PUBLISHED

UNITED STATES COURT OF APPEALS

FOR THE FOURTH CIRCUIT

No. 19-6200

QUENTIN ROBERT BRASWELL,

Petitioner - Appellant,

v.

DONNA M. SMITH,

Respondent - Appellee.

Appeal from the United States District Court for the Eastern District of North Carolina, at 

Raleigh. Terrence W. Boyle, Chief District Judge. (5:18-hc-02085-BO) 

Argued: January 28, 2020 Decided: March 4, 2020

Before DIAZ, THACKER, and QUATTLEBAUM, Circuit Judges.

Reversed and remanded by published opinion. Judge Thacker wrote the opinion, in which 

Judge Diaz and Judge Quattlebaum joined.

ARGUED: Jennifer Claire Leisten, OFFICE OF THE FEDERAL PUBLIC DEFENDER, 

Raleigh, North Carolina, for Appellant. Evan Rikhye, OFFICE OF THE UNITED 

STATES ATTORNEY, Raleigh, North Carolina, for Appellee. ON BRIEF: G. Alan 

DuBois, Federal Public Defender, OFFICE OF THE FEDERAL PUBLIC DEFENDER, 

Raleigh, North Carolina, for Appellant. Robert J. Higdon, Jr., United States Attorney, 

Jennifer P. May-Parker, Assistant United States Attorney, OFFICE OF THE UNITED 

STATES ATTORNEY, Raleigh, North Carolina, for Appellee.
2

THACKER, Circuit Judge:

In United States v. Wheeler, this court set forth a four part test to determine whether 

an individual can seek relief from an erroneous sentence in a 28 U.S.C. § 2241 habeas 

corpus petition via the “savings clause” of 28 U.S.C. § 2255(e). 886 F.3d 415 (4th Cir. 

2018). The savings clause provides that a court may entertain a traditional § 2241 petition 

if the petitioner can demonstrate a § 2255 motion is “inadequate or ineffective to test the 

legality of his detention.” Id. at 419 (quoting § 2255(e)). In order for a petitioner to meet 

this standard, he must demonstrate: 

(1) at the time of sentencing, settled law of this circuit or the 

Supreme Court established the legality of the sentence; (2) 

subsequent to the prisoner’s direct appeal and first § 2255 

motion, the aforementioned settled substantive law changed 

and was deemed to apply retroactively on collateral review; (3) 

the prisoner is unable to meet the gatekeeping provisions of § 

2255(h)(2) for second or successive motions; and (4) due to 

this retroactive change, the sentence now presents an error 

sufficiently grave to be deemed a fundamental defect. 

Id. at 429 (the “Wheeler test”).

In this case, Quentin Braswell (“Appellant”) appeals from the district court’s denial 

of his § 2241 petition, which he sought to file via the savings clause. The district court 

reasoned that Appellant could not meet the second prong of the Wheeler test because 

Appellant filed his first § 2255 motion after the applicable change in settled substantive 

law, even though that § 2255 motion was resolved before that change in law was deemed 

to apply retroactively on collateral review. 

We reverse. In applying the second Wheeler prong, we look to the time of the

“retroactive change in law,” i.e., the combination of the change in law and its retroactivity. 
3

886 F.3d at 429. Thus, for the reasons that follow, in the unique circumstance where the 

change in settled substantive law occurred before a petitioner filed his or her first § 2255 

motion, but such change was deemed retroactive after the resolution of the petitioner’s first 

§ 2255 motion, the petitioner satisfies the second prong of Wheeler. We remand for 

proceedings consistent with this opinion. 

I.

On July 9, 2009, a federal grand jury in the Eastern District of North Carolina 

indicted Appellant on gun and drug charges. The Government filed an Information of Prior 

Convictions for Enhancement of Sentence pursuant to 21 U.S.C. § 851 (the “Information”), 

which stated that Appellant was subject to an enhanced sentence based on a 1997 North 

Carolina conviction for possession with intent to sell cocaine (the “1997 Conviction”). The

Information alleged that the 1997 Conviction was a “felony drug offense[]” that subjected

Appellant to an enhanced sentence pursuant to 21 U.S.C. § 841(b).1

 J.A. 21.2 

 1 At the time Appellant was charged, convicted, and sentenced, § 841(b) provided

that “any person who violates [§ 841(a) for possession or distribution of drugs involving 

five grams or more of crack cocaine]” and “commits such violation after a prior conviction 

for a felony drug offense has become final . . . shall be sentenced to a term of imprisonment 

which may not be less than 10 years and not more than life imprisonment.” 21 U.S.C. 

§ 841(b)(1)(B) (2009). In the absence of a prior felony drug offense, the term of 

imprisonment “may not be less than 5 years and not more than 40 years.” Id. 

“Felony drug offense” was, and still is, defined as “an offense that is punishable by 

imprisonment for more than one year under any law . . . of a State.” 21 U.S.C. § 802(44). 

2 Citations to the “J.A.” refer to the Joint Appendix filed by the parties in this appeal.
4

On September 11, 2009, the grand jury returned a superseding indictment charging 

Appellant with two counts of distribution of five grams or more of crack cocaine and aiding 

and abetting pursuant to 21 U.S.C. § 841(a)(1) and 18 U.S.C. § 2 (Counts One and Two); 

one count of possession with the intent to distribute a quantity of cocaine pursuant to

§ 841(a)(1) (Count Three); one count of possession of firearms in furtherance of a drug 

trafficking crime pursuant to 18 U.S.C. § 924(c)(1)(A) (Count Four); and possession of 

firearms by a felon pursuant to 18 U.S.C. § 922(g)(1) (Count Five). Appellant pled guilty 

to Counts Two and Four of the superseding indictment on November 4, 2009.

Appellant’s sentencing hearing took place on May 10, 2010. Because of the 

Information, the statutory range to which Appellant was subjected on Count Two was ten

years to life imprisonment, to be followed by a term of supervised release of eight years. 

See 21 U.S.C. § 841(b)(1)(B) (2009). Absent the Information, Braswell’s statutory 

sentencing range on Count Two would have been five to 40 years, and his term of 

supervised release would have been four years. See id. 

At sentencing, the district court accepted the Presentence Investigation Report, 

which designated Appellant as a career offender pursuant to § 4B1.1 of the United States 

Sentencing Guidelines (the “Guidelines”).

3

 Appellant’s resulting advisory Guidelines

range was 262 to 327 months of imprisonment on Count Two, and a consecutive sentence 

 3 The career offender enhancement applies when a defendant has two or more prior 

felony convictions of either a “controlled substance offense” or “crime of violence,” each 

of which was “punishable by imprisonment for a term exceeding one year.” U.S.S.G. 

§§ 4B1.1(a), 4B1.2(a), (b) (2009).
5

of 60 months of imprisonment on Count Four, for a total of 322 to 387 months, plus eight 

years of supervised release. The district court sentenced Appellant to 262 months on Count 

Two, and 60 months on Count Four, for a total of 322 months. On March 18, 2011, this 

court affirmed Appellant’s conviction and dismissed his challenge to his sentence based on 

the appellate waiver in his plea agreement. See United States v. Braswell, 418 F. App’x 

195, 196 (4th Cir. 2011).

On August 17, 2011, five months after Appellant’s direct appeal proceedings ended, 

this court held that, in considering whether North Carolina drug convictions are “felony 

drug offense[s]” pursuant to 21 U.S.C. § 802(44), the Government cannot rely on a 

hypothetical maximum term of imprisonment to determine if the crime was punishable by 

“imprisonment for more than one year.” United States v. Simmons, 649 F.3d 237, 239 (4th 

Cir. 2011) (en banc) (quoting § 802(44)) (hereinafter “Simmons”). Rather, the sentencing 

court “may only consider the maximum possible sentence that the particular defendant 

could have received.” Wheeler, 886 F.3d at 420 (discussing Simmons) (emphasis in 

original) (internal quotation marks omitted). 

On March 10, 2012, Appellant moved to vacate his sentence pursuant to § 2255. He 

argued that he should not have been deemed a career offender because, based on Simmons, 

Appellant did not “have a predicate offense.” J.A. 88. In response, the Government

“concede[d] that, as a result of Simmons, [Appellant’s 1997 Conviction] is not punishable 

by more than one year imprisonment, and therefore he lacks the necessary predicates for 

career offender status.” Id. at 101–02. The Government also “concede[d] that, as a result 

of Simmons, th[e] [1997] [C]onviction could not form the basis for a § 851 enhancement. 
6

The statutory punishment range on Count Two therefore should have been 5 years to 40 

years, not 10 years to life. However, the sentence actually imposed on Count Two -- 262 

months -- was still within the correct statutory range.” Id. at 103 n.1.

On February 19, 2013, the district court adopted the magistrate judge’s 

recommendation and dismissed the § 2255 motion. This recommendation was based on 

three grounds: (1) Appellant was barred from challenging his sentence by the waiver in his 

plea agreement; (2) even if the 1997 Conviction was no longer a qualifying prior offense 

for a career offender enhancement, Appellant was nonetheless sentenced within the 

unenhanced statutory maximum of 40 years and thus, his § 2255 claim was “not cognizable

and should be dismissed”; and (3) Simmons had not been deemed retroactive on collateral 

review. J.A. 124. Six months later, on August 21, 2013, this court held that Simmons 

applied retroactively on collateral review. See United States v. Miller, 735 F.3d 141, 147

(4th Cir. 2013). 

After Simmons, Appellant filed at least one other § 2255 motion, arguing that 

Simmons “would prevent [Appellant’s] [1997 Conviction] from being used to support a 21 

U.S.C. § 851 [Information] because [Appellant’s] prior drug convictions were not 

punishable by a term of imprisonment exceeding one year.” J.A. 163–64 (filed Nov. 21, 

2016) (emphases omitted). The district court denied the motion because Appellant did not 

seek the proper authorization from this court to file a successive § 2255 petition. 

This court decided United States v. Wheeler on March 28, 2018, developing a test 

for petitioners seeking to file a § 2241 petition. In that case, Gerald Wheeler attempted to 

use § 2241 via the savings clause of § 2255(e) to challenge the use of his prior North 
7

Carolina drug conviction for a § 851 sentencing enhancement. While his petition was 

pending, this court decided Miller. Unlike Appellant, Wheeler filed his first § 2255 motion 

before Simmons was decided, not after. 

Based on Wheeler, on April 11, 2018, Appellant filed a pro se § 2241 petition for 

writ of habeas corpus. On January 29, 2019, the district court dismissed the petition. The 

district court concluded that Appellant could not meet the second prong of Wheeler and 

pass through the savings clause because “Wheeler requires both the substantive law to 

change and for that change to be retroactive subsequent to petitioner’s first § 2255 motion.” 

J.A. 236. Thus, the district court concluded, because “the substantive law set forth in 

Simmons changed prior to [Appellant’s] § 2255,” he could not satisfy prong two. The 

district court also explained in a footnote that Appellant’s Simmons claim was barred by 

the waiver in his plea agreement. Appellant timely noted this appeal. 

II.

We review legal issues concerning the savings clause of § 2255(e) de novo. See 

United States v. Wheeler, 886 F.3d 415, 422 (4th Cir. 2018).

III.

A.

The Wheeler Test

Again, the Wheeler test provides that a petitioner can pass through the savings 

clause if:

(1) at the time of sentencing, settled law of this circuit or the 

Supreme Court established the legality of the sentence; (2) 

subsequent to the prisoner’s direct appeal and first § 2255 
8

motion, the aforementioned settled substantive law changed 

and was deemed to apply retroactively on collateral review; (3) 

the prisoner is unable to meet the gatekeeping provisions of § 

2255(h)(2) for second or successive motions; and (4) due to 

this retroactive change, the sentence now presents an error 

sufficiently grave to be deemed a fundamental defect. 

United States v. Wheeler, 886 F.3d 415, 429 (4th Cir. 2018). “[T]he savings clause 

requirements are jurisdictional,” id. at 426, so we independently examine whether all four 

prongs of the Wheeler test are met. See United States v. Urutyan, 564 F.3d 679, 684 (4th 

Cir. 2009) (a federal court is “obliged to satisfy [itself] of subject-matter jurisdiction”).

1.

Prong One

The first Wheeler prong requires that, “at the time of sentencing, settled law of this 

circuit or the Supreme Court established the legality of the sentence.” 886 F.3d at 429. 

Appellant easily satisfies this prong because in May 2010, the Simmons panel decision had 

been vacated and the en banc decision had not yet been issued. The then-prevailing

decision of United States v. Harp held, “[T]o determine whether a conviction is for a crime 

punishable by a prison term exceeding one year [under North Carolina law], . . . we 

consider the maximum aggravated sentence that could be imposed for that crime upon a 

defendant with the worst possible criminal history.” 406 F.3d 242, 246 (2005) (emphasis 

in original). A defendant theoretically could have received a sentence of more than one 

year in prison for the 1997 Conviction; thus, it was a prior offense that could validly 

enhance Appellant’s sentence pursuant to § 841(b) and § 851.
9

2.

Prong Two

a.

The second prong of Wheeler requires, “[S]ubsequent to the prisoner’s direct appeal 

and first § 2255 motion, the . . . settled substantive law changed and was deemed to apply 

retroactively on collateral review.” 886 F.3d at 429. As to prong two, the district court 

concluded:

[Appellant] is unable to establish prong two of Wheeler 

because Simmons was issued before [he] pursued his first § 

2255 motion. In fact, [Appellant] unsuccessfully raised a 

Simmons claim in his first § 2255 motion. Although Simmons

was made retroactively applicable to cases on collateral review 

subsequent to the denial of [Appellant’s] § 2255 motion, 

Wheeler requires both the substantive law to change and for 

that change to be retroactive subsequent to [Appellant’s] first 

§ 2255 motion. Because the substantive law set forth in 

Simmons changed prior to [Appellant’s] § 2255, he cannot 

satisfy Wheeler.

J.A. 236 (citations omitted). 

Appellant’s direct appeal concluded in March 2011; the Simmons en banc decision 

was issued in August 2011; Appellant’s first § 2255 was filed in March 2012 and his first 

§ 2255 proceedings ended in February 2013; and Simmons was made retroactive in Miller

six months later, in August 2013. Appellant argues that, even though the “settled 

substantive law” did not change (i.e., the Simmons en banc decision was not issued) 

“subsequent to the prisoner’s . . . first § 2255 motion,” Wheeler, 886 F.3d at 429, “the date 

of retroactivity -- not the date of the substantive change in law -- is the controlling 

consideration in determining whether the second prong is met.” Appellant’s Br. 21. The 
10

Government, in contrast, asks us to read prong two literally and in isolation from the rest 

of the opinion. 

b.

Although prong two could be read literally such that the change in settled law and

the retroactivity determination should both occur after the first § 2255 motion, the Wheeler

test should not be interpreted so rigidly. Wheeler did not address the unique situation at 

hand, where the first § 2255 motion was filed between the change in substantive law and 

the declaration of its retroactivity. In considering these rare facts, we look to the entirety 

of the Wheeler opinion and conclude that, in order for a petitioner to satisfy prong two, the 

combination of the change in settled substantive law and its retroactivity must occur after 

the first § 2255 motion has been resolved. 

i.

Wheeler demonstrates that the change in settled substantive law and retroactivity 

determination work together as a package deal. The change in settled substantive law 

“must have been made retroactive on collateral review. Otherwise, the prisoner would not 

be able to ‘test the legality of his detention’ in a § 2241 proceeding, which is the ultimate 

goal of the savings clause.” Wheeler, 886 F.3d at 429 (quoting 28 U.S.C. § 2255(e)). We 

explained that on prong two, we look to the “retroactive change in law” as one moment in 

time. Id. For example, when discussing whether Wheeler met prong two, we explained: 

[T]he en banc Simmons decision, which abrogated Harp, was 

decided August 17, 2011, and was made retroactive on 

collateral review by Miller on August 21, 2013. This all 

occurred after Appellant’s direct appeal, filed March 2008, and 

his first § 2255, filed June 2010. Although Appellant actually 
11

raised a Simmons type claim in his first § 2255 on ineffective 

assistance of counsel grounds, the Simmons en banc decision 

itself could not have been invoked at that time because it did 

not exist.

Id. at 429–30 (emphasis supplied). Therefore, because the retroactivity determination

occurred after the first chance Appellant had to “invoke[]” the change in settled law in a 

§ 2255 motion, § 2255 remained “inadequate or ineffective” to test the legality of his 

detention. 

Furthermore, prong four of Wheeler demonstrates that the date of retroactivity is the 

trigger for savings clause relief. That requirement states, “due to this retroactive change 

[in settled law], the sentence now presents an error sufficiently grave to be deemed a 

fundamental defect.” 886 F.3d at 429 (emphasis supplied). It is the retroactive change, 

not just the change, in settled law that renders the sentence fundamentally defective. 

ii.

Appellant’s reading of prong two also furthers the purpose and policy behind the 

Wheeler opinion. Wheeler could not receive the benefit of Simmons because it “did not 

exist.” 886 F.2d at 430. Here, Appellant could not receive the benefit of Simmons because 

it was not applicable retroactively on collateral review. In fact, the legal landscape existing 

at the time of Appellant’s first § 2255 motion all but foreclosed this possibility. See 

Carachuri-Rosendo v. Holder, 560 U.S. 563, 575–76 (2010) (in holding that defendant’s 

second Texas offense of simple drug possession was not an “aggravated felony,” rejecting 

the “hypothetical approach” to prior convictions where “all conduct punishable as a felony” 

would be treated as “the equivalent of a conviction of a felony” (internal quotation marks 
12

omitted)). But see United States v. Powell, 691 F.3d 554, 560 (4th Cir. 2012) (holding that 

Carachuri-Rosendo is not retroactive on collateral review). In this case and Wheeler, the 

petitioners in their first § 2255 motions could not rely upon the change in substantive law 

to correct their fundamental sentencing errors; thus, such motions were inadequate and 

ineffective to test the legality of their detention. 

To hold otherwise would strip all meaning and purpose from § 2241 and Wheeler

itself. “[T]he privilege of habeas corpus entitles the prisoner to a meaningful opportunity 

to demonstrate that he is being held pursuant to the erroneous application or interpretation 

of relevant law.” Boumediene v. Bush, 553 U.S. 723, 779 (2008) (emphasis supplied) 

(internal quotation marks omitted). Accepting the Government’s inflexible reading of 

prong two of the Wheeler test would deny relief to Appellant merely because he could cite 

to Simmons in his first § 2255 motion, even though the state of the law at the time precluded 

him from using it in his favor. This is not a meaningful opportunity. 

c.

In support of a literal and isolated reading of prong two, the Government posits,

“The use of the word ‘and’ as opposed to ‘or’ is significant.” Gov’t’s Br. 17. It also 

contends, “[T]here was no settled Fourth Circuit barrier or other barrier under the 

Antiterrorism and Effective Death Penalty Act of 1996 (AEDPA), to the Fourth Circuit’s 

making a retroactivity determination on [Appellant’s] first § 2255 motion,” and therefore, 

“the absence of a holding of retroactivity at the time of a § 2255 motion would not present 

the kind of ‘exceptional circumstance[]’ that would require a § 2241 to step in and take the 
13

place of § 2255.” Id. at 18 (quoting Wheeler, 886 F.3d at 428) (citation omitted). We reject 

these arguments.

First, the Government believes it is significant that the Wheeler test contains “and” 

rather than “or.” But if the test used the word “or,” prong two would state: “subsequent to 

the prisoner’s direct appeal and first § 2255 motion, the aforementioned settled substantive 

law changed [or] was deemed to apply retroactively on collateral review.” 886 F.3d at 

429. This argument misses the point. No party is contending that prong two should be 

read in the disjunctive. Indeed, this reading would completely eliminate the retroactivity 

requirement altogether. 

Second, the Government maintains that this court could have deemed Simmons

retroactive during the proceedings on Appellant’s first § 2255 motion, and therefore, 

Appellant does not present an “exceptional circumstance” worthy of habeas relief. But the 

same can be said for Wheeler himself. When Wheeler filed his first § 2255 motion before 

Simmons, he raised a Simmons-like argument. This court could have decided, as it did in 

Simmons, that the method of analyzing North Carolina prior felony convictions was 

erroneous, and Wheeler would have received relief. 

Besides, this argument also misses the point. We explained in Wheeler that the 

purpose of traditional habeas relief was to “remedy statutory, as well as constitutional, 

claims presenting . . . exceptional circumstances where the need for the remedy afforded 

by the writ of habeas corpus is present.” 886 F.3d at 428 (internal quotation marks 

omitted). Further, “if we held that a prisoner was foreclosed from seeking collateral relief 

from a fundamentally defective sentence, and ‘through no fault of his own, has no source 
14

of redress,’ this purpose would remain unfulfilled.” Id. (quoting In re Jones, 226 F.3d 328, 

333 n.2 (4th Cir. 2000)) (emphasis omitted). Thus, Appellant, like Wheeler, presents an 

exceptional circumstance -- at the time of his first § 2255 motion, he was foreclosed from 

collateral relief because Simmons was inaccessible to him. If we adopted the Government’s 

contrary view, we would in essence punish Appellant for being too diligent or for 

submitting his petition to an efficient court. If Appellant had waited longer to file his first 

§ 2255 motion, or if the district court had processed his case more slowly, his claims could 

have been successful. 

For these reasons, Appellant has satisfied prong two of the Wheeler test.

3.

Prong Three

Prong three of the Wheeler test provides that the prisoner must be “unable to meet 

the gatekeeping provisions of § 2255(h)(2) for second or successive motions.” 886 F.3d at 

429. Appellant easily meets this requirement because he is invoking Simmons, which is 

not a rule of constitutional law made retroactive by the Supreme Court on collateral review. 

See § 2255(h)(2).

4.

Prong Four

Finally, Wheeler prong four requires that “due to th[e] retroactive change [in settled 

substantive law], the sentence now presents an error sufficiently grave to be deemed a 

fundamental defect.” 886 F.3d at 429. The Government concedes that Appellant satisfies 
15

prong four under Wheeler, but it takes issue with Wheeler’s established holding that an 

increase in a mandatory minimum is a fundamental defect. 

In both Wheeler and this case, the mandatory minimum was increased from five to 

ten years. And in Wheeler, we specifically rejected the argument (which the Government 

attempts to rehash here) that “any sentence that falls at or below the statutory maximum

does not present a fundamental defect.” 886 F.3d at 432. We explained, “An increase in 

the congressionally mandated sentencing floor implicates separation of powers principles 

and due process rights fundamental to our justice system.” Id. at 430. The defect is 

fundamental because it “wrongly prevent[s] [the sentencing court] from exercising the 

proper range of [its] sentencing discretion.” Lester v. Flournoy, 909 F.3d 708, 713 (4th 

Cir. 2018) (discussing Wheeler prong four). Because Appellant’s mandatory minimum 

was erroneously increased, according to Wheeler, his sentence “presents an error 

sufficiently grave to be deemed a fundamental defect.” 886 F.3d at 433. Therefore, 

Appellant satisfies prong four as well.

We make clear, however, that Appellant’s satisfaction of prong four is based on the 

increase in his mandatory minimum, not on his career offender designation. As we stated 

in United States v. Foote, a “fundamental defect or a complete miscarriage of justice” has 

not occurred where the petitioner was sentenced as a career offender “under an advisory 

Guidelines scheme.” 784 F.3d 931, 932, 941 (4th Cir. 2015). But see Lester, 909 F.3d at 

716 (holding that the petitioner was entitled to proceed pursuant to § 2241 on his claim that 

he had been improperly sentenced as a career offender under the Guidelines when they 

were mandatory). Here, Appellant was deemed a career offender under an advisory 
16

Guidelines scheme; thus, to the extent Appellant bases his Wheeler claim on his career 

offender designation, he does not satisfy prong four. 

B.

Plea Agreement Waiver

The district court noted that Appellant’s § 2241 petition is barred by the waiver in 

his plea agreement, which stated in relevant part:

The Defendant agrees . . . [t]o waive all rights conferred by 18 

U.S.C. § 3742 to appeal whatever sentence is imposed, 

including any issues that relate to the establishment of the 

advisory Guideline range, reserving only the right to appeal 

from a sentence in excess of the applicable advisory Guideline 

range that is established at sentencing, and further to waive all 

rights to contest the conviction or sentence in any postconviction proceeding, including one pursuant to 28 U.S.C. 

§ 2255, excepting an appeal or motion based upon grounds of 

ineffective assistance of counsel or prosecutorial misconduct 

not known to the Defendant at the time of the Defendant’s 

guilty plea. The foregoing appeal waiver does not constitute or 

trigger a waiver by the United States of any of its rights to 

appeal provided by law.

J.A. 241 (sealed) (emphasis supplied). On direct appeal, this court found the waiver to be 

knowing and voluntary. See United States v. Braswell, 418 F. App’x 195, 196 (4th Cir. 

2011). However, this Court will not enforce an otherwise valid waiver if “to do so would 

result in a miscarriage of justice,” United States v. Adams, 814 F.3d 178, 182 (4th Cir. 

2016), or where there is an “illegal sentence . . . involv[ing] fundamental issues,” United 

States v. Copeland, 707 F.3d 522, 530 (4th Cir. 2013) (alteration and internal quotation 

marks omitted). But see United States v. Archie, 771 F.3d 217, 223 (4th Cir. 2014) (“[W]e 

. . . decline[] to enforce a valid appeal waiver only where the sentencing court violated a 
17

fundamental constitutional or statutory right that was firmly established at the time of 

sentencing.” (emphasis supplied)). 

Although a heading in the Government’s brief states that the district court “did not 

err in determining that the waiver in his plea agreement effectively bars [Appellant] from 

challenging his sentence,” Gov’t’s Br. 18, it fails to develop this argument. Rather, the 

Government concedes that Wheeler renders the plea agreement waiver invalid as to 

Appellant’s § 2241 petition. See id. at 19 n.4 (“Although[] this argument is now foreclosed 

by Wheeler, the United States believes that the waiver in the plea agreement signed by 

[Appellant] remains valid.” (emphasis supplied)). In the entirety of its response brief, and 

even during oral argument, the Government failed to invoke the waiver or claim that the 

appeal should be dismissed based thereon under current law. Rather, it argues that an 

increase in a mandatory minimum sentence is not a fundamental defect resulting in a 

miscarriage of justice. As the Government also acknowledges, however, this argument is 

wholly foreclosed by Wheeler. Therefore, we decline to hold that Appellant is foreclosed 

from bringing this § 2241 petition based on the Government’s enforcement of the waiver 

in his plea agreement. See United States v. Brock, 211 F.3d 88, 90 (4th Cir. 2000) 

(declining to address plea agreement waiver issue where “the Government expressly 

elected not to argue waiver”); see also United States v. Poindexter, 492 F.3d 263, 271 (4th 

Cir. 2007) (noting the government can elect not to enforce an appeal waiver and instead 

contest the merits of a defendant’s argument).
18

IV.

For these reasons, we reverse the dismissal of Appellant’s § 2241 petition, and 

remand for proceedings consistent with this opinion. 

REVERSED AND REMANDED