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

BRIEFS

No. 16-424

In the Supreme Court of the Anited States

RODNEY CLASS,

Petitioner,

V.

UNITED STATES OF AMERICA,

Respondent.

On Writ of Certiorari to the

United States Court of Appeals for the

District of Columbia Circuit

BRIEF OF THE NATIONAL ASSOCIATION OF

CRIMINAL DEFENSE LAWYERS AND THE

AMERICAN CIVIL LIBERTIES UNION AS AMICI

CURIAE IN SUPPORT OF PETITIONER

JONATHAN HACKER DANIEL N. LERMAN

Co-CHAIR, AMICUS Counsel of Record

COMMITTEE KATHLEEN SHEN

NATIONAL ASSOCIATION ROBBINS, RUSSELL, ENGLERT,

OF CRIMINAL DEFENSE ORSECK, UNTEREINER & SAUBER

LAWYERS LLP

1625 Eye Street, N.W. : 1801 K Street, N.W.

Washington, DC 20006 ' Washington, DC 20006

(202) 775-4500

dlerman@Grobbinsrussell.com

DAVID D. COLE RUTHANNE M. DEUTSCH

AMERICAN CIVIL LIBERTIES HYLAND HUNT

UNION FOUNDATION DEUTSCH HUNT PLLC

915 15th Street N.W. 300 New Jersey Avenue, N.W.

Washington, DC 20005 Suite 900

Washington, DC 20001

ADDITIONAL COUNSEL LISTED ON INSIDE COVER

a SS esa

EZEKIEL EDWARDS

AMERICAN CIVIL LIBERTIES

UNION FOUNDATION

126 Broad Street

New York, NY 10004

Il.

i

TABLE OF CONTENTS

THE MENNA-BLACKLEDGE

DOCTRINE SERVES THE PUBLIC

INTEREST IN TESTING THE

CONSTITUTIONALITY OF CRIMINAL

hers ciicislbnisinciiinsantkieniunniiimidesenneivense

A. Plea Bargaining Dominates The

Criminal Justice System ......................

B. Post-Plea Challenges To

Unconstitutional Statutes Are

THE GOVERNMENT'S PROPOSED

ALTERNATIVES ARE NO SUBSTITUTE

Pe Ee BE EI scccescsccecsesscescsensenezcnes

A. Rule 11(a)(2) Does Not Provide A

Meaningful Alternative To Direct

FREE EERE SESS a a

B. Collateral Review Is No Substitute

For Direct Appeal Under Menna and

EEL SRE LR Pe

CONCLUSION

SCHEER HR OO OO OTe eee mew ee

ee ee ee

il

TABLE OF AUTHORITIES

Cases

Blackledge v. Perry,

I ca canis ictsgenieninidinindimpdiopesisines

Board of Trustees of State Univ. of NLY. v.

Fox,

Seer

Bordenkircher v. Hayes,

en Si I scircsnivanssl cehsssinstsinéoansieded

Bousley v. United States,

Se i CN I acsccnccesicsssesncsesesoreseeece

Bowers v. Hardwick,

Be es MIE ctccesccccncscocsscecceseosecnsses

Brady v. United States,

I ircichcncounecatntetiteensisessensie

Broadrick v. Oklahoma,

ne I is srdincin eiessiinccsnnnaincchionslasin

Edwards vy. Carpenter,

ee

Gould v. United States,

657 F. Supp. 2d 321 (D. Mass. 2009)...................

Haynes v. United States,

a II ctertere<sepesmsesientesesicencsses

Page(s)

il

TABLE OF AUTHORITIES—Continued

Lafler v. Cooper,

Se CS BU SIPEED vcrnsscccceasnesescecseseoscs

Lawrence v. Texas,

539 U.S. 558 (2003) .................. poeikeedant

Loving v. Virginia,

Ee IE cickceninioninees siercniemneemeine

Mackey v. United States,

eit & gd. | RR eeweneneennnnn

Mackins v. United States,

No. 04-cv-261, 2009 WL 1563920

(W.D.N.C. June 1, 2009) .....................

Menna v. New York,

Be a Ie GED hcesccseriesiereennscnssssoreee

Missouri v. Frye,

BY Ss IE ID oe ccsccveenscnensacsseoesses

Montgomery v. Louisiana,

ee

Murray v. Giarratano,

NE i vidindiapenanivennntonionsinens

Padilla v. Kentucky,

EE: EP IED ences scccsnncecccdesnccacees

Penn. v. Finley,

a SR , renee

Page(s)

lV

TABLE OF AUTHORITIES—Continued

People v. Neuhaus,

240 P.3d 391 (Colo. Ct. App. 2009)............

Ex Parte Siebold,

I io itis ids wavtincinunuaionesion

State v. Keohane,

FR ge 8 eee

Steffel v. Thompson,

Se OE iciascecccessescsesessssvorsessvevncs

Susan B. Anthony List v. Driehaus,

ee I IED snessinicnernicvesotesesssssasess

Town of Newton v. Rumery,

I isc snicesexsucetcssarsecounsbestoes

United States v. Broce,

Ie GN IID va reser scctesess scssesivecesanse wea

United States v. Carvajal-Mora,

No. 08-CR-0059-CVE, 2009 WL 5171822

(N.D. Okla. Dec. 21, 2O08)................00.2000-0-

United States v. Davis,

900 F.2d 1524 (10th Cir. 1990)...........0......

United States v. Drayton,

No. 12-2568-KHV, 2013 WL 789027

= ee Ie ee

Page(s)

Vv

TABLE OF AUTHORITIES—Continued

United States v. Fisher,

772 F.2d 371 (7th Cir. 1985) .................

United States v. Knowles,

29 F.3d 947 (5th Cir. 1994)...........0.......

United States v. Stevens,

CE TFT, GE GD neo ss cccsevescsnnesesiscisencoanplinntata

Welch v. United States,

oy Se REESE

White v. United States,

371 F.3d 900 (7th Cir. 2004) .................

Wooley v. Maynard,

GE SEs Pe CE OD ck ctnsds penocenencvesciecsnats

Ex parte Young,

Be Oe a Re CID venice yctécssnctinonaans

Statutes, Rules, ané Guidelines

SR TEAS, Bree cikanisinieensncocsenatinnst

BB ETA Ee seve secsniiorsicisissineneieaan

Rk 5 oe SNe iEe Saaeriee oe

BD UE TG. © Be sh vn ciciscsscivcnssnncomandonmnaa

Fed. R. Crim. P. 11, Advisory Committee’s

Notes to 1983 Amendment....................

Page(s)

ey

vi

TABLE OF AUTHORITIES—Continued

Page(s)

ces mmnenorccney passim

Tex. Code Crim. P. Art. 44.02 .............0000..0..0..0s00000 14

U.S. Sentencing Guidelines Manual § 3F1.1.............. 8

U.S. Sentencing Guidelines Manual § 5K1.1 ............. 9

Other Authorities

Dept. of Educ., Nat'l Ctr. for Educ.

Statistics, Literacy Behind Bars: Results

From the 2003 National Assessment of

Adult Literacy Prison Survey (2007).................... 24

Dept. of Justice, Bureau of Justice

Statistics, Felony Sentences in State

Se sensunocenence 7

Dept. of Justice, Bureau of Justice

Statistics, Special Report, Defense

Counsel in Criminal Cases (2000) ................-...006.. i)

Dept. of Justice, Bureau of Justice

Statistics, Special Report, Education and

Correctional Populations (2003) .....................000+. 24

Dept. of Justice, Bureau of Justice

Statistics, Special Report, Mental Health

Problems of Prison and Jail Inmates

i cnlameensececosvscouse 25

vil

TABLE OF AUTHORITIES—Continued

Dept. of Justice, Memorandum for All

Federal Prosecutors from the Att’y Gen.,

Department Charging and Sentencing

Fe Fe i erbiitnniddtrtrtctdsntetsseienctes

Nancy J. King, et al., Final Technical

Report: Habeas Litigation in U.S. District

Courts: An Empirical Study of Habeas

Corpus Cases Filed By State Prisoners

Under the Antiterrorism and Effective

Death Penalty Act of 1996 (August 2007)...

Rachel E. Barkow, Separation of Powers and

the Criminal Law,

58 Stan. L. Rev. 989 (2006)....................-....

Robert E. Scott & William J. Stuntz, Plea

Bargaining as Contract,

101 Yale L. J. 1909 (1992)......................006-

Ronald F. Wright, Federal Criminal

Workload, Guilty Pleas, and Acquittals:

Statistical Background, Wake Forest

Univ. Legal Studies Paper (Sept. 2005) .....

Ronald F. Wright, Trial Distortion and the

End of Innocence in Federal

Criminal Justice,

154 U. Pa. L. Rev. 79 (2008)........................

Page(s)

peskens .. 26

viii

TABLE OF AUTHORITIES—Continued

Page(s)

Stephanos Bibas, Plea Bargaining Outside

the Shadow of Trial,

117 Harv. L. Rev. 2463 (2004) ......................06 9, 10

Stephanos Bibas, Regulating the Plea-

Bargaining Market: From Caveat Emptor

to Consumer Protection,

Tes I Oe I ETD viniscinattrccnscncnsintutsdedninenane 8

Susan R. Klein et al., Waiving the Criminal

Justice System: An Empirical and

Constitutional Analysis,

52 Am. Crim. L. Rev. 73 (2015)..................0:000000. 25

University at Albany, Sourcebook of

Criminal Justice Statistics Online, Table

Sa RE REE EE PAIR oN a EE 7

BRIEF OF THE NATIONAL ASSOCIATION OF

CRIMINAL DEFENSE LAWYERS AND THE

AMERICAN CIVIL LIBERTIES UNION AS

AMICI CURIAE IN SUPPORT OF PETITIONER

INTEREST OF AMICI CURIAE '

The National Association of Criminal Defense

Lawyers (NACDL) is a_=e nonprofit voluntary

professional bar association that works on behalf of

criminal defense attorneys to ensure justice and due

process for those accused of crime or misconduct.

NACDL was founded in 1958. It has a nationwide

membership of many thousands of direct members,

and up to 40,000 with affiliates. NACDL’s members

include private criminal defense lawyers, public

defenders, military defense counsel, law professors,

and judges. NACDL is the only nationwide

professional bar association for public defenders and

private criminal defense lawyers.

NACDL is dedicated to advancing the proper,

efficient, and just administration of justice. NACDL

files numerous amicus briefs each year in the U.S.

Supreme Court and other federal and state courts,

| Petitioner’s blanket letter of consent to the filing of amicus

briefs has been filed with this Court. Respondent has consented

to the filing of this brief; written documentation of that consent

is being submitted concurrently. No counsel for a party has

written this brief in whole or in part, and no counsel or party

made a monetary contribution intended to fund the preparation

or submission of this brief. No person or entity, other than the

amici curtae or their counsel, has made a monetary contribution

to this brief’s preparation or submission.

2

seeking to provide amicus assistance in cases that

present issues of broad importance to criminal

defendants, criminal defense lawyers, and the

criminal justice system as a whole.

This case presents a question of great importance

to NACDL and the clients its attorneys represent

because the vast majority of criminal prosecutions

end in guilty pleas. NACDL has a strong interest in

protecting the fairness of plea bargains through clear

default rules that help to level the playing field

between prosecutors and defendants.

The American Civil Liberties Union (ACLU) is a

nationwide, nonprofit, nonpartisan organization with

more than 1.5 million members dedicated to the

principles of liberty and equality embodied in the

Constitution and this nation’s civil rights laws. In

furtherance of those principles, the ACLU has

appeared in numerous cases before this Court, both

as direct counsel and as amicus. This case implicates

several issues of importance to the ACLU’s members,

including ensuring that unconstitutional statutes

that may deter or chill constitutionally protected

activity are reviewed at the earliest possible

opportunity.

Here, NACDL and the ACLU seek this Court’s

confirmation of the Menna-Blackledge default rule

under which a defendant’s right to appellate review

of a claim that a statute is unconstitutional is not

waived sub silentio through an unconditional guilty

plea.

3

INTRODUCTION AND

SUMMARY OF ARGUMENT

Unconditional guilty pleas do not implicitly waive

constitutional challenges to the underlying statute of

conviction. A holding to the contrary would

contravene this Court’s precedents and hinder the

judiciary’s ability to review and strike down

unconstitutional statutes, leaving invalid laws on the

books to wrongly chill lawful conduct. There is no

good reason to shield an unconstitutional criminal

statute from judicial review at the earliest possible

opportunity.

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

(per curiam), and Blackledge v. Perry, 417 U.S. 21

(1974), a guilty plea is “an admission of factual guilt,”

which “simply renders irrelevant those constitutional

violations not logically inconsistent with the valid

establishment of factual guilt.” Menna, 423 U.S. at

62 n.2. Thus, a defendant’s claim that his confession

was unconstitutionally coerced is rendered irrelevant

by a guilty plea because it is not logically inconsistent

with factual guilt. See Blackledge, 417 U.S. at 30.

But when “the claim is that the State may not convict

petitioner no matter how validly his factual guilt is

established,” that claim is preserved even after an

unconditional guilty plea. Menna, 423 at 62 n.2. The

claim at issue here—that the statute on which the

conviction is premised is unconstitutional—falls

squarely in the latter category, and therefore should

be preserved.

A guilty plea forecloses trial and sets a new

course, after which a defendant can challenge case-

specific procedural errors relating to his factual guilt

only by expressly preserving his appeal rights under

4d

Rule 11(a)(2). But a guilty plea, without more, poses

no bar to a substantive constitutional challenge to the

statute of conviction, because such a claim goes to the

State’s very power to impose charges and precludes

conviction notwithstanding factual guilt. That is true

both with respect to claims that the statute of

conviction is unconstitutional on its face and those

that the statute is unconstitutional as applied. In

both settings, whether the defendant is factually

guilty is of no moment, because the claim is that the

government lacks the power to prohibit his conduct.

See Haynes v. United States, 390 U.S. 85, 87 n.2

(1968).

Amici therefore fully support Petitioner’s

argument on the merits: An unconditional guilty

plea concedes only factual guilt, and does not,

standing alone, relinquish the right to challenge the

constitutionality of the statute that forms the basis of

the conviction. We write separately to emphasize

that there is nothing to be gained—and much to be

lost—by letting unconditional guilty pleas, like

Petitioner’s here, silently foreclose such challenges.

I. As this Court has recognized, today’s criminal

justice system is largely a system of pleas, not trials.

And plea bargaining does not take place on a level

playing field. Prosecutors typically have greater

resources, more information, and vast discretion in

making charges, thus maximizing their leverage

during negotiations. Studies show that even

defendants who would otherwise be acquitted are

likely to plead guilty, given the realities of an under-

resourced defense bar and the extraordinary power

that prosecutors wield. Both the ubiquity of pleas

and the structural imbalances inherent in the

5

bargaining process demand rules that ensure that

constitutional protections are not too readily elided

through the guilty plea process.

It would make little sense to require a defendant

who does not contest his factual guilt to undertake a

trial merely to preserve a constitutional challenge to

the statute of conviction. Clarifying that

unconditional guilty pleas do not by default waive

substantive challenges to the State’s very power to

bring charges in the first place will ensure that

substantive challenges to the statute of conviction are

heard at the earliest opportunity. Getting

unconstitutional laws off the books sooner rather

than later serves the public interest—and not just the

individual interest of the criminal defendant. This

Court has long recognized that the public interest in

preventing punishment of constitutionally protected

conduct is so strong that it outweighs even the

finality of a conviction. Ex Parte Siebold, 100 U.S.

371, 375-377 (1879). There is no basis for denying

the opportunity to raise the same challenge on direct

appeal.

II. The government’s proposed alternatives to a

presumption of prompt judicial review—relying upon

the prosecutors noblesse oblige to secure a

conditional guilty plea under Rule 11(a)(2), or

attempting to raise a substantive challenge on

collateral review—are inferior alternatives. Neither

procedure guarantees criminal defendants who plead

guilty what is theirs by right: the opportunity to raise

a timely challenge to the State’s imposition of a

punishment that is beyond its authority to impose. If

such a right is waivable at all, it is only through a

knowing, intelligent, and voluntary waiver expressly

6

provided in the plea agreement itself. No such

waiver occurred here.

ARGUMENT

I. THE MENNA-BLACKLEDGE DOCTRINE

SERVES THE PUBLIC INTEREST IN

TESTING THE CONSTITUTIONALITY OF

CRIMINAL STATUTES

Plea bargaining is central to today’s criminal

justice system. Who goes to prison, and for how long,

is largely determined through the plea-bargaining

process. In that context, the Menna-Blackledge

doctrine plays a critical role in preserving challenges

to the constitutionality of criminal statutes—and

ensuring that lawful conduct is not chilled—by

helping to strike down unconstitutional laws as soon

as possible.

A. Plea Bargaining Dominates The Criminal

Justice System

This Court has recognized that the criminal

justice system is “for the most part a system of pleas,

not a system of trials.” Lafler v. Cooper, 566 U.S.

156, 170 (2012). Following decades of decline, the

percentage of federal criminal cases culminating in a

plea of guilty or nolo contendere has risen since 1980,

as many cases that previously would have gone to

trial are resolved through guilty pleas instead—

including cases that would have resulted in

acquittals. See Ronald F. Wright, T7rial Distortion

and the End of Innocence in Federal Criminal Justice,

154 U. Pa. L. Rev. 79, 90-91, 105-106 (2005). In 1980,

7

just 81% of federal criminal convictions were the

result of guilty pleas.2 According to the most recent

figures available, guilty pleas now account for 97% of

federal convictions.®

State felony convictions tell a similar story. In

1970, it was estimated that between 70 and 85% of

state felony convictions were the result of guilty

pleas. See Brady v. United States, 397 U.S. 742, 752

n.10 (1970). By 2006, 94% of state felony convictions

resulted from pleas of guilty or nolo contendere.‘

Critical constitutional guarantees thus cannot be

given effect without accounting for “the central role

plea bargaining plays in securing convictions and

determining sentences.” Lafler, 566 U.S. at 170; see

also Missouri v. Frye, 566 U.S. 133, 143-144 (2012);

Padilla v. Kentucky, 559 U.S. 356, 373-374 (2010).

Defendants plead guilty at such high rates

because broad criminal statutes and_ severe,

mandatory sentences give prosecutors enormous

leverage over them. See Wright, 154 U. Pa. L. Rev.

at 85. As a result of overlapping criminal statutes, “a

single episode may fall within the definition of

several criminal offenses, ranging from trivial

2 See Ronald F. Wright, Federal Criminal Workload, Guilty

Pleas, and Acquittals: Statistical Background, Wake Forest

Univ. Legal Studies Paper (Sept. 2005), Appendix 1 (Disposition

of Federal Criminal Cases and Defendants, 1871-2002),

http://bit.ly/2r8Q8tg.

3 See University at Albany, Sourcebook of Criminal Justice

Statistics Online, Table 5.34.2010, http://bit.ly/2pPBmnb.

+ Dept. of Justice, Bureau of Justice Statistics, Felony Sentences

in State Courts, 2006, at 1 (2010), http://bit.ly/20oSOEC2.

8

misdemeanors to serious felonies.” Robert E. Scott &

William J. Stuntz, Plea Bargaining as Contract, 101

Yale L. J. 1909, 1962 (1992). At the same time,

mandatory minimum penalties and_ structured

sentencing make sentencing outcomes predictable,

particularly in the federal system. See Stephanos

Bibas, Regulating the Plea-Bargaining Market: From

Caveat Emptor to Consumer Protection, 99 Cal. L.

Rev. 1117, 1128 (2011).

Prosecutors thus have the power to determine the

length of a defendant’s likely sentence through their

charging decisions—and are free to invoke the threat

of greater punishment to induce a plea of guilty. See

Bordenkircher v. Hayes, 434 U.S. 357 (1978). Indeed,

one of the very purposes of longer statutory sentences

is to enhance the already-significant power of

prosecutors by giving them more “plea-bargaining

chips.” Bibas, Regulating the Plea-Bargaining

Market, 99 Cal. L. Rev. at 1128; see also Rachel E.

Barkow, Separation of Powers and the Criminal Law,

58 Stan. L. Rev. 989, 1034 (2006) (“[Ljonger

sentences exist on the books largely for bargaining

purposes.”). And federal prosecutors are required to

use every chip at their disposal: Just last week, the

Attorney General issued a memorandum announcing

that “it is a core principle that prosecutors should

charge and pursue the most serious, readily provable

offense.” Dept. of Justice, Memorandum for All

Federal Prosecutors from the Att’y Gen., Department

Charging and Sentencing Policy (May 10, 2017),

http://bit.ly/2qaeaTG.

On the other side of the ledger, significant

sentencing discounts are available to defendants who

comply with prosecutors’ demands. See, e.g., U.S.

9

Sentencing Guidelines Manual § 3E1.1 (decreasing

the offense level where the defendant “clearly

demonstrates acceptance of responsibility for his

offense”); id. § 5K1.1 (providing for departure from

the guidelines recommendation “[u]pon motion of the

government stating that the defendant has provided

substantial assistance in the investigation or

prosecution of another person”). These developments

have made it extraordinarily costly for a criminal

defendant to refuse a guilty plea. It is therefore

unsurprising that “fewer [have] paid the price each

year.” Wright, 154 U. Pa. L. Rev. at 85.

The pressure to plead guilty is particularly acute

for indigent defendants. Overburdened public

defenders often lack the time and resources necessary

to try cases or to negotiate more favorable plea

agreements for their clients. See Stephanos Bibas,

Plea Bargaining Outside the Shadow of Trial, 117

Harv. L. Rev. 2463, 2479-2480 & n.60 (2004). Court-

appointed counsel are subject to similar pressures.

See id. at 2477. Indigent defendants therefore plead

guilty at higher rates than other defendants. See

Dept. of Justice, Bureau of Justice Statistics, Special

Report, Defense Counsel in Criminal Cases, at 8

(2000), http://bit.ly/2oQCWES8 (“State and Federal

inmates who used public attorneys were less likely

than those with private attorneys to have been tried

by jury.”).

These dynamics—broad and overlapping criminal

statutes, severe mandatory minimum sentences,

“acceptance of responsibility” sentencing discounts,

and often-inadequate representation—not only place

increased pressure upon indigent defendants to plead

guilty, but may also decrease the quality of bargains

10

that are offered to them. After all, prosecutors have

little reason to offer concessions to defendants who

are already under tremendous pressure to plead. See

Bibas, Plea Bargaining Outside the Shadow of Trial,

117 Harv. L. Rev. at 2477.

Given these power imbalances, and assuming it is

even constitutionally permissible to foreclose

substantive constitutional challenges to criminal

statutes when defendants elect to concede factual

guilt and forgo a trial, it should be the government’s

burden to negotiate an express waiver, rather than

the defendant’s obligation to try to secure a

conditional plea. See also infra, at 21-22. That

default rule helps to cabin the “coercive power of

criminal process” that prosecutors already exert.

Town of Newton v. Rumery, 480 U.S. 386, 400 (1987)

(O’Connor, J., concurring).

B. Post-Plea Challenges To Unconstitutional

Statutes Are Important

Given the preeminent role of pleas in the criminal

justice system, it would make little sense to require a

defendant who does not contest his factual guilt to

undertake a trial merely to preserve a constitutional

challenge to the statute of conviction. And that

applies to both facial and as-applied challenges:

Whether facial or as-applied, challenges to the

constitucionality of the statute of conviction place at

issue the government’s power to prohibit conduct, not

factual guilt. See Pet’r’s Br. at 42-44. This Court’s

precedents confirm as much, as Menna and Haynes,

where the Court heard substantive constitutional

challenges on direct appeal notwithstanding a guilty

plea, were both as-applied challenges. Id. at 42-43.

11

But aside from wasting judicial resources, the

D.C. Circuit’s holding that an unconditional guilty

plea forfeits a constitutional challenge to the statute

of conviction deprives courts of the opportunity to

resolve important constitutional issues at the earliest

possible opportunity—and within a context devoid of

factual disputes. Landmark rulings been made in

cases involving post-plea constitutional challenges,

and permitting such challenges is consistent with the

admonition that, when the Constitution places

certain conduct beyond the power of the government

to punish, there “is little societal interest in

permitting the criminal process to rest at a point

where it ought properly never to repose.” Welch v.

United States, 136 S. Ct. 1257, 1266 (2016) (quoting

Mackey v. United States, 401 U.S. 667, 693 (1971)

(opinion of Harlan, J.)).

1. Permitting challenges to the constitutionality of

a statute on direct appeal following a guilty plea

furthers the strong public interest in determining the

constitutionality of criminal statutes sooner rather

than later. This Court has often recognized the

imperative to provide early relief from an

unconstitutional statute, lest protected behavior—.e.,

behavior beyond the government’s power to punish—

be chilled or deterred. That principle applies with

special force where, as here, a criminal conviction,

and the consequent loss of liberty, are at stake.

Thus, for example, this Court’s precedents permit

pre-enforcement review of the constitutionality of

criminal statutes, even in the face of federalism

concerns. When prosecution is threatened under a

statute, it “is not necessary that {a person] first

expose himself to actual arrest or prosecution to be

12

entitled to challenge a statute that he claims deters

the exercise of his constitutional rights.” Susan B.

Anthony List v. Driehaus, 134 S. Ct. 2334, 2342

(2014) (quoting Steffel v. Thompson, 415 U.S. 452,

459 (1974)); see also Wooley v. Maynard, 430 U.S.

705, 710 (1977). That is so even when it is a state

prosecution that is threatened, because “a refusal on

the part of the federal courts to intervene when no

state proceeding is pending may place the hapless

plaintiff between the Scylla of intentionally flouting

state law and the Charybdis of forgoing what he

believes to be constitutionally protected activity.”

Steffel, 415 U.S. at 462.

Relatedly, in the First Amendment context, courts

may review claims that a statute is facially overbroad

even when presented by a plaintiff to whom the

statute could constitutionally be applied. Under the

overbreadth doctrine, “persons who are themselves

unharmed by the defect in a_ statute” may

“nevertheless . . . challenge that statute on the

ground that it may conceivably be applied

unconstitutionally to others, in other situations not

before the Court.” Board of Trustees of State Univ. of

N.Y. v. Fox, 492 U.S. 469, 484 (1989) (internal

quotation marks omitted). Waiting for the perfect

plaintiff—who may never materialize because the

statute deters his or her protected speech—makes no

sense when the constitutional harm would otherwise

go unremedied. “|The possible harm to society in

permitting some unprotected speech to _ go

unpunished is outweighed by the possibility that

protected speech of others may be muted and

perceived grievances left to fester because of the

possible inhibitory effects of overly broad statutes.”

Broadrick v. Oklahoma, 413 U.S. 601, 612 (1973).

13

Similarly, the foundational doctrine of Ex parte

Young, 209 U.S. 123 (1908), permitting federal courts

to enjoin the enforcement of state statutes on any

constitutional ground, rests on the premise that

federal courts should be open early to claims that a

state prosecution would be unconstitutional, rather

than require an individual or company to “await

proceedings against the company in a state court,

grounded upon a disobedience of the act, and then, if

necessary, obtain a review in this court by writ of

error to the highest state court.” Jd. at 165. The

“great risk” of wrongly imposed punishment,

including fines and imprisonment, overrides even

Eleventh Amendment concerns. Ibid.

A direct appeal challenging the constitutionality

of a statute following an unconditional guilty plea

serves this same goal of preventing unnecessary

constitutional harm. In such a case, the individual

has risked more than those for whom prosecution is

merely threatened, by conceding his factual guilt (and

the authority of the government to punish him if his

constitutional argument is wrong). There is no

reason to require a defendant to expend resources on

a trial when there are no facts to find, just to bring a

challenge on direct appeal. And there is every reason

not to: Post-plea appeals further the strong public

interest in early invalidation of unconstitutional

statutes and present an excellent opportunity to

resolve constitutional questions in a case where the

facts are undisputed.

This Court’s cases reveal as much. Landmark

rulings have been made in cases in which individuals

entered unconditional guilty pleas and _ then

challenged the constitutionality of the statutes under

14

which they were convicted. For example, after their

motions to dismiss the charges on constitutional

grounds were denied, the petitioners in Lawrence v.

Texas, 539 U.S. 558 (2003), both entered pleas of nolo

contendere to the criminal charges against them for

violating the Texas anti-sodomy law, id. at 563,

which under Texas law automatically preserved all

issues previously asserted by written motion, Tex.

Code Crim. P. Art. 44.02. Their appeals following

those pleas resulted in this Court’s ruling that the

petitioners’ “right to liberty under the Due Process

Clause gives them the full right to engage in their

[private sexual] conduct without intervention of the

government,” Lawrence, 539 U.S. at 578, overruling

Bowers v. Hardwick, 478 U.S. 186 (1986). Moreover,

because it appears that the Lawrence petitioners

were sentenced only to fines, federal habeas review

would not have been available to them.

There are other examples, too, in which a

defendant who did not contest his or her factual guilt

vindicated important constitutional rights. In the

landmark decision Loving v. Virginia, 388 U.S. 1

(1967), this Court struck down Virginia’s

unconstitutional antimiscegnation statute and

reversed the convictions of the petitioners on

collateral review, notwithstanding the fact that they

had pleaded guilty. See id. at 3; see also United

States v. Knowles, 29 F.3d 947, 950-951 (5th Cir.

1994) (reversing conviction under Gun Free School

Zones Act on direct appeal following unconditional

plea).

It is not uncommon for a defendant to concede

factual guilt, even if he has a_ substantial

constitutional claim that he should be allowed to

15

engage in the conduct the state seeks to prohibit.

Permitting direct appeals on such claims following

unconditional guilty pleas allows the courts to

vindicate both the individual’s interest in not being

prosecuted for protected conduct, and _ society’s

interest in removing unconstitutional statutes from

the books at the earliest opportunity.

2. The government appears to concede that a

defendant who pleaded guilty and “seeks the benefit

of a substantive ruling establishing that the statute

of conviction is unconstitutional” could “seek” relief

on collateral review—if a different defendant secured

that constitutional ruling first. Br. in Opp. at 18.

That is the correct rule, provided that the petitioner

is otherwise able to overcome the procedural hurdles

to relief. In Bousley v. United States, 523 U.S. 614

(1998), for example, this Court held that a defendant

who pleaded guilty to use of a firearm was entitled to

review of his habeas petition on the merits, if he

could show that a subsequent decision limiting the

scope of conduct proscribed by the statute of

conviction rendered him actually innocent of the

charge. Id. at 616. In reaching that conclusion, this

Court emphasized that, where there has been a

subsequent decision holding that “a substantive

federal criminal statute does not reach certain

conduct,” such that the petitioner is able to show that

he is actually innocent of the crime with which he has

been convicted, it would be “inconsistent with the

doctrinal underpinnings of habeas review’ to

preclude a court from reaching his claim on the

merits. /d. at 620-621.

But the government’s suggestion that defendants

like Petitioner simply wait for somebody else to

16

challenge the statute of conviction is hardly sufficient

to protect the relevant constitutional interests. The

reason why substantive rules can be used to vacate

even decades-old convictions (and thus override the

State’s interest in finality), is that they conclusively

establish that a defendant’s confinement is

unlawful—and has always been unlawful—rather

than simply raise the risk that it might be inaccurate.

Montgomery v. Louisiana, 136 S. Ct. 718, 729-730

(2016). That rationale applies with equal force in the

context of a direct appeal where, as here, a defendant

maintains that a statute is unconstitutional—a

paradigmatic substantive rule. Welch, 136 S. Ct. at

1265 (“[Cjonstitutional determinations that place

particular conduct or persons covered by the statute

beyond the State’s power to punish” are substantive

rules.).

Whatever finality interest might be secured by a

guilty plea, it is manifestly less than the interest in

finality of convictions after direct review, which must

nevertheless give way to claims of substantive

unconstitutionality. Montgomery, 136 S. Ct. at 730.

The government should not be able to insist that a

defendant wait in jail for someone else to secure a

substantive constitutional ruling (see Br. in Opp. at

18), simply because the defendant does not contest

the factual allegations against him.

This Court has explained that collateral attack is

available after a guilty plea when the plea was not

knowing and voluntary, or “where on the face of the

record the court had no power to enter the conviction

or impose the_ sentence’—citing Menna and

Blackledge as examples of the latter condition.

United States v. Broce, 488 U.S. 563, 569, 574 (1989).

17

A court therefore lacks the power to enter a

conviction where, as here, the statute of conviction is

unconstitutional. See Montgomery, 136 S. Ct. at 730

(A “conviction under an unconstitutional law is not

merely erroneous, but is illegal and void, and cannot

be a legal cause of imprisonment.”) (internal

quotation marks omitted).

The Menna-Blackledge distinction between claims

that are inconsistent with factual guilt (barred) and

claims that require relief even if factual guilt is

established (not barred) is therefore analogous to the

procedural/substantive distinction in the habeas

context. Procedural rules regulate the “manner of

determining the defendant’s culpability” and merely

“raise the possibility that someone convicted with use

of the invalidated procedure might have been

acquitted otherwise.” Montgomery, 1368. Ct. at 730

(emphasis and internal quotation marks omitted).

They are “not logically inconsistent” with factual

guilt. Menna, 423 U.S. at 62 n.2. Substantive rules,

on the other hand, “stand in the way of conviction”

even “if factual guilt is validly established.” I[bid.; see

also Montgomery, 136 S. Ct. at 730 (recognizing that

there is no possibility of a “valid result” “where a

substantive rule has eliminated a State’s power to

proscribe the defendant’s conduct”).

The same societal interest and constitutional

imperative recognized in habeas cases as requiring

relief from even decades-old convictions also favors

not barring adjudication of substantive constitutional

claims on direct appeal simply because a defendant

18

entered an unconditional guilty plea.© To deprive a

defendant of his right to challenge the statute of

conviction on direct appeal merely because he does

not contest factual guilt would allow the State to

punish conduct that it may not be permitted to

punish in the first place—all without appellate

review. There is no legitimate rationale for

precluding such claims on direct appeal.

Il. THE GOVERNMENT’S PROPOSED

ALTERNATIVES ARE NO SUBSTITUTE FOR

DIRECT APPEAL

The government has suggested that curtailing the

Menna-Blackledge doctrine will have “limited

practical importance” because defendants can choose

to enter a conditional guilty plea under Federal Rule

of Criminal Procedure 11(a)(2) or seek collateral relief

from their convictions in the event that some other

defendant has succeeded in a constitutional challenge

to the same statute. Br. in Opp. at 18. But neither

the conditional plea mechanism set forth in Rule

’ The Menna-Blackledge test turns upon whether the claim at

issue is “logically inconsistent with the valid establishment of

factual guilt.” Menna, 423 U.S. at 62 n.2. The language from

Menna referring to the State being precluded “from haling a

defendant into court on a charge,” id. at 62, was not meant to

limit the scope of issues appealable from unconditional pleas.

But even if the Court were to agree that only those

constitutional challenges that prohibit a State “from haling a

defendant into court” can be appealed, challenges to the

constitutionality of the convicting statute would satisfy that

test. When a statute is unconstitutional, the government never

had the power to proscribe that conduct, and the government

violates the Constitution by haling a defendant into court to

defend conduct that is constitutionally protected.

19

11(a)(2) nor collateral review procedures provide

meaningful alternatives to direct appeal. If this

Court affirms the limitations that the D.C. Circuit

grafted on to the Menna-Blackledge doctrine, a

crucial mechanism for assessing the constitutionality

of criminal] statutes will simply be lost.

A. Rule’ 11(a)(2) Does Not Provide A

Meaningful Alternative To Direct Appeal

The government maintains that Rule 11(a)(2)

provides an adequate opportunity for defendants to

preserve constitutional claims in the context of a

guilty plea, and that, in effect, the burden should be

on the defendant to invoke this rule if he or she seeks

to pursue a constitutional challenge. But that

argument places too much weight on the availability

of Rule 11(a)(2).

To begin with, Rule 11(a)(2) has no bearing on a

state defendant's guilty plea, and therefore provides

no general solution to the problem. Conditional plea

mechanisms vary by state, see People v. Neuhaus,

240 P.3d 391, 394-395 (Colo. Ct. App. 2009)

(surveying state law of conditional pleas), and several

states do not permit them at all, see, e.g., State v.

Keohane, 814 A.2d 327, 329 (R.I. 2003) (per curiam).

Thus, even assuming that the government is correct

that Rule 11(a)(2) obviates the need for the Menna-

Blackledge doctrine (and it is not), that argument, by

its own terms, applies only to those defendants lucky

enough to be charged in jurisdictions that allow

conditional pleas in the first place.

In any event, while Rule 11(a)(2) provides a

limited mechanism for federal defendants who plead

guilty to preserve certain claims for appeal, it does

20

nothing to alter a federal criminal defendant’s right

to challenge the constitutionality of the statute under

which he has been convicted. Nothing in the text of

the rule even suggests that such challenges are

irrevocably waived if not preserved in the form of a

conditional plea. To the contrary, the Advisory

Committee on Rules has expressly stated that,

contrary to the government’s position here,

“[s]ubdivision 11(a)(2)...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 Notes to 1983 Amendment (emphasis

added).

That is not surprising. The conditional plea

mechanism provided for by Rule 11(a)(2) is a poor

substitute for direct appeal. The practical effect of

requiring defendants to obtain conditional pleas

would be the near-elimination of such challenges

altogether. Rule 11(a)(2) is “intended to benefit

courts and prosecutors, not defendants.” Gould v.

United States, 657 F. Supp. 2d 321, 330 (D. Mass.

2009). Thus, the rule provides that a conditional

guilty plea may be entered only “[w]ith the consent of

the court and the government.” Fed. R. Crim. P.

1l(a)(2). A prosecutor may withhold such consent

“for any reason or for no reason at all.” United States

v. Fisher, 772 F.2d 371, 374 (7th Cir. 1985) (per

curiam). Moreover, “[clonditional pleas are not

commonly offered by most prosecutors.” United

States v. Drayton, No. 12-2568-KHV, 2013 WL

789027, at *5 n.5 (D. Kan. Mar. 1, 2013); see also

United States v. Carvajal-Mora, No. 08-CR-0059-

CVE, 2009 WL 5171822, at *6 (N.D. Okla. Dec. 21,

21

2009); Mackins v. United States, No. 04-cv-261, 2009

WL 1563920, at *5 (W.D.N.C. June 1, 2009).

Nor are courts under any obligation to enter such

pleas. Even a “blanket prohibition” on the entry of all

conditional pleas may not “constitute error in any

given case.” United States v. Davis, 900 F.2d 1524,

1527-1528 (10th Cir.), cert. denied, 498 U.S. 856

(1990) (finding no error where district court refused

to enter conditional plea on the ground that it would

enable the defendant to appeal pretrial orders

“while ... serving his time”). Requiring a defendant

to follow the procedure set forth in Rule 11(a)(2) to

preserve constitutional challenges to his statutes of

conviction would effectively leave him “at the mercy

of noblesse oblige.” United States v. Stevens, 559 U.S.

460, 480 (2010). Fundamental constitutional rights

should not be so readily swept aside based on the

mere possibility that prosecutors—who already have

enormous leverage to extract unconditional guilty

pleas—might choose to offer federal defendants a

conditional plea under Rule 11(a)(2).

To be sure, some constitutional mghts can be

waived, assuming that waiver is knowing, intelligent,

and voluntary, and made with sufficient awareness of

the likely consequences. See Brady v. United States,

397 U.S. 742, 748 (1970); Bousley, 523 U.S. at 620.

The Menna-Blackledge doctrine is best read as

providing a default rule: A guilty plea, without more,

cannot waive challenges that are not inconsistent

with factual guilt, such as challenges to the

constitutionality of the statute of conviction. That

default rule does not bar waivers of substantive or

constitutional claims, but puts the burden on the

prosecutor to obtain from the defendant an express,

22

unambiguous waiver rather than tasking an already

out-leveraged defendant with seeking’ the

prosecutor's uncertain permission to preserve claims

under a Rule 11(a)(2) conditional plea. Because plea

bargains, like any contract, are negotiated in the

shadow of the law, placing the burden on prosecutors

to secure knowing waivers helps level the playing

field.

The facts of this case illustrate why such a clear

default rule is necessary—and why any ambiguity as

to the scope of the rights being waived should be

construed against the government, which holds most

of the cards in the plea bargaining process.

Petitioner, proceeding pro se, vigorously litigated his

claims challenging the _ constitutionality of

Section 5104 before accepting a plea agreement.

That plea agreement did not expressly waive

Petitioner’s right to appeal the trial court’s resolution

of those constitutional claims. To the contrary, the

agreement expressly disavowed any “promises,

understandings, or representations .. . other than

those contained in writing herein.” J.A. 159.

The government relies on language in the

agreement stating “[y]ou understand that by pleading

guilty in this case you agree to waive certain rights

afforded by the Constitution.” J.A. 156. But that

language does not on its face explain which “certain”

constitutional claims were being waived, and is

included in a section of the plea agreement entitled

“Trial Rights”—strongly indicating that what

Petitioner was waiving was only his constitutional

trial rights, not his right to challenge the

constitutionality of Section 5104. The “Appeal

Rights” section of the agreement, moreover, states

23

only that Petitioner waived “the right to appeal the

sentence in this case.”® J.A. 157.

That is not an express waiver of all appeal rights.

It is a fair reading of this record that the government

knew or should have known that Petitioner did not

intend to give up his claims’ regarding the

constitutionality of Section 5104—and that he might

have refused to plead guilty if he understood that to

be the case. The government had ample opportunity

to clarify these issues, both in drafting the plea

agreement and during the course of the colloquy. It

should not now benefit from its failure to do so—

much less from its decision not to offer Petitioner,

who proceeded pro se below, a Rule 11(a)(2)

conditional plea deal.

B. Collateral Review Is No Substitute For

Direct Appeal Under Menna And

Blackledge

The government also suggests that a defendant

raising a substantive constitutional challenge to the

statute of his conviction could, under certain

circumstances, seek relief from conviction on

collateral review, based on a constitutional ruling

secured by some other defendant. Br. in Opp. at 18.

But a defendant should not have to wait for someone

6 Nor was Petitioner clearly informed that those claims were

being waived. To the contrary, he was told that he could

“appeal... if [he] believe[{d] that [his] guilty plea was somehow

unlawful.” S.A. 102 (emphasis added). Petitioner immediately

thereafter challenged the lawfulness of his conviction on appeal,

providing further evidence that he never intended to waive

those claims.

24

else to obtain a constitutional ruling—an uncertain

prospect at best-—-in order to challenge his statute of

conviction. Furthermore, collateral review, if it is

available at all, provides a wholly inadequate

substitute for direct appeal. Collateral review

procedures present enormous, often insurmountable,

obstacles to prisoners. Forcing defendants who

contest the constitutionality of their statute of

conviction to pursue their claims on collateral review

would drastically reduce the likelihood of those

claims being heard at all.

To begin with, there are considerable practical

hurdles even to bringing a petition for collateral

relief. Most significantly, prisoners seeking collateral

review of their convictions have limited resources at

their disposal—and most importantly, no right to

counsel, see Murray v. Giarratano, 492 U.S. 1, 3-4

(1989); Penn. v. Finley, 481 U.S. 551, 555 (1987).

Prisoners are thus largely on their own when it comes

to navigating the various legal] hurdles to collateral

relief, of which there are many.’

7 Navigating the complex collateral review process can be

challenging even for an experienced advocate. For many state

and federal prisoners, those challenges may well be

insurmountable. State and federal prison populations are

significantly less educated than the general population. See

Dept. of Justice, Bureau of Justice Statistics, Special Report,

Education and Correctional Populations, at 2 (2003),

http://bit.ly/2kRy7dn. Prisoners are also more likely to have

diagnosed learning disabilities, less likely to have basic literacy

skills, See Dept. of Educ., Nat'l Ctr. for Educ. Statistics, Literacy

Behind Bars: Results From the 2003 National Assessment of

Adult Literacy Prison Survey, at 27, 29 (2007),

http://bit.ly/2oGboX6, and more likely to suffer from mental

25

As an initial matter, most U.S. Attorney’s offices

now include collateral attack waivers in their

boilerplate plea agreements (as does the plea

agreement in this case, see J.A. 157). See Susan R.

Klein et al., Waiving the Criminal Justice System: An

Empirical and Constitutional Analysis, 52 Am. Crim.

L. Rev. 73, 87 (2015) (in survey of 114 boilerplate plea

agreements including at least one from each federal

district, seventy-seven contained collateral attack

waiver). Whether raising their own constitutional

claims or seeking the benefit of a substantive rule

secured by another defendant, federal prisoners who

have not waived their right to collateral review must

still overcome an array of procedural obstacles,

including a strict, one-year limitations period, 28

U.S.C. § 2255(f), and a near-total bar on subsequent

or successive petitions, id. § 2255(h). Put simply, it

would be exceedingly difficult for a federal prisoner to

obtain relief from his conviction on collateral review.

State prisoners seeking habeas relief have an even

more arduous path. In addition to facing many of the

same obstacles as federal prisoners, see 28 U.S.C.

§ 2254(b) (limitation on successive habeas corpus

applications), id. § 2244(d)(1) (one-year statute of

limitations), state prisoners must also contend with

requirements “ranging from exhaustion of remedies,

to fair presentment obligations, to procedural default

rules, and above all, to the strong deference to the

conclusions of fact and law reached by the state

—.—$—$ Sr

illness. See Dept. of Justice, Bureau of Justice Statistics, Special

Report, Mental Health Problems of Prison and Jail Inmates, at

1, 3 (2006), http://bit.ly/2eRfbf2.

26

courts,” White v. United States, 371 F.3d 900, 903

(7th Cir. 2004) (Wood, J., concurring).

Any one of these requirements standing alone

would present a significant barrier to relief. For

example, it takes the average non-capital habeas

petitioner more than six years just to exhaust state

remedies. See Nancy J. King, et al., Final Technical

Report: Habeas Litigation in U.S. District Courts: An

Empirical Study of Habeas Corpus Cases Filed By

State Prisoners Under the Antiterrorism and Effective

Death Penalty Act of 1996, at 4 (August 2007),

http://bit.ly/2pHigef. Cumulatively, these hurdles

will often prove insuperable. See Edwards v.

Carpenter, 529 U.S. 446, 454 (2000) (Breyer, J.,

concurring) (“[T]he complexity of this Court’s habeas

corpus jurisprudence...in practice can deny the

fundamental constitutional protection that habeas

corpus seeks to assure.”).

The government never explains why its proposed

wait-for-a-substantive-decision-in-another-case rule

could possibly promote judicial efficiency or public

policy. But given the practical and legal barriers

discussed above, its suggestion that the availability of

collateral review somehow minimizes the impact of

the lower court’s evisceration of the Menna-

Blackledge doctrine rings hollow.

CONCLUSION

The judgment of the court of appeals should be

reversed.

27

Respectfully submitted.

JONATHAN HACKER DANIEL N. LERMAN

Co-CHAIR, AMICUS Counsel of Record

COMMITTEE KATHLEEN SHEN

NATIONAL ASSOCIATION ROBBINS, RUSSELL,

OF CRIMINAL DEFENSE ENGLERT, ORSECK,

LAWYERS UNTEREINER & SAUBER

1625 Eye Street, N.W. LLP

Washington, DC 20006 1801 K Street, N.W.

Washington, DC 20006

DAVID D. COLE (202) 775-4500

AMERICAN CIVIL dlerman@robbinsrussell.com

LIBERTIES UNION

FOUNDATION Counsel for the National

Association of Criminal

915 15th Street N.W. Dutnee Lamers

Washington, DC 20005

RUTHANNE M. DEUTSCH

— a HYLAND Hunt

- ERICAN cao DEUTSCH HUNT PLLC

IBERTIES UNION 300 New Jersey Avenue,

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125 Broad Street Suite 900

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