Amicus Curiae Brief — Jayren Jakar Wynn, Petitioner v. United States

No. 21-5714

In the Supreme Court of the United States

_____________

JAYREN WYNN,

Petitioner,

v.

UNITED STATES OF AMERICA,

Respondent.

_____________

ON PETITION FOR A WRIT OF CERTIORARI

TO THE UNITED STATES COURT OF APPEALS

FOR THE SECOND CIRCUIT

_____________

AMICI CURIAE BRIEF OF

THE NEW CIVIL LIBERTIES ALLIANCE

& DUE PROCESS INSTITUTE

IN SUPPORT OF PETITIONER

_____________

SHANA-TARA O’TOOLE

DUE PROCESS INSTITUTE

700 Pennsylvania Ave.

SE, #560

Washington, DC 20003

(202) 558-6683

Shana@idueprocess.org

JARED MCCLAIN

Counsel of Record

MARK CHENOWETH

KARA ROLLINS

NEW CIVIL LIBERTIES ALLIANCE

1225 19th St. NW, Suite 450

Washington, DC 20036

(202) 869-5210

Jared.McClain@NCLA.legal

Counsel for Amici Curiae

i

QUESTIONS PRESENTED

The New Civil Liberties Alliance and Due Process

Institute, as amici curiae, address the following

questions necessary to resolving the circuit splits at

issue in Mr. Wynn’s petition:

(1) Do courts owe deference to Commission

commentary that expands the Guidelines?

(2) Do the rule of lenity and the right to due process

preclude Stinson deference when commentary to a

Sentencing Guideline would increase a sentence?

ii

TABLE OF CONTENTS

Questions Presented ........................................................... i

Table of Contents................................................................ ii

Table of Authorities...........................................................iii

Interest of Amici Curiae .................................................... 1

Statement of the Case ........................................................ 2

Discussion............................................................................ 5

I. STINSON DEFERENCE CANNOT INCREASE

CRIMINAL PENALTIES .................................................... 5

A. Stinson Did Not Implicate the Rule of

Lenity ....................................................................... 5

B. The Constitution Compels Lenity ........................ 8

C. Traditional Tools of Interpretation Apply

Lenity Before Deference ....................................... 10

D. Lower Courts Disagree over Lenity’s

Application in Stinson Cases............................... 12

II. THIS COURT SHOULD GRANT THE PETITION TO

NARROW OR OVERRULE STINSON ............................... 18

A. Interpretive Deference Is Unconstitutional ...... 18

1. Stinson Deference Contradicts Judicial

Independence and the Judicial Office ........ 18

2. Stinson Violates Due Process by

Institutionalizing Judicial Bias..................... 22

B. Deference to Commission Commentary Is

Uniquely Unlawful ............................................... 23

Conclusion ......................................................................... 24

iii

TABLE OF AUTHORITIES

Cases

Abramski v. United States,

573 U.S. 169 (2014) ................................................. 7

Aposhian v. Wilkinson,

989 F.3d 890 (10th Cir. 2021) (en banc) ............... 16

Babbit v. Sweet Home Chapter of Cmts. for a Great

Ore., 515 U.S. 687 (1995) ...................................... 17

Bifulco v. United States,

447 U.S. 381 (1980) ................................................. 6

Bray v. Atalanta,

4 F. Cas. 37 (D.S.C. 1794) ....................................... 6

Carter v. Welles-Bowen Realty, Inc.,

736 F.3d 722 (6th Cir. 2013) ................................. 10

Christensen v. Harris Cty.,

529 U.S. 576 (2000) ................................................. 9

Com. Coatings Corp. v. Cont’l Cas. Co.,

393 U.S. 145 (1968) ............................................... 22

De Lima v. Sessions,

867 F.3d 260 (1st Cir. 2017)............................ 10, 14

Edward J. DeBartolo Corp. v. Fla. Gulf Coast Bldg.

& Constr. Trades Council,

485 U.S. 568, 575 (1988) ....................................... 11

iv

Esquivel-Quintana v. Sessions,

137 S. Ct. 1562 (2017) ....................................... 7, 17

Georgia v. Brailsford,

2 U.S. (2 Dall.) 416 (1793) ..................................... 20

Guedes v. Bureau of Alcohol, Tobacco, Firearms &

Explosives, 140 S.Ct. 789 (2020) ............................. 7

In re Murchison,

349 U.S. 133 (1955) ............................................... 23

Kisor v. Wilkie,

139 S. Ct. 2400 (2019) ..................................... passim

Leocal v. Ashcroft,

543 U.S. 1 (2004) ................................................... 17

Liparota v. United States,

471 U.S. 419 (1985) ................................................. 8

M. Kraus & Bros. v. United States,

327 U.S. 614 (1946) ................................................. 6

Marbury v. Madison,

5 U.S. (1 Cranch) 137 (1803)........................... 18, 21

Marshall v. Jerrico, Inc.,

446 U.S. 238 (1980) ............................................... 22

Masterpiece Cake Shop, Ltd. v. Colo. Civil Rights

Comm’n, 138 S.Ct. 1719 (2018) ............................ 22

McBoyle v. U.S.,

283 U.S. 25 (1931) ................................................... 8

v

Miller v. Johnson,

515 U.S. 900 (1995) ............................................... 21

Mistretta v. United States,

488 U.S. 361 (1995) ............................................... 24

Perez v. Mortgage Bankers Ass’n,

572 U.S. 92 (2015) ................................................. 21

Peugh v. United States,

569 U.S. 530 (2013) ................................................. 9

Prohibition del Roy,

12 Co. Rep. 63, 65 (1608)....................................... 19

Skilling v. United States,

561 U.S. 358 (2010) ................................................. 6

Smith v. United States,

2020 WL 4211284 (S.D. W.Va. June 26, 2020) .... 15

Solid Waste Agency of N. Cook Cty. v. U.S. Army

Corps of Eng’rs, 531 U.S. 159 (2001) .................... 17

The Julia,

14 F. Cas. 27 (C.C.D. Mass. 1813) ........................ 20

Tumey v. Ohio,

273 U.S. 510 (1927) ............................................... 23

United States v. Adams,

934 F.3d 720 (7th Cir. 2019) ................................. 14

United States v. Bass,

404 U.S. 336 (1971) ........................................... 8, 12

vi

United States v. Booker,

543 U.S. 220 (2005) ............................................. 6, 9

United States v. Broadway,

815 Fed. App’x 95 (8th Cir. 2020) ............................ 15

United States v. Cantu,

423 F. Supp. 3d 345 (S.D. Tex. 2019) ................... 15

United States v. Cingari,

952 F.3d 1301 (11th Cir. 2020) ..................... 3, 4, 16

United States v. Crum,

934 F.3d 963 (9th Cir. 2019) ................................. 16

United States v. Cruz-Flores,

799 F. App’x 245 (5th Cir. 2020).............................. 12

United States v. Davis,

39 S.Ct. 2319 (2019) .............................................. 11

United States v. Faison,

2020 WL 815699 (D. Md. Feb. 18, 2020) .......... 7, 12

United States v. Goodin,

835 Fed. App’x 771 (5th Cir. 2021) ....................... 15

United States v. Havis,

907 F.3d 439 (6th Cir. 2018) ................. 7, 11, 18, 21

United States v. Jackson,

60 F.3d 128 (2d Cir. 1995)..................................... 15

United States v. Lewis,

963 F.3d 16 (1st Cir. 2020).................................... 14

vii

United States v. Lovato,

950 F.3d 1337 (10th Cir. 2020).......................... 12, 16

United States v. Martinez,

602 F.3d 1166 (10th Cir. 2010) ............................. 16

United States v. McClain,

23 F. App’x 544 (7th Cir. 2001) ............................. 14

United States v. Moss,

872 F.3d 304 (5th Cir. 2017) ................................. 15

United States v. Nasir,

2021 WL 5173485 (3d Cir. 2021) (en banc) ..... passim

United States v. Rodriguez-Arreola,

313 F.3d 1064 (8th Cir. 2002).................................. 14

United States v. Santos,

553 U.S. 507 (2008) ................................................. 9

United States v. Thompson/Ctr. Arms Co.,

504 U.S. 505 (1992) ............................................... 10

United States v. Wiltberger,

18 U.S. (1 Wheat.) 76 (1820) ............................... 4, 6

United States v. Winstead,

890 F.3d 1082 (D.C. Cir. 2018) ............................. 13

United States. v. Burr,

25 F. Cas. 2 (C.C.D. Va. 1807) .............................. 20

Webster v. Fall,

266 U.S. 507 (1925) ................................................. 7

viii

Whitman v. United States,

574 U.S. 1003 (2014) ............................................... 4

Yarborough v. Alvarado,

541 U.S. 652 (2004) ............................................... 21

Yi v. Fed. Bureau of Prisons,

412 F.3d 526 (4th Cir. 2005) ................................. 15

Statutes

18 U.S.C. § 3553(b) ................................................... 21

Other Authorities

A DISCOURSE UPON THE EXPOSICION &

UNDERSTANDINGE OF STATUTES (Samuel E.

Thorne ed. 1942) ...................................................... 6

James Iredell, To the Public,

N.C. Gazette (Aug. 17, 1786) ................................. 19

Philip Hamburger, Chevron Bias,

84 GEO. WASH. L. REV. 1187 (2016) ...................... 22

Philip Hamburger, LAW AND JUDICIAL DUTY

(2008) ..................................................................... 19

Quick Facts: Career Offenders, U.S. Sentencing

Comm’n (FY 2019) ................................................... 5

Records of the Federal Convention of 1787

(Max Farrand ed., Yale Univ. Press 1911)........... 19

The Declaration of Independence ............................ 19

ix

THE FEDERALIST No. 78 ............................................. 20

INTEREST OF AMICI CURIAE1

The New Civil Liberties Alliance (“NCLA”) is a

nonpartisan, nonprofit civil rights organization and

public-interest law firm. Professor Philip Hamburger

founded NCLA to challenge multiple constitutional

defects in the modern administrative state through

original litigation, amicus curiae briefs, and other

advocacy.

NCLA views the administrative state as an

especially serious threat to civil liberties. No other

current legal development denies more rights to more

Americans. Although we still enjoy the shell of our

Republic, a very different sort of government has

developed within it—a type, in fact, that our

Constitution was designed to prevent. NCLA aims to

defend civil liberties—primarily by asserting

constitutional

constraints

on

the

modern

administrative state.

Due Process Institute is a nonprofit, bipartisan,

public-interest organization that works to honor,

preserve, and restore procedural fairness in the

criminal legal system because due process is the

guiding principle that underlies the Constitution’s

solemn promises to “establish justice” and to “secure

the blessings of liberty.” U.S. Const., pmbl. The

issues raised in this brief are essential to protecting

the principles of due process and fundamental

fairness in America’s federal sentencing regime.

1 Both parties consented to the filing of this brief.

No one other than the amici curiae and their counsel

authored or financed the preparation or the

submission of this brief.

2

Amici are disturbed by the widespread judicial

“deference” to the commentary of the United States

Sentencing Commission. See Stinson v. United

States, 508 U.S. 36 (1993). Stinson deference raises

grave constitutional concerns that this Court has

never considered.

STATEMENT OF THE CASE

Every Justice in Kisor v. Wilkie agreed on the need to

“reinforce” and “further develop” the limitations on the

deference that courts owe to an agency’s interpretation

of its own rules. 139 S. Ct. 2400, 2408, 2415 (2019); id.

at 2424 (Roberts, C.J., concurring); id. at 2448

(Gorsuch, J., concurring in judgment); id. at 2448-49

(Kavanaugh, J., concurring in judgment). Kisor held

that, before courts defer to an agency’s interpretation,

they must (1) exhaust their interpretive tools and

conclude the text is “genuinely ambiguous”; (2)

determine that the agency interpretation is “reasonable”;

and (3) conduct an “independent inquiry” to confirm that

“the character and context of the agency interpretation

entitles it to controlling weight.” Id. at 2415-16.

Prior to Kisor, courts were deferring “reflexive[ly]”

to agency interpretations, without first conducting

the exhaustive textual analysis that the Constitution

requires. See ibid. This reflexive deference was likely

the result of “mixed messages” this Court sent in

cases that “applied Auer deference without significant

analysis of the underlying regulation.” Id. at 2414.

Of all this Court’s mixed messages about agency

deference, Stinson has been among the most

damaging, given its application during criminal

sentencing. 508 U.S. at 38. Stinson requires courts

to defer to the United States Sentencing Commission’s

3

commentary interpreting the Sentencing Guidelines

unless that commentary “is inconsistent with, or a

plainly erroneous reading of, that guideline.” Ibid. Such

deference was appropriate, according to Stinson, even if

the interpretation “may not be compelled by the

guideline text.” Id. at 47.

Applying Stinson, courts have given “nearly

dispositive weight” to Commission commentary over “the

Guidelines’ plain text.” United States v. Nasir, 2021 WL

5173485, at *9 (3d Cir. 2021) (en banc) (Bibas, J.,

concurring, with Ambro, Jordan, Greenaway, Krause,

Restrepo, JJ.). That these courts have deferred

reflexively is no coincidence—they rely on Stinson’s

explicit language. Take the Eleventh Circuit for

example. Even after Kisor’s admonishment, the

Eleventh Circuit still quotes Stinson for its rule that

“the commentary for a guideline remains

authoritative ‘unless it violates the Constitution or a

federal statute, or is inconsistent with, or a plainly

erroneous reading of, that guideline.’” United States

v. Cingari, 952 F.3d 1301, 1308 (11th Cir. 2020)

(citation omitted).

Commentary loses its

“authoritative … status” in the Eleventh Circuit only

“if it is ‘inconsistent with, or a plainly erroneous

reading of, that guideline.’” Ibid. There’s no textual

inquiry into a Guideline’s ambiguity, only deference.

To their credit, the Third, Sixth, and D.C. Circuits

(and several district courts in the Fourth Circuit) have

recognized that strict adherence to Stinson is

inconsistent with this Court’s modern administrativelaw jurisprudence, the Commission’s authority, and the

Constitution. The other circuits, however, perpetuate

Stinson’s outdated language and refuse to reconsider

circuit precedent that contradicts Kisor. More time for

4

percolation will not resolve this circuit split. The dispute

stems from this Court’s mixed signals, and the

recalcitrant circuits have made clear they won’t act

before this Court does.

Moreover, only this Court can resolve the “broader

problem” that arises once the other seven circuits awake

“from [their] slumber of reflexive deference.” Nasir, 2021

WL 5173485, at *9 (Bibas, J.). Courts must exhaust the

“traditional tools of construction” before deferring to an

agency. Kisor, 139 S. Ct. at 2415. Lenity is a traditional

tool of construction “perhaps not much less old than

construction itself” that protects core liberties against

government intrusion. United States v. Wiltberger, 18

U.S. (1 Wheat.) 76, 95 (1820). The courts of appeals,

however, are divided on whether lenity applies before

deference or if it applies at all. Compare Nasir, 2021

WL 5173485, at *9 (Bibas, J.) (“A key tool in that

judicial toolkit is the rule of lenity.”), with Cingari,

952 F.3d at 1310-11 (“cast[ing] doubt” on whether

lenity applies before Stinson deference).

Like the primary circuit split, the lower courts’

confusion about how to sequence lenity stems from

this Court’s muddling of the issue. See, e.g., Whitman

v. United States, 574 U.S. 1003 (2014) (Scalia J., with

Thomas, J., respecting denial of certiorari)

(establishing that this Court’s anti-lenity statements

“contradict[] the many cases before and since holding

that, if a law has both criminal and civil applications,

the rule of lenity governs its interpretation in both

settings”).

Mr. Wynn’s petition presents a critical opportunity

to clarify once and for all that courts do not owe

deference to Commission commentary that expands

the Guidelines. Each passing term, seven circuits

5

systematically violate the due-process rights of criminal

defendants by applying Stinson deference to increase the

Guideline range approved by Congress. The CareerOffender Guideline alone, which starts at a presumptive

15-year prison term, adds thousands of years to the

sentences of almost 2,000 defendants each year.2 With

the liberty of so many at stake, there is no excuse to keep

waiting.

DISCUSSION

I. STINSON DEFERENCE CANNOT INCREASE CRIMINAL

PENALTIES

The lower courts should have applied Kisor’s holding

to all derivatives of Seminole Rock/Auer deference. But

Mr. Wynn’s petition, like the similar petitions this Court

denied last June, show that widespread misapplication

of Stinson deference will persist until this Court

intervenes.

Lower-court judges openly disagree about whether

Kisor limited Stinson and how rigorously they must

analyze a Guideline before deferring to Commission

commentary. This disparity would be unacceptable for

any rules that require uniformity, but it is completely

inexcusable in sentencing, when liberty is at stake. See

Nasir, 2021 WL 5173485, at *10-11 (Bibas, J.). The

Constitution demands that all judges interpret

ambiguous Guidelines in a defendant’s favor.

A. Stinson Did Not Implicate the Rule of Lenity

The rule of lenity dictates that “ambiguity

concerning the ambit of criminal statutes should be

2 Quick Facts: Career Offenders, U.S. Sentencing

Comm’n (FY 2019), https://bit.ly/2PSzYlX.

6

resolved in favor of lenity.” Skilling v. United States,

561 U.S. 358, 410 (2010).

This concept is not new; few interpretive tools

have lenity’s tradition. See Wiltberger, 18 U.S. (1

Wheat.) at 95; see also Bray v. Atalanta, 4 F. Cas. 37,

38 (D.S.C. 1794) (ruling that “a penal law [] must be

construed strictly”).

Early-15th Century jurist

William Paston abided by the maxim that “a penalty

should not be increased by interpretation.”

A

DISCOURSE UPON THE EXPOSICION & UNDERSTANDINGE

OF STATUTES (Samuel E. Thorne ed. 1942) (“[W]hen

the law is penall, for in those it is true that Paston

saiethe, Poenas interpretation augeri non debere[.]”).

Lenity “applies not only to interpretations of the

substantive ambit of criminal prohibitions, but also to

the penalties they impose.” Bifulco v. United States,

447 U.S. 381, 387 (1980); M. Kraus & Bros. v. United

States, 327 U.S. 614, 621-22 (1946) (plurality)

(holding, one year after Seminole Rock, “the same

strict rule of construction that is applied to statutes

defining criminal action” must apply to agency

regulations). In fact, lenity “first arose to mitigate

draconian sentences.” Nasir, 2021 WL 5173485, at *10

(Bibas, J.). The rule similarly requires courts to

resolve ambiguous Guidelines—which “exert a lawlike gravitational pull on sentences”—in a defendant’s

favor. Id. at *11 (citing United States v. Booker, 543

U.S. 220, 265 (2005) (Breyer, J., majority opinion on

remedy)).

Stinson did not consider lenity’s priority over

deference because the commentary at issue there

favored a more lenient sentence. See 508 U.S. at 47-48.

The Court, therefore, did not grapple with the

constitutional issues inherent when the deference it

established increases a criminal penalty. Nor has any

7

subsequent decision of this Court. Cf. EsquivelQuintana v. Sessions, 137 S. Ct. 1562, 1572 (2017)

(declining to “resolve whether the rule of lenity or

Chevron receives priority”); see also Webster v. Fall,

266 U.S. 507, 511 (1925) (“Questions which merely

lurk in the record, neither brought to the attention of

the court nor ruled upon, are not to be considered as

having been so decided as to constitute precedents.”).

Unlike in Stinson, deference to the Commission in

this case required the court to impose a stricter

sentence on Mr. Wynn, so “alarm bells should be going

off.” United States v. Havis, 907 F.3d 439, 459 (6th

Cir. 2018) (Thapar, J.).

“[W]hen liberty is at stake,” deference “has no role to

play.” Guedes v. Bureau of Alcohol, Tobacco, Firearms

& Explosives, 140 S. Ct. 789, 790 (2020) (Gorsuch, J.,

statement regarding denial of certiorari). As six

Third Circuit judges just recognized, “[p]enal laws

pose the most severe threats to life and liberty, as the

Government seeks to brand people as criminals and

lock them away.” Nasir, 2021 WL 5173485, at *10

(Bibas, J.). “Liberty is the norm; every moment of

incarceration should be justified.” United States v.

Faison, 2020 WL 815699, at *1 (D. Md. Feb. 18, 2020).

For a defendant, “every day, month and year that was

added to the ultimate sentence will matter.” Ibid.

Any increase in a criminal sentence must comport

with due process. “[I]t is crucial that judges give

careful consideration to every minute that is added to

a defendant’s sentence.” Ibid. “The critical point is

that criminal laws are for courts, not for the

Government, to construe.” Abramski v. United States,

573 U.S. 169, 191 (2014) (“[W]e have never held that

the Government’s reading of a criminal statute is

entitled to any deference.”).

8

B. The Constitution Compels Lenity

Three “core values of the Republic” compel the rule

of lenity: (1) due process; (2) the separation of

governmental powers; and (3) “our nation’s strong

preference for liberty.” Nasir, 2021 WL 5173485, at

*10-11 (Bibas, J.). Due process requires that “a fair

warning should be given to the world in language that

the common world will understand, of what the law

intends to do if a certain line is passed. To make the

warning fair, so far as possible the line should be

clear.” McBoyle v. United States, 283 U.S. 25, 27

(1931). By construing ambiguities in the defendant’s

favor, lenity prohibits criminal punishment without a

fair warning through clear statutory language.

Lenity also protects the separation of powers: the

legislature criminalizes conduct and sets statutory

penalties, the executive prosecutes crimes and can

recommend a sentence, and the judiciary sentences

defendants within the applicable statutory

framework. United States v. Bass, 404 U.S. 336, 348

(1971). The rule “strikes the appropriate balance

between the legislature, the prosecutor, and the court

in defining criminal liability.” Liparota v. United

States, 471 U.S. 419, 427 (1985). Finally, and

“perhaps most importantly,” Nasir, 2021 WL 5173485,

at *10 (Bibas, J.), lenity “embodies ‘the instinctive

distaste[] against men languishing in prison unless

the lawmaker has clearly said they should.’” Bass,

404 U.S. at 347 (citation omitted). This “presumption

of liberty remains crucial to guarding against

overpunishment.” Nasir, 2021 WL 5173485, at *11

(Bibas, J.). By promoting liberty, lenity “fits with one

of the core purposes of our Constitution, to ‘secure the

Blessings of Liberty’ for all[.]” Id. (quoting U.S.

Const. pmbl.).

9

Additionally, lenity also serves the practical

purpose of “plac[ing] the weight of inertia upon the

party that can best induce [law-makers] to speak

more clearly[.]” United States v. Santos, 553 U.S. 507,

514 (2008).

Stinson deference undermines this

incentive by allowing Commission commentary to

resolve ambiguous Guidelines in the government’s

favor.

The dispositive weight that seven circuits afford to

Commission commentary—regardless of textual

ambiguity—exacerbates the problems inherent in

ignoring lenity. These circuits elevate the

Commission’s interpretation over the actual text of

the Guidelines. Cf. Booker, 543 at 258 (striking the

portion of the Sentencing Reform Act that made the

Guidelines mandatory). And by doing so, these courts

permit the Commission to effectively amend

congressionally approved Guidelines by simply reinterpreting the Commission’s own ambiguous

language. See Christensen v. Harris Cty., 529 U.S.

576, 588 (2000) (deferring to an agency’s position on

an unambiguous rule “would be to permit the agency,

under the guise of interpreting a regulation, to create

de facto a new regulation”). In this way, Stinson

“insulate[s]” the Commission’s commentary “from

legislative interference,” Peugh v. United States, 569

U.S. 530, 545 (2013), undermining the very political

accountability that this Court created deference to

promote.

C. Traditional Tools of Interpretation Apply

Lenity Before Deference

Kisor reiterated that deference to an agency is

inappropriate until a court empties its “legal toolkit”

of “all the ‘traditional tools’ of construction.” 139 S.

10

Ct. at 2418. Two such interpretative tools prioritize

lenity over deference.

First, lenity itself is a traditional “rule of statutory

construction” in the courts’ toolkit. United States v.

Thompson/Ctr. Arms Co., 504 U.S. 505, 518 (1992)

(cleaned up). Like other “presumptions, substantive

canons and clear-statement rules,” lenity must “take

precedence over conflicting agency views.” Carter v.

Welles-Bowen Realty, Inc., 736 F.3d 722, 731 (6th Cir.

2013) (Sutton, J., concurring) (collecting cases).

Agency deference must come last because “[r]ules of

interpretation bind all interpreters, administrative

agencies included.” Ibid. “That means an agency, no

less than a court, must interpret a doubtful criminal

statute in favor of the defendant.” Ibid.; see also De

Lima v. Sessions, 867 F.3d 260, 265 (1st Cir. 2017)

(“Courts that say lenity doesn’t apply until last miss

the fact that agencies, like courts, are supposed to

apply statutory canons of interpretation, which

include lenity.”).

Accordingly, “lenity takes precedence” over

Stinson deference. Nasir, 2021 WL 5173485, at *11

(Bibas, J.). When a Guideline is ambiguous, the court

must adopt the more lenient reading—regardless of

what the commentary says. Ibid.

Second, lenity implicates a related tool of

construction: it allows courts to avoid the

constitutional concerns concomitant in construing

ambiguity against a criminal defendant. When “an

otherwise acceptable construction of a statute would

raise serious constitutional problems,” courts

“construe the statute to avoid such problems unless

such construction is plainly contrary to the intent of

Congress.” Edward J. DeBartolo Corp. v. Fla. Gulf

11

Coast Bldg. & Constr. Trades Council, 485 U.S. 568,

575 (1988).

Lenity and constitutional avoidance operate

symbiotically when interpreting an ambiguous

criminal statute. See United States v. Davis, 139 S.

Ct. 2319, 2333 (2019) (describing the doctrines as

“traditionally sympathetic” to one another). Like

lenity, constitutional avoidance resolves ambiguity

against the government to avoid violating a

defendant’s due-process rights and the separation of

powers. See ibid. (“Applying constitutional avoidance

to narrow a criminal statute, as this Court has

historically done, accords with the rule of lenity.”).

No similar constitutional concerns necessitate the

application of Stinson deference, which lacks any

constitutional underpinning. See Nasir, 2021 WL

5173485, at *11 (Bibas, J.) (“There is no compelling

reason to defer to a Guidelines comment that is

harsher than the text.”); Havis, 907 F.3d at 451

(Thapar, J.) (“Such deference is found nowhere in the

Constitution—the document to which judges take an

oath.”). Rather than the Constitution, agency

deference is “rooted in a presumption about [the

drafter’s] intent”; though, the presumption is “always

rebuttable.” Kisor, 139 S. Ct. at 2412. In the criminal

context, this presumption must give way to a strict

reading of the statute. Wiltberger, 18 U.S. at 95.

Prioritizing deference over lenity offends due process

and violates the judicial oath to uphold the

Constitution. DeBartolo Corp., 485 U.S. at 575

(construing ambiguity to avoid constitutional

infirmity because “Congress, like this Court, is bound

by and swears an oath to uphold the Constitution”).

“Whatever the virtues” of agency deference in civil

12

cases, “in criminal justice those virtues cannot

outweigh life and liberty. Efficiency and expertise do

not trump justice.” Nasir, 2021 WL 5173485, at *11

(Bibas, J.).

When criminal penalties are ambiguous, “doubts

are resolved in favor of the defendant.” Bass, 404 U.S.

at 347. Lenity leaves no room for deference.

D. Lower Courts Disagree over

Application in Stinson Cases

Lenity’s

The circuit split has two dimensions: (1) whether

Kisor’s methodology applies in Stinson cases and (2)

whether lenity applies before deference in that

analysis. This misunderstanding affects all Stinson

cases—not just those construing the Career Offender

Guideline. See, e.g., United States v. Riccardi, 989 F.3d

476, 485, 488 (6th Cir. 2021) (rejecting the government’s

“attempts to distinguish” career-offender cases); United

States v. Lovato, 950 F.3d 1337 (10th Cir. 2020) (rejecting

Kisor-based arguments to Crime-of-Violence Guideline);

United States v. Cruz-Flores, 799 F. App’x 245 (5th Cir.

2020) (rejecting Kisor-based arguments to UnlawfulEntry Guideline ); Faison, 2020 WL 815699 (refusing

to defer to commentary to the Firearms-Transactions

Guideline).

The Sixth Circuit’s recent decision in Riccardi

illustrates the lower courts’ disagreement. The court

refused to defer to § 2B1.1’s commentary on gift-card

theft because “Kisor’s clarification of [Auer’s] plain-error

test applies just as much to Stinson (and the

Commission’s guidelines) as it does to Auer (and an

agency’s regulations).” 989 F.3d at 485. But Judge

Nalbandian wrote separately to opine that Stinson is “its

own free-standing directive,” under which courts should

still defer to commentary “as long as the interpretation

13

does not violate the Constitution or a federal statute and

is not plainly erroneous or inconsistent with the

provision’s text.” Id. at 491 & n.4. He disputed that

Kisor was “a command … to apply such deference in

[Stinson] cases.” Ibid. In Judge Nalbandian’s view, the

old Stinson standard should prevail, unaltered by Kisor’s

clarifications, until this Court “expand[s] its own

precedent.” Id. at 492.

At least six Third Circuit judges disagree with

Judge Nalbandian. Awakened by Kisor from their

“slumber of reflexive deference,” those judges agreed

that, at step 1 of the court’s analysis, the rule of lenity

“displaces”

deference

to

the

Commission’s

commentary. Nasir, 2021 WL 5173485, at *11 (Bibas,

J.).

Judge Thapar expressed a similar view in his

Havis concurrence. He explained that deference has

no place in construing sentencing commentary

because lenity should apply when the commentary

would render a sentence harsher and, even when not,

deference would still “deprive the judiciary of its

ability to check the Commission’s exercise of power.”

Havis, 907 F.3d at 450-51 (Thapar, J.).

And the panel in United States v. Winstead opined

that, although it was unnecessary to apply lenity

because Guideline § 4B1.2 is unambiguous, “it is not

obvious how the rule of lenity is squared with

Stinson’s description of the commentary’s authority to

interpret guidelines. We are inclined to believe that

the rule of lenity still has some force.” 890 F.3d 1082,

1092 n.14 (D.C. Cir. 2018) (Silberman, Garland,

Edwards, JJ.).

Other courts prioritize lenity over deference in

other Auer cases but refuse to revisit Stinson

precedent that conflicts with Kisor. The Seventh

14

Circuit, for example, “consider[s] rule of lenity

arguments when a defendant argues that a particular

sentencing guideline is ambiguous.” United States v.

McClain, 23 F. App’x 544, 548 (7th Cir. 2001)

(collecting cases). But that court has refused to revisit

its decision to defer to Application Note 1, even

though it deferred based on the Guideline’s silence

about “whether inchoate offenses are included or

excluded.” See United States v. Adams, 934 F.3d 720,

729 (7th Cir. 2019) (citation omitted).

The First Circuit has also expressly prioritized

lenity over deference in Auer cases. De Lima, 867

F.3d at 265. Yet, the court still applied its pre-Kisor

precedent over the concerns of Judges Torruella and

Thompson that reflexive Stinson deference carries

“troubling implications for due process, checks and

balances, and the rule of law.” United States v. Lewis,

963 F.3d 16, 27-28 (1st Cir. 2020) (Torruella &

Thompson, JJ., concurring).

There’s a similar story in the Eighth Circuit,

which has held that “lenity applies when an

ambiguous section of the Sentencing Guidelines may

be given either of two plausible readings.” United

States v. Rodriguez-Arreola, 313 F.3d 1064, 1067 (8th

Cir. 2002). But the court has denied at least five postKisor petitions to reconsider that precedent en banc,3

despite recognizing that Kisor was a “major development

since 1995” when the circuit established its Stinson

precedent, United States v. Broadway, 815 Fed. App’x 95,

96 n.2 (8th Cir. 2020).

Likewise, the Fifth Circuit has held that lenity

precludes Auer deference in criminal cases. United

3 See Reply Br. n.1, Broadway v. United States, Pet.

No. 20-836 (collecting cases).

15

States v. Moss, 872 F.3d 304, 308, 314 (5th Cir. 2017);

see also United States v. Cantu, 423 F. Supp. 3d 345,

352 (S.D. Tex. 2019) (applying lenity over Guideline

§ 1B1.13 cmt. n.1(D)). Yet, the court recently

acknowledged the circuit split on Stinson deference,

reasoning that it “would be inclined to agree with the

Third Circuit” in Nasir if “not constrained by circuit

precedent” and the specific facts of the defendant’s

case. United States v. Goodin, 835 Fed. App’x 771,

782 n.1 (5th Cir. 2021).

On the other side of the methodological dispute sit

the Second, Fourth, Ninth, Tenth, and Eleventh

Circuits.

The Second Circuit panel below explicitly rejected

Mr. Wynn’s arguments that Kisor undermined the

Second Circuit’s uncritical rationale in United States

v. Jackson, 60 F.3d 128, 133 (2d Cir. 1995). App. A at

4.

The Fourth Circuit prioritizes deference over

lenity in other contexts. See Yi v. Fed. Bureau of

Prisons, 412 F.3d 526, 535 (4th Cir. 2005)

(“[D]eference trumps lenity when courts are called

upon to resolve disputes about ambiguous statutory

language.”) (citation omitted). But that court “has not

yet addressed” whether to defer to Application Note 1.

See Smith v. United States, 2020 WL 4211284, at n.3

(S.D. W.Va. June 26, 2020) (collecting district-court

cases refusing deference).

For its part, the Ninth Circuit has said it “would

follow the Sixth and D.C. Circuits’ lead” if “free to do

so.” United States v. Crum, 934 F.3d 963, 966 (9th

Cir. 2019). Although, that circuit’s current approach

of searching beyond the Guidelines’ text to add crimes

to the Career Offender Guideline is antithetical to

lenity. See ibid.

16

The Tenth Circuit still adheres to pre-Kisor

deference when commentary “can be reconciled with

the language of the guideline.” United States v.

Martinez, 602 F.3d 1166, 1174 (10th Cir. 2010) (cited

by Lovato, 950 F.3d at 1347). As for the priority of

lenity, the circuit is decidedly undecided. Cf.

Aposhian v. Wilkinson, 989 F.3d 890 (10th Cir. 2021)

(en banc) (vacating as improvidently granted an en

banc rehearing to consider the lenity/deference issue),

cert. pending sub nom., Aposhian v. Garland, No. 21159 (filed Aug. 2, 2021); but see id. at 899 (Tymkovich,

C.J., dissenting, with Hartz, Holmes, Eid, and

Carson, JJ.) (“I am admittedly lost as to why Chevron

gets to cut in front of the rule of lenity in the statutory

interpretation line.”).

And the Eleventh Circuit has “cast doubt” on

whether the rule of lenity applies to the interpretative

commentary to the Guidelines. Cingari, 952 F.3d at

1310-11.

Given the methodological nature of the lower

courts’ disagreements,4 this Court’s intervention is

necessary to clarify that lenity is a traditional tool of

interpretation that applies before Stinson deference.

4 Whenever the Commission eventually regains a

quorum, it still cannot resolve this methodological

dispute by amending a particular Guideline. Even

after how long it takes to nominate and confirm

Commissioners (there are currently six vacancies and

no nominations pending), an amendment cycle and

congressional review takes about a year. Waiting in

vain for the Commission to solve a problem that this

Court created will add decades of unconstitutional

prison terms to thousands of defendants.

17

Only this Court can resolve the issue because this

Court’s own statements caused the confusion. In

dictum, the Court once said that, although it had

applied lenity to “specific factual disputes” regarding

“a statute that contains criminal sanctions,” the

Court had “never suggested that the rule of lenity

should provide the standard for reviewing facial

challenges to administrative regulations whenever

the

governing

statute

authorizes

criminal

enforcement.” Babbitt v. Sweet Home Chapter of

Cmts. for a Great Ore., 515 U.S. 687, 704 n.18 (1995).

Justice Scalia, joined by Justice Thomas, later

described Babbitt’s footnote as a “drive-by ruling” that

“deserves little weight” because it “contradicts the

many cases before and since holding that, if a law has

both criminal and civil applications, the rule of lenity

governs its interpretation in both settings.” Whitman,

574 U.S. 1003 Scalia, J., statement respecting denial

of certiorari) (citing Leocal v. Ashcroft, 543 U.S. 1, 1112 n.8 (2004); Thompson/Ctr. Arms, 504 U.S. at 518

n.10). At least twice since Babbitt, the Court has

granted a petition that raised the issue of whether

lenity takes priority over deference but then disposed

of the case on other grounds. See Esquivel-Quintana,

137 S. Ct. at 1572; Barber v. Thomas, 560 U.S. 474,

488 (2010); see also Solid Waste Agency of N. Cook

Cty. v. U.S. Army Corps of Eng’rs, 531 U.S. 159, 174

n.8 (2001) (declining to consider lenity’s application

because the challenged regulation exceeded the

agency’s authority).

This Court should grant Mr. Wynn’s petition and

clarify the proper methodology for all Stinson cases.

Denying yet another petition on this issue will further

signal to the lower courts that they can continue to

disregard Kisor’s edicts.

18

II. THIS COURT SHOULD GRANT THE PETITION TO

NARROW OR OVERRULE STINSON

Obligatory deference regimes like Stinson are

antithetical to the independent judgment that Article

III requires, and they violate the Fifth Amendment’s

Due Process Clause by exhibiting bias toward one

party.

As Judge Thapar explained in his Havis concurrence,

deference to the Commission’s commentary “both

transfer[s] the judiciary’s power to say what the law is to

the Commission and deprive[s] the judiciary of its ability

to check the Commission’s exercise of power.” Havis, 907

F.3d at 450-51 (Thapar, J.). Stinson also allows the

Commission to interpret its own Guidelines. But “just as

a pitcher cannot call his own balls and strikes, an agency

cannot trespass upon the court’s province to ‘say what

the law is.’” Id. at 450 (quoting Marbury v. Madison, 5

U.S. (1 Cranch) 137, 177 (1803)).

A. Interpretive Deference Is Unconstitutional

1. Stinson

Deference

Violates

Judicial

Independence and the Judicial Office

Judicial independence has been a touchstone of

legitimate governance at least since English judges

resisted King James I’s insistence that “[t]he King

being the author of the Lawe is the interpreter of the

Lawe.” See Philip Hamburger, Law and Judicial Duty

149-50, 223 (2008).

The judges insisted that,

although they exercised the judicial power in the

name of the monarch, the power rested solely in the

judges. Prohibition del Roy, 12 Co. Rep. 63, 65 (1608).

During the revolt against tyranny, the American

Declaration of Independence objected to judges

19

“dependent on [King George III’s] will alone.” The

Declaration of Independence, ¶ 3. The Founders then

cast their first substantive vote at the Constitutional

Convention of 1787 to create a government that

separated power among three co-equal branches. See

1 Records of the Federal Convention of 1787, 30-31

(Max Farrand ed., Yale Univ. Press 1911). Dividing

governmental power preserves liberty, in part,

because each branch jealously checks the other

branches’ attempts to accumulate power at the

expense of the constitutional balance.

No branch is more vital to protecting liberty from

factious politics than the judiciary.

As our

constitutional backstop, the independent judiciary

ensures that the political branches cannot diminish

constitutional liberties.

Article III guards the

judiciary’s independence by adopting the common-law

tradition of an independent judicial office, secured by

life tenure and undiminished salary. U.S. CONST.,

ART. III, § 1. To hold the judicial office, an Article III

judge swears an oath to the Constitution and is dutybound to exercise his or her office independently. See

Law and Judicial Duty 507-12.

The judicial office includes a duty of independent

judgment. See James Iredell, To the Public, N.C.

Gazette (Aug. 17, 1786) (describing the duty of judges

as “[t]he duty of the power”).

Through the

independent judicial office, the Founders ensured

that judges would not administer justice based on

someone else’s interpretation of the law. See 2

Records of the Federal Convention of 1787, 79

(Nathaniel Gorham) (“[T]he Judges ought to carry

into the exposition of the laws no prepossessions with

regard to them”); THE FEDERALIST No. 78 (Alexander

20

Hamilton) (“The interpretation of laws is the proper

and peculiar province of the courts.”). The opinions of

the founding era’s finest jurists recognize this

obligation of independence. See, e.g., Georgia v.

Brailsford, 2 U.S. (2 Dall.) 415, 416 (1793) (Iredell, J.,

dissenting) (“It is my misfortune to dissent … but I

am bound to decide, according to the dictates of my

own judgment.”); The Julia, 14 F. Cas. 27, 33 (C.C.D.

Mass. 1813) (Story, J.) (“[M]y duty requires that

whatsoever may be its imperfections, my own

judgment should be pronounced to the parties.”);

United States v. Burr, 25 F. Cas. 2, 15 (C.C.D. Va.

1807) (Marshall, J.) (“[W]hether [the point] be

conceded by others or not, it is the dictate of my own

judgment, and in the performance of my duty I can

know no other guide.”).

Judicial independence, as a duty and obligation,

persists today. This principle is so axiomatic that it

seldom appears in legal argument; the mere

suggestion that a judge might breach his or her duty

of independent judgment is scandalous. But that is

exactly what deference regimes like Stinson require:

judicial dependence on a non-judicial entity’s

interpretation of the law.5

Faithful application of Stinson requires judges to

abdicate the duty of their judicial office by forgoing

their independent judgment in favor of an agency’s

legal interpretation. See Perez v. Mortgage Bankers

Ass’n, 572 U.S. 92, 110 (2015) (Scalia, J., concurring

5 Those judges who serve on the Commission are

not acting as judges but as part-time Commissioners,

even if their expertise as judges informs their decisions. See Havis, 907 F.3d at 451 (Thapar, J.).

21

in judgment) (deference requires courts “to ‘decide’

that the text means what the agency says”).

Deference diminishes the judicial office and, with it,

the structural safeguards the Framers erected as a

bulwark against tyranny. Cf. Miller v. Johnson, 515

U.S. 900, 922-23 (1995) (holding that deference to the

Department of Justice’s statutory interpretation

would impermissibly “surrender[] to the Executive

Branch [the Court’s] role in enforcing the

constitutional limits [at issue]”).

Even when Congress has tasked an agency with

promulgating binding rules or guidelines, it remains

the judiciary’s role to “say what the law is” in any case

or controversy about the meaning and application of

those agency-made provisions. Marbury, 5 U.S. at

177. The duty of independent judgment is the very

office of an Article III judge; Stinson cannot lawfully

require judges to abdicate that duty. Cf. Yarborough

v. Alvarado, 541 U.S. 652, 663-64 (2004) (discussing

the “substantial element of judgment” that federal

judges must exercise “when applying a broadly

written rule to a specific case”). The Commission’s

opinion of how to best interpret its guidelines

deserves no more weight than the heft of its

persuasiveness.

See, e.g., 18 U.S.C. § 3553(b)

(allowing but not requiring courts to “consider” the

“official commentary of the Sentencing Commission”

when deciding whether to depart from a guidelines

range).

2. Stinson

Violates

Due

Process

Institutionalizing Judicial Bias

by

Deference to Commission commentary also

jeopardizes the judicial impartiality that due process

requires. Cf. Marshall v. Jerrico, Inc., 446 U.S. 238,

22

242 (1980); Com. Coatings Corp. v. Cont’l Cas. Co.,

393 U.S. 145, 149 (1968) (explaining that judicial

bodies “not only must be unbiased but also must avoid

even the appearance of bias.”); Masterpiece Cake

Shop, Ltd. v. Colo. Civil Rights Comm’n, 138 S. Ct.

1719, 1734 (2018) (Kagan, J., concurring) (agreeing

the Constitution forbids adjudicatory proceedings

that are “infected by … bias”).

Judicial bias need not be personal to violate due

process—it can also be institutional.

In fact,

institutionalized judicial bias is more pervasive, as it

systematically subjects parties across the entire

judiciary to bias rather than only a party before a

particular judge. Stinson institutionalizes bias by

requiring courts to “defer” to the government’s legal

interpretation in violation of a defendant’s right to

due process of law. Cf. Philip Hamburger, Chevron

Bias, 84 GEO. WASH. L. REV. 1187 (2016). Rather than

exercise their own judgment about what the law is,

judges under Stinson defer as a matter of course to

the judgment of one of the litigants before them: the

federal government. The government litigant wins

merely by showing that its preferred interpretation of

the commentary “is not plainly erroneous or

inconsistent with” the Guidelines. Stinson, 508 U.S.

at 47; see also Martinez, 602 F.3d at 1173 (deferring

when commentary “can be reconciled with the

language of [the] guideline”). A judge cannot simply

find the defendant’s reading more plausible or think

the government’s reading is wrong—the government

must be plainly wrong.

Most judges recognize that personal bias requires

recusal. It is equally inappropriate for a judge to

decide a case based on a deference regime that

23

institutionalizes bias by requiring judges to favor the

legal interpretation of a government litigant. See In

re Murchison, 349 U.S. 133, 136 (1955) (reasoning

that the “stringent” due-process requirement of

impartiality may require recusal by “judges who have

no actual bias and who would do their very best to

weigh the scales of justice equally between

contending parties”).

No rationale can defend a practice that weights

the scales in favor of a government litigant—the most

powerful party—and commands systematic bias in

favor of the government’s preferred interpretations of

the Sentencing Guidelines. Government-litigant bias

doctrines like Stinson deny due process by favoring

the prosecution’s litigating position. Tumey v. Ohio,

273 U.S. 510, 532 (1927) (“Every procedure” that

might lead a judge “not to hold the balance nice, clear,

and true between the state and the accused denies the

latter due process of law.”).

B. Deference to Commission Commentary Is

Uniquely Unlawful

Keeping in mind that reflexive agency deference is

never appropriate and is particularly injurious in

criminal cases, there is yet another reason that the

Second Circuit’s deference to Application Note 1

warrants

this

Court’s

review:

Commission

commentary cannot expand the Guidelines.

The Commission is constitutional only because (1)

Congress reviews amendments to the Guidelines

before they take effect and (2) the Commission must

promulgate its amendments through notice-andcomment rulemaking. Mistretta v. United States, 488

U.S. 361, 393-94 (1989).

24

Convenience or expediency cannot justify the

commentary’s expansion of the Guidelines. Under

Mistretta, any text the Commission issues without

notice-and-comment rulemaking or congressional

review cannot bind the Judiciary without offending

the separation of powers. The lower courts’ disregard

of the strict limitations outlined in Mistretta

undermines the Commission’s “unusual” special place

in our constitutional system and creates something

untenable. See ibid.

It’s time for this Court to reconsider Stinson, reject

the “deference” that compromises the judiciary, and

allow conscientious judges to uphold their

constitutional oath. Deference has no role in criminal

sentencing, where the government can deprive a

defendant of liberty only if all three branches agree

separately and independently that the sanction is

justified.

CONCLUSION

This Court should grant Mr. Wynn’s petition and rule

that Stinson deference cannot increase criminal

sentences, or else abandon such deference altogether.

Respectfully submitted,

SHANA-TARA O’TOOLE

DUE PROCESS INSTITUTE

700 Pennsylvania Ave.

SE, #560

Washington, DC 20003

(202) 558-6683

Shana@idueprocess.org

November 2021

JARED MCCLAIN

Counsel of Record

MARK CHENOWETH

KARA ROLLINS

NEW CIVIL LIBERTIES ALLIANCE

1225 19th St. NW, Suite 450

Washington, DC 20036

(202) 869-5210

Jared.McClain@NCLA.legal

Counsel for Amici Curiae