equitable principles." Id. at 648. In light of this, the Court held that the AEDPA's statutes of limitations " do[] not set forth 'an inflexible rule requiring dismissal whenever' its 'clock has run.'" Id. at 645 (quoting Day v. McDonough, 547 U.S. 198, 205, 126 S.Ct. 1675, 164 L.Ed.2d 376 (2010)). The Court further explained that, while courts of equity are of course governed by " rules and precedents," equity also requires " flexibility" and the avoidance of " mechanical rules." Id. at 649-50 (internal quotation marks and citations omitted); see also id. at 650 (courts must " exercise judgment in light of prior precedent, but with awareness of the fact that specific circumstances, often hard to predict in advance, could warrant special treatment in an appropriate case" ).

Although Holland dealt with attorney misconduct, an issue not before this Court, the decision's broader point was that the " exercise of a court's equity powers . . . must be made on a case-by-case basis . . . ." Id. at 649-50; See also Jones v. United States, 689 F.3d 621, 626-28 (6th Cir. 2012) (citing Holland and applying equitable tolling where inmate filed petition within three months of Supreme Court's decision in Begay v. United States, 553 U.S. 137, 128 S.Ct. 1581, 170 L.Ed.2d 490 (2008), entitling him to relief). To the extent Minter created a bright-line rule that futility may not constitute an extraordinary circumstance, Holland requires that we at least apply such a rule on a case-by-case basis.[5]

Page 548

When examining the particular circumstances of Whiteside's case, we find that he satisfies the requirements necessary for equitable tolling. He has successfully demonstrated that his sentence amounted to a fundamental miscarriage of justice. Correcting unjust incarcerations is the whole purpose of § 2255. As the Supreme Court explained in Holland, the AEDPA's time limitations do not foreclose this relief to all those who are unable to meet the statute's deadlines. Had Whiteside filed within the one-year statute of limitations, he likely would have been forced to suffer the injustice with no future chance at relief. The timing of our decisions should not be the sole determinant of a petitioner's access to justice. Whiteside's inability to obtain meaningful relief prior to our decision in Simmons is an extraordinary circumstance that warrants some flexibility on our behalf in order " to accord all the relief necessary to correct . . . particular injustices." Id. at 650 (quoting Hazel-Atlas Glass Co. v. Hartford-Empire Co., 322 U.S. 238, 248, 64 S.Ct. 997, 88 L.Ed. 1250, 1944 Dec. Comm'r Pat. 675 (1944)).[6] Accordingly, we equitably toll the limitations period and review Whiteside's claim.


Turning to the merits of the case, we are asked to decide whether a petitioner may challenge his sentence on collateral review based on an incorrect application of the career offender enhancement. Because it is the only response that is both consistent with the realities of federal sentencing and just, we answer yes.

Section 2255 allows federal prisoners to move to set aside sentences that are imposed " in violation of the Constitution or laws of the United States." Thus, § 2255 relief is not limited to constitutional errors. See Davis v. United States, 417 U.S. 333, 345-56, 94 S.Ct. 2298, 41 L.Ed.2d 109 (1974). However, a non-constitutional error may only serve as a basis for collateral attack when it involves " a fundamental defect which inherently results in a complete miscarriage of justice." United States v. Addonizio, 442 U.S. 178, 185, 99 S.Ct. 2235, 60 L.Ed.2d 805 (1979) (internal quotation marks omitted). The Supreme Court has provided only the general contours of what constitutes a complete miscarriage of justice. For example, in Hill v. United States, 368 U.S. 424, 429, 82 S.Ct. 468, 7 L.Ed.2d 417 (1962), the Court reviewed a sentencing judge's failure to inform a defendant that he had the right to speak at his sentencing hearing. The Court characterized this mistake as a mere failure to follow the formal requirements of a rule, and held that it did not constitute a basis for habeas relief. Id.; See also Peguero v. United States, 526 U.S. 23,

Page 549

119 S.Ct. 961, 143 L.Ed.2d 18 (1999) (failure to inform defendant of the right to appeal where defendant knew of the right); United States v. Timmreck, 441 U.S. 780, 99 S.Ct. 2085, 60 L.Ed.2d 634 (1979) (failure to mention a special parole term at Rule 11 hearing). In contrast, in Davis the Court held that a post-conviction change in the law that rendered the defendant's conduct no longer criminal is correctable on collateral review because " [t]here can be no doubt that such a circumstance inherently results in a complete miscarriage of justice . . . ." 417 U.S. at 346 (internal quotation marks omitted).

Like a number of our sister circuits, we have held that " ordinary misapplication of the guidelines does not amount to a miscarriage of justice." United States v. Mikalajunas, 186 F.3d 490, 496 (4th Cir. 1999) (collecting cases); see also United States v. Pregent, 190 F.3d 279, 283-84 (4th Cir. 1999). However, we have not offered a considered explanation of what constitutes an " ordinary" Guidelines error as opposed to something more fundamental. In Mikalajunas, we held that an improper two-level enhancement for restraint of the victim did not amount to a complete miscarriage of justice. 186 F.3d at 496. In Pregent, we considered whether a defendant whose criminal history had been wrongly calculated resulting in a sentence four months too long was entitled to seek relief from the supervised release portion of his sentence. 190 F.3d at 283 & n.4. Although we assumed that the error was cognizable on collateral review, we dismissed the defendant's claim as untimely. We have not had occasion to address the specific issue presented in this case: whether the career offender enhancement is so significant that its improper application amounts to a fundamental miscarriage of justice.[7]

Three courts of appeals have, however, confronted this precise question, albeit with differing results. In Sun Bear v. United States, 644 F.3d 700 (8th Cir. 2011) (en banc), the Eighth Circuit considered the question following the Supreme Court's decision in Begay, which limited the category of defendants eligible for career offender status by narrowing the definition of a crime of violence. See 553 U.S. at 148.[8] Sun Bear held that career offender status is an " ordinary question[] of [G]uideline interpretation," and that misapplication of this status is not an error that results " in a complete miscarriage of justice." 644 F.3d at 704 (citation omitted).[9]

Page 550

The Seventh Circuit initially reached a different conclusion. In Narvaez, the court held that because of changes to the law under Begay and Chambers v. United States, 555 U.S. 122, 129 S.Ct. 687, 172 L.Ed.2d 484 (2009), the defendant " never should have been classified as a career offender and never should have been subjected to the enhanced punishment reserved for such repetitive and violent offenders." Narvaez, 674 F.3d at 627 (emphasis omitted). The court deemed the resulting career offender sentence a miscarriage of justice even though it fell beneath the applicable statutory maximum. Id. at 629. The court explained:

The imposition of the career offender status branded Mr. Narvaez as a malefactor deserving of far greater punishment than that usually meted out for an otherwise similarly situated individual who had committed the same offense. It created a legal presumption that he was to be treated differently from other offenders because he belonged in a special category reserved for the violent and incorrigible. No amount of evidence in mitigation or extenuation could erase that branding or its effect on his sentence. His designation as a career offender simply took as unchallenged a premise that was not true and gave him no way of avoiding the consequences of that designation.


Narvaez, however, dealt with a sentence issued prior to United States v. Booker, 543 U.S. 220, 125 S.Ct. 738, 160 L.Ed.2d 621 (2005), when the Guidelines remained mandatory. Shortly after the Narvaez decision, the Seventh Circuit limited its holding to sentences issued under the mandatory Guidelines. See Hawkins v. United States, 706 F.3d 820, 824 (7th Cir. 2013) supplemented on denial of reh'g, 724 F.3d 915 (7th Cir. 2013), cert. denied, 134 S.Ct. 1280, 188 L.Ed.2d 299 (Feb. 24, 2014). In Hawkins, the court held that post-Booker, Guidelines errors were " less serious," and that as long as the sentence imposed was beneath the statutory maximum it was not subject to correction on collateral review.

The Eleventh Circuit then reached the opposite conclusion of both the Eighth and Seventh Circuits. In a case that was recently vacated pending rehearing en banc, Spencer v. United States, 727 F.3d 1076, 1087 (11th Cir. 2013), vacated pending reh'g en banc, (11th Cir. Mar. 7, 2014), the court stated that an erroneous career offender enhancement amounts to a fundamental miscarriage of justice because " categorization as a career offender is not merely a formal requirement of a criminal procedural rule." This was true because, even post-Booker, " the Guidelines are the heart of the substantive law of federal sentencing." Id. at 1087. Central to the panel's reasoning was the Supreme Court's recent decision in Peugh v. United States, __ U.S. __, 133 S.Ct. 2072, 186 L.Ed.2d 84 (2013).

In Peugh, the Court held that retroactive application of a Guideline that increases a defendant's applicable Guidelines range violates the Ex Post Facto Clause of the Constitution. Id. at 2084. In the process, the Court reaffirmed the important role that the Guidelines play in sentences issued post-Booker. The Court stated that the Guidelines remain " the lodestone of sentencing," id., and that " [t]he post-Booker federal sentencing scheme aims to achieve uniformity by ensuring that sentencing

Page 551

decisions are anchored by the Guidelines . . . ." Id. at 2083 (emphasis added). The Court also noted the requirement that " 'district courts must begin their analysis with the Guidelines and remain cognizant of them throughout the sentencing process.'" Id. (quoting Gall v. United States, 552 U.S. 38, 50 n.6, 128 S.Ct. 586, 169 L.Ed.2d 445 (2007)). The Court explained that this and other hurdles " make the imposition of a non-Guidelines sentence less likely," id. at 2083-84, and that an increase in the Guidelines range still creates a " significant risk of a higher sentence." Id. at 2088. In support, the Court cited Sentencing Commission data showing that, absent a government motion for a variance, roughly eighty percent of defendants since 2007 have received within-Guidelines sentences. Id. at 2084.

Relying on the Supreme Court's recent pronouncements and citing additional statistical data concerning the career offender enhancement, the Spencer panel held, " [w]e cannot pretend that, because of Booker, career offender status no longer matters to sentence length." 727 F.3d at 1088. Instead, " an erroneous career offender Guideline calculation, even though ...

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