Petitioners Brief — Class v. United States, 137 S. Ct. 1065 (2017) (No. 16-424)

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No. 16-424 OFFICE OF THE CLERK

IN THE

Supreme Court of the United States

mensine Cnsan

Petitioner,

UNITED STATES OF AMERICA,

Respondent.

On Writ of Certiorari to the

United States Court of Appeals

for the District of Columbia Circuit

BRIEF OF PETITIONER

JESSICA RING AMUNSON

Counsel of Record

ERICA L. ROSS

JOSHUA M. PARKER

CORINNE M. SMITH

LEONARD R. POWELL*

JENNER & BLOCK LLP

1099 New York Ave., NW

Suite 900

Washington, DC 20001

(202) 639-6000

jamunson@jenner.com

* Admitted in California only;

supervised by principals of the firm

QUESTION PRESENTED

In Blackledge v. Perry, 417 U.S. 21 (1974), and

Menna v. New York, 423 U.S. 61 (1975), this Court held

that a defendant who pleads guilty can still raise on

appeal any constitutional claim that does not depend on

challenging his “factual guilt.” In Blackledge and

Menna, the Court held that double jeopardy and

vindictive prosecution are two such claims that are not

inherently resolved by pleading guilty, because those

claims do not challenge whether the government could

properly meet its burden of proving each element of the

crime.

In the years since this Court decided Blackledge and

Menna, the circuit courts have deeply divided on

whether a defendant’s challenge to the constitutionality

of his statute of conviction survives a plea, or instead is

inherently waived as part of the concession of factual

guilt.

The question presented is:

Whether a guilty plea inherently waives defendant’s

right to challenge the constitutionality of his statute of

conviction.

‘3

TABLE OF CONTENTS

QUESTION PRESENTE D.............0...:-scssccosossersseseosenseeee i

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CONSTITUTIONAL AND STATUTORY

PROVISIONS INVOLVED ............ccccceseesesseeeeees 4

ene 4

I. TE 4

Il. ‘Petitioner Challenges The

Constitutionality Of 40 U.S.C. § 5104(e) In

Ne ee hictniicctncnnnteimnannnntiiintetsnmmaiensiios 5

A 8

IV. The D.C. Cireuit Holds That A Plea

Inherently Waives All Constitutional

SUMMARY OF ARGUMENT............cccccsesssseereneenensenes 14

BO, 16

Il.

iii

Defendants Do Not Inherently Waive The

Ability To Challenge The

Constitutionality Of The Statute Of

Conviction By Pleading Guilty. ...................0.00- 16

It Is Undisputed That Petitioner’s

Guilty Plea Did Not Expressly Waive

His Right To Challenge The

Constitutionality Of The Statute Of

Sei inscictasniinstbiscenbtiishntindeietanticesionanes 18

A Constitutional Challenge To The

Statute Of Conviction Calls Into

Question Whether The Government

Can Ever Obtain A Valid Conviction,

And Therefore Is Not Waived Or

Foreclosed By A Guilty Plea. ................. 20

This Court’s Retroactivity

Jurisprudence Confirms That

Constitutional Challenyes To

Criminal Statutes Raise Heightened

EY ciiternetsnvtnsnnsinsnnneginanseneninsoresteorces 29

Rule 11(a)(2) Does Not Require That A

Constitutional Challenge To The Statute

Of Conviction—Facial Or As-Applied—Be

Expressly Preserved In A_ Plea

Ill. In The Alternative, The Court Should

Remand For A Determination Of Whether

Petitioner's Plea Was _ Voluntary,

Knowing, And Intelligent. ................csescessereeees 44

CEPI ccscccsscnssnnssncessasrenssnsnerorunenneeentganemeneennneste 47

TABLE OF AUTHORITIES

CASES

Blackledge v. Perry, 417 U.S. 21 (1974)............ passim

Bousley v. United States, 523 U.S. 614 (1998)......... 46

Boykin v. Alabama, 395 U.S. 238 (1969)..............0+. 20

Bradshaw v. Stumpf, 545 U.S. 175 (2005).............0+. 44

Brady v. United States, 397 U.S. 742 (1970)...... 16, 21

Chevron U.S.A. Inc. v. Echazabal, 536 U.S. 73

IIT scscsistichceaitieilasiiaintanbaeniapieiahiidiienliadaintidniaihebidteinguaen 18

Christian Legal Society Chapter of the

University of California, Hastings College

of the Law v. Martinez, 561 U.S. 661 (2010)....... 46

Citizens United v. FEC, 558 U.S. 310 (2010)........... 43

District of Columbia v. Heller, 554 U.S. 570

STITT soselichaiesiasiecineeiainatecinieinhspiaiibniigsintibiineunimenscecieneupentents 7

Florida v. Nixon, 543 U.S. 175 (2004)........ccccccceceeee 20

Haring v. Prosise, 462 U.S. 306 (1983) ............... 20, 22

Haynes v. United States, 390 U.S. 85

SIIUTIE crncepsatnsensnnseinigemdineeteninnimmmeniaenniinien 27, 28, 43

Haynes v. United States, 372 F.2d 651 (5th Cir.

1967), judgment rev'd, 390 U.S. 85 (1968)..... 27, 28

Henderson v. Morgan, 426 U.S. 637 (1976).............. 44

Kontrick v. Ryan, 540 U.S. 448 (2004).......... 39, 40, 41

Lafler v. Cooper, 566 U.S. 156 (2012)............0000.. 16, 20

Loving v. Virginia, 388 U.S. 1 (1967) ss... 28, 29

Loving v. Commonwealth, 147 S.E.2d 78 (Va.

1966), judgment rev'd, 388 U.S. 1 (1967)........0++. 29

McDonald v. City of Chicago, 561 U.S. 742

STITT icsieathinatintaniavisionsnitaiinigtashitisininedipaiibiaaisepetmemncneenenenes 7

McMann v. Richardson, 397 U.S. 759 (1970) .... 21, 33

Menna v. New York, 423 U.S. 61 (1975)........... passim

Missouri v. Frye, 566 U.S. 133 (2012)............ccccceseeeee 1

Montgomery v. Louisiana, 136 8S. Ct. 718

TT ailorindiaetiennibtedadcidieaiiaasttsitmeidanitarninattntcesen 1, 26, 33

Palmer v. District of Columbia, 59 F’. Supp. 3d

ee ls SIE cieresntncsunsesrensesecteensensdnenntenenenccee 6

Parker v. North Carolina, 397 U.S. 790 (1970)....... 21

Puckett-v. United States, 556 U.S. 129 (2009).......... 18

Schriro v. Summerlin, 542 U.S. 348 (2004)........ 31, 32

Ex parte Siebold, 100 U.S. 371 (1880)................. 29, 30

Teague v. Lane, 489 U.S. 288 (1989).............. 30, 31, 33

Tollett v. Henderson, 411 U.S. 258

TIE biciasinsieniieindiiiiaisahiiaamnmnienpitanentdndnndate 13, 21, 22, 44

United States v. Andrade, 83 F.3d 729 (5th Cir.

iaiiicnschtetihenscatastininiipcenapinaiiniguasnintbipedeiennecmeas 39

United States v. Aranda, 612 F. App’x 177 (4th

aT siincnsindiicsinieibiiaigpiecanseenmnicncctanniandenetinnserdesnenes 42

United States v. Baucum, 80 F.3d 539 (D.C.

chair icsedicteiaetee acid rtliaadoeaiiges ciltiiinenes 41

United States v. Broce, 488 U.S. 563

vii

United States v. Curcio, 712 F.2d 1532 (2d Cir.

United States v. DeVaughn, 694 F.3d 1141

NE IEEE ovcninnnsiseieeninintbtcodscesidnnmpnseentineneiainne 40,

United States v. Johnston, 199 F.3d 1015 (9th

United States v. Ruiz, 536 U.S. ss

United States v. Seay, 620 F.3d 919 (8th Cir.

United States v. Stevens, 559 U.S. 460 (2010)..........

United States v. Warwar, 478 F.2d 1188 (ist

United States v. Williams, 341 U.S. 58 (1951).........

Washington State Grange v. Washington State

Republican Party, 552 U.S. 442 (2008)...............

Welch v. United States, 136 S. Ct. 1257

CONSTITUTIONAL PROVISIONS AND STATUTES

III OF sivecientsnpesirceneneteenindsenenesnntmenteiians

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OTHER AUTHORITIES

Albert W. Alschuler, Plea Bargaining And Its

History, 79 Colum. L. Rev. 1 (1979) ..........:ses00 16

ee passim

Fed. R. Crim. P. 11 advisory committee’s note

to 1983 amendments..............cccccccereeeseeeees 37, 38, 39

5 Margaret N. Kniffin, Corbin on Contracts

(Joseph M. Perillo ed., rev. ed. 1998) .................. 18

11 Richard A. Lord, Williston on Contracts

IE III sstthcniernnuiensecsibititninanetninnepmtianginatnmimmesen 18

U.S. Dep’t of Justice, U.S. Attorneys’ Manual,

Criminal Resource Manual § 626....................000+5 18

Ronald F. Wright, Trial Distortion and the

End of Innocence in Federal Criminal

Justice, 154 U. Pa. L. Rev. 79 (2005).................-. 38

INTRODUCTION

Plea bargaining today is not just “some adjunct to the

criminal justice system; it is the criminal justice

system.” Missouri v. Frye, 566 U.S. 133, 144 (2012)

(emphasis in original) (quotation marks omitted). The

default rules of plea bargaining “determine[] who goes

to jail[,] for how long,” and for what crimes. Id.

(quotation marks omitted). This case asks the Court to

answer a question regarding the application of these

default rules: whether a defendant who has not

expressly waived the right to challenge on appeal the

constitutionality of his statute of conviction nonetheless

inherently waives this right merely by pleading guilty.

The answer to that question is no. In Blackledge v.

Perry, 417 U.S. 21 (1974), and Menna v. New York, 423

U.S. 61 (1975), this Court held that where a defendant

pleads guilty, but then asserts a right that would have

prevented the government from prosecuting him at all—

such as the right not to be vindictively prosecuted or to

be put into double jeopardy—the assertion of that right

is not inherently waived or foreclosed by the guilty plea.

A defendant’s right not to be convicted pursuant to an

unconstitutional statute plainly falls into this category.

As this Court recognized more than a century ago and

reaffirmed as recently as last year, “an unconstitutional

law is void, and is as no law,” and any penalty imposed

pursuant to that law “is, by definition, unlawful.”

Montgomery v. Louisiana, 136 S. Ct. 718, 730-31 (2016)

(quoting Ex parte Siebold, 100 U.S. 371, 376 (1880)).

Unlike core trial rights (like the right to cross-

examine witnesses), and procedural and evidentiary

rights (like rights under the Fourth Amendment), which

may be waived by a guilty plea or foreclosed because of

a defendant’s admissions in the plea, a challenge to the

constitutionality of the statute of conviction goes to the

very power of the government to prosecute the

defendant. The default rule is that a defendant’s ability

to raise such a challenge does not automatically

disappear merely because the defendant has chosen to

admit he engaged in conduct that he asserts is

constitutionally protected.

The government and the court below argue for a

different default rule, claiming that a guilty plea does

inherently waive a defendant’s right to raise a

constitutional challenge to the statute of conviction on

appeal, unless the defendant expressly preserves his

right to bring that challenge by entering a conditional

plea pursuant to Federal Rule of Criminal Procedure

11(a)(2). Rule 11(a)(2) permits the defendant to reserve

in writing the right to appeal a conviction on specified

grounds if the defendant is able to secure the approval

of the prosecutor and the court. But, as its drafters

explicitly noted, Rule 11(a)(2) does not displace this

Court’s decisions in Blackledge and Menna, which make

clear that a challenge to the State’s very power to bring

the prosecution is preserved regardless of whether the

defendant enters a conditional guilty plea.

Petitioner’s interpretation of the default rules is

dictated by this Court’s precedent. But even if it were

not, Petitioner’s is the only interpretation that makes

sense. There is no reason to leave unconstitutional

criminal statutes on the books and unchallenged, which

is where they will remain if defendants who plead

guilty—the vast majority of defendants in the criminal

justice system—bear the burden of obtaining the

permission of the prosecutor to reserve the right to

bring a constitutional challenge on appeal. That rule

would not only chill constitutionally protected conduct;

it would also lead to a substantial waste of resources as

defendants pursue unnecessary trials in which no factual

disputes are at issue in order to challenge the

constitutionality of their statutes of conviction. This

Court should reaffirm its prior decisions and hold that a

guilty plea does not inherently waive a post-plea

challenge to the constitutionality of the statute of

conviction.

OPINIONS BELOW

The July 5, 2016, opinion of the United States Court

of Appeals for the District of Columbia Circuit (Pet.

App. la) is unpublished. The District Court for the

District of Columbia’s October 27, 2014 oral order

denying Petitioner’s motion to dismiss the indictment

(Pet. App. 6a) is unreported. The district court’s April

16, 2014 memorandum order denying in part Petitioner’s

motion to dismiss the indictment (Pet. App. 10a) is

reported at 38 F. Supp. 3d 19.

JURISDICTION

This Court has jurisdiction under 28 U.S.C. § 1254(1).

The D.C. Circuit entered its judgment on July 5, 2016.

The petition for writ of certiorari was timely filed on

September 30, 2016 and granted on February 21, 2017.

CONSTITUTIONAL AND STATUTORY

PROVISIONS INVOLVED

This case involves U.S. Const. amend. V, and 40

U.S.C. §§ 5101, 5102, 5104, and 5109. These provisions

are reproduced in the Petition Appendix at 17a.

STATEMENT

I, Factual Background

Petitioner is a retired veteran who resides in North

Carolina and has a concealed-carry permit from that

State. See D.C. Cir. J.A. 30, 50, 101, 130.1 On Thursday,

May 30, 2013, Petitioner was driving from Virginia to

Pennsylvania when he stopped en route to visit the U.S.

Capitol. Jd. at 57, 102, 162. Petitioner parked his Jeep

on the 200 block of Maryland Avenue, SW, which is

located just north of the United States Botanic Garden

and approximately 1,000 feet from the entrance to the

Capitol building. Jd. at 162 ¢ 1. The parking lot is

publicly accessible, but a permit is usually required to

park there on weekdays. /d. at 101, 128. Although

Petitioner did not know it at the time he parked there,

the parking lot is statutorily included within the Capito}

Grounds, where all weapons are prohibited pursuant to

40 U.S.C. § 5104(e). It is undisputed that there was no

sign stating that the parking lot was part of the Capitol

Grounds or that weapons were prohibited there. Jd. at

125 n.1.

Petitioner’s Jeep contained several lawfully-owned

firearms. See id. at 130. After parking, Petitioner locked

! Citations to “D.C. Cir. J.A.” refer to the Joint Appendix filed in the

D.C. Cireuit on November 20, 2015.

his vehicle, leaving those firearms inside, secured out of

sight. See id. at 162-63. He then proceeded, unarmed, to

visit the House and Senate buildings. Jd. at 125.

Approximately an hour later, a Capitol Police officer

noticed that Petitioner’s Jeep had North Carolina plates,

and she determined that it did not have a parking permit

on the front windshield. Jd. She also noticed what

appeared to be a large blade strapped to a roller bar

inside the vehicle and what appeared to be an empty gun

holster in the map pocket of the driver’s side door. Jd.

The officer determined that the Jeep was registered

to Petitioner, and she radioed for additional officers to

assist her. Jd. When Petitioner returned to his vehicle

later that afternoon, he confirmed to the officers that he

owned the Jeep, and he freely admitted that there were

weapons inside the vehicle, for which he had lawful

permits. Jd. The officers informed Petitioner that it was

“legal to have weapons on Capitol grounds” and

arrested him. Jd. at 126. They transported him to

Capitol Police headquarters and subsequently searched

his Jeep pursuant to a warrant, /d. at 103. The search

recovered three firearms, stored out of sight, as well as

several knives. /d.

II. Petitioner Challenges The Constitutionality Of

40 U.S.C. § 5104(e) In The District Court.

Petitioner was charged in the U.S. District Court for

the District of Columbia with one count of violating 40

U.S.C. § 5104(e), which makes it a crime to “carry on or

have readily accessible to any individual] on the [Capitol]

Grounds or in any of the Capitol Buildings a firearm .. .”

40 U.S.C. § 5104(e)(1)(A)G); see also J.A. 20-21%

Petitioner was also charged with violating D.C. Code

§ 22-4504(a), which prohibited carrying a pistol in public

without a license, but that charge was later dropped

after § 22-4504(a) was declared unconstitutional. See

Palmer v. District of Columbia, 59 F. Supp. 3d 173

(D.D.C. 2014); J.A. 22.

On August 15, 2013, Petitioner voluntarily testified

before a grand jury. D.C. Cir. J.A. 127. Petitioner

explained that he had previously parked in the same spot

without issue, that he was not aware he had parked

within the Capitol Grounds, and that there was no sign

indicating the area was restricted. /d. at 128-29.

Petitioner testified that he did not notice any sign

indicating a permit was required to park in that lot until

Capitol Police pointed it out to him. /d. at 129.

Petitioner was nonetheless indicted. J.A. 20.

Representing himself pro se, with appointed stand-

by counsel, Petitioner filed numerous motions to dismiss

the indictment, arguing inter alia that his storage of

lawfully-owned weapons inside his locked vehicle was

protected by the Second Amendment. For example,

Petitioner argued that “[t]he 2nd Amendment to our

Const.iution states that ‘the Right of the People to keep

and bear Arms, shall not be infringed,” and accordingly

“there can be no legislation which would abrogate

(abolish) them.” D.C. Cir. J.A. 32-33 (emphasis omitted);

see also id. at 36, 42-43, 46. He also raised a due process

notice claim, arguing that he had not been given fair

warning that weapons were banned in the parking lot,

® Citations to “J.A.” refer to the Joint Appendix filed with this brief.

which was freely accessible to the public. See id. at 39,

128. Petitioner presented argument on these motions at

a hearing held April 7, 2014. He contended that his

conduct had been “well within [his] protected rights of

[the] Second Amendment,” id. at 69, and that he had no

way of knowing weapons were forbidden where he

parked, id. at 65.

The court ordered the government to file responsive

briefing on the Second Amendment issue. See id. at 92.

The government extensively addressed the question of

whether the Second Amendment, as interpreted by this

Court’s decisions in District of Columbia v. Heller, 554

U.S. 570 (2008), and McDonald v. City of Chicago, 561

U.S. 742 (2010), prohibited Petitioner’s prosecution. See

D.C. Cir. J.A. 106-13. The government argued that all

government property is inherently a “sensitive place”

where there is no right to armed self-defense under the

Second Amendment. /d. at 112.

The government also filed motions that addressed

many of the due process notice arguments Petitioner

had raised. The government argued that there could be

no notice or warning concerns because: (1) § 5104(e) has

no “knowledge and/or intent requirements” (i.e., the

statute has “no ... mens rea element”), id. at 124, 130;

and (2) the statute defining the Capitol Grounds makes

a “clear reference” to the relevant parking lot when it

designates “all grounds bounded by the curblines of

First Street, Southwest on the east; Washington

Avenue, Southwest to its. intersection with

Independence Avenue, and Independence Avenue from

such intersection to its intersection with Third Street,

Southwest on the south; Third Street, Southwest on the

west; and Maryland Avenue, Southwest on the north,”

40 U.S.C. § 5102(c)(1)(C), as being part of the Capitol

Grounds, D.C. Cir. J.A. 138.

On October 27, 2014, the district court orally denied

Petitioner’s claim that his Second Amendment rights

had been violated, concluding that a government-owned

parking lot was the same as a “government building[],”

where all weapons could presumptively be banned. Pet.

App. 9a. The court also declined to accept Petitioner’s

due process notice argument.

Ill. Petitioner Pleads Guilty.

Petitioner’s case was set for trial, but he sent a letter

to the court indicating that he would be unable to appear.

D.C. Cir. J.A. 145. Subsequently, he pled guilty to the

charge of violating §5104(e). The plea conceded

Petitioner’s factual guilt—that he had violated § 5104(e)

by parking his vehicle, which contained several firearms

and knives, within the area statutorily designated as the

Capitol Grounds. See J.A. 24-26, 30-31. The plea

agreement expressly waived Petitioner’s trial rights, as

well as Petitioner’s right to appeal his sentence or to

collaterally attack his conviction or sentence—uniless he

claimed the sentence was above the statutory maximum

or guidelines range determined by the court, or unless

his collateral attack was based on newly discovered

evidence or a claim of ineffective assistance of counsel.

See id. at 39-41. The plea agreement did not, however,

contain any express waiver of the right to directly

appeal the conviction, nor did it concede in any way that

§ 5104 itself was constitutional. See id. at 30-31, 38-41.

The plea agreement also included an integration clause

stating that the plea comprised the “[clomplete

[ajgreement” between the parties and that no

“promises, understandings, or representations have

been made... other than those contained in writing

herein.” Jd. at 45.

At the plea colloquy on November 21, 2014, the

district court reviewed with Petitioner the rights

waived by the plea agreement. /d. at 54, 61-79. As part

of that review, the court explained to Petitioner that he

retained the right to “appeal a conviction after a guilty

plea if [he] believe[d] that [his] guilty plea was somehow

unlawful.” Jd. at 63. Petitioner agreed that he was

willing to give up “most of [his] rights to an appeal .. .

[o]ther than what [the court] mentioned.” Jd. at 66.

IV. TheD.C. Circuit Holds That A Plea Inherently

Waives All Constitutional Claims.

Four days after he was sentenced, Petitioner filed a

notice of appeal with the D.C. Circuit. See D.C. Cir. J.A.

24-25. He then filed a pro se opening merits brief,

focusing on his claim that his Second Amendment rights

had been violated. See J.A. 16-17. The government did

not move to dismiss the appeal as being either waived or

foreclosed by Petitioner’s guilty plea, nor did it

otherwise respond in any manner to Petitioner’s brief.

Approximately seven months later, the D.C. Circuit set

a new briefing schedule and appointed counsel to serve

as amicus curiae to argue in favor of Petitioner. Jd. at

17.

Amicus fully briefed the primary constitutional

challenges that Petitioner had raised at the district

court, and Petitioner expressly adopted amicus’s

arguments as his own. See id. at 18. Petitioner argued

that the Second Amendment protects the right to “keep

and bear arms” for self-defense, and that § 5104(e)

infringes on that right by effectively banning law-

abiding citizens from securely storing lawfully-owned

weapons in their vehicles parked in a publicly accessible

lot. Amicus D.C, Cir. Br. 22, 25. Petitioner also argued

that § 5104(e), both facially and as-applied, violates the

Due Process Clause because it fails to give fair warning

as to what areas are considered the Capitol Grounds

where weapons are banned. 7d. at 54-56. And further,

Petitioner argued, the lack of any notice, especially when

combined with the government’s argument that

§ 5104(e) has no mens rea requirement, violates due

process. /d. at 55.

In response, the government argued—for the first

time, nearly one year after Petitioner had filed his

opening brief—that even though Petitioner’s plea did

not contain any express waiver of the right to appeal his

conviction, the plea inherently waived Petitioner’s right

to raise any constitutional claims that accrued before he

pled guilty, including his constitutional challenges to the

statute. See Gov't D.C. Cir. Br. 28 & n.15. The

government therefore urged the D.C. Circuit not to

reach the merits of Petitioner’s claims on appeal.

Petitioner countered that because the plain terms of

his plea agreement did not include a waiver of his right

to directly appeal with a constitutional challenge to the

statute of conviction, the court should not interpret the

contract between the parties to waive that right.

Amicus D.C. Cir. Reply 1-8. Petitioner further argued

that his constitutional challenges survived his guilty plea

pursuant to this Court’s holdings in Blackledge v. Perry,

417 U.S. 21 (1974), and Menna v. New York, 423 U.S. 61

(1975). Amicus D.C. Cir. Reply 8-13.

In Blackledge, a state prosecutor charged a

defendant with felony assault with a deadly weapon

after the defendant appealed his conviction of a lesser-

included offense. 417 U.S. at 22-23. The defendant pled

guilty to the charge but later filed a habeas petition

alleging that the felony indictment constituted

vindictive prosecution in violation of his due process

rights. Id. at 23-26. The Court held that the defendant’s

guilty plea did not foreclose his due process claim

because, as opposed to claims that could be “cured” by

the government, the Blackledge defendant’s claim “went

to the very power of the State to bring the defendant

into court to answer the charge brought against him.”

Id. at 30. If the defendant had succeeded with his

vindictive prosecution claim, it would have had the

“practical result” of “prevent[ing] a trial from taking

place at all.” Jd. at 30-31 (internal quotation marks

omitted). In other words, the State was categorically

“forbid[den}” from “bring[ing] [the] more serious

charges against the defendant” because of the

“sufficiently serious due process concerns” raised by

“the potential for prosecutorial vindictiveness.” United

States v. Broce, 488 U.S. 563, 574-75 (1989) (citing

Blackledge, 417 U.S. at 30-31).

Similarly, in Menna, this Court held that pleading

guilty does not preclude a defendant from subsequently

raising a double jeopardy claim where “judged on its face

the charge is one which the State may not

constitutionally prosecute.” 423 U.S. at 62 n.2. That is

because, in such a circumstance, “the State may not

convict” the defendant “no matter how validly his factual

guilt is established.” Jd. Menna further clarified that a

guilty plea does not “inevitably ‘waive’ all antecedent

constitutional violations,” but rather represents the

defendant’s concession of his “factual guilt.” Jd. Thus,

the plea “renders irrelevant” any claim that depends on

challenging the government’s evidence of guilt, i.e.,

those claims that “do not stand in the way of conviction,

if factual guilt is validly established,” such as procedural

defects or Fourth Amendment violations. I/d.; see

Blackledge, 417 U.S. at 30. By contrast, where “the

claim is that the State may not convict [the defendant]

no matter how validly his factual guilt is established”—

that is, where the defendant contends that “the charge

is one that the State may not constitutionally prosecute”

at all—“{t)Jhe guilty plea . . . does not bar the claim.”

Menna, 423 U.S. at 62 n.2.

As Petitioner explained to the D.C. Circuit, his

constitutional challenges to § 5104 were akin to the

claims the Court held were not inherently precludeu by

guilty pleas in Blackledge and Menna. Like the

defendants in those cases, Petitioner was not

challenging his “factual guilt”: he did not contest

whether the government could show, for example, that

Petitioner’s car was parked on the Capitol Grounds, or

that it contained firearms. Amicus D.C. Cir. Reply 9, 12.

Rather, Petitioner asserted that even assuming the

elements of the statute were satisfied, he still couid not

be validly prosecuted or convicted because § 5104 itself

was unconstitutional both on its face and as applied to

his particular circumstances. See id. at 15, 27. Thus,

Petitioner argued that under Blackledge and Menna,

the court should reach the merits of his Second

Amendment and due process challenges to the statute.

Id. at 13-14.

After oral argument, the D.C. Circuit affirmed

Petitioner’s conviction, refusing to address the merits of

any of his constitutional claims. Pet. App. la-ba. The

court acknowledged that Petitioner’s plea agreement

did not include any “explicit waiver of appeal rights . . .

as to alleged errors in the indictment or in proceedings

before the sentencing.” Jd. at 4a. The court nonetheless

held that simply by entering a guilty plea, Petitioner had

inherently waived his right to bring an appeal

challenging the constitutionality of the statute under

which he was convicted. Jd. at 3a.

The court’s holding was based on two premises.

First, the court cited this Court’s decision in Tollett v.

Henderson, 411 U.S. 258, 266-68 (1973), for the

“universally recognized law” that a guilty plea

inherently “waive[s] the pleading defendant’s claims of

error on appeal, even constitutional claims.” /d. at 3a-4a

(alteration omitted) (quoting United States v. Delgado-

Garcia, 374 F.3d 1337, 13841 (D.C. Cir. 2004)). The court

did not acknowledge that this Court’s later decisions ir

Blackledge and Menna expressly rejected this reading

of Tollett. Blackledge, 417 U.S. at 30-31; Menna, 423

U.S. at 62 n.2. In particular, the D.C. Circuit did not

address Menna’s statement that Tollett does not “stand

for the proposition that counseled guilty pleas inevitably

‘waive’ all antecedent constitutional violations,” but

rather stands for the proposition that a valid guilty plea

admits factual guilt and thus removes that issue from the

case. 423 U.S. at 62 n.2.

Second, the D.C. Circuit stated that where a

defendant pleads guilty and does not expressly

“reserv(e! in writing the right to have an appellate court

review an adverse determination of a specified pretrial

motion” pursuant to Federal Rule of Criminal] Procedure

11(aX2), the only claims that can be raised on appeal are

“the defendant’s claimed right not to be haled into court

at all,” and a claim “that the court below lacked subject-

matter jurisdiction over the case.” Pet. App. 4a (quoting

Delgado-Garcia, 374 F.3d at 1341). The court found

neither category relevant to Petitioner and therefore

refused to reach the merits of his claims regarding the

unconstitutionality of § 5104. Id.

SUMMARY OF ARGUMENT

1. Petitioner’s guilty plea did not expressly waive his

right to directly appeal his conviction or to challenge the

constitutionality of the statute under which he was

convicted, Under the principles of contract law that

generally govern guilty pleas, that should be the end of

the matter: a court should not read into the parties’

contract a term to which they did not agree.

The government and the court below nonetheless

take the position that Petitioner’s guilty plea inherently

waived his right to challenge his statute of conviction.

This Court’s cases dictate otherwise. In a series of

decisions, this Court has repeatedly and clearly

distinguished between trial rights that can be waived,

procedural or evidentiary claims that can be rendered

irrelevant, and claims that go to the State’s very power

to prosecute the defendant for the crime alleged, which

are neither waived nor rendered irrelevant by a

voluntary, knowing, and intelligent guilty plea.

Petitioner’s claim that he was convicted under an

unconstitutional statute falls in this last category.

Petitioner attacks the State’s very power to validly

prosecute and convict him; he does not take issue with

his failure to receive a trial, or with the procedures by

which the government might have attempted te convict

him. Simply put, Petitioner’s claim is that, no matter

what procedures the government employed or what

evidence the government amassed, the government

could not validly prosecute and convict him for the crime

alleged. Under this Court’s precedent, Petitioner’s mere

act of pleading guilty does not waive or foreclose that

claim.

The Court has drawn a similar line in its retroactivity

jurisprudence. In that context, the Court has recognized

that because a decision invalidating a criminal statute as

unconstitutional leaves no valid basis for a prisoner’s

conviction, it is a “substantive” rule that should apply

retroactively to cases on collateral review, even though

most new “procedural” rules do not.

2. The court below failed to appreciate the

distinction between different types of rights implicated

by a guilty plea and held instead that a defendant cannot

seek to invalidate his voluntary, knowing, and intelligent

plea based on any alleged constitutional violation unless

he has secured the permission of the prosecutor and the

court to enter a conditional plea pursuant to Federal

Rule of Criminal Procedure 11(a)(2). But as that Rule’s

drafters made clear, the Rule has no applicability when

the alleged constitutional violation would render it

impossible for the government to obtain or sustain the

conviction. Although the drafters also referred to the

“jurisdictional” nature of such claims, the drafters were

using the term in a less-than-meticulous manner: a

defendant is not limited to raising post-plea only those

claims that implicate subject-matter or personal

jurisdiction. Nor should a defendant be limited to

raising only facial challenges to the statute under which

he is convicted when an as-applied challenge would

likewise bar a prosecution from ever taking place.

3. This Court should hold, as its precedent compels,

that a guilty plea does not inherently waive or foreclose

a defendant’s right to challenge the constitutionality of

his statute >f conviction. If this Court holds otherwise,

it should remand for a determination of whether

Petitioner’s plea was actually voluntary, knowing, and

intelligent—an argument that Petitioner raised below,

but the Court of Appeals failed to address.

ARGUMENT

I. Defendants Do Not Inherently Waive The

Ability To Challenge The Constitutionality Of

The Statute Of Conviction By Pleading Guilty.

Although courts disfavored plea agreements for

many decades, see, ¢g., Albert W. Alschuler, Plea

Bargaining And Its History, 79 Colum. L. Rev. 1, 5, 19-

24 (1979), “the reality [is] that criminal justice today is

for the most part a system of pleas, not a system of

trials.” Lafler v. Cooper, 566 U.S. 156, 170 (2012). As of

2012, approximately “[nJinety-seven percent of federal

convictions and ninety-four percent of state convictions

[were] the result of guilty pleas.” IJd.; see also Brady v.

United States, 397 U.S. 742, 752 n.10 (1970) (noting that

by 1970, it “ha[d] been estimated that about 90%, and

perhaps 95%, of all criminal convictions [were] by pleas

of guilty,” including “between 70% and 85% of all felony

convictions”). Given that the vast majority of criminal

cases today are resolved through plea agreements, this

Court has addressed the contours and consequences of

guilty pleas on numerous occasions.

This Court has explained that plea agreements are

essentially contracts, and thus must be enforced as

written. Where, as here, the defendant has not

expressly waived his right to bring a direct appeal

challenging the constitutionality of the statute of

conviction, the plea may be read to waive that right only

if there is a default rule that the mere act of pleading

guilty inherently precludes such challenges. This

Court’s cases make clear that no such default rule exists.

In so doing, they draw a line between rights that are

rendered irrelevant by the defendant’s voluntary,

knowing, and intelligent admission of factual guilt, and

thus cannot be subsequently raised as a basis to

invalidate the conviction, and rights that call into

question the government’s power to validly convict the

defendant of the crime alleged.

This line is analogous to the line the Court has drawn

in its retroactivity jurisprudence, in which the Court has

held that decisions that invalidate the statute of

conviction on constitutional grounds are substantive

rules that must apply retroactively because they

implicate the government’s power to hold the defendant

at all. The same reasoning applies in the context of

guilty pleas: a constitutional challenge to the statute of

conviction questions the State’s power to hold the

defendant at all, no matter how perfect the procedures

it employs or how strong the evidence of factual guilt. It

therefore survives a guilty plea.

A. It Is Undisputed That Petitioner’s Guilty Plea

Did Not Expressly Waive His Right To

Challenge The Constitutionality Of The

Statute Of Conviction.

“Plea bargains are essentially contracts.” Puckett v.

United States, 556 U.S. 129, 137 (2009); accord U.S. Dep’t

of Justice, U.S. Attorneys’ Manual, Criminal Resource

Manual § 626(2) (“A plea bargain is a contract between

the prosecutor and the defendant” that “will depend

upon the precise language used.”). Consequently, plea

agreements should ordinarily be interpreted in

accordance with contract principles. Absent “mistake,

fraud, unconscionability, or another invalidating cause,”

a court “must enforce [a contract] as drafted by the

parties.” 11 Richard A. Lord, Williston on Contracts §

31:5, at 461 (4th ed. 2012). This “general rule... prevents

a court from adding terms or provisions to the contract.”

Id. § 31:6. Additionally, as in the case of statutory

interpretation, when a contract contains “a series of two

or more terms or things that should be understood to go

hand in hand,” the “sensible inference” is that “the term

left out must have been meant to be excluded.” Chevron

U.S.A. Inc. v. Echazabal, 536 U.S. 73, 81 (2002); see also

5 Margaret N. Kniffin, Corbin on Contracts § 24.28, at

315-16 (Joseph M. Perillo ed., rev. ed. 1998) (affirming

the applicability of the expressio unius canon to

contracts).

As both the government and the D.C. Circuit have

acknowledged, Petitioner’s plea agreement did not

expressly waive his right to challenge’ the

constitutionality of the statute of conviction on appeal.

Pet. App. 4a; see also Gov’t D.C. Cir. Br. 16 (arguing that

“it is not necessary for the plea agreement to contain an

explicit waiver of appellate review” of claims that the

statute of conviction is unconstitutional). Petitioner’s

plea agreement includes an “explicit waiver of appeal

rights as to sentencing errors,” but no explicit waiver of

appeal rights as to the constitutionality of the statute of

conviction, § 5104(e). Pet. App. 4a; J.A. 40-41. Indeed,

Petitioner’s plea agreement includes an entire section on

“Appeal Rights” that describes the waived appeal rights

in great detail, but does not include any mention of

appeal rights as to Petitioner’s conviction, or as to the

constitutionality of § 5104(e). J.A. 40-41. In the courts

of appeals, “there are numerous examples of appellate

waivers that clearly encompass both the defendant’s

right to appeal his sentence and his right to appeal his

conviction.” United States v. Spear, 753 F.3d 964, 968

(9th Cir. 2014) (emphasis in original). Not so here.

To hold that Petitioner waived his right to challenge

the constitutionality of the statute of conviction on

appeal, this Court therefore would have to read an

implicit waiver into the explicit terms of the parties’

contract—it would have to hold, as the government

argued below, that despite Petitioner’s failure to

explicitly waive his right to appeal his conviction on the

grounds that the statute under which he was convicted

was unconstitutional, “the guilty plea itself effects a

waiver as a matter of law.” Gov’t D.C. Cir. Br. 16. As

discussed below, such a reading of the plea agreement

would be inconsistent with the default rules governing

guilty pleas set forth in decades of this Court’s

precedent.

B. A Constitutional Challenge To The Statute Of

Conviction Calls Into Question Whether The

Government Can Ever Obtain A Valid

Conviction, And Therefore Is Not Waived Or

Foreclosed By A Guilty Plea.

1. In establishing the default rules governing guilty

pleas, the Court has generally divided the rights at issue

into three categories. First, there are constitutional

rights that simply “inhere in a criminal trial, including

the right to trial by jury, the protection against self-

incrimination, and the right to confront one’s accuser.”

Florida v. Nixon, 543 U.S. 175, 187-88 (2004) (citing

Boykin v. Alabama, 395 U.S. 238, 243 (1969)); United

States v. Ruiz, 5386 U.S. 622, 628-29 (2002). The default

rule is that these basic trial rights are automatically

waived by a guilty plea so long as that plea is voluntary,

knowing, and intelligent: because a guilty plea forecloses

the possibility of a trial, it necessarily forecloses the

assertion of the associated constitutional trial rights.

See, e.g., Boykin v. Alabama, 395 U.S. 238, 243 & n.5

(1969). However, the assertion of appellate rights does

not fall within this category, because an appeal “cannot

in any way be characterized as part of the trial.” Lafler,

566 U.S. at 165.

Second, there are procedural rights that inhere in a

criminal prosecution, but are rendered irrelevant

(rather than waived) by a valid guilty plea. These rights

include, for example, the Fourth Amendment’s

protection against unreasonable searches and seizures,

Haring v. Prosise, 462 U.S. 306, 320-21 (1983); the Fifth

Amendment’s guarantee against involuntary

confessions, McMann v. Richardson, 397 U.S. 759, 771-

72 (1970); and the Fourteenth Amendment’s safeguard

against racial discrimination in grand jury selection,

Tollett, 411 U.S. at 266-68. These are fundamental

constitutional protections that a defendant is ordinarily

entitled to rely upon, but that become irrelevant after a

defendant pleads guilty and thereby admits his factual

guilt. The default rule with respect to this class of rights

is that they cannot be asserted after a defendant has

entered a voluntary, knowing, and intelligent guilty

plea.

In Tollett v. Henderson, 411 U.S. 258 (1973), and in

the so-called “Brady trilogy” of Brady v. United States,

397 U.S. 742 (1970), McMann v. Richardson, 397 U.S.

759 (1970), and Parker v. North Carolina, 397 U.S. 790

(1970), this Court explained that when a defendant

pleads guilty, his right to assert that a violation of these

procedural rights should invalidate his conviction is

necessarily foreclosed. Because a criminal defendant

has voluntarily, knowingly, and intelligently admitted

his factual guilt—.e., he has “solemnly admitted in open

court that he is in fact guilty of the offense with which he

is charged”—he may not invalidate the plea based on

mere procedural defects that the government could have

remedied through different pre-trial procedures. 411

U.S. at 267-68. This is because such procedural defects

might “only [have] delay[ed] the inevitable date of

prosecution” rather than prohibited it entirely. Jd.

Unlike the core trial rights in the first category that

are inherently waived by a guilty plea, the procedural

rights in this second category are not “waived” at all.

Rather, the concept at issue is akin to forfeiture. “A

guilty plea represents a break in the chain of events

which has preceded it in the criminal process,” such that

it forecloses further inquiry into most constitutional

deprivations that occurred before the plea. Jd. at 267-68.

This Court has therefore held that “when a defendant is

convicted pursuant to his guilty plea rather than a trial,

the validity of that conviction cannot be affected by”

procedural or evidentiary errors like “an alleged Fourth

Amendment violation because the conviction” rests on

the defendant’s admission of guilt, not “on evidence that

may have been improperly seized.” Haring, 462 U.S. at

321.

Finally, there are rights that go to the very power of

the government to bring the prosecution and secure the

conviction at all. These include, for example, the Fifth

Amendment rights not to be put into double jeopardy or

to be vindictively prosecuted. As this Court explained

in Blackledge and Menna, these rights go to “the very

power of the State to bring the defendant into court to

answer the charge brought against him.” Blackledge,

417 U.S. at 30. The default rule with respect to these

rights is that they are neither waived nor foreclosed by

the act of pleading guilty.

The Blackledge/Menna rights in this third category

are “fundamental{ly] distinct[]’ from the Tollett/Brady

rights in the second category, as this Court explained

with the following illustration: “The defendants in

McManzxn v. Richardson, for example, could surely have

been brought to trial without the use of the allegedly

coerced confessions, and even a tainted indictment of the

sort alleged in Tollett could have been ‘cured’ through a

new indictment by a properly selected grand jury.”

Blackledge, 417 U.S. at 30. However, with respect to

Blackledge/Menna rights, “the nature of the underlying

constitutional infirmity is markedly different.” Jd.

Defendants in this category are not “complaining of

‘antecedent constitutional violations’ or of a ‘deprivation

of constitutional rights that occurred prior to the entry

of the guilty plea.” Jd. Instead, the right asserted is one

“not to be haled into court at all upon the felony charge,”

having the “practical result” of “prevent[ing] a trial from

taking place at all, rather than .. . prescrib[ing]

procedural rules that govern the conduct of a trial.” Jd.

at 30-31 (internal quotation marks omitted).

In Menna, this Court expanded upon this distinction

between substantive rights that go to the very power of

the State to bring the prosecution and procedural rights

that do not, noting that with respect to the constitutional

rights in the latter category, a guilty plea “simply

renders irrelevant those constitutional violations not

logically inconsistent with the valid establishment of

factual guilt and which do not stand in the way of

conviction if factual guilt is validly established.” 423

U.S. at 62 n.2. With respect to the rights in the former

category, “the claim is that the State may not convict

petitioner no matter how validiy his factual guilt is

established,” because “the charge is one which the State

may not constitutionally prosecute.” Jd.*

5 Judge Friendly summarized this Court’s decisions in a similar

manner. Reviewing Blackledge, Menna, Tollett, and the Brady

trilogy, he described “the guiding principle of these decisions” as

follows:

Most recently, this Court distinguished among these

types of claims in United States v. Broce, 488 U.S. 563

(1989). The defendants in Broce pled guilty to two

counts of conspiracy contained in two separate

indictments, but later tried to raise a double jeopardy

claim to vacate one of the conspiracy counts because a

subsequent prosecution of a different defendant

suggested that there may have been only one

conspiracy. Jd. at 566-67, 576. This Court declined to

entertain the double jeopardy claim, emphasizing that it

was “foreclosed by the admissions inherent in

[defendants’] guilty pleas,” including that the

defendants entered into “two agreements which started

at different times and embraced separate objectives.”

Id. at 571, 576.

In reaching this conclusion, the Court distinguished

the double jeopardy claims at issue in Broce from the

double jeopardy claims at issue in Menna. In Broce, the

defendants could not “prove their claim without

contradicting” the indictments to which they pled guilty,

meaning that their claims were foreclosed under the

A defendant who has been convicted on a plea of guilty

may challenge his conviction cn any constitutional ground

that, if asserted before trial, would forever preclude the

state from obtaining a valid conviction against him,

regardless of how much the state might endeavor to

correct the defect. In other words, a plea of guilty may

operate as a forfeiture of all defenses except those that,

once raised, cannot be cured.

United States v. Curcio, 712 F.2d 1532, 1538-39 (2d Cir. 1983)

(alterations and internal quotation marks omitted).

logic of Tollett and the Brady trilogy. Jd. at 576. By

contrast, in Menna, “the indictment was facially

duplicative of the earlier offense of which the defendant

had been convicted”; the facts the defendant admitted

could not “conceivably be construed” as anything other

than “a redundant confession to the earlier offense” and

thus, a double jeopardy violation. /d. at 575-76. Broce

therefore follows the Tollet/Brady line of cases in finding

that a guilty plea prohibits further inquiry into

constitutional violations that become irrelevant once a

defendant admits that he is guilty of facts the

government may criminalize. At the same time, it

reaffirms that under Blackledge and Menna, “a plea of

guilty to a charge does not waive a claim that—judged

on its face—the charge is one which the State may not

constitutionally prosecute.” Jd. at 575 (emphasis in

original) (quoting Menna, 423 U.S. at 62 n.2).

2. The right not to be prosecuted and convicted

pursuant to an unconstitutional statute clearly falls into

the Blackledge/Menna category of rights and is neither

waived nor foreclosed automatically by a plea of guilty.

Such a challenge goes to the government’s very power

to prosecute or convict a defendant. It, by contrast, does

not concern the evidentiary disputes and procedural

errors that formed the basis of the constitutional

challenges in Tollett and the Brady trilogy.

As noted above, a guilty plea forecloses further

inquiry only into “constitutional violations not logically

inconsistent with the valid establishment of factual guilt

and which do not stand in the way of conviction, if factual

guilt is validly established.” Menna, 423 U.S. at 62 n.2.

Here, however, Petitioner’s claim is that the statute

under which he has been convicted is unconstitutional

and thus “the charge is one which the State may not

constitutionally prosecute”; in other words, “the State

may not convict [Petitioner] no matter how validly his

factual guilt is established.” Jd. “The guilty plea,

therefore does not bar the claim.” Jd.

As this Court recently reaffirmed, a “conviction

under an unconstitutional law is not merely erroneous,

but is illegal and void, and cannot be a legal cause of

imprisonment.” Montgomery, 136 S. Ct. at 730-31

(quoting Ex parte Siebold, 100 U.S. at 376) (internal

quotation marks omitted). Put another way, “an

unconstitutional law is void, and is as no law,” and any

penalty imposed pursuant to that law “is, by definition,

unlawful.” Jd. (quoting Ex parte Siebold, 100 U.S. at

376). Thus, the assertion that the underlying statute is

unconstitutional most certainly would “stand in the way

of conviction, [even] if factual guilt is validly

established,” Menna, 423 U.S. at 62 n.2, since the State

has no lawful basis for convicting a defendant in the

absence of a valid statute criminalizing his conduct.

Because Petitioner’s due process and Second

Amendment claims are challenges to the very power of

the government to criminalize his conduct, he retained

the right to pursue those challenges after pleading

guilty. If Petitioner is correct that the Second

Amendment precludes the government from enacting a

law that criminalizes storage of lawfully-owned firearms

in a locked vehicle in a publicly accessible parking lot

approximately 1,000 feet from the entrance to the

Capitol building, then Petitioner’s conviction cannot

stand. So too with respect to Petitioner’s due process

notice challenge. For these reasons, Petitioner’s guilty

plea did not foreclose his right to appeal his conviction

with a challenge to the constitutionality of § 5104.

3. That Petitioner’s guilty plea did not implicitly

waive his challenge to § 5104 is particularly clear

because, at the time it decided Blackledge and Menna,

this Court had already recognized that a defendant’s

challenge to the constitutionality of the statute of

conviction survives a guilty plea. In Haynes v. United

States, 390 U.S. 85 (1968), the defendant was a convicted

felon charged with failing to register a firearm under the

National Firearms Act, id. at 86-87. The defendant

moved to dismiss the indictment, arguing that because

he was a convicted felon and thus prohibited from

owning a firearm, requiring him to register that firearm

violated his Fifth Amendment right against self-

incrimination. Jd. at 86,90. The court denied the motion

to dismiss the indictment and the defendant thereafter

pled guilty, admitting that he had indeed failed to

The defendant then appealed his conviction on the

grounds that the registration requirement was

unconstitutional both on its face and as applied to him.

Id. at 87; see also Haynes v. United States, 372 F.2d 651,

652-54 (5th Cir. 1967), judgment rev'd, 390 U.S. 85 (1968).

The Fifth Circuit reached the merits of his claims, noting

that while a “guilty plea is a waiver of all

nonjurisdictional defects and defenses and admits the

facts charged, .. . [wJhere, prior to his guilty plea, a

defendant appropriately raises the unconstitutionality

of the applicable statute, an appeal, directed to that

issue, is not foreclosed.” Haynes, 372 F.2d at 652 (citing

Ex parte Siebold, 100 U.S. 371).

After the Fifth Circuit upheld the defendant’s

conviction, this Court granted certiorari. Like the Fifth

Circuit, this Court also reached the merits of defendant’s

claims, considering it quite obvious that “Petitioner’s

plea of guilty did not, of course, waive his previous claim

of the constitutional privilege.” Haynes, 390 U.S. at 87

n.2. While the Court did not further explain its rationale

for this statement, it seems clear that the Court was

animated by the same concerns in Haymes as it was in

Blackledge and Menna—a guilty plea conceding factual

guilt does not resolve questions about the government’s

very ability to bring the prosecution. Ultimately, this

Court not only reached the merits of the defendant's

claims in Haynes, it held the statute unconstitutional as

applied to the defendant and reversed, finding it

unnecessary to remand because “any proceeding in the

District Court must inevitably result in the reversal] of

petitioner’s conviction.” Jd. at 101. Like Blackledge and

Menna, Haynes thus demonstrates that a guilty plea is

not an automatic bar to a constitutional challenge to the

statute of conviction.

4. Indeed, some of this Court’s most historic rulings

on constitutional rights arose from circumstances in

which defendants pled guilty and later mounted

constitutional challenges to their statutes of conviction.

In Loving v. Virginia, 388 U.S. 1 (1967), for example,

Richard and Mildred Loving pled guilty to violating

Virginia’s ban on interracial marriages. Jd. at 3. After

they were sentenced, the Lovings filed a motion to

vacate the judgment against them and set aside their

sentences, “asserting that the statute under which they

were convicted was unconstitutional and that the

sentences imposed upon them were invalid.” Loving v.

Commonwealth, 147 S.E.2d 78, 79 (Va. 1966), judgment

rev'd, 388 U.S. 1 (1967). The government never argued

that the Lovings’ pleas foreclosed their constitutional

challenge, and this Court certainly did not view their

pleas as a bar, ultimately holding that because “[t]he

Fourteenth Amendment requires that the freedom of

choice to marry not be restricted by invidious racial

discriminations . . . [t]hese convictions must be

reversed.” 388 U.S. at 12.

C. This Court’s Retroactivity Jurisprudence

Confirms That Constitutional Challenges To

Criminal Statutes Raise Heightened

Concerns.

In several other contexts discussed by Petitioner’s

amici, such as standing doctrine and pre-enforcement

review of criminal statutes, this Court has recognized

that challenges to the constitutionality of criminal

statutes raise heightened concerns and warrant special

solicitude. This is particularly true in the context of the

Court’s retroactivity jurisprudence. This parallel body

of case law supports a holding that a guilty plea does not

inherently waive a defendant’s challenge to the

constitutionality of the statute of conviction.

1. As early as Ex parte Siebold, 100 U.S. 371 (1879),

this Court recognized that while a prisoner generally

could not use the writ of habeas corpus to attack “a

conviction and sentence by a court having jurisdiction of

the cause,” he could obtain relief in habeas if “the want

of jurisdiction . . . or some other matter render[ed] [the

original court’s} proceedings void.” Jd. at 375.4 The

Court then held that a challenge to the constitutionality

of the statute of conviction fell within this narrow class

of cases in which a court could afford habeas relief. As

the Court explained, if the petitioners’ argument was

“well taken, it affects the foundation of the whole

proceedings. An unconstitutional law is void, and is as

no law. An offence created by it is not a crime. A

conviction under it is not merely erroneous, but is illegal

and void, and cannot be a legal cause of imprisonment.”

Id. at 376-77.

The Court’s modern retroactivity jurisprudence

recognizes the same principle. In Teague v. Lane, 489

U.S. 288 (1989), the Court held that as a general matter,

“new constitutional rules of criminal procedure will not

be applicable to those cases which have become final

before the new rules are announced,” but are challenged

in collateral proceedings. /d. at 310 (plurality opinion).

The Court imposed two exceptions, however: “a new

rule” applies retroactively on collateral review if it

“places ‘certain kinds of primary, private individual

conduct beyond the power of the criminal law-making

authority to prosecute”—what has become known as a

4 Siebold stated that “if the laws [of conviction] are unconstitutional

and void, the Circuit Court acquired no jurisdiction of the causes.”

Id. at 377. As discussed infra, however, the use of the term

“jurisdiction” has not always been consistent, and the Siebold

Court's invocation of that word is best understood as meaning that

the government lacked authority to criminalize the defendants’

actions—not that the court lacked jurisdiction in the modern sense

of authority to decide the case. See United States v. Williams, 341

U.S. 58, 66 (1951).

“substantive rule”—or if it “alter[s] our understanding

of the bedrock procedural elements essential to the

fairness of a proceeding”—what the Court termed a

“watershed rule[] of criminal procedure.” /d. at 311

(plurality opinion) (quoting Mackey v. United States, 401

U.S. 667, 693 (1971)).

Subsequent cases have expanded on the distinction

between substantive rules, which apply retroactively,

and most procedural rules, which do not. Substantive

rules “include[] decisions that narrow the scope of a

constitutional statute by interpreting its terms, ... as

well as constitutional determinations that place

particular conduct or persons covered by the statute

beyond the State’s power to punish.” Schriro v.

Summerlin, 542 U.S. 348, 351-52 (2004) (citing Bousley

v. United States, 523 U.S. 614, 20-21 (1998); Saffle v.

Parks, 494 U.S. 484, 494-95 (1990); Teague, 489 U.S. at

311 (plurality opinion)). “Such rules apply retroactively

because they ‘necessarily carry a significant risk that a

defendant stands convicted of an act that the law does

not make criminal’ or faces a punishment that the law

cannot impose upon him.” Jd. at 352 (quoting Bousley,

523 U.S. at 620). While the government might be able to

proscribe the same conduct under a more aptly or

narrowly drawn law going forward, the government

cannot continue to hold the defendant under a statute

that is not constitutionally drawn. See, e.g., Welch v.

United States, 136 S. Ct. 1257, 1265-67 (2016).

By contrast, new rules of procedure generally do not

apply retroactively. That is because “[t]hey do not

produce a class of persons convicted of conduct the law

does not make criminal, but merely raise the possibility

that someone convicted with use of the invalidated

procedure might have been acquitted otherwise.” Jd. at

1265 (quoting Schrivo, 542 U.S. at 352) (quotation marks

omitted). New procedural rules, in other words, do not

impact the State’s ability to prosecute the specific

defendant for the conduct at issue, and they are

generally surmountable by the government: even if the

defendant shows that a different procedure should have

been followed, the government normally would be free

to re-try the defendant using those procedures, or to

show that any error was harmless. For this reason,

procedural rules have a “speculative connection to

innocence.” Schriro, 542 U.S. at 352. Unlike substantive

rules, they do not necessarily undermine the

determination that the defendant is guilty of the crime.

In this way, the Court’s distinction between

substantive rules, which always apply retroactively, and

procedural rules, which usually do not, echoes the

distinction between the Blackledge/Menna and

Tollet/Brady lines of cases. Substantive rules apply

retroactively because they go to the State’s very power

to validly prosecute the defendant, just as

Blackledge/Menna claims survive a guilty plea because

they too challenge the State’s power to hold the

defendant for the crime alleged. By contrast, procedural

challenges generally do not apply retroactively, because,

like Tollett/Brady claims, they raise concerns that go to

the particular procedures used to obtain a conviction.

Concerns with the finality of a conviction are also

parallel in the two contexts. In the retroactivity cases,

this Court has explained that while the State often has a

“weighty interest[] in ensuring the finality of convictions

and sentences,” Montgomery, 136 S. Ct. at 732, where

the conviction or sentence is not authorized by law,

“finality interests are at their weakest,” Welch, 136 S.

Ct. at 1266. “As Justice Harlan wrote, ‘[tjhere is little

societal interest in permitting the criminal process to

rest at a point where it ought properly never to repose.”

Id. (quoting Mackey, 401 U.S., at 693 (opinion of Harlan,

J.)); see also Montgomery, 136 S. Ct. at 732 (noting that

Teague’s concerns with finality and expenditure of

State’s resources “has no application in the realm of

substantive rules, for no resources marshaled by a State

could preserve a conviction or sentence that the

Constitution deprives the State of power to impose”).

The same is true in the context of a challenge to the

constitutionality of a statute following a guilty plea:

because the State simply cannot convict someone of an

act the law does not make criminal, the State lacks a

viable interest in maintaining the finality of such a

conviction on appeal.

Finality interests are stronger, however, for both

Tollett/Brady claims and claims relying on the

retroactive application of procedural rules. See

McMann, 397 U.S. at 774 (explaining that permitting

defendants to pursue claims of antecedent constitutional

violation post-plea “would be an improvident invasion of

the State’s interests in maintaining the finality of guilty-

plea convictions”); Teague, 489 U.S. at 309 (plurality

opinion) (“Application of constitutional rules not in

existence at the time a conviction became final seriously

undermines the principle of finality which is essential to

the operation of our criminal justice system.”). In those

cases, “{i]f a new rule regulates only the procedures for

determining culpability ... [t]he chance of a more

accurate outcome under the new procedure normally

does not justify the cost of vacating a conviction whose

only flaw is that the procedures ‘conformed to then-

existing constitutional standards.” Welch, 136 S. Ct. at

1266 (quoting Teague, 489 U.S. at 310 (plurality

opinion)). Therefore, the “balance generally tips in favor

of finality.” Id.

In sum, this Court has recognized in the retroactivity

context that challenges to the constitutionality of the

statute of conviction are different in kind from

challenges to the particular procedures followed to

prove a defendant’s factual guilt. The retroactivity case

law thus supports holding that a defendant who pleads

guilty may nonetheless raise a challenge to the

constitutionality of the underlying statute on appeal,

just as a habeas petitioner may benefit in post-conviction

proceedings from the invalidation of an unconstitutional

statute after his own conviction has become final.

2. To hold otherwise would make little sense. In its

Brief in Opposition, the government argued that if this

Court were to conclude that a defendant who pleads

guilty is inherently precluded from challenging on direct

appea! the constitutionality of the statute of conviction,

he could nonetheless “seek[] the benefit of a substantive

ruling establishing that the statute of conviction is

unconstitutional [by] seek{ing] relief under 28 U.S.C.

2255.” BIO 18. However, as Petitioner noted in reply,

the government likely would contend at that point that

the defendant had forfeited the claim by failing to raise

it on direct review. See Pet. Reply 6 n.4 (citing Massaro

v. United States, 538 U.S. 500, 504 (2003)). That would

place the defendant in an impermissible Catch-22: on

direct appeal, the government would argue that the

constitutional claims can be raised only in habeas—and

then in habeas, the government would take the position

that the claims were procedurally improper for having

not been raised on direct review.

Moreover, even if a defendant who is barred from

raising a claim on direct appeal were able to do so on

collateral review, that rule would result in a substantial

waste of resources. It would require courts to address

claims on collateral review that easily could have been

resolved on direct appeal. It also would force defendants

who have been prosecuted under unconstitutional

statutes to further languish in the criminal justice

system while they await relief in habeas. And it would

leave unconstitutional statutes on the books for longer,

chilling protected conduct. Such a result would extract

great cost from defendants and the judicial system alike

with little or no corresponding benefit.

Il. Rule 11(a)(2) Does Not Require That A

Constitutional Challenge To The Statute Of

Conviction—Facial Or As-Applied—Be

Expressly Preserved In A Plea Agreement.

The court below got the default rules wrong.

Without even mentioning this Court’s decisions in

Blackledge and Menna, the D.C. Circuit erroneously

held that it could not entertain Petitioner’s

constitutional challenges to the statute under which he

was convicted. The court rested its decision on the fact

that Petitioner did not enter a conditional plea pursuant

to Federal Rule of Criminal Procedure 11(a)(2), which

provides that “[w]ith the consent of the court and the

government, a defendant may enter a conditional plea of

guilty ..., reserving in writing the right to have an

appellate court review an adverse determination of a

specified pretrial motion.” See Pet. App. 4a. The D.C.

Circuit held that in the absence of a conditional plea

entered under Rule 11(a)(2), all claims of error are

waived by a guilty plea, and that there were only “two

recognized exceptions to this rule”: “the defendant’s

claimed right not to be haled into court at all” and a claim

that the court lacked subject-matter jurisdiction over

the case. Pet. App. 4a (quoting Delgado-Garcia, 374

F.3d at 1341). The court then found that neither

“exception” applied in this case.

By not engaging with Blackledge and Menna or

Petitioner’s arguments, the D.C. Circuit failed to

appreciate that Rule 11(a)(2) has no application to this

case. As explained by the Advisory Committee that

drafted it, Rule 11(a)(2) applies only when Blackledge

and Menna do not. For the reasons set forth in Part I,

Petitioner’s Second Amendment and due process

challenges fall squarely within the Blackledge/Menna

doctrine, and therefore he did not need to expressly

reserve those claims in writing or obtain the

government’s or the court’s permission to preserve

those claims for appeal. Nor does it matter, as some

lower courts and the government have suggested,

whether those claims are considered “jurisdictional,” or

whether they are presented as facial or as-applied

challenges.

1. Like the D.C. Circuit, the government has relied

on Federal Rule of Criminal Procedure 11(a)(2) to

support the argument that a defendant who pleads

guilty inherently waives his right to challenge the

statute of conviction on appeal. BIO 7-8. Yet the Rule

in fact favors Petitioner’s view, because it reiterates the

distinction between Tollett/Brady claims, to which the

Rule applies, and Blackledge/Menna claims, to which it

does not.

Adopted in 1983, Rule 11(a)(2) was enacted to resolve

a circuit split on the permissibility of conditional pleas

that reserve a defendant’s right to “have an appellate

court review an adverse determination of a specified

pretrial motion.” Fed. R. Crim. P. 11(a)(2); see also Fed.

R. Crim. P. 11 advisory committee’s note to 1983

amendments. Rule 11(a)(2) sanctioned the practice, but

it imposed two conditions on defendants who wished to

take advantage of the new rule. First, defendants were

required to “reserv[e] in writing” those claims that they

wished to preserve. Second, they had to obtain “the

consent of the court and the government.” Fed. R. Crim.

P. 11(a)(2).

Importantly, the Advisory Committee explained

that Rule 11(a)(2)’s new requirements did not apply to

all pretrial motions—specifically, the requirements did

not apply to pretrial motions raising Blackledge/Menna

claims about the very power of the State to prosecute

the defendant. As the Advisory Committee explicitly

noted: “The Supreme Court has held that certain kinds

of constitutional objections may be raised after a plea of

guilty. .. . Subdivision 11(a)(2) has no application to

such situations, and should not be interpreted as either

broadening or narrowing the Menna-Blackledge

doctrine or as _ establishing procedures for its

application.” Fed. R. Crim. P. 11 advisory committee’s

note to 1983 amendments (emphasis added). Thus, the

Advisory Committee clarified that where a

constitutional objection fails into the Blackledge/Menna

category, there is no need for a defendant to reserve in

writing his right to bring the constitutional objection, or

to obtain the permission of the court or the government

to appeal.

Such a qualification is eminently reasonable given

the nature of claims under Blackledge and Menna. It

would make little sense to require the defendant to

obtain the permission of the prosecutor to preserve a

challenge to the very power of the prosecutor over the

defendant. Such a requirement would leave defendants

“at the mercy of noblesse oblige.” United States v.

Stevens, 559 U.S. 460, 480 (2010). Considering the vast

leverage that prosecutors wield in plea negotiations, see,

e.g., Ronald F. Wright, Trial Distortion and the End of

Innocence in Federal Criminal Justice, 164 U. Pa. L.

Rev. 79, 109-12 (2005), establishing a default rule that

would require defendants to affirmatively preserve a

constitutional challenge to the statute of conviction

would not only render the Advisory Committee’s notes

about Blackledge and Menna meaningless, it would

render the very doctrine of Blackledge and Menna

meaningless.

2. Although the Advisory Committee was explicit

about the inapplicability of Rule 11(a)(2)’s requirements

to Blackledge/Menna claims, the Committee unhelpfully

couched its broader discussion of Rule 11(a)(2) in terms

of “jurisdiction.” In discussing Rule 11(a)(2) generally,

the Advisory Committee noted that “the availability of

a conditional plea under specified circumstances will aid

in clarifying the fact that traditional, unqualified pleas

do constitute a waiver of nonjurisdictional defects.”

Fed. R. Crim. P. 11 advisory committee’s note to 1983

amendments (emphasis added). Many lower courts have

also used this language, holding that only challenges to a

court’s “jurisdiction” survive a guilty plea, and pointing

to Blackledge and Menna as examples of such

“jurisdictional” challenges. See, e.g., United States v.

Phillips, 645 F.3d 859, 862 (7th Cir. 2011); United States

v. Andrade, 83 F.3d 729, 731 (5th Cir. 1996) (“A plea of

guilty typically waives all non-jurisdictional defects in

the proceedings below’). By using the terms

“jurisdictional” and “nonjurisdictional” in a “less than

meticulous” manner, Kontrick v. Ryan, 540 U.S. 4438, 454

(2004), the Advisory Committee and the lower courts

have generated significant confusion.

The Advisory Committee’s note does not mean that

the class of rights protected by Blackledge and Menna

implicates a court’s jurisdiction in the formal sense of

subject-matter or personal jurisdiction. See Kontrick,

540 U.S. at 454. Rather, the Advisory Committee and

those courts that have properly understood the scope of

Blackledge and Menna have used the term “jurisdiction”

as shorthand for the idea that the government has no

power to criminalize the conduct at issue.’ The Seventh

®* The D.C. Circuit appears to have understood that

Blackledge/Menna claims are not themselves “jurisdictional,”

because it conceptualized the “exception” for “jurisdictional” claims

as distinct from the “exception” for claims that raise the defendant’s

right “not to be haled into court at all,” like those in Blackledge and

Menna. See Pet. App. 4a (discussing Delgado-Garcia, 374 F.3d at

Circuit has acknowledged as much with respect to its

own use of the term in the guilty plea context, noting

that “jurisdictional’ . . . does not refer to subject matter

jurisdiction.” Phillips, 645 F.3d at 862. Instead, “[a]

jurisdictional issue is one that stands in the way of

conviction—even when factual guilt is validly

established—and prevents a court from entering any

judgment in the case.” Id. (citing Blackledge, 417 U.S.

at 30). Other courts have similarly explained their use

of the words “jurisdictional” and “nonjurisdictional” in

this context. See, e.g., United States v. DeVaughn, 694

F.3d 1141, 1152-53 (10th Cir. 2012) (acknowledging that

the court’s previous statement that guilty pleas waive all

“nonjurisdictional defects” is a misnomer in light of

Blackledge and Menna); United States v. Johnston, 199

F.3d 1015, 1019 n.3 (9th Cir. 1999) (“jurisdictional”

defects in the context of a guilty plea include “claims in

which .. . the charge in question is one which the state

may not constitutionally prosecute”).

Blackledge and Menna themselves make clear that

they are not limited to claims that are formally

“jurisdictional” in nature—i.e., those “prescriptions

delineating the class of cases (subject-matter

jurisdiction) and the persons (personal jurisdiction)

falling within a court’s adjudicatory authority.”

Kontrick, 540 U.S. at 455, After all, the due process and

double jeopardy challenges in those cases would not

meet that test: they are not jurisdictional in the sense

that, if valid, they would demonstrate that the court

1341). As discussed infra, however, the D.C. Circuit interpreted the

“haled into court” language in an unduly narrow fashion.

lacks “adjudicatory authority” over the case. See id.;

DeVaughn, 694 F.3d at 1153-54; Phillips, 645 F.3d at

862-63; United States v. Baucum, 80 F.3d 5389, 542-43

(D.C. Cir. 1996).

3. Similarly misguided was the D.C. Circuit’s holding

that Petitioner’s claims were foreclosed because they did

not involve the “right not to be haled into court at all.”

Pet. App. 4a (quotation marks omitted). Although it did

not mention Blackledge, the court was presumably

referencing Blackledge’s statement that the due process

right asserted in that case was “the right not to be haled

into court at all upon the felony charge.” 417 U.S. at 30.

The D.C. Circuit offered an extraordinarily narrow view

of that statement, apparently holding that Petitioner

forfeited his constitutional claims by appearing in court

to answer the charges against him. That is, of course,

not what Blackledge held. Rather, as explained above,

Blackledge was about the power of the State to obtain a

valid conviction. See id. at 30-31; Menna, 423 U.S. at 62

& n.2.

Again, Blackledge and Menna themselves make

clear that the “haled into court” language does not

literally limit the types of challenges that may be raised

following a guilty plea to those in which a defendant

never has to appear in court to answer the charges

against him. In both Blackledge and Menna, the

defendants were in fact “haled into court” and required

to litigate their constitutional challenges following their

guilty pleas from the trial courts through the courts of

appeals and to the Supreme Court. 417 U.S. at 30; 423

U.S. at 61-62. As explained above, the correct inquiry

under Blackledge and Menna is not about being

physically “haled into court.” Rather, it is about

whether the defendant’s claim, if successful, would

forever prevent a valid prosecution or trial from taking

place. Petitioner’s constitutional challenges meet this

test, and he should have been permitted to pursue them

on appeal without expressly reserving them pursuant to

Rule 11(a)(2).

4. Although the D.C. Circuit did not reach the issue,

some other courts of appeals have further confused the

scope of Blackledge and Menna by holding that guilty

pleas inherently waive as-applied, but not facial,

constitutional challenges to the statute of conviction.

See United States v. Aranda, 612 F. App’x 177, 178 n.1

(4th Cir. 2015); Phillips, 645 F.3d at 863; United States

v. Seay, 620 F.3d 919, 922-23 (8th Cir. 2010). This

distinction makes little sense and contravenes this

Court’s own precedent. Where the claim is that the

State is without power to prosecute, it does not matter

whether the challenge is facial or as applied.

Blackledge and Menna themselves involved as-

applied challenges. In Blackledge, the claim was that the

State was, “under the facts of this case, simply precluded

by the Due Process Clause from calling upon the

respondent to answer to the more serious charge in the

Superior Court.” 417 U.S. at 30 (emphasis added).

Likewise, in Menna, the defendant’s claim was that

because of the particular facts of that case, the “Double

Jeopardy Clause precluded the State from haling him

into court on the charge to which he had pleaded guilty.”

423 U.S. at 62. Similarly, in Haynes, this Court reversed

the petitioner’s conviction following a guilty plea even

though it agreed with the government that a facial

challenge to the statute at issue was “inappropriate.”

390 U.S. at 99.

To the extent the Blackledge/Menna category is

limited to “facial” claims, it is limited only by the concept

of “facia]” set forth in Broce, in which the Court declined

to entertain defendants’ claim of double jeopardy

because the defendants could not “prove their claim by

relying on those indictments and the existing record” at

the time of the plea. 488 U.S. at 576. Thus, Broce held

that the Blackledge/Menna claim must be apparent “on

the face” of the record as it exists at the time of the plea.

Id. at 569 (majority opinion); id. at 583 (Blackmun, J.,

dissenting). Broce’s holding that defendants cannot rely

on later-established facts should not be misconstrued as

a categorical prohibition of as-applied claims.

It would be odd indeed to allow a defendant to bring

facial but not as-applied constitutional challenges post-

plea, given that facial challenges are generally

“disfavored” by the Court. Wash. State Grange v. Wash.

State Republican Party, 552 U.S. 442, 450 (2008). Facial

challenges can “run contrary to the fundamental

principle of judicial restraint” because they often ask the

court to “formulate a rule of constitutional law broader

than is required by the precise facts to which it is to be

applied.” Jd. (internal quotation marks omitted); see also

Citizens United v. FEC, 558 U.S. 310, 331 (2010) (noting

that the “distinction between facial and as-applied

challenges is not so well defined that it has some

automatic effect”). There is no reason to hold that a

defendant must seek to invalidate a statute in all

instances in order to argue that the statute cannot make

him a criminal in a particular circumstance. This Court

should clarify that Petitioner is permitted to bring both

his facial and as-applied challenges on appeal.

Ill. In The Alternative, The Court Should Remand

For A Determination Of Whether Petitioner’s

Plea Was Voluntary, Knowing, And

Intelligent.

For all of the reasons discussed above, this Court

should hold that a guilty plea does not inherently waive

the defendant’s right to challenge the constitutionality

of the statute of conviction. Nonetheless, if this Court

disagrees and establishes a new default rule requiring

defendants to expressly preserve such rights in their

plea agreements pursuant to Rule 11(a)(2), the Court

should remand for the lower courts to determine

whether Petitioner’s plea was voluntary, knowing, and

intelligent—an issue that Petitioner raised below, but

that the Court of Appeals failed to address.

This Court has long held that a guilty plea “is valid

only if done voluntarily, knowingly, and intelligently,

‘with sufficient awareness of the relevant circumstances

and likely consequences.” Bradshaw v. Stumpf, 545

U.S. 175, 183 (2005) (quoting Brady, 397 U.S. at 748); see

also, e.g., Henderson v. Morgan, 426 U.S. 637, 644-45

(1976). If the Court concludes that despite the lack of

any express waiver in his plea agreement, Petitioner’s

guilty plea nonetheless waived his right to directly

appeal the constitutionality of the statute of conviction,

serious questions remain regarding whether the plea

was voluntary, knowing, and intelligent. See Tollett, 411

US. at 267 (reaffirming principle that even where a

guilty plea eliminates the right to raise a challenge based

on a preceding constitutional violation, the defendant

remains free to “attack the voluntary and intelligent

character of the guilty plea”).

Although Petitioner consulted “off and on” with

stand-by counsel, he was pro se when he pled guilty. J.A.

53. Yet rather than receive a clear explanation of the

consequences of his plea from the district court, he was

informed that he could “appeal a conviction after a guilty

plea if [he] believe[d] that [his] guilty plea was somehow

unlawful.” JA. 63. Thereafter, when the court asked

Petitioner if he “want[ed] to give up most of [his] rights

to an appeal,” Petitioner responded that he was willing

to give up those rights “{o]ther than what [the court]

mentioned.” J.A. 66. The court did not seek to establish

what Petitioner meant by this statement or whether

Petitioner understood what the court meant when it

informed Petitioner that he could “appeal [his]

conviction after a guilty plea if [he] believe[d] that [his]

guilty plea was somehow unlawful.” J.A. 63, 66; cf.

United States v. Warwar, 478 F.2d 1183, 1184-85 (1st Cir.

1973) (“[WJhen it affirmatively appears that the

defendant may be under a misapprehension as to the

effect of a guilty plea upon the preservation of any of his

rights, it becomes the duty of the court to take

appropriate corrective action. In the present case, the

court should have informed the appellant that, by

pleading guilty, he might be waiving a claim which he

apparently intended to preserve ... .”).

The court’s statement, coupled with the plea

agreement’s omission of an express waiver of the right

to appeal his conviction among the express listing of

other waived rights, strongly corroborates Petitioner’s

assertion that he did not make a voluntary, knowing, and

intelligent decision to waive his right to appeal. That

Petitioner did not understand the scope of his plea’s

appellate waiver to include a challenge to the

constitutionality of his statute of conviction is

particularly clear considering Petitioner’s course of

conduct in filing a notice of appeal four days after he was

sentenced. See D.C. Cir. J.A. 24-25.

Although Petitioner challenged below the voluntary,

knowing, and intelligent nature of his plea, the D.C.

Circuit never addressed the issue. It did not find the

argument waived or lacking on the merits; it simply did

not discuss it at all. In these circumstances, if this Court

holds that Petitioner’s plea waived his right to challenge

the constitutionality of the statute of conviction on

appeal, it should nonetheless remand for a determination

as to whether the plea was voluntary, knowing, and

intelligent. See, e.g., Christian Legal Soc. Chapter of the

Univ. of Cal., Hastings Coll. of the Law v. Martinez, 561

U.S. 661, 697 n.28 (2010) (“When the lower courts have

failed to address an argument that deserved their

attention, our usual practice is to remand for further

consideration . . . .”); Bousley v. United States, 523 U.S.

614, 623 (1998) (remanding for consideration of actual

innocence claim not addressed by lower courts).

CONCLUSION

The judgment of the District of Columbia Circuit

should be reversed.

Respectfully submitted,