Petition for Writ of Certiorari — Kenneth J. Jouppi, Petitioner v. Alaska

Supreme Court briefAug 29, 2025

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No. ________

In the Supreme Court of the United States

KENNETH JOHN JOUPPI, PETITIONER

STATE OF ALASKA

On Petition for a Writ of Certiorari

to the Supreme Court of Alaska

PETITION FOR A WRIT OF CERTIORARI

ROBERT JOHN

LAW OFFICE OF ROBERT

JOHN

P.O. Box 73750

Fairbanks, AK 99707

(907) 456-6056

rjohn@gci.net

SAMUEL B. GEDGE

Counsel of Record

MICHAEL N. GREENBERG

INSTITUTE FOR JUSTICE

901 North Glebe Road,

Suite 900

Arlington, VA 22203

(703) 682-9320

sgedge@ij.org

mgreenberg@ij.org

(i)

QUESTION PRESENTED

The “touchstone of the constitutional inquiry under

the Excessive Fines Clause” is that the amount of the fine

“must bear some relationship to the gravity of the offense

that it is designed to punish.” United States v. Bajakajian, 524 U.S. 321, 334 (1998). Below, the Alaska Supreme Court upheld the forfeiture of petitioner’s $95,000

airplane because, the court reasoned, petitioner knew

that one of his passenger’s grocery bags contained a sixpack of Budweiser.

In so holding, the court captured vividly a lower-court

conflict over the standard for evaluating the gravity of a

property owner’s offense under the Excessive Fines

Clause. Aligning with the Eleventh Circuit, the Alaska

Supreme Court examined the gravity of the defendant’s

offense at a stratospheric level of abstraction. Meanwhile,

the federal circuit in which Alaska sits—in line with many

other state and federal courts—holds that “[i]t is critical”

to “review the specific actions of the violator rather than

by taking an abstract view of the violation.”

The question presented is whether, in determining

whether a fine contravenes the Excessive Fines Clause,

courts may consider the gravity of the underlying offense

purely in the abstract or should consider the gravity of

the specific defendant’s wrongdoing.

RELATED PROCEEDINGS

Supreme Court of Alaska:

Kenneth John Jouppi v. State, No. S-18598 (Apr. 18,

2025)

State v. Kenneth John Jouppi, No. S-18637 (Apr. 18,

2025)

Alaska Court of Appeals:

State v. Kenneth John Jouppi, No. A-13147 (Sept.

23, 2022)

State v. Kenneth John Jouppi and Ken Air, LLC,

Nos. A-11819, A-11829, A-11830 (May 12, 2017)

District Court of Alaska, Fourth Judicial District:

State v. Kenneth John Jouppi, No. 4FA-12-3228CR

(May 3, 2018) (trial-court order on remand)

State v. Kenneth John Jouppi, No. 4FA-12-3228CR

(Dec. 18, 2013) (original trial-court judgment)

State v. Ken Air, LLC, No. 4FA-12-3659CR (May 3,

2018) (trial-court order on remand)

State v. Ken Air, LLC, No. 4FA-12-3659CR (Dec. 18,

2013) (original trial-court judgment)

State v. Helen Celia Nicholia, No. 4FA-12-3226CR

(July 19, 2013) (passenger’s trial-court judgment)

iii

TABLE OF CONTENTS

Page

Introduction ........................................................................ 1

Opinions below ................................................................... 4

Jurisdiction ......................................................................... 4

Constitutional provision involved ..................................... 5

Statement ............................................................................ 5

A. Background ............................................................ 5

B. Facts and procedural history................................ 7

Reasons for granting the petition .................................. 15

A. The decision below sharpens a conflict over

the standard for whether a fine is excessive ..... 15

1. Four state high courts and most federal

courts of appeals agree that the gravity of

a defendant’s offense must be evaluated by

reference to his or her specific culpability .. 16

2. The decision below joins the Eleventh

Circuit in evaluating the gravity of the

offense in purely abstract terms .................. 23

B. The decision below is erroneous ......................... 27

C. The question presented raises an issue of

national importance, and this case is an ideal

vehicle for addressing it ...................................... 29

Conclusion ......................................................................... 33

Appendix A—Opinion of the Alaska Supreme Court

(Apr. 18, 2025)........................................... 1a

Appendix B—Opinion of the Alaska Court of Appeals

(Sept. 23, 2022) ....................................... 30a

Appendix C—Order of the District Court for the

State of Alaska, Fourth Judicial

District (May 3, 2018) .......................... 152a

TABLE OF AUTHORITIES

Page

Cases:

Alexander v. United States, 509 U.S. 544 (1993)........ 11

Bullock v. Goodall, 7 Va. 44 (1801)............................... 29

Commonwealth v. 1997 Chevrolet,

160 A.3d 153 (Pa. 2017) .................................... 17, 18, 30

Cripps v. La. Dep’t of Agric. & Forestry,

819 F.3d 221 (5th Cir. 2016) ........................................ 22

Culley v. Marshall, 601 U.S. 377 (2024) .................. 4, 32

Harmelin v. Michigan, 501 U.S. 957 (1991) ............ 5, 32

Hintz v. State, 627 P.2d 207 (Alaska 1981) ............ 13-14

Jones v. Commonwealth, 5 Va. 555 (1799) ..................29

Leonard v. Texas, 580 U.S. 1178 (2017) .......................32

One 1995 Toyota Pick-Up Truck v. District of

Columbia, 718 A.2d 558 (D.C. 1998).................... 19, 20

Pimentel v. City of Los Angeles,

974 F.3d 917 (9th Cir. 2020) ........................................ 15

R. v. Mosley, 111 Eng. Rep. 499 (K.B. 1835) ................. 5

Robson 200, LLC v. City of Lakeland,

593 F. Supp. 3d 1110 (M.D. Fla. 2022) .......................25

Sessions v. Dimaya, 584 U.S. 148 (2018) ................. 3, 31

Sparger-Withers v. Taylor,

No. 21-cv-2824, 2024 WL 473719 (S.D. Ind. Feb. 7,

2024), appeal pending, No. 24-1367 (7th Cir.) ..........32

State v. Jouppi,

397 P.3d 1026 (Alaska Ct. App. 2017) ........................ 10

State v. Real Prop., 994 P.2d 1254 (Utah 2000) .... 18, 19

16, 17,

State v. Timbs, 134 N.E.3d 12 (Ind. 2019) ............. 23, 32

2, 16, 17

State v. Timbs, 169 N.E.3d 361 (Ind. 2021) ........... 23, 24

Thomas v. County of Humboldt,

124 F.4th 1179 (9th Cir. 2024) ............................ 1, 7, 20

2-5, 16,

Timbs v. Indiana, 586 U.S. 146 (2019) ............. 29, 31, 32

Toth v. United States, 143 S. Ct. 552 (2023) ..................4

Tyler v. Hennepin County, 598 U.S. 631 (2023) ........... 5

United States ex rel. Grant v. Zorn,

107 F.4th 782 (8th Cir. 2024),

cert. denied, Nos. 24-549, 24-845 (June 23, 2025) .....22

United States v. $100,348.00,

354 F.3d 1110 (9th Cir. 2004) ................................ 20, 31

United States v. 3814 NW Thurman St.,

164 F.3d 1191 (9th Cir. 1999) ......................................24

United States v. 6380 Little Canyon Rd.,

59 F.3d 974 (9th Cir. 1995) .......................................... 21

United States v. 817 N.E. 29th Drive,

175 F.3d 1304 (11th Cir. 1999) .................................... 24

United States v. Abair,

746 F.3d 260 (7th Cir. 2014) ........................................ 22

United States v. Bajakajian,

1, 2, 5-7, 11, 16,

524 U.S. 321 (1998) ......................... 17, 21, 26, 27, 28, 30

United States v. Beecroft,

825 F.3d 991 (9th Cir. 2016) ........................................ 20

vii

United States v. Carpenter,

317 F.3d 618 (2003),

opinion reinstated in relevant part, 360 F.3d 591

(6th Cir. 2004) ...............................................................22

United States v. Facteau,

89 F.4th 1 (1st Cir. 2023),

cert. denied, 145 S. Ct. 137 (2024) ..............................21

United States v. Jalaram, Inc.,

599 F.3d 347 (4th Cir. 2010) ........................................ 22

United States v. Schwarzbaum,

127 F.4th 259 (11th Cir. 2025) .............................. 25-27

United States v. Wagoner Cnty. Real Est.,

278 F.3d 1091 (10th Cir. 2002) .................................... 22

United States v. Wallace,

389 F.3d 483 (5th Cir. 2004) ........................................ 21

von Hofe v. United States,

492 F.3d 175, 187 (2d Cir. 2007) .................................22

Yates v. Pinellas Hematology & Oncology, P.A.,

21 F.4th 1288 (11th Cir. 2021) ................................ 3, 25

Yskamp v. DEA, 163 F.3d 767 (3d Cir. 1998) ............. 21

Statutes:

28 U.S.C. § 1257(a) ...................................................... 5, 14

Alaska Stat. § 04.11.491(a)(1)...........................................7

Alaska Stat. § 04.11.491(a)(2) ...........................................7

Alaska Stat. § 04.11.491(a)(3) ...........................................7

Alaska Stat. § 04.11.491(a)(5)...........................................7

Alaska Stat. § 04.11.499(a) ...............................................8

Alaska Stat. § 04.16.200(e)(1)-(3) ..................................... 8

viii

Alaska Stat. § 04.16.200(g)(1)(A) ...................................10

Alaska Stat. § 04.16.220(a)(3)(C) ............................... 8, 10

Other Authorities:

2 Matthew Bacon, A New Abridgement of the Law

(4th ed. 1778) ................................................................28

Beth A. Colgan, Reviving the Excessive Fines

Clause, 102 Calif. L. Rev. 277 (2014) ......................... 30

David Pimentel, Forfeitures and the Eighth

Amendment: A Practical Approach to the

Excessive Fines Clause as a Check on

Government Seizures,

11 Harv. L. & Pol’y Rev. 541 (2017) ..................... 30, 31

Ex. 1 to U.S. Mot. for Judgment, United

States v. Schwarzbaum, No. 18-cv-81147

(S.D. Fla. Sept. 15, 2022) (Doc. 152-1) ....................... 26

Historical Manuscripts Comm’n, The Manuscripts

of the House of Lords, 1690-1691 (1892) ...................28

Kristen A. Ogilvie, Unintended Consequences of

Local Alcohol Restrictions in Rural Alaska,

17(1) J. Ethnicity in Substance Abuse 16 (2018) ........7

Pamela S. Karlan, “Pricking the Lines”: The Due

Process Clause, Punitive Damages, and

Criminal Punishment,

88 Minn. L. Rev. 880 (2004) ..........................................7

Stephen M. Shapiro et al., Supreme Court Practice

(11th ed. 2019) ................................................................ 2

Transcript, Timbs v. Indiana (No. 17-1091) .................3

(1)

INTRODUCTION

This case presents a threshold question concerning

the standard for whether a fine or forfeiture contravenes

the Eighth Amendment’s Excessive Fines Clause. For

over a decade, the State of Alaska has been trying to forfeit bush pilot Ken Jouppi’s 1969 Cessna airplane. The basis: One of Jouppi’s passengers had beer in her luggage,

and the State maintained that one six-pack, at least,

would have been visible to Jouppi. For certain Alaskan

villages, it’s a crime to bring in alcohol. And when the

means of importation is an airplane, the plane is subject

to forfeiture. No matter that the offense is a misdemeanor. As here. No matter that the pilot is a first-time

offender. As here. No matter that the alcohol is a six-pack

of Budweiser. As here. No matter that it belonged to a

customer. As here. The result: an airplane forfeited for a

six-pack.

The Excessive Fines Clause was built for cases like

this.

In holding otherwise “as a matter of law,” the Alaska

Supreme Court broke with this Court’s precedent and

with that of many lower courts. “[A] punitive forfeiture,”

this Court has held, “violates the Excessive Fines Clause

if it is grossly disproportional to the gravity of a defendant’s offense.” United States v. Bajakajian, 524 U.S. 321,

334 (1998). And in evaluating the gravity of the offense,

many courts—including Alaska’s home circuit—start

from a shared premise: “It is critical” to “review the specific actions of the violator rather than by taking an abstract view of the violation.” Thomas v. County of Humboldt, 124 F.4th 1179, 1193 (9th Cir. 2024) (citation omitted). Starting from that same premise, in fact, the Indiana

Supreme Court on remand in Timbs v. Indiana “focus[ed] on the specific harms of specific acts” and held

that forfeiting Tyson Timbs’s Land Rover was excessive.

State v. Timbs, 169 N.E.3d 361, 373 (2021); see also

Timbs v. Indiana, 586 U.S. 146 (2019).

With the decision below, the Alaska Supreme Court

adopted a minority view and embraced a fundamentally

different standard: It examined the gravity of Ken

Jouppi’s offense in paradigmatically abstract terms. It

dismissed as “not particularly relevant whether Jouppi’s

offense was part of a larger pattern of criminal activity”—

despite this Court’s describing as “highly relevant”

whether a defendant’s offense “was unrelated to any

other crime.” Bajakajian, 524 U.S. at 338 n.12. It compared the airplane’s value to the very sort of theoretical

statutory-maximum sentences this Court in Bajakajian

abjured. It ignored the “extent of the harm caused by

Jouppi’s illegal conduct” in favor of “the harm . . . addressed in the legislative history” decades before. Only

thus could it hold that “the illegal importation of even a

six-pack of beer causes grave societal harm” and that forfeiting Jouppi’s airplane “does not violate the Excessive

Fines Clause.”

The split is real, and it is a compelling one for this

Court’s intervention. Given the Ninth Circuit’s longstanding view of the Excessive Fines Clause, Alaska’s contrary

standard “pits a highest state court against the court of

appeals whose circuit includes that state.” Stephen M.

Shapiro et al., Supreme Court Practice, 4-72 (11th ed.

2019). Fines and forfeitures in Alaska are thus subject to

two different Eighth Amendment regimes depending on

whether the forum is state court or federal. That conflict

also promises different real-world outcomes. Under the

defendant-focused standard of federal courts like the

Ninth Circuit and state courts like Indiana’s, Pennsylva-

nia’s, D.C.’s, and Utah’s, Jouppi’s forfeiture almost certainly would not have been upheld. Meanwhile, forfeitures that those courts have invalidated would surely be

blessed in Alaska. Tyson Timbs, for instance, unquestionably would have lost his Land Rover had he been in

Alaska instead of Indiana. For that matter, Hosep Bajakajian would have lost his $357,000. Justice Breyer

could well have lost his (hypothetical) Bugatti. Tr. 43-44,

Timbs v. Indiana (No. 17-1091) (“[Court]: So what is to

happen if a state needing revenue says anyone who

speeds has to forfeit the Bugatti, Mercedes, or a special

Ferrari or even jalopy? (Laughter.)”). The scope of a Bill

of Rights protection should not vary radically based on

geography. Yet Alaska’s plane-for-a-six-pack standard

conflicts starkly with the standard articulated in Bajakajian and recognized by many courts nationwide.

The Court’s intervention is urgently needed now,

moreover, in an era of “more and more civil laws bearing

more and more extravagant punishments.” Sessions v.

Dimaya, 584 U.S. 148, 184 (2018) (Gorsuch, J., concurring

in part and concurring in the judgment). Only once (in Bajakajian) has the Court considered the standard for determining whether a fine is excessive. In the twentyseven years since, some courts—like Alaska’s—have

locked themselves into a “hyper-deferential” standard

that provides virtually no check on exorbitant fines. Yates

v. Pinellas Hematology & Oncology, P.A., 21 F.4th 1288,

1318 (11th Cir. 2021) (Newsom, J., joined by Jordan, J.,

concurring). Many others have become mired in “disorder,” with “a patchwork of inconsistent tests” and “a large

degree of uncertainty regarding current excessive fines

jurisprudence.” See p. 30, infra. And all the while, enforcement agencies “increasingly depend heavily on fines

and fees as a source of general revenue.” Timbs, 586 U.S.

at 154 (citation omitted); see also Culley v. Marshall, 601

U.S. 377, 405-06 (2024) (Sotomayor, J., dissenting); Toth

v. United States, 143 S. Ct. 552, 553 (2023) (Gorsuch, J.,

dissenting from denial of certiorari) (noting that unwarranted narrowing of the Excessive Fines Clause “incentivizes governments to impose exorbitant civil penalties

as a means of raising revenue”).

This case offers the rare clean vehicle for the Court to

correct the course in a narrow but important way. The decision below implicates a critical first-order question: not

the virtues of one multi-factor test over another, but,

more fundamentally, whether courts should evaluate the

gravity of a defendant’s offense in the abstract or should

instead evaluate the specific defendant’s wrongdoing.

This issue goes to the core of the Excessive Fines Clause’s

guarantee. It is a pure question of law. It is presented

squarely—the decision below cleared aside all possible

fact disputes—and it can be addressed narrowly. Doing

so would not only reorient jurisdictions like Alaska, but

also provide much-needed direction for courts nationwide. The petition should be granted.

OPINIONS BELOW

The opinion of the Alaska Supreme Court (App. 1a29a) is reported at 566 P.3d 943. The opinion of the Alaska

Court of Appeals (App. 30a-63a) is reported at 519 P.3d

653. The order of the trial court (App. 152a-69a) is not reported.

JURISDICTION

The Alaska Supreme Court entered judgment on

April 18, 2025. On June 26, 2025, Justice Kagan extended

the time within which to file a petition for a writ of certiorari to September 2, 2025. This Court’s jurisdiction is invoked under 28 U.S.C. § 1257(a).

CONSTITUTIONAL PROVISION INVOLVED

The Eighth Amendment to the U.S. Constitution provides: “Excessive bail shall not be required, nor excessive

fines imposed, nor cruel and unusual punishments inflicted.”

STATEMENT

A. Background

“Protection against excessive punitive economic sanctions” is “both ‘fundamental to our scheme of ordered liberty’ and ‘deeply rooted in this Nation’s history and tradition.’” Timbs v. Indiana, 586 U.S. 146, 154 (2019).

“[U]niquely of all punishments,” fines stand to make governments money, in turn raising special risk of being “imposed in a measure out of accord with the penal goals of

retribution and deterrence.” Harmelin v. Michigan, 501

U.S. 957, 979 n.9 (1991) (opinion of Scalia, J.); see also R.

v. Mosley, 111 Eng. Rep. 499, 500 (K.B. 1835). It is against

this backdrop that the Eighth Amendment singles out

fines for special mention: “They cannot be excessive.” Tyler v. Hennepin County, 598 U.S. 631, 650 (2023) (Gorsuch, J., concurring).

As this Court articulated in 1998, “[t]he touchstone of

the constitutional inquiry under the Excessive Fines

Clause is the principle of proportionality.” United States

v. Bajakajian, 524 U.S. 321, 334. A fine is unconstitutionally excessive “if it is grossly disproportional to the gravity of a defendant’s offense,” id., and isolating “the gravity

of the defendant’s offense” (id. at 337) is particularly

critical when the penalizing statute applies with equal

force to a wide range of misconduct.

The Court’s analysis in Bajakajian well illustrates

the standard in practice. The statute Hosep Bajakajian

violated requires people to submit a report before bringing more than $10,000 into or out of the country. The accompanying penalty provisions mandate forfeiture of all

unreported currency—for Bajakajian, $357,144. That

provision reaches all sorts of offenders. And given that

sweep, the Court’s excessive-fines analysis focused on locating Bajakajian—specifically—on the statute’s broad

spectrum of culpability. The Court first considered the

gravity of his particular misconduct. His “crime was

solely a reporting offense,” the Court observed, and his

money “was the proceeds of legal activity.” Id. at 337-38.

That his violation “was unrelated to any other crime” was

also “highly relevant.” Id. at 338 n.12. The Court also

looked to his (relatively lenient) sentencing-guidelines

range, which, the Court remarked, refuted the government’s emphasis on the maximum theoretical punishments set by Congress. Id. at 339 & n.14. “That the maximum fine and Guideline sentence to which [he] was subject were but a fraction of the penalties authorized,” the

Court reasoned, “undercuts any argument based solely

on the statute.” Id. at 339 n.14. For “they show that [his]

culpability relative to other potential violators of the reporting provision—tax evaders, drug kingpins, or money

launderers, for example—is small indeed.” Id.

The Court also evaluated “[t]he harm that [Bajakajian] caused.” Id. at 339. Here, too, the Court homed

in on the man: It focused, not on the generalized harms of

Bank Secrecy Act violations in the abstract, but on the

harm caused by Bajakajian himself. Id. On the record

before it, the Court concluded, that harm was “minimal.”

Id. All told, forfeiting Bajakajian’s $357,144 bore “no articulable correlation to any injury suffered by the Government” and was “grossly disproportional to the gravity of

his offense.” Id. at 339-40.

In the decades since, many courts—though not all—

have faithfully distilled Bajakajian’s central teaching: “It

is critical,” as the Ninth Circuit recently put it, “that the

court review the specific actions of the violator rather

than by taking an abstract view of the violation.” Thomas

v. County of Humboldt, 124 F.4th 1179, 1193 (2024) (citation omitted); see generally Pamela S. Karlan, “Pricking

the Lines”: The Due Process Clause, Punitive Damages,

and Criminal Punishment, 88 Minn. L. Rev. 880, 901

(2004) (“[T]he Court seems to analyze the gravity of Bajakajian’s offense solely from a retributivist perspective—asking how much harm his particular violation of

the statute caused.”).

B. Facts and procedural history

1. In the 1980s, the State of Alaska authorized municipalities and villages to declare themselves “dry villages.”

Since then, some have voted simply to regulate the sale of

alcohol, limiting it to restaurants, package stores, and the

like. Alaska Stat. § 04.11.491(a)(2), (3). Others prohibit

selling alcohol but not possessing it. Id. § 04.11.491(a)(1).

Still others select a more stringent level of restriction:

banning the sale, importation, and possession of alcohol

altogether. Id. § 04.11.491(a)(5); see generally Kristen A.

Ogilvie, Unintended Consequences of Local Alcohol Restrictions in Rural Alaska, 17(1) J. Ethnicity in Substance Abuse 16-31 (2018).

For these most restrictive villages, it is a state-level

crime to “knowingly send, transport, or bring an alcoholic

beverage” there. Alaska Stat. § 04.11.499(a). The resulting penalties depend primarily on the amount of alcohol

and whether the defendant is a repeat offender. Transporting 10.5 liters of spirits or 12 gallons of beer is a class

C felony. Two-time recidivists face class C felony charges

too, no matter the quantity involved. On the less serious

end of the spectrum, first-time offenders who transport

less than the quantities of alcohol above are guilty of only

a class A misdemeanor. Id. § 04.16.200(e)(1)-(3). For that

first-time offender, the minimum sentence is three days’

imprisonment and a $1,500 fine. Id. § 04.16.200(g)(1)(A).

And, potentially, forfeiture. Using a plane to transport

the alcohol subjects the plane to mandatory forfeiture—

no matter the quantity and no matter the seriousness of

the offense. Id. § 04.16.220(a)(3)(C). Airplanes are “always subject to mandatory forfeiture under the statute,

regardless of whether the conviction is a misdemeanor or

felony or is the defendant’s first conviction.” App. 22a.

2. Now 82 years old, petitioner Ken Jouppi has been

fascinated with flying since childhood. After serving four

years in the Air Force, mainly as a mechanic for B-52s, he

got his pilot’s license in the late 1960s. In the late ’70s, he

moved to Alaska. R. p. 99.1

For those who love flying, there’s no better place.

Ever since Captain Joseph Martin first flew an opencockpit biplane over Fairbanks in 1913 (helped by his wife

and fellow pilot, Lily), aviation has held a special place in

Alaska’s heritage. Ken Jouppi fit right in. Starting out, he

“R.” refers to the trial-court record on file with the Alaska Court of

Appeals, Case No. A-13147.

flew for a small company out of Ketchikan, working with

the U.S. Forest Service, flying charters, and occasionally

piloting medevac and search missions. R. pp. 676-77. In

time, he started his own company (“KenAir”), and for

years, he made a living using his 1969 Cessna U206D as a

one-man air-taxi service, shuttling tourists and locals

alike over the Alaskan wilderness.

As a pilot, Jouppi knew of Alaska’s dry-village system,

and he would not deliberately fly alcohol illegally. But nor

would he preemptively rifle through passengers’ luggage

to hunt for alcohol. No law required him to search their

belongings, and, in his view, it would be “invasive and demeaning” to do so. R. pp. 154, 677-78.

On the morning of April 3, 2012, he was scheduled to

fly a repeat passenger from Fairbanks to the village of

Beaver—a fully “dry” village that bans selling, importing,

and possessing alcohol. Along with many other groceries,

Jouppi’s passenger had three cases of beer packed in her

luggage. She herself was not a drinker. But she was travelling to Beaver to spend her birthday with her husband,

who worked there; the beer (Budweiser and Bud Light)

was for him. 8/22/2013 Tr. 247-48, 256.

As Jouppi was loading the plane, state troopers arrived on scene, searched it, and found the beer. While

Jouppi insisted he had no idea there was any beer in his

passenger’s luggage, the officers maintained that, at a

minimum, one six-pack of Budweiser was visible in a

shopping bag. So the State charged Jouppi, his company,

and the passenger with the misdemeanor offense of knowingly transporting an alcoholic beverage into a dry community. The passenger pleaded guilty. Jouppi and the

company went to trial and were found guilty by way of a

verdict that expressed no finding on how much alcohol he

knew was aboard his plane. App. 5a. The trial judge imposed the minimum executed sentence allowed by statute: a $1,500 fine for Jouppi (and another $1,500 for his

company) and three days’ imprisonment. App. 5a (“The

court sentenced Jouppi to 180 days in jail with 177 suspended, a $3,000 fine with $1,500 suspended, and three

years of probation.”); see also R. p. 686 (“Mr. Jouppi, I

learned by reading 33 letters that he’s 70 years old and he

has a stellar criminal record. Clean.”).

3.a. Much more was to come: For the past thirteen

years, the State has been pursuing Jouppi’s plane

through in personam criminal forfeiture. (The plane belongs to Jouppi, not his company. App. 6a.) At first, the

trial court held that the forfeiture was not authorized by

the statute. The plane hadn’t flown a foot toward the village of Beaver, the court reasoned, so it could not be said

to have “transport[ed] or facilitate[d] the transportation

of . . . alcoholic beverages imported into a” dry village.

Alaska Stat. § 04.16.220(a)(3)(C). The Alaska Court of Appeals disagreed, construing the statute to mandate forfeiture “regardless of whether the alcoholic beverages are

actually transported toward their destination.” State v.

Jouppi, 397 P.3d 1026, 1033 (2017).

b. On remand, the trial court held a hearing on

whether the forfeiture amounted to an unconstitutionally

excessive fine. The court then ruled that it did. See generally App. 154a-55a (detailing that the federal excessivefines issue was raised before sentencing in 2013 and renewed on remand in 2017).

As an initial matter, the court concluded that Jouppi’s

in personam criminal forfeiture is a fine under the

Excessive Fines Clause. App. 156a; see also Alexander v.

United States, 509 U.S. 544, 558 (1993). The court then

held that the forfeiture was unconstitutionally excessive.

Much like this Court in United States v. Bajakajian, the

trial court “assess[ed] the gravity” of Jouppi’s “actual

conduct” against the severity of the forfeiture. App. 160a.

On the punishment side of the ledger, forfeiting Jouppi’s

airplane was a severe economic sanction. App. 163a (“The

court concludes that the plane is worth $95,000.”). On the

other side of the ledger, his “culpability relative to other

potential violators of the [statute]” was low. See United

States v. Bajakajian, 524 U.S. 321, 339 n.14 (1998). The

criminal statute, the trial court remarked, “recognize[s] a

hierarchy of seriousness among . . . offenses,” yet the airplane-forfeiture provision applies “with equal force to

all.” App. 160a-61a. And while Jouppi’s conduct was “serious,” it “was not nearly as egregious as other conduct

that could result in mandatory forfeiture of a plane under

the applicable statutes.” App. 168a.

“The gravity of the harm” was likewise “low relative

to other AS 04.11.499(a) offenses.” App. 161a. Jouppi “was

convicted of a class A misdemeanor,” the court reasoned,

and even among the universe of misdemeanors, “[o]ne

could imagine more egregious” ones. App. 161a, 168a. The

passenger’s alcohol was not “wine or distilled spirits,” but

“two cases of Budweiser beer, and four six packs of sixteen ounce cans of Budweiser and Bud Light beer.” App.

159a. The court even put a thumb on the government’s

side of the scale and “assume[d]” without deciding that

Jouppi’s “culpability extends to all of the alcohol on the

aircraft, and not merely the six beers that were in plain

view.” App. 161a; see also App. 160a. Even on that assumption, the total amount of beer was “still well within

the limit set forth in” the misdemeanor-tier of the statute.

App. 161a. Consistent with the testimony of Jouppi’s passenger, moreover, the beer “could have plausibly all been

intended for [her] personal consumption, or her family’s

personal consumption.” App. 160a. The court found it

“easy to imagine much more egregious AS 04.11.499(a) violations” and held that “the forfeiture is an excessive fine,

and hence unconstitutional.” App. 161a, 169a.

c. The State appealed, and the court of appeals vacated the trial court’s judgment. App. 30a-63a. The court

shared the trial court’s view that the excessiveness standard rightly focuses on “the particular facts of Jouppi’s

case and his specific level of culpability.” App. 56a. In the

court of appeals’ view, however, the trial court’s factual

findings were “incomplete.” App. 43a. Rather than assuming without deciding that Jouppi’s culpability extended to all of the beer in his passenger’s luggage, the

trial court should have resolved whether his crime “was,

in substance, attempting to bring [only] a six pack of beer

to a local option community.” App. 43a (citation omitted;

alteration in original). The trial court also should have

“address[ed] whether Jouppi’s violation of the bootlegging statute was related to, or comprised part of, other

illegal activities.” App. 44a. And the trial court should

have “made clearer findings regarding the extent of the

harm caused by Jouppi’s illegal conduct.” App. 46a. The

court of appeals thus remanded for further proceedings.2

One member of the panel issued an 83-page separate opinion expressing his view that certain in personam criminal forfeitures are

immune from review under the Excessive Fines Clause. App. 64a151a (Mannheimer, J., concurring in part and dissenting in part). As

that judge acknowledged, however, “Bajakajian holds that the excessive fines clause does govern all in personam forfeitures.” App.

d. The Alaska Supreme Court granted review and vacated the court of appeals’ judgment. App. 1a-29a. Where

the court of appeals called for further fact-finding, the supreme court held unanimously that forfeiting Jouppi’s

airplane was constitutional “as a matter of law.” App. 2a.

Throughout, the court made plain that its analysis was

premised on Jouppi’s having violated the dry-village statute only as to one “six-pack of beer.” App. 24a; see also

App. 20a, 25a. With that as its starting point, the court

then developed an excessiveness standard that reflected

a paradigmatically abstract view of Jouppi’s crime. The

court acknowledged, for example, that “Jouppi was convicted of only one instance of alcohol importation unconnected to other criminal activity.” App. 19a. But the court

considered it “not particularly relevant whether Jouppi’s

offense was part of a larger pattern of criminal activity”

because, whatever the degree of his wrongdoing, “a pilot

knowingly transporting a passenger’s alcohol to a dry village is precisely the kind of person and conduct that the

legislature was concerned about.” App. 26a. The court

also asserted that Jouppi “was clearly within the class of

persons targeted by the statute” because the statute applied to him (App. 20a)—a characteristic true of anyone

punished under it.

More followed along similar lines. The court compared

the value of Jouppi’s plane to the $10,000 maximum fine

allowed by statute (App. 23a)—a maximum reserved for

“the worst type of offender ‘within the group of persons

committing the offense in question.’” Hintz v. State, 627

131a. The judge’s additional views about civil in rem forfeitures

(which this case is not) are likewise foreclosed by precedent. App.

126a (acknowledging as much).

P.2d 207, 210 (Alaska 1981). That the plane’s value was

“only” nine and a half times that theoretical maximum,

the court remarked, “suggests that the forfeiture is not

grossly disproportional.” App. 23a. In evaluating “the nature and extent of the harm caused by the defendant’s offense,” App. 24a, the court then looked, not to the harm

caused by Jouppi, but to “the harm . . . addressed in the

legislative history of the forfeiture provision” decades

ago, App. 25a n.94. Having done so, it saddled Jouppi with

the ills of alcohol abuse statewide: “increased crime,” “alcoholism,” “fetal alcohol spectrum disorder,” “substantial

costs on public health and the administration of justice,”

and “death.” App. 24a.

For the avoidance of doubt, the court closed by

spelling out the breadth of its reasoning: “It is clear to

us,” the court stated, “that the legislature determined

that the harm from even a six-pack of beer knowingly imported into a dry village is severe enough to warrant forfeiture of an aircraft.” App. 25a. On that basis, the court

“h[e]ld that the forfeiture of Jouppi’s airplane is not

grossly disproportional to the gravity of the offense for

which he has been convicted and, therefore, the forfeiture

does not violate the Excessive Fines Clause of the Eighth

Amendment.” App. 27a.3

The court’s decision is a final judgment under 28 U.S.C. § 1257(a).

Based on that decision, the court of appeals confirmed that “there are

no further issues to be resolved,” Order 1, No. A-13147 (Alaska Ct.

App. May 9, 2025), and the trial court entered an order for forfeiture.

Order for Forfeiture of Airplane, No. 4FA-12-03228CR (Alaska Dist.

Ct. June 17, 2025).

REASONS FOR GRANTING THE PETITION

In upholding the forfeiture of an airplane for a sixpack, the decision below encapsulates a division in the

lower courts over how to evaluate the gravity of a defendant’s offense under the Excessive Fines Clause. Most

courts, following this Court’s lead, share the same premise: that the standard focuses, not on the gravity of the

offense in the abstract, but on the actual defendant’s conduct. The Alaska Supreme Court, meanwhile, hews to a

minority view that instead looks to the gravity of the defendant’s offense at a stratospheric level of generality.

That standard contravenes this Court’s precedent and the

text and history of the Excessive Fines Clause. The question presented is important—not least because Alaska’s

standard conflicts with that of its home circuit—and this

case is an ideal vehicle in which to resolve it.

A. The decision below sharpens a conflict over the

standard for whether a fine is excessive.

In assessing the gravity of a defendant’s offense—a

key input for any excessive-fines case—many state and

federal courts agree that the standard looks to “the specific actions of the violator rather than . . . taking an abstract view of the violation.” Pimentel v. City of Los Angeles, 974 F.3d 917, 923 (9th Cir. 2020). Aligning with the

Eleventh Circuit, the decision below embraced a different

approach: one that examines the gravity of the defendant’s offense purely in abstract terms. The result: a neardispositive thumb on the government’s side of the scale

and a blank check for forfeitures like the one below.

1. Four state high courts and most federal

courts of appeals agree that the gravity of a

defendant’s offense must be evaluated by reference to his or her specific culpability.

a. The decision below splits most strikingly with the

decisions of the Indiana Supreme Court following this

Court’s remand in Timbs v. Indiana. As the Court is

aware, Tyson Timbs pleaded guilty to a relatively lowlevel drug offense and received a modest sentence: home

detention, probation, and addiction treatment. 586 U.S.

146, 148-49 (2019). Alongside that, however, Indiana also

sought to forfeit his Land Rover, recently purchased for

$42,000. Id. at 149. Following this Court’s intervention (on

whether the Excessive Fines Clause applies to the

States), the Indiana Supreme Court issued two opinions

marking out the “analytical framework” for evaluating

whether a forfeiture is unconstitutionally excessive. State

v. Timbs, 134 N.E.3d 12, 21 (2019); State v. Timbs, 169

N.E.3d 361 (2021).

In evaluating the gravity of Timbs’s offense, the Indiana Supreme Court took its cue from this Court’s decision

in United States v. Bajakajian, 524 U.S. 321 (1998). As a

general matter, the court acknowledged, drug offenses

(like most crimes) “threaten[] society.” Timbs, 169

N.E.3d at 373. But for purposes of assessing the excessiveness of a specific forfeiture, the court emphasized that

“focusing on the specific harms of specific acts” is most

“in line with the Supreme Court’s reasoning in United

States v. Bajakajian.” Id. “In Bajakajian,” after all, this

Court had “pointed out that currency-reporting crimes

might generally include serious violations by ‘tax evaders,

drug kingpins, or money launderers.”’ Id. Yet in evaluating the gravity of Bajakajian’s offense, this Court “did not

impute to [him] the offenses of others,” but “rather considered what specific harms his specific acts had caused.”

Id.

The Indiana Supreme Court followed suit: Applying a

“fact intensive” standard, id. at 368, it concluded that “the

severity of [Timbs’s] underlying offense” was “minimal,”

id. at 375. While Timbs was undisputedly an addict, the

record showed that he “wasn’t a drug ‘kingpin.’” Id. at

374. He had sold only a small quantity of drugs—and only

at the behest of undercover officers. Id. at 375-76. Those

transactions were not part of a broader dealing operation.

And he received a “minimum sentence” in his criminal

case—far below “the maximum statutory penalty” reserved for “those who commit the worst variants of the

crime.” Id. at 375 (quoting Timbs, 134 N.E.3d at 37). On

this record, the court reasoned, “it follows that Timbs . . .

committed a crime that was much less severe ‘relative to

other potential violators.’” Id. (quoting Bajakajian, 524

U.S. at 339 n.14). All told, “the seriousness of Timbs’s specific crime, for which he received the minimum possible

sentence; the harm caused by dealing two grams of heroin

to an undercover police officer; and the relationship of the

dealing to Timbs’s earlier actions in purchasing drugs to

feed his addiction” combined to confirm “the minimal severity of Timbs’s offense.” Id. at 376.

b. In focusing on the specific defendant’s culpability,

the Indiana Supreme Court embraced a standard shared

by at least three other state high courts.

In 2017, the Pennsylvania Supreme Court articulated

a standard that aligns with Indiana’s and cannot be reconciled with Alaska’s. Commonwealth v. 1997 Chevrolet,

160 A.3d 153. Under Bajakajian, the court reasoned, the

excessiveness standard is “defendant-culpability focused,

rather than centered on the severity of the crime in the

abstract.” Id. at 189. Thus, the court looked, not to the

“maximum authorized sentence” in a vacuum, but to how

that theoretical maximum compares to “the actual penalty imposed (sentence, fine) upon the offender giving rise

to the forfeiture.” Id. at 190. “[T]he regularity of the criminal conduct must be considered” as well, the court added,

“including whether the illegal acts were isolated or frequent, constituting a pattern of misbehavior.” Id. Likewise for “the actual harm resulting from the crime

charged,” which, the court explained, focuses on the harm

caused by the defendant, not the “generalized harm to society” of crime writ large. Id. at 192; see also id. (remanding for trial court to determine whether Excessive Fines

Clause precluded forfeiting elderly woman’s home and

minivan based on son’s marijuana dealing).

The Utah Supreme Court embraced the same framework in holding excessive the forfeiture of a home based

on the owner’s commission of low-level drug offenses.

State v. Real Prop., 994 P.2d 1254 (2000). In “gauging the

gravity of the offense,” the court construed Bajakajian

as focusing on the specific defendant’s level of culpability.

Id. at 1259. The court acknowledged, for example, “the

broad-scale effect of drug trafficking on society.” Id. at

1260. But even so, the court focused on the seriousness of

the particular defendant’s wrongdoing. “Measured by

any standard,” the court reasoned, “[her] drug operation

was small, involving possession of less than two pounds of

marijuana for sale in an eighteen month span.” Id. And,

as in Bajakajian, her modest criminal sentence reinforced that her culpability was low compared to other potential violators of the statute. Id. at 1259. At the same

time, the court explicitly rejected the government’s comparison of the forfeited property to the “‘maximum possible penalties.’” Id. at 1260. Those “theoretical figures”

have “limited relevance in determining proportionality,”

the court wrote, since “two separate individuals, convicted of an ‘identical’ crime may receive vastly different

sentences based on inherently individualized facts.” Id. at

1259-60, 1261. Comparing the $80,000 value of the defendant’s home against the relatively minor gravity of her offenses, the court “conclude[d] that there is a gross disproportionality here under the standards set forth in Bajakajian, and the forfeiture cannot be sustained.” Id. at

1261.

The standard of the D.C. Court of Appeals is similarly

keyed to the specific defendant’s wrongdoing. In considering the forfeiture of a vehicle for the owner’s solicitation

of prostitution, the court read Bajakajian as “plac[ing]

its primary emphasis on the culpability of Bajakajian himself rather than on the severity of the crime in the abstract.” One 1995 Toyota Pick-Up Truck v. District of

Columbia, 718 A.2d 558, 565 (D.C. 1998). While the court

acknowledged that “the maximum penalty authorized by

the legislature” is “one indicium of the gravity of a criminal offense,” it highlighted that “the actual penalty range

applicable to the particular defendant” is a better indicator of their wrongdoing. Id. at 565 n.16. Unlike the Alaska

Supreme Court, moreover, the D.C. Court of Appeals refused to ascribe to a single defendant the ills of prostitution District-wide. As with any crime, the court reasoned,

prostitution presents “multi-faceted problems”—from

traffic congestion to depressed property values to reduced quality of life more broadly. Id. at 566. In evaluating the excessiveness of one forfeiture, however, the court

held that a single property owner “can not be made to

bear grossly disproportionate responsibility for the problem of prostitution in the District” as a whole. Id. As with

Hosep Bajakajian, the court concluded, “[t]he forfeiture

here impose[d] punishment on [the defendant] which

greatly outweighs his particular contribution to these

multi-faceted problems.” Id.

c. Most federal courts of appeals to have engaged with

the question start from a similar premise: The gravity of

a defendant’s offense is determined, not in the abstract,

but by reference to the specific defendant’s actions.

In Alaska’s home circuit, the federal courts hold that

“[i]t is critical . . . that the court review the specific actions

of the violator rather than by taking an abstract view of

the violation.” Thomas v. County of Humboldt, 124 F.4th

1179, 1193 (9th Cir. 2024) (citation omitted). For federal

courts in Alaska, therefore, “[t]he culpability of the offender should be examined specifically, rather than examining the gravity of the crime in the abstract.” United

States v. $100,348.00, 354 F.3d 1110, 1123 (9th Cir. 2004)

(citation omitted). These courts evaluate where a specific

defendant falls on the “gravity spectrum” compared to

other potential violators. Id. Rather than comparing the

value of forfeited property to the maximum theoretical

sentence, these courts follow Bajakajian’s lead in

“giv[ing] greater weight” to guidelines ranges, which

“take into account the specific culpability of the offender.”

Id. at 1122; see also United States v. Beecroft, 825 F.3d

991, 1001 (9th Cir. 2016) (O’Scannlain, J.) (singling out

guidelines as “especially instructive as they reflect the

particular circumstances of [the defendant’s] crimes”).

And—again contra the Alaska Supreme Court—federal

courts in the Ninth Circuit are admonished to “not put

‘full responsibility for the “war on drugs” on the shoulders

of every individual claimant.’” United States v. 6380 Little Canyon Rd., 59 F.3d 974, 986 n.13 (9th Cir. 1995), abrogated in part on other grounds by Bajakajian, 524

U.S. at 333-34.

Nor is the Ninth Circuit an outlier in this regard. The

circuits’ precise formulations and applications of the excessive-fines standard vary, sometimes in important

ways. (More on that below, pp. 29-31.) But most start

from the shared premise above: The gravity of an offense

is to be determined with reference to “the culpability of

the individual defendant.” United States v. Facteau, 89

F.4th 1, 45 (1st Cir. 2023) (citation omitted), cert. denied,

145 S. Ct. 137 (2024). “Even before the Bajakajian opinion,” for instance, the Third Circuit had “look[ed] at the

overall circumstances, including seriousness of the offense and personal benefit or culpability, to decide excessiveness.” Yskamp v. DEA, 163 F.3d 767, 773 (1998). In

upholding forfeiture of an unregistered airplane, the

Fifth Circuit undertook a similarly defendant-focused

analysis, emphasizing that the defendant “owned the airplane for some seven years without registering it,” that

the registration failure reflected no “mere spur of the moment lapse in judgment,” and that the out-of-date registration on file (to a state agency) “increased the damage

to the integrity of federal aviation safety and security systems” because the agency of record could “engage in lowlevel flight, below radar coverage, without attracting a

law enforcement response.” United States v. Wallace,

389 F.3d 483, 487 (2004).4

For pecuniary fines (though not for forfeitures), the Fifth Circuit

has adopted an unreasoned, blanket rule that a fine “does not violate

Along similar lines is the Sixth Circuit, which has rejected as an “oversimplified approach” merely comparing

the value of a forfeiture to the maximum statutory fine.

United States v. Carpenter, 317 F.3d 618, 627 (2003),

opinion reinstated in relevant part, 360 F.3d 591 (2004).

The Seventh Circuit has voiced “serious doubts that the

forfeiture of [a] home’s entire $67,000 value comports

with the ‘principle of proportionality’” based on the actions of the specific defendant—“at most a one-time offender who committed an unusually minor violation of the

structuring statute not tied to other wrongdoing.” United

States v. Abair, 746 F.3d 260, 268 (2014). And last year,

the Eighth Circuit likewise stressed that “the ‘most important indicium’” in its analysis is “the reprehensibility

of the defendant’s conduct.” United States ex rel. Grant

v. Zorn, 107 F.4th 782, 800 (2024), cert. denied, Nos. 24549, 24-845 (June 23, 2025); see also United States v.

Jalaram, Inc., 599 F.3d 347, 357 (4th Cir. 2010) (concluding that defendant’s “offense was serious and its individual culpability significant”); von Hofe v. United States,

492 F.3d 175, 187 (2d Cir. 2007) (“The statutory maximum, designed as an outer limit on the punishment available, does not necessarily reflect an individual offender’s

culpability or the gravity of the actual offense giving rise

to forfeiture.”); United States v. Wagoner Cnty. Real

Est., 278 F.3d 1091, 1101 (10th Cir. 2002) (noting that

evaluating “the severity of the offense” includes such considerations as “the nature and scope of the illegal

the Eighth Amendment—no matter how excessive the fine may appear—if it does not exceed the limits prescribed by the statute authorizing it.” Cripps v. La. Dep’t of Agric. & Forestry, 819 F.3d 221,

234 (2016).

operation at issue” and “the value of any contraband involved in the offense” (citation omitted)).

2. The decision below joins the Eleventh Circuit in evaluating the gravity of the offense

in purely abstract terms.

a. The Alaska Supreme Court stands in contrast. Its

standard looks, not to the culpability of the person before

it, but to the culpability of an abstract violator of the statute—the theoretical worst-case offender.

Each of what the court described as its “factors” illustrates that premise. App. 18a. Where other courts have

cautioned that “the maximum statutory penalty for an offense suggests the appropriate sentence for those who

commit the worst variants of the crime,” Timbs, 134

N.E.3d at 37, the Alaska Supreme Court compared by

rote the value of Jouppi’s airplane to “the maximum fine

that could have been imposed” on a worst-case violator,

App. 23a. Nowhere did it consider the sentence Jouppi

himself received—not the maximum or anything close,

but the minimum executed fine and jail term permitted

by law. Under the standard of Indiana, Pennsylvania,

Utah, and D.C., that consideration would have signaled a

level of culpability “much less severe ‘relative to other potential violators’” of the statute. Timbs, 169 N.E.3d at

375. Under Alaska’s standard? Irrelevant.

In similar vein, the Alaska Supreme Court’s standard

nowhere accounts for how the defendant’s violation “compare[s] to other variants of the offense.” Timbs, 134

N.E.3d at 37. The court assumed, for instance, that

Jouppi’s culpability extended to one six-pack of beer

alone. App. 24a-25a. Yet under the Alaska Supreme

Court’s standard, it does not matter that a property

owner’s offense is conspicuously “at the low end of the severity spectrum.” United States v. 3814 NW Thurman

St., 164 F.3d 1191, 1198 (9th Cir. 1999). Nor does the

court’s standard consider “the relationship of the offense

to other criminal activity.” Timbs, 169 N.E.3d at 374.

Quite the opposite: The court repudiated that consideration. It acknowledged that “Jouppi was convicted of only

one instance of alcohol importation unconnected to other

criminal activity.” App. 19a. Yet it wrote off as “not particularly relevant whether Jouppi’s offense was part of a

larger pattern of criminal activity.” App. 26a. For, whatever the gravity of his offense, “a pilot knowingly transporting a passenger’s alcohol to a dry village is precisely

the kind of person and conduct that the legislature was

concerned about.” App. 26a.

As for the harm caused: more of the same. Unlike the

courts above, the Alaska Supreme Court looked, not to

the harm caused by Jouppi, but to “the harm . . . addressed in the legislative history of the forfeiture provision” decades ago. App. 25a n.94. From that level of generality, it saddled Jouppi with the social ills of alcohol

abuse writ large. Increased crime. Public-health costs.

Death. App. 24a. Only thus could the court conclude that

“the illegal importation of even a six-pack of beer causes

grave societal harm” and “strongly suggests that the forfeiture is not grossly disproportional.” App. 24a.

b. The Eleventh Circuit, too, has trended toward evaluating the gravity of defendants’ offenses in impossibly

abstract terms. Starting in the late ’90s, the Eleventh Circuit maintained that “excessiveness is determined in relation to the characteristics of the offense, not in relation

to the characteristics of the offender.” United States v.

817 N.E. 29th Drive, 175 F.3d 1304, 1311 (1999). Since

then, the court has increasingly bound itself to a mode of

analysis much like Alaska’s. The outcome is much the

same as well: reducing an enumerated constitutional protection to a “hyper-deferential” check on government

overreach. Yates v. Pinellas Hematology & Oncology,

P.A., 21 F.4th 1288, 1318 (11th Cir. 2021) (Newsom, J.,

joined by Jordan, J., concurring); see also Robson 200,

LLC v. City of Lakeland, 593 F. Supp. 3d 1110, 1120-22

(M.D. Fla. 2022) (criticizing the Eleventh Circuit’s precedent as inconsistent with Bajakajian).

A recent Eleventh Circuit decision shows the standard in practice. Earlier this year, the court upheld $12.2

million of a $12.5 million penalty for a defendant’s failure

to file foreign-bank-account reports, or “FBARs.” United

States v. Schwarzbaum, 127 F.4th 259, 265 (11th Cir.

2025). For “willful” FBAR violations, the government can

impose civil penalties totaling half the balance of unreported funds. Id. And like the forfeiture provision in Bajakajian—and the one here—the FBAR penalty regime

has been construed to capture a wide range of wrongdoers, from knowing and deliberate violators to the merely

reckless. Id. at 282 n.7.

In upholding the $12.2 million penalty in Schwarzbaum, the Eleventh Circuit anticipated the Alaska Supreme Court with a standard that evaluates the gravity of

the defendant’s offense purely in abstract terms. The

court asserted that Isac Schwarzbaum fell “squarely in

the [FBAR statute’s] crosshairs” because the statute applied to him, a fact equally true in Bajakajian and in almost every case where the Excessive Fines Clause is implicated. Id. at 282 (citation omitted). Nowhere did the

court’s standard account for the fact that Schwarzbaum’s

mens rea was on the low end of the spectrum—reckless,

not knowing or deliberate. Id. at 267. Nor did the court’s

standard account for the fact that Schwarzbaum had no

“intention of evading United States tax reporting requirements.” Id. at 266. Nor did it matter that the unreported

funds were not “believed to be from illegal sources or

used for a criminal purpose.” Ex. 1 to U.S. Mot. for Judgment at 4, United States v. Schwarzbaum, No. 18-cv81147 (S.D. Fla. Sept. 15, 2022) (Doc. 152-1). Rather than

evaluate where Schwarzbaum landed on the spectrum of

“potential violators of the reporting provision,” Bajakajian, 524 U.S. at 339 n.14, the Eleventh Circuit confirmed that the provision applied to him and left it at that.

The rest of the court’s analysis was of a piece. Again

like the Alaska Supreme Court, the Eleventh Circuit compared Schwarzbaum’s penalty to the maximum sentence

that a criminal FBAR defendant could theoretically face:

several tiers of $250,000 criminal fines plus three consecutive five-year prison terms. Schwarzbaum, 127 F.4th at

282-83. In this way, the court looked to the very statutory

maximums this Court in Bajakajian abjured. 524 U.S. at

339 n.14 (“That the maximum fine and Guideline sentence

to which respondent was subject were but a fraction of the

penalties authorized . . . undercuts any argument based

solely on the statute . . . .”). And it did so even though

Schwarzbaum himself did not in fact violate the comparator criminal statute. Compare 127 F.4th at 282 n.7, with

id. at 267. In “consider[ing] the harm caused by the defendant,” id. at 283, the Eleventh Circuit then repeated

its level-of-generality error for a final time. Rather than

evaluating the harm caused by Schwarzbaum, the court

resorted to commentary in the 1970 legislative record to

the effect that foreign accounts can be used to further “organized criminal operations,” “evade income taxes,”

violate securities laws, and launder “illegally obtained

monies.” Id. (citation omitted). The very legislative history invoked in Bajakajian—by the dissent. 524 U.S. at

351 (Kennedy, J., dissenting).

B. The decision below is erroneous.

The Alaska Supreme Court’s standard contravenes

this Court’s precedent and the Excessive Fines Clause’s

text and history.

1. Bajakajian’s fundamental lesson is straightforward: In assessing the gravity of a defendant’s offense,

courts should evaluate the actions of the person before

them. The Alaska Supreme Court’s standard breaks with

this mode of analysis at every turn. The court dismissed

as “not particularly relevant whether Jouppi’s offense

was part of a larger pattern of criminal activity” (App.

26a)—despite this Court’s describing as “highly relevant”

whether a defendant’s offense “was unrelated to any

other crime.” Bajakajian, 524 U.S. at 338 n.12. It compared the airplane’s value to the very sort of maximum

sentences Bajakajian eschewed. Compare id. at 339

n.14, with App. 23a (“[T]he value of Jouppi’s airplane is

only 9.5 times the maximum fine that could have been imposed.”). It ignored that, with a six-pack violation to his

name, Jouppi’s “culpability relative to other potential violators” of the statute was glaringly “small indeed.” Bajakajian, 524 U.S. at 339 n.14. And it turned its back on

the “extent of the harm caused by Jouppi’s illegal conduct” in favor of “the harm . . . addressed in the legislative

history” decades before. App. 25a n.94 (citation omitted).

At base, the Alaska Supreme Court’s standard looks

less like that of Bajakajian’s majority and far more like

that of its dissent. On the Alaska court’s reasoning, in fact,

Hosep Bajakajian himself would have lost. Like Ken

Jouppi, Bajakajian was “within the class of persons targeted by the statute.” App. 20a. Bank Secrecy Act violations—in the abstract—likewise could be said to cause

“grave societal harm.” App. 24a; see also 524 U.S. at 351

(Kennedy, J., dissenting). And proportionally, Bajakajian’s forfeiture was far nearer his maximum statutory fine ($357,114 compared to $250,000) than was

Jouppi’s ($95,000 compared to $10,000). Boxes checked.

That Alaska’s standard would almost surely support a reversal in Bajakajian rather than the Court’s affirmance

spotlights how far afield the decision below strayed.

2. Alaska’s standard contravenes text and history as

well. Ratified with the Anglo-American legal tradition in

mind, the Excessive Fines Clause would have been well

understood in 1791 (and later) to denote “excessive” in relation to the specific defendant’s wrongdoing. In fact, that

premise dates to 1215, when Magna Carta pronounced

that “[a] free man shall be amerced for a small fault only

according to the measure thereof, and for a great crime

according to its magnitude.”

The Great Charter’s guarantee claimed renewed urgency centuries later, following the depredations of the

Stuart kings. With the enactment of the English Bill of

Rights in 1689, Parliament resolved itself to permit fines

only “according to the quantity and quality of [the offender’s] misdeeds.” Historical Manuscripts Comm’n,

The Manuscripts of the House of Lords, 1690-1691, at

104 (1892). As Matthew Bacon would later recount,

judges’ power to fine had to be guided by their duty “to

make it adequate to the Offence,” taking into “Consideration . . . the Baseness and Enormity, and dangerous Tendency of it,” along with the “Malice, Deliberation and

Wilfulness with which it was committed” and “the Age,

Quality, and Degree of the Offender, &c.” 2 A New

Abridgement of the Law 517 (4th ed. 1778).

Across the Atlantic, the same understanding took root

in America. A “fine or amercement ought to be according

to the degree of the fault and the estate of the defendant,”

wrote Judge Carrington, of Virginia, in 1799. Jones v.

Commonwealth, 5 Va. 555, 557. “[I]t is clear,” he reasoned, that the “makers of the [Virginia] constitution, as

well as the Legislature contemplated, that no addition,

under any pretext whatever was to be imposed, upon the

offender, beyond the real measure of his own offence.” Id.

at 557-58; Timbs, 586 U.S. at 152 (discussing Virginia’s

Declaration of Rights). Nor was Judge Carrington alone

in this view. Simply, the Excessive Fines Clause conceived of by the Alaska Supreme Court—one indifferent

to the degree of a defendant’s “offence and injury”—

would have been unrecognizable to those who ratified it.

Bullock v. Goodall, 7 Va. 44, 49 (1801) (Pendleton, J.).

C. The question presented raises an issue of national importance, and this case is an ideal vehicle for addressing it.

The question presented implicates the Constitution’s

most textually explicit check on extravagant economic

sanctions—including both civil and criminal forfeitures.

It has great legal and practical importance, and this case

is a perfect vehicle in which to consider it.

1. Like other Bill of Rights guarantees, the Eighth

Amendment’s “[p]rotection against excessive punitive

economic sanctions” is “both ‘fundamental to our scheme

of ordered liberty’ and ‘deeply rooted in this Nation’s history and tradition.’” Timbs, 586 U.S. at 154. With only one

precedent from this Court giving shape to the excessiveness standard, however, twenty-seven years’ worth of

lower-court decisions have staked out “a patchwork of inconsistent tests” even among the federal courts of appeals

catalogued above. David Pimentel, Forfeitures and the

Eighth Amendment: A Practical Approach to the Excessive Fines Clause as a Check on Government Seizures, 11 Harv. L. & Pol’y Rev. 541, 543-44 (2017). Often,

it’s hard to discern whether or not one court’s multi-factor

test differs materially from another’s. And with many

such cases appearing highly fact-bound, suitable vehicles

for this Court’s review are rare. Meanwhile, the lower

courts’ increasingly baroque tests risk losing sight of

“[t]he touchstone of the constitutional inquiry”: “The

amount of the forfeiture must bear some relationship to

the gravity of the offense that it is designed to punish.”

Bajakajian, 524 U.S. at 334. The upshot? Nationwide, “a

large degree of uncertainty regarding current excessive

fines jurisprudence.” 1997 Chevrolet, 160 A.3d at 178. Or

more colorfully: “a quagmire.” Beth A. Colgan, Reviving

the Excessive Fines Clause, 102 Calif. L. Rev. 277, 295

n.92 (2014); see also id. at 295 (“The jurisprudence has

created disorder in the lower courts and left jurists feeling hamstrung.” (footnotes omitted)).

Against that backdrop, the decision below implicates

a critical first-order question: not the relative virtues of

one multi-factor test over another, but, more fundamentally, whether the courts should evaluate the gravity of a

defendant’s offense purely in the abstract or should evaluate the specific defendant’s wrongdoing. Refocusing the

lower courts on that baseline inquiry would not only correct jurisdictions like Alaska and the Eleventh Circuit,

but also offer an important data point for the many courts

whose buildup of multi-factor tests risks “muddl[ing] the

issue.” Pimentel, supra, 11 Harv. L. & Pol’y Rev. at 54344. And as the decision below highlights, the question presented goes to the core of the Excessive Fines Clause’s

proportionality guarantee. If “[t]he culpability of the offender . . . [is] examined specifically,” $100,348.00, 354

F.3d at 1123 (citation omitted), the Excessive Fines

Clause is well-designed to check exorbitant economic

sanctions on an as-applied basis. If, in contrast, the gravity of a defendant’s offense is evaluated purely in the abstract—asking whether a crippling forfeiture could be

valid for an imagined worst-case offender—the Clause secures at best notional protection for the flesh-and-blood

people invoking it.

This case shows the stakes. On Alaska’s standard, forfeiting an airplane over a six-pack “clearly” comports with

the Excessive Fines Clause. App. 25a. And it’s unclear

what forfeiture wouldn’t. Tyson Timbs unquestionably

would have lost had he been in Alaska instead of Indiana.

Likewise for the homeowner in Utah. And the vehicle

owner in D.C. And Hosep Bajakajian. That the Alaska Supreme Court’s standard would yield different outcomes in

all those cases spotlights not just the importance of the

split, but that Alaska’s approach degrades a Bill of Rights

protection that “has been a constant shield throughout

Anglo-American history.” Timbs, 586 U.S. at 153.

2. The Court’s intervention is urgently needed now,

in an era of “more and more civil laws bearing more and

more extravagant punishments.” Sessions v. Dimaya,

584 U.S. 148, 184 (2018) (Gorsuch, J., concurring in part

and concurring in the judgment). State and federal courts

alike rightly understand Bajakajian’s proportionality

standard to apply not just to criminal-court sanctions, but

to civil forfeitures as well. Timbs, 134 N.E.3d at 26 (cataloguing authority). And as Justice Scalia remarked in the

early ’90s, the fact that “fines are a source of revenue”

gives “good reason to be concerned that [they], uniquely

of all punishments, will be imposed in a measure out of

accord with the penal goals of retribution and deterrence.” Harmelin v. Michigan, 501 U.S. 957, 979 n.9

(1991) (opinion of Scalia, J.).

Those concerns have only multiplied in the decades

since, as all levels of government “increasingly depend

heavily on fines and fees as a source of general revenue.”

Timbs, 586 U.S. at 154 (citation omitted). Nationwide, police departments rely on fines and forfeitures for their

budgets. So, too, do prosecutors. In the most extreme instances, individual prosecutors are even given a personal

financial stake in their forfeiture cases. Sparger-Withers

v. Taylor, No. 21-cv-2824, 2024 WL 473719 (S.D. Ind.

Feb. 7, 2024), appeal pending, No. 24-1367 (7th Cir.).

In turn, those bearing the brunt are most often our

Nation’s most vulnerable, “the poor and other groups

least able to defend their interests.” Leonard v. Texas,

580 U.S. 1178, 1180 (2017) (statement of Thomas, J., respecting the denial of certiorari). Five Members of the

Court commented on this phenomenon just last year.

Culley v. Marshall, 601 U.S. 377, 397 (2024) (Gorsuch, J.,

concurring); id. at 406-07 (Sotomayor, J., dissenting).

More than ever, the Excessive Fines Clause stands as a

key check on the power to punish. With a standard like

Alaska’s, however, it serves as no check at all.

3. This case is an ideal vehicle in which to decide the

question presented. Each level of the Alaska judiciary addressed the excessiveness issue. Under the trial court’s

view, Ken Jouppi prevailed; under the state supreme

court’s, he lost “as a matter of law.” App. 2a. And as this

petition comes to the Court, it is the rare excessive-fines

case with no factual wrinkles. Having cleared the table of

all possible fact disputes, the Alaska Supreme Court teed

up the question presented perfectly: It deployed a standard that looked to the gravity of the defendant’s crime

only at the highest level of abstraction. Few excessivefines cases will present the issue so sharply; a decision upholding the forfeiture of an airplane for a six-pack is a

self-recommending candidate for review. The petition

should be granted, the Alaska Supreme Court’s startinggate misconception corrected, and the case remanded for

further proceedings.

CONCLUSION

The petition for a writ of certiorari should be granted.

Respectfully submitted.