Petition for Writ of Certiorari — Cyrano R. Irons, Petitioner v. United States

No.

In the Supreme Court of the United States

CYRANO R. IRONS, PETITIONER

v.

UNITED STATES OF AMERICA

ON PETITION FOR A WRIT OF CERTIORARI

TO THE UNITED STATES COURT OF APPEALS

FOR THE EIGHTH CIRCUIT

PETITION FOR A WRIT OF CERTIORARI

JOHN P. ELWOOD

ARNOLD & PORTER

KAYE SCHOLER LLP

601 Massachusetts Ave., NW

Washington, DC 20001

(202) 942-5000

LAINE CARDARELLA

Federal Public Defender

Daniel P. Goldberg

Assistant Federal Public

Defender

Counsel of Record

OFFICE OF THE FEDERAL

PUBLIC DEFENDER

WESTERN DISTRICT OF

MISSOURI

1000 Walnut St., Suite 600

Kansas City, MO 64106

(816) 471-8282

Dan_Goldberg@fd.org

QUESTION PRESENTED

Whether errors in calculating the Sentencing Guidelines are rendered categorically harmless by the district

court’s assertion that the Guidelines would make no difference to the choice of sentence.

(I)

II

RELATED PROCEEDINGS

United States v. Irons, 4:19-CR-00390 (W.D. Mo. July

27, 2021)

United States v. Irons, 21-2750 (8th Cir. Mar. 23, 2022)

III

TABLE OF CONTENTS

Page

Opinion Below .......................................................................... 1

Jurisdiction .............................................................................. 1

Statutes And Rules Involved................................................. 1

Introduction ............................................................................. 2

Statement ................................................................................. 6

Reasons For Granting The Petition ..................................... 9

A. The Circuits Are Deeply Divided Over Whether

All Sentencing Guidelines Errors Are Rendered

Harmless By The District Court’s Assertion

That The Guidelines Were Irrelevant To Its

Choice Of Sentence ......................................................... 9

1. Six Circuits Have Held That Blanket

Harmless Error Findings By The District

Court Cannot Immunize Guideline

Miscalculations From Appellate Scrutiny............ 9

2. Two Circuits Give Some Deference To The

District Court’s Harmless Error Findings,

But Will Not Find The Guidelines Error

Harmless Unless The Sentence Is Also

Substantively Reasonable .................................... 13

3. Two Circuits Conclude That All Guidelines

Errors Are Rendered Harmless By The

District Court’s Blanket Assertion That The

Guidelines Did Not Matter To Its Sentence ...... 13

B. The Eighth Circuit’s Rule Is Wrong .......................... 16

1. This Court’s Precedent Provides That

Sentencing Courts Must Properly Calculate

The Sentencing Guidelines, And That

Reviewing Courts Should Ordinarily Correct

Guidelines Errors .................................................. 16

IV

2. Rule 52(a), Like Rule 52(b), Requires That

Guidelines Errors Should Ordinarily Be

Corrected ................................................................ 18

C. The Question Presented Is Important And

Recurring........................................................................ 20

D. This Case Is An Ideal Vehicle ..................................... 22

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

APPENDIX CONTENTS

Page

Appendix A: Court of appeals opinion

(Mar. 23, 2022) ............................................. 1a

Appendix B: Court of appeals order denying

rehearing

(Apr. 26, 2022) .............................................. 3a

Appendix C: Excerpts of transcript of sentencing

hearing (July 27, 2021) ............................... 4a

V

TABLE OF AUTHORITIES

Cases

Page(s)

Gall v. United States,

552 U.S. 38 (2007) ..................................... 3, 4, 5, 16, 17, 18

Greer v. United States,

141 S. Ct. 2090 (2021) ....................................................... 19

Hughes v. United States,

138 S. Ct. 1765 (2018) ....................................................... 21

Kimbrough v. United States,

552 U.S. 85 (2007) ............................................................. 17

Molina-Martinez v. United States,

136 S. Ct. 1338 (2016) ....................................... 2, 11, 17, 18

Neder v. United States,

527 U.S. 1 (1999) ............................................................... 22

Peguero v. United States,

526 U.S. 23 (1999) ............................................................. 22

Pepper v. United States,

562 U.S. 476 (2011) ............................................................. 3

Peugh v. United States,

569 U.S. 530 (2013) ................................................. 3, 17, 18

Rosales-Mireles v. United States,

138 S. Ct. 1897 (2018) ............................. 5, 6, 17, 18, 19, 22

Spears v. United States,

555 U.S. 261 (2009) ............................................................. 5

United States v. Asbury,

27 F.4th 576 (7th Cir. 2022) ................................... 9, 10, 21

United States v. Bah,

439 F.3d 423 (8th Cir. 2006) ............................................ 14

United States v. Bennett,

839 F.3d 153 (2d Cir. 2016) .............................................. 11

United States v. Booker,

543 U.S. 220 (2005) ............................................. 2, 3, 17, 18

VI

Cases—Continued

Page(s)

United States v. Brown,

No. 20-2847, 2021 WL 3732369

(8th Cir. Aug. 24, 2021) .................................................... 23

United States v. Collins,

800 F. Appx. 361 (6th Cir. 2020) ..................................... 13

United States v. Davila,

569 U.S. 597 (2013) ................................................. 6, 19, 22

United States v. Foston,

No. 21-2435, 2022 WL 1510689

(8th Cir. May 13, 2022)............................................... 14, 16

United States v. Gieswein,

887 F.3d 1054 (10th Cir. 2018) ........................................ 12

United States v. Gomez,

690 F.3d 194 (4th Cir. 2012) ............................................ 13

United States v. Grady,

18 F.4th 1275 (11th Cir. 2021) ......................................... 15

United States v. Hasting,

461 U.S. 499 (1983) ........................................................... 20

United States v. Henry,

1 F.4th 1315 (11th Cir. 2021) ................................. 4, 15, 16

United States v. Icaza,

492 F.3d 967 (8th Cir. 2007) ............................................ 14

United States v. Keene,

470 F.3d 1347 (11th Cir. 2006) ........................................ 15

United States v. Khatallah,

41 F.4th 608 (D.C. Cir. 2022) .................................... 16, 17

United States v. Loving,

22 F.4th 630 (7th Cir. 2022) ............................................. 10

United States v. Miranda-Zarco,

836 F.3d 899 (8th Cir. 2016) ............................................ 23

VII

Cases—Continued

Page(s)

United States v. Montes-Flores,

736 F.3d 357 (4th Cir. 2013) ............................................ 21

United States v. Ortiz-Santizo,

766 F. App’x 890 (11th Cir. 2019) ................................... 15

United States v. Ouellette,

985 F.3d 107 (1st Cir. 2021) ............................................ 15

United States v. Peterson,

887 F.3d 343 (8th Cir. 2018) ................................ 14, 19, 20

United States v. Porter,

928 F.3d 947 (10th Cir. 2019) ................................ 4, 22, 24

United States v. Seabrook,

968 F.3d 224 (2d Cir. 2020).............................................. 11

United States v. Smalley,

517 F.3d 208 (3d Cir. 2008).............................................. 12

United States v. Still,

6 F.4th 812 (8th Cir. 2021) ......................................... 14, 20

United States v. Tampas,

493 F.3d 1291 (11th Cir. 2007) ........................................ 15

United States v. Tanksley,

848 F.3d 347 (5th Cir. 2017) ............................................ 12

United States v. Vonn,

535 U.S. 55 (2002) ............................................................. 19

United States v. Williams,

5 F.4th 973 (9th Cir. 2021) ............................................... 12

United States v. Wright,

642 F.3d 148 (3d Cir. 2011).............................................. 12

Williams v. United States,

503 U.S. 193 (1992) ..................................................... 20, 22

Statutes and Rules

18 U.S.C. § 922 ................................................................... 6, 7

18 U.S.C. § 3553 ......................................... 1, 4, 5, 7, 8, 10, 15

VIII

Statutes and Rules—Continued

Page(s)

28 U.S.C. § 1254 ..................................................................... 1

Fed. R. Crim. P. Rule 11(c)(1) ........................................... 22

Fed. R. Crim. P. Rule 52(a) ................2, 6, 16, 18, 19, 20, 22

Fed. R. Crim. P. Rule 52(b) ..................................... 2, 18, 19

Mo. Rev. Stat. § 571.015 ................................................. 7, 23

Miscellaneous

U.S. Sentencing Comm’n, Table 29,

“Sentence Imposed Relative to the

Guidelines Range,” FY2020 Sourcebook

of Federal Sentencing ...................................................... 21

U.S. Sentencing Guidelines (2021)

§3E1.1................................................................................... 7

§4A1.1(e) .............................................................................. 7

§4B1.2 ................................................................................... 7

In the Supreme Court of the United States

CYRIL R. IRONS, PETITIONER

v.

UNITED STATES OF AMERICA

ON PETITION FOR A WRIT OF CERTIORARI

TO THE UNITED STATES COURT OF APPEALS

FOR THE EIGHTH CIRCUIT

PETITION FOR A WRIT OF CERTIORARI

OPINION BELOW

The opinion of the court of appeals (App. 1a–2a) is

unreported, but available at 2022 WL 852853.

JURISDICTION

The judgment of the court of appeals was entered on

March 23, 2022. The court denied a timely petition for

rehearing on April 26, 2022. App. 3a. On June 21, 2022,

Justice Kavanaugh extended the time for filing a petition

for a writ of certiorari until September 13, 2022. The

jurisdiction of this Court is invoked under 28 U.S.C.

§ 1254(1).

STATUTES AND RULES INVOLVED

1. Title 18, United States Code, Section 3553 provides,

in relevant part:

(a) Factors to be considered in imposing a sentence.

— * * * The court, in determining the particular sentence to be imposed, shall consider — * * *

(4) the kinds of sentence and the sentencing range

established for—

(1)

2

(A) the applicable category of offense committed

by the applicable category of defendant as set

forth in the guidelines—

(i) issued by the Sentencing Commission * * *.

(5) any pertinent policy statement—

(A) issued by the Sentencing Commission * * *.

2. Federal Rule of Criminal Procedure 52 provides:

(a) Harmless error. Any error, defect, irregularity,

or variance that does not affect substantial rights

must be disregarded.

(b) Plain error. A plain error that affects substantial rights may be considered even though it was not

brought to the court’s attention.

INTRODUCTION

Every year, tens of thousands of individuals are sentenced to terms of imprisonment for violations of federal

law. This case concerns what courts of appeals must do in

the all-too-common situation when the district court has

made a mistake in calculating the defendant’s sentencing

range, after asserting that the Sentencing Guidelines

would make no difference to its choice of sentence. The

courts of appeals are divided on how to handle that frequently recurring situation. Most have held that such calculation errors must be corrected, vacating the sentence

and remanding for resentencing. Others—like the Eighth

Circuit below—hold that a judge’s boilerplate disclaimer

categorically makes any Guidelines calculation errors per

se harmless and immune from appellate review.

The Guidelines play a “central role in sentencing” and

frequently are determinative of the actual sentence. Molina-Martinez v. United States, 136 S. Ct. 1338, 1341

(2016). “The post-Booker federal sentencing scheme aims

to achieve uniformity by ensuring that sentencing

3

decisions are anchored by the Guidelines and that they remain a meaningful benchmark through the process of appellate review.” Peugh v. United States, 569 U.S. 530, 541

(2013).

Because of the centrality of the Guidelines, “district

courts must begin their analysis with the Guidelines and

remain cognizant of them throughout the sentencing process,” and “improperly calculating[] the Guidelines range”

constitutes “significant procedural error.” Gall v. United

States, 552 U.S. 38, 50 n.6, 51 (2007) (emphasis added).

Even if the sentencing court “decides that an outsideGuidelines sentence is warranted,” it “must give serious

consideration” to “the extent of the deviation” and variances from the Guidelines range must be accompanied by

a “justification * * * sufficiently compelling to support the

degree of the variance.” Id. at 50; see also Pepper v.

United States, 562 U.S. 476, 508 (2011) (Breyer, J., concurring in part and concurring in judgment) (“[T]he law

permits the court to disregard the Guidelines only where

it is ‘reasonable’ for a court to do so.” (citing United States

v. Booker, 543 U.S. 220, 261–262 (2005)). After all, the

Guidelines warrant respect as “the product of careful

study based on extensive empirical evidence derived from

the review of thousands of individual sentencing decisions.” Gall, 552 U.S. at 46. They therefore serve as the

“benchmark” for any sentence, even a non-Guidelines one.

Id. at 49.

This Court has squarely held that “a district court

should begin all sentencing proceedings by correctly calculating the applicable Guidelines range.” Gall, 552 U.S.

at 49. And when reviewing a sentence on appeal, “the appellate court * * * must first ensure that the district court

committed no significant procedural error, such as failing

to calculate (or improperly calculating) the Guidelines

range * * * or failing to adequately explain the chosen

4

sentence—including an explanation for any deviation

from the Guidelines range.” Id. at 51.

Despite this unequivocal guidance, there is an entrenched circuit split over whether “improperly calculating[] the Guidelines range” is rendered categorically

harmless if the sentencing court announces that it considers the Guidelines unimportant for its sentence. In the decision below, the Eighth Circuit, applying long-established circuit precedent, held that when the sentencing

court states that it would have imposed the same sentence

regardless of the Guidelines, any error by the sentencing

court in calculating the Guidelines is categorically harmless. App. 2a. The Eleventh Circuit disposes of sentencing

appeals similarly. See United States v. Henry, 1 F.4th

1315, 1327 (11th Cir. 2021).

But had petitioner been sentenced in the Second,

Third, Fifth, Seventh, Ninth, or Tenth Circuits, the court

of appeals would have vacated the sentence and remanded

so that the sentencing court could resentence the defendant having first considered the presumptively reasonable

properly calculated Guidelines sentencing range. Indeed,

in courts just four miles to the west of where petitioner

was sentenced, “[i]t is not enough for the district court to

say that its conclusion would be the same even if all the

defendant's objections to the presentence report had been

successful” because “simply citing the § 3553 factors does

not insulate the sentence from procedural error.” United

States v. Porter, 928 F.3d 947, 963 (10th Cir. 2019) (adopting government’s argument that Guidelines error was not

harmless).

And while the Fourth and Sixth Circuits give some

deference to the district court’s assertion that any Guidelines miscalculations would be harmless, they additionally

require an independent assessment of the reasonableness

of the sentence to be “certain” the error was harmless on

appeal. Thus, in most circuits, petitioner’s case would

5

have been reversed and remanded for a new sentencing

hearing. Only in the Eighth and Eleventh Circuits can a

district court effectively opt out of Guidelines sentencing

and immunize its Guidelines calculation errors by announcing that “the Sentencing Commission’s expert judgment” (Spears v. United States, 555 U.S. 261, 266 (2009)

(per curiam)) matters so little to it that the sentencing

court need not even bother calculating that benchmark

correctly.

The Eighth Circuit’s rule is wrong—grievously

wrong, fundamentally incompatible with Congress’s decision to adopt a nationwide system of Guidelines sentencing to promote uniformity. It conflicts with Congress’s establishment of defined sentencing factors which provide

that sentence courts must consider “the sentencing range

established * * * by the Sentencing Commission.” 18

U.S.C. § 3553(a)(4)(A)(i). And it conflicts with this Court’s

precedent, which establishes that sentencing “should

begin” with “correctly calculating the applicable Guidelines range,” and that appellate courts “must first ensure”

the district court did not “improperly calculat[e] the

Guidelines range,” Gall, 552 U.S. at 49–51, to facilitate appellate review and ensure it can assess the substantive

reasonableness of the sentence. See Rosales-Mireles v.

United States, 138 S. Ct. 1897, 1910 (2018) (“Before a

court of appeals can consider the substantive reasonableness of a sentence, ‘[i]t must first ensure that the district

court committed no significant procedural error, such as

failing to calculate (or improperly calculating) the Guidelines range.’ ” (quoting Gall, 552 U.S. at 51)).

The Guidelines remain the benchmark for sentencing; regardless of what they say, judges tend to sentence

in the shadow of the Guidelines, and so changes in calculation matter even to non-Guidelines sentences. Reflecting that fact, this Court has repeatedly held that even unobjected-to Guidelines calculations errors must ordinarily

6

be corrected under the more-exacting rubric of plain error review because the failure to correctly calculate the

range “can, and most often will, be sufficient to show a

reasonable probability of a different outcome absent the

error.” Rosales-Mireles, 138 S. Ct. at 1907 (emphasis

added). And by creating an irrebuttable presumption that

the district court’s blanket statement as to the irrelevance

of the Guidelines is dispositive to the harmless error analysis, the Eighth Circuit’s rule is contrary to Rule 52(a),

which places the burden on the government to prove error

is harmless after reviewing the entire record. United

States v. Davila, 569 U.S. 597, 607 (2013).

The question recurs frequently and is unquestionably

important in light of the centrality of the Guidelines in

sentencing. Petitioner’s case is an ideal vehicle to settle

this frequently occurring issue. The sole reason offered by

the Eighth Circuit to affirm the sentence was the district

court’s statement it would have “come out in the same

place” even if the defendant had “won every one” of his

objections to the Guidelines calculations. App. 2a. There

is no question that this issue was squarely presented and

addressed below. And this case starkly illustrates the consequences of the split; if petitioner had been sentenced in

Kansas City, Kansas instead of Kansas City, Missouri, he

would have had the benefit of the Tenth Circuit’s diametrically different rule. This Court’s review is warranted to

restore uniformity to federal sentencing law.

STATEMENT

1. Petitioner pleaded guilty to being a felon in possession of a firearm, in violation of 18 U.S.C. § 922(g)(1). App.

1a.

Before the sentencing hearing, petitioner objected

that the Probation Office’s presentence report (PSR) calculated his advisory Guidelines range improperly. App.

6a–15a. Petitioner argued that the PSR miscalculated his

7

criminal history score by improperly counting two of his

prior state convictions for Missouri armed criminal action,

Mo. Rev. Stat. § 571.015, as “crime[s] of violence,” although they did not qualify under the definition set forth

in United States Sentencing Guideline (“U.S.S.G.”)

§4B1.2, because the offense did not have “as an element

the use, attempted use, or threatened use of physical force

against the person of another.” App. 6a–9a. Without the

additional criminal history point per conviction provided

under U.S.S.G. §4A1.1(e), his criminal history category

would have been IV, as opposed to V. Ibid. Petitioner also

objected that the PSR failed to lower his base level offense

three levels for acceptance of responsibility because of his

guilty plea under U.S.S.G. §3E1.1. App. 10a–13a. The

PSR concluded petitioner’s sentencing range was 77–96

months; without the “crime of violence” enhancement, it

would have been 63–78 months; with acceptance of responsibility also, it would have been 46–57 months. Pet.

C.A. Br. 34.

The district court overruled both of petitioner’s objections. App. 11a–12a. The court de-emphasized the importance of calculating the Guidelines, concluding that

while “we do calculate the [G]uidelines,” “really the

main—the main analysis we do here is—has to do with

this statute called 18 U.S.C. 3553(a), and in that—in that

statute Congress has given the [c]ourt factors to consider

in every case * * * .” App. 16a. The district court sentenced petitioner to 108 months’ imprisonment, close to

the 10-year statutory maximum penalty for the offense,

see 18 U.S.C. § 922(g). App. 18a. As factors supporting its

non-Guidelines sentence, the court cited petitioner’s

“criminal history,” the “fact that [petitioner was] on supervision” at the time of his offense, and his “behavior

while incarcerated” (petitioner had been involved in

fights) as “the drivers of [the] large sentence.” App. 17a–

19a. The court stated at the outset of his explanation that

8

“notwithstanding any of these guideline calculations, if

you had won every one of the [objections] that [defense

counsel] had advanced, I would come out in the same place

because of 18 U.S.C. 3553(a). So this is more dependent

on the factors, I guess, in my sentence.” App. 17a.

2. The court of appeals affirmed. App. 1a–2a. The

panel did not reach the sole issue petitioner had raised regarding whether his Guidelines range was properly calculated. Rather, in two sentences of analysis, the court concluded that it did not need to determine whether the

Guidelines were correctly calculated because any error

was categorically harmless. The panel relied on the fact

that the district court had “explained that ‘notwithstanding any of these calculations, if [petitioner] had won every

one of the objections advanced, it would have come out in

the same place because of 18 U.S.C. [§] 3553(a),’ meaning

that petitioner’s sentence was based on the statutory sentencing factors rather than the allegedly erroneous criminal-history calculation.” App. 2a (quoting sentencing

transcript). The panel reasoned, “[t]his is as clear a statement as any that [petitioner] would have received the

same sentence regardless of which criminal-history score

applied.” Ibid.

The panel examined no facts about petitioner’s criminal history, or the crime for which he was sentenced. App.

1a–2a. Nor did it analyze the 18 U.S.C. § 3553 factors. Nor

did the panel consider whether petitioner’s sentence was

substantively reasonable—even though petitioner had

pleaded guilty and was sentenced to nearly the statutory

maximum sentence. Ibid.

9

REASONS FOR GRANTING THE PETITION

A.

The Circuits Are Deeply Divided Over Whether All

Sentencing Guidelines Errors Are Rendered Harmless

By The District Court’s Assertion That The Guidelines

Were Irrelevant To Its Choice Of Sentence

In the Eighth and Eleventh Circuits, all errors in

calculating a defendant’s Sentencing Guidelines are

rendered categorically harmless by the district court’s

assertion that the Guidelines made no difference to the

choice of sentence. But the Second, Third, Fourth, Fifth,

Sixth, Seventh, Ninth, and Tenth Circuits have rejected

district courts’ efforts to exempt themselves from

appellate scrutiny, and require a more extensive and

detailed harmless error analysis before affirming a

defendant’s sentence notwithstanding the Guidelines

error. Other courts have taken intermediate positions.

This entrenched circuit split warrants this Court’s

immediate review.

1.

Six Circuits Have Held That Blanket Harmless

Error Findings By The District Court Cannot

Immunize Guideline Miscalculations From

Appellate Scrutiny

The majority approach—adopted by the Second,

Third, Fifth, Seventh, Ninth, and Tenth Circuits—provides that a Guidelines calculation error is not harmless

merely because the district court stated it would have sentenced the defendant to the same sentence regardless of

any Guidelines errors.

The Seventh Circuit’s recent analysis of the issue exemplifies the majority rule’s rationale for rejecting district judges’ efforts to exempt their non-Guidelines sentences from appellate scrutiny. In United States v. Asbury, the sentencing court rejected the defendant’s objections to the PSR, and added: “[I]f I made an error in the

guideline calculation in terms of offense level, that would

10

not affect my sentence. I’m basing my sentence on the

Section 3553(a) factors and the exercise of my discretion

after placing a lot of thought into this sentencing hearing.”

27 F.4th 576, 579 (2022). The Seventh Circuit rejected the

conclusion that the sentencing court’s statement rendered

its sentencing errors harmless, holding that while sentencing courts have discretion to fashion sentences under

18 U.S.C. § 3553, this discretion does not “permit the

judge to nullify the guidelines by way of a simple assertion

that any latent errors in the guidelines calculation would

make no difference to the choice of sentence.” Id. at 581.

Reasoning that sentencing decisions at every level of the

judiciary must be made by reference to the appropriate

Guidelines calculation, “ ‘a conclusory comment tossed in

for good measure’ is not enough to make a guidelines error harmless.” Ibid.; accord United States v. Loving, 22

F.4th 630, 636 (7th Cir. 2022) (“[W]e cannot infer, based

on the district court’s terse comments about the sentencing factors under 18 U.S.C. § 3553(a) that the court believed a 71-month prison sentence would be appropriate

regardless of the correct guideline range.”).

As the Seventh Circuit explained, permitting such

conclusory assertions to insulate sentencing errors from

appellate review would circumvent the need for the judge

in every case to correctly calculate a baseline Guidelines

sentencing range and explain sentencing decisions departing from that range, and therefore is fundamentally

inconsistent with Guidelines sentencing. “There are no

‘magic words’ in sentencing.” Asbury, 27 F.4th at 581. “If

there were, the judge would have no incentive to work

through the guideline calculations: she could just recite at

the outset that she does not find the [G]uidelines helpful

11

and proceed to sentence based exclusively on her own

preferences.” Ibid.1

Similarly, the Second Circuit has held “the district

court cannot insulate its sentence from our review by commenting that the Guidelines range made no difference to

its determination” because “the Guidelines, although advisory, are not a body of casual advice, to be consulted or

overlooked at the whim of a sentencing judge.” United

States v. Seabrook, 968 F.3d 224, 233–34 (2d Cir. 2020).

The Second Circuit has “often recognized the powerful

‘anchor[ing]’ effect of a ‘miscalculated Guidelines range’

on a district court's thinking about the appropriate sentence, even where the court ‘asserted it was not moved by

the Guidelines.’ ” Id. (quoting United States v. Bennett,

839 F.3d 153, 163 & n.8 (2d Cir. 2016)). This is important

because a Guidelines error can affect substantial rights

when the judge rejects the Guidelines: “ ‘[e]ven if the sentencing judge sees a reason to vary from the Guidelines,

if the judge uses the sentencing range as the beginning

point to explain the decision to deviate from it, then the

Guidelines are in a real sense the basis for the sentence.’ ”

Bennett, 839 F.3d at 163 (quoting Molina-Martinez, 136

S. Ct. at 1345 (emphasis original)).

The Seventh Circuit went on to explain that “a district court's

statement purporting to inoculate its chosen sentence against errors identified on appeal will be effective only if two conditions are

satisfied. First, the inoculating statement must be ‘detailed,’ meaning that the judge “must give specific * * * attention to the contested guideline issue in her explanation” rather than “[a] generic

disclaimer of all possible errors.” 27 F.4th at 581. “Second, the inoculating statement must explain * * * why the potential error would

not ‘affect the ultimate outcome.’ When an inoculating statement

fails to satisfy either of these two criteria, we cannot say with confidence that the district court would have reached the same sentence

despite the [G]uidelines error. It follows that we cannot say whether

the error was harmless.” Id. at 581–582.

1

12

The Third, Fifth, Ninth, and Tenth Circuits have

reached similar holdings. See, e.g., United States v.

Wright, 642 F.3d 148, 154 n.6 (3d Cir. 2011) (“a statement

by a sentencing court that it would have imposed the same

sentence even absent some procedural error does not

render the error harmless” because “it must still begin by

determining the correct alternative Guidelines range and

properly justify the chosen sentence” in relation to it);

United States v. Smalley, 517 F.3d 208, 212 (3d Cir. 2008)

(sentencing error was not harmless despite district

court’s statement that “it would have given the same

sentence * * * if it had applied” the Guidelines as the

defendant requested does not make the error harmless);

United States v. Williams, 5 F.4th 973, 978 (9th Cir. 2021)

(reversing because of district court’s Guidelines

miscalculation notwithstanding the district court’s

statements “that it would have imposed the same

sentence” regardless of the Guidelines); United States v.

Tanksley, 848 F.3d 347, 353 (5th Cir. 2017) (remanding for

new sentencing because “it is not enough for the district

court to say the same sentence would have been imposed

but for the error”). Most noteworthy here, if petitioner

had been prosecuted a few miles to the west in Kansas

City, Kansas, the Tenth Circuit undoubtedly would have

addressed his claim on the merits: That “court has

rejected the notion that district courts can insulate

sentencing decisions from review by making * * *

statements” that “its conclusion would be the same ‘even

if all of the defendant’s objections to the presentence

report had been successful.’ ” United States v. Gieswein,

887 F.3d 1054, 1062–1063 (2018) (collecting cases).

13

2.

Two Circuits Give Some Deference To The District

Court’s Harmless Error Findings, But Will Not

Find The Guidelines Error Harmless Unless The

Sentence Is Also Substantively Reasonable

By contrast, the Fourth and Sixth Circuits give some

degree of deference to the district court’s assertion that

any errors in Guidelines calculations would be harmless,

yet still require a more probing analysis than the Eighth

or Eleventh Circuits before concluding any error was

harmless. The Fourth Circuit has explained: “For us to

find harmless error, we must be certain that “(1) the district court would have reached the same result even if it

had decided the [G]uidelines issue the other way, and (2)

[make] a determination that the sentence would be reasonable even if the Guidelines issue had been decided in

the defendant’s favor.” United States v. Gomez, 690 F.3d

194, 203 (2012) (emphasis added).

The Sixth Circuit has taken a similar approach, under

which Guidelines errors are reversed unless there is

“certainty that the error at sentencing did not cause the

defendant to receive a more severe sentence.” United

States v. Collins, 800 F. Appx. 361, 362 (2020). That

“showing is not easy,” requiring the appellate court to find

that “an upward variance from the correct [G]uidelines

range would have been reasonable.” Ibid.

3.

Two Circuits Conclude That All Guidelines Errors

Are Rendered Harmless By The District Court’s

Blanket Assertion That The Guidelines Did Not

Matter To Its Sentence

In sharp contrast, the Eighth and Eleventh Circuits

affirm all Guidelines error based solely on the district

court’s assertion that the Guidelines made no difference

to its choice of sentence. The Eighth Circuit has repeatedly held that “a district court’s incorrect application of

the Guidelines is harmless error when the court specifies

the resolution of a particular issue did not affect the

14

ultimate determination of a sentence, such as when the

district court indicates it would have alternatively imposed the same sentence even if a lower [G]uideline range

applied.” United States v. Still, 6 F.4th 812, 818 (8th Cir.

2021). Thus, even a cursory assertion that the Guidelines

calculation would not affect the sentence—such as the one

in this case—suffice to insulate mistaken Guidelines calculations from appellate review.

The Eighth Circuit often avoids reaching the merits

of whether there was a Guidelines miscalculation because

“[w]hen the district court explicitly states that it would

have imposed the same sentence of imprisonment regardless of the underlying Sentencing Guideline range, any

error on the part of the district court is harmless.” United

States v. Peterson, 887 F.3d 343, 349 (2018) (emphasis

added). In this context, the Eighth Circuit does not require review of the record as a whole, or ensure that the

sentence was grounded in an alternative Guidelines

range, or even determine if the sentence was substantively reasonable. Ibid.; see also Still, 6 F.4th at 818;

United States v. Foston, No. 21-2435, 2022 WL 1510689,

at *1 (May 13, 2022) (unpublished) (concluding in two sentences of analysis that any Guidelines error was harmless

because “the district court stated that it ‘would still impose [the same] sentence’ ” regardless of the error).2

The Eleventh Circuit takes a similar approach.

“[B]ecause the district court stated on the record that it

would have imposed the same sentence either way, that is

all we need to know to hold that any potential error was

In two cases decided more than 15 years ago, the Eighth Circuit

required more probing harmless error analysis from the district

court before affirming. See United States v. Icaza, 492 F.3d 967,

970–71 (2007); United States v. Bah, 439 F.3d 423, 432 (2006). But

the Eighth Circuit treats those cases as a dead letter and instead

follows inconsistent later precedent. No panel of the Eighth Circuit

has reversed on this basis since Icaza.

2

15

harmless.” United States v. Henry, 1 F.4th 1315, 1327

(2021); accord United States v. Grady, 18 F.4th 1275, 1291

(2021) (“a [G]uidelines error is harmless if the district

court unambiguously expressed that it would have imposed the same sentence * * * regardless of how the

guidelines objections had come out”).3

The First Circuit takes an intermediate position. It

has held that a district court’s conclusory statement that

“I would impose precisely the same sentence even if the

applicable sentencing [G]uidelines range would have

been reduced by any or all of the objections made” is

enough to render error generally harmless, at least

where the sentence is “outside of the Guidelines range.”

See United States v. Ouellette, 985 F.3d 107, 110–111

(2021). However, before affirming, the court must “still

review the sentence for substantive reasonableness” before it may affirm. Ibid.

* * * * *

The circuits thus are intractably divided on a frequently recurring and fundamental question regarding

the review of sentencing errors on appeal. The split is sufficiently deep that there is no prospect that the courts will

At times, the Eleventh Circuit has added “one thing” to its harmless error analysis: “that the sentence imposed through the alternative or fallback reasoning of Section 3553(a) must be reasonable.”

United States v. Keene, 470 F.3d 1347, 1349 (2006). But the Eleventh

Circuit has only rarely granted relief as it pertains to the substantive reasonableness of a sentence as part of it harmless error analysis, as highlighted in Henry and Grady. See also United States v.

Tampas, 493 F.3d 1291, 1304–1305 (2007) (district court’s improper

imposition of 16-level enhancement after government conceded district court’s calculation was “imprecise” was harmless error because

“the district court would have imposed the same sentence regardless of the Guidelines”); United States v. Ortiz-Santizo, 766 F. App’x

890, 896 (2019) (unpublished) (refusing to address guidelines calculation error “because the district court said expressly that it would

impose the same sentence regardless”).

3

16

resolve the split absent this Court’s intervention. And the

Eighth and Eleventh Circuits have both declined to reconsider their positions en banc, even when litigants have

pointed out that their positions diverge from most other

courts of appeals. See App. 3a; Order, United States v.

Foston, No. 21-2435 (June 21, 2022) (Eighth Circuit denied petition for rehearing, rejecting argument that sentencing courts “should not be allowed to inoculate a Guideline” error through blanket statements); United States v.

Henry, 18-15251 (Aug. 17, 2021) (Eleventh Circuit denied

petition for rehearing en banc). Only this Court can restore uniformity to federal sentencing law.

B. The Eighth Circuit’s Rule Is Wrong

The Eighth Circuit is wrong in holding that when a

sentencing court states it would have imposed the same

sentence regardless of the Guidelines, a reviewing court

may conclude that any Guidelines calculation error is

rendered categorically harmless. Blanket harmless error

findings conflict with what Congress and this Court

require courts to perform at every sentencing hearing,

and also conflict with how harmless error review must be

conducted under Federal Rule of Criminal Procedure

52(a).

1.

This Court’s Precedent Provides That Sentencing

Courts Must Properly Calculate The Sentencing

Guidelines, And That Reviewing Courts Should

Ordinarily Correct Guidelines Errors

Properly calculating the Guidelines is not an optional

step for sentencing courts. “[D]istrict courts must begin

their analysis with the Guidelines and remain cognizant of

them throughout the sentencing process.” Gall, 552 U.S.

at 50 n.6. (emphasis added). “The starting point of any

federal sentencing proceeding is ‘correctly calculating the

applicable Guidelines range[,]’ which serves as the ‘initial

benchmark’ in determining an appropriate sentence.”

United States v. Khatallah, 41 F.4th 608, 643 (D.C. Cir.

17

2022) (quoting Gall, 552 U.S. at 49). The Guidelines are

central to sentencing, even when the sentencing judge

chooses to depart or vary the sentence imposed, because

“while not binding, the Guidelines are “the product

of careful study based on extensive empirical evidence

derived from the review of thousands of individual

sentencing decisions.” Ibid. (quoting Gall, 552 U.S. at 46).

And the Sentencing Commission “base[s] its

determinations on empirical data and national experience,

guided by a professional staff with appropriate expertise.”

Kimbrough v. United States, 552 U.S. 85, 109 (2007).

Thus, even when a sentencing court chooses not to

impose a Guidelines sentence, it ordinarily must explain

its sentencing decision in relation to the properly

calculated Guidelines sentence because it is

“uncontroversial” that a “major departure [from the

Guidelines] should be supported by a more significant

justification that a minor one,” and sentencing courts

“must adequately explain the chosen sentence * * * to

promote the perception of fair sentencing.” Gall, 552 U.S.

at 50. And determining substantive reasonableness

ordinarily requires knowing the correct Guidelines

sentencing range because “[e]ven if the sentencing judge

sees a reason to vary from the Guidelines, if the judge uses

the sentencing range as the beginning point to explain the

decision to deviate from it, then the Guidelines are in a

real sense the basis for the sentence.” Peugh, 569 U.S. at

542 (emphasis in original). Stated another way, although

the district court has discretion to depart from the

Guidelines, the court “must consult those Guidelines and

take them into account when sentencing.” Booker, 543

U.S. at 264.

Similarly, in Molina-Martinez and Rosales-Mireles,

this Court twice held that properly calculating the

Guidelines range is the touchstone of all sentencing

hearings. So central to sentencing are the Guidelines that

18

“[w]hen a defendant is sentenced under an incorrect

Guidelines range—whether or not the defendant’s

ultimate sentence falls within the correct range—the

error itself can, and most often will, be sufficient to show

a reasonable probability of a different outcome absent the

error.” Molina-Martinez, 578 U.S. at 203 (emphasis

added); accord Rosales-Mireles, 138 S. Ct. at 1903

(holding a plain Guidelines error “in the ordinary case”

warrants a remand for a new sentencing hearing because

“it seriously affect[s] the fairness, integrity, or public

reputation of the judicial proceedings.”). Those holdings

reflect the “anchoring” effect of the Guidelines—shaping

judges’ sentencing decisions whether or not they choose

to impose a Guidelines sentence.

The Guidelines also play a critical role in reviewing

sentences on appeal. “The post-Booker federal sentencing

scheme aims to achieve uniformity by ensuring that

sentencing decisions are anchored by the Guidelines and

that they remain a meaningful benchmark through the

process of appellate review.” Peugh, 569 U.S. at 541

(emphasis added). And when reviewing a sentence on

appeal, “the appellate court * * * must first ensure that

the district court committed no significant procedural

error, such as failing to calculate (or improperly

calculating) the Guidelines range * * * or failing to adequately explain the chosen sentence—including an

explanation for any deviation from the Guidelines range.”

Gall, 552 U.S. at 51.

2.

Rule 52(a), Like Rule 52(b), Requires That

Guidelines Errors Should Ordinarily Be Corrected

Knowing the correct Guidelines range is of such paramount importance to sentencing that Rule 52(b) ordinarily requires Guidelines miscalculations to be corrected

even on plain error review when a defendant fails to object. Rosales-Mireles, 138 S. Ct. at 1907. The error also

should ordinarily be corrected on harmless-error review

19

because “ensuring the accuracy of Guidelines determinations also serves the purpose of providing certainty and

fairness in sentencing on a greater scale,” in light of the

fact that “[w]hen sentences based on incorrect Guidelines

ranges go uncorrected, the Commission’s ability to make

appropriate amendments is undermined.” Id. at 1908. Finally, Guidelines errors should ordinarily be corrected because the anchoring effect of the guidelines means that

“the risk of unnecessary deprivation of liberty particularly undermines the fairness, integrity or public reputation of judicial proceedings in the context of plain Guidelines error because the role the district court plays in calculating the range and the relative ease of correcting the

error.” Ibid.

Those principles a fortiori require reversal when, as

here, the defendant has preserved the error and the claim

is “governed by the more lenient harmless-error standard

of Rule 52(a) rather than the more exacting plain-error

standard of Rule 52(b).” Greer v. United States, 141 S. Ct.

2090, 2093 (2021). “When Rule 52(a)’s ‘harmless-error

rule’ governs, the prosecution bears the burden of showing harmlessness.” United States v. Davila, 569 U.S. 597,

607 (2013) (quoting United States v. Vonn, 535 U.S. 55, 62

(2002)). However, the Eighth Circuit’s test has the effect

of improperly flipping the burden under Rule 52(a), placing it on the defendant to prove prejudice when the district court has stated “that it would have imposed

the same sentence of imprisonment regardless of the underlying Sentencing Guideline range.” Peterson, 887 F.3d

at 349. This is a burden the defendant cannot overcome on

appeal because the Eighth Circuit uncritically accepts

even boilerplate assertions at face value, without otherwise examining the record. Ibid. (“Here, the district court

specifically stated at the sentencing hearing that it would

have imposed the same sentence regardless of the Sentencing Guidelines calculations. Therefore, we find that

20

any procedural error on the part of the district court in

calculating Peterson's sentence was harmless.”). Thus,

the Eighth Circuit’s harmless error review is tantamount

to no review at all on appeal, because it always affirms if

the judge has made a boilerplate disavowal of the Guidelines’ importance.

The Eighth Circuit’s application of Rule 52(a) is also

improper because it neglects that “the Court has consistently made clear that it is the duty of a reviewing court to

consider the trial record as a whole” when conducting

harmless error review. United States v. Hasting, 461 U.S.

499, 509 (1983) (citations omitted and emphasis added).

This Court held of the mandatory Guidelines that “once

the court of appeals has decided that the district court

misapplied the Guidelines, a remand is appropriate unless

the reviewing court concludes, on the record as a whole,

that the error was harmless.” Williams v. United States,

503 U.S. 193, 203 (1992) (emphasis added). But in finding

Guidelines calculation errors harmless, the Eighth Circuit

looks only to the district court’s harmless error statements, instead of the entire record. Peterson, 887 F.3d at

349; see also Still, 6 F.4th at 818.

Finally, unlike almost every other circuit, the Eighth

Circuit does not bother determining whether the sentence

imposed was substantively reasonable once the district

judge makes a boilerplate recitation that the Guidelines

were unimportant in its sentence. Thus, it appears that

the Eighth Circuit routinely affirms Guidelines

miscalculation errors even when the final sentence is

unreasonable, because of its reflexive deference to the

district court’s harmless error findings.

C.

The Question Presented Is Important And Recurring

The disagreement over the proper scope of harmless

error review regarding Guidelines error has severe

consequences for individual liberty, frustrates proper

21

application of the Sentencing Guidelines, and undermines

uniformity in federal sentencing, which was Congress’s

“principal purpose” in adopting Guidelines sentencing.

Hughes v. United States, 138 S. Ct. 1765, 1774 (2018).

Federal sentencing procedures affect the lives of tens

of thousands of individuals every year. Nearly 65,000

federal defendants were sentenced in 2020 alone, and

more than a quarter of defendants—nearly 17,000—

received sentences that represented variances from the

Guidelines. U.S. Sentencing Comm’n, Table 29, “Sentence

Imposed Relative to the Guidelines Range,” FY2020

Sourcebook of Federal Sentencing, https://bit.ly/

3zAXFCz. Across broad areas of the United States, the

sentencing judge could avoid appellate scrutiny of such

sentences through the simple expedient of claiming it

would impose the same sentence regardless of the

Guidelines. In such areas, judges effectively can simply

“opt out” of the Guidelines sentencing system that

Congress sought to establish.

Just this year, the Seventh Circuit “noticed the frequency with which sentencing judges are relying on inoculating statements” in an effort to immunize Guidelines

miscalculations on appeal. Asbury, 27 F.4th at 581. District judges face incentives that encourage them to make

blanket assertions about their sentencing conclusions to

insulate their Guidelines calculations from appellate review. Indeed, one Fourth Circuit judge has even “encourage[d] district courts to consider announcing alternate

sentences in cases * * * where the guidelines calculation

is disputed.” United States v. Montes-Flores, 736 F.3d

357, 374 (4th Cir. 2013) (Shedd, J., dissenting). It is important for this Court to resolve whether that practice is

proper, and how appellate courts should assess such situations for harmlessness.

Ensuring that harmless error review of Guidelines

miscalculations is properly conducted also benefits the

22

government when it appeals Guidelines miscalculations.

See Porter, 928 F.3d at 968 (remanding after the government demonstrated the Guidelines miscalculation was not

harmless, even though district court made blanket harmless error findings). Because Guidelines errors “seriously

affect[s] the fairness, integrity, or public reputation of the

judicial proceedings,” Rosales-Mireles, 138 S. Ct. at 1903,

the entire justice system has an interest to make sure that

harmless error review of Guidelines miscalculations is

properly conducted.

This Court has often granted certiorari to resolve

circuit conflicts to ensure harmless error review is

properly conducted under Rule 52(a). See, e.g., Williams,

503 U.S. at 203 (whether incorrect application of the

mandatory Guidelines is harmless error); Davila, 569

U.S. at 605 (whether violations of Rule 11(c)(1) are

harmless); Neder v. United States, 527 U.S. 1, 7 (1999)

(whether an erroneous jury instruction is harmless error);

Peguero v. United States, 526 U.S. 23, 24 (1999) (whether

the failure to advise a defendant of his right to appeal is

harmless error).

D. This Case Is An Ideal Vehicle

This case is an excellent vehicle for resolving this

important and recurring question. The case presents a

single purely legal issue. Petitioner squarely preserved

the issue that the judge’s boilerplate statement did not

insulate claims of error from appellate review. And the

Eighth Circuit squarely rejected the argument, holding

that the district court’s blanket statement it would have

“come out in the same place” regardless of the Guidelines,

App. 2a, rendered any sentencing errors categorically

harmless. Solely because of a happenstance of geography,

Eighth Circuit law foreclosed a claim that would have

succeeded if petitioner had been sentenced less than four

miles to the west. There are no disputed issues of fact nor

any jurisdictional questions that would prevent the Court

23

from resolving the issue. And nearly every circuit has

thoroughly analyzed the issue, creating an entrenched

split. The issue is ripe for review, and nothing would be

gained from delaying review.

This case is also a compelling vehicle to decide the

question because it highlights how blanket harmless error

findings can insulate substantial claims of error from review. The Eighth Circuit reversed and remanded for a

new sentencing hearing on the very same underlying sentencing issue that petitioner presented on appeal—that

Missouri armed criminal action, Mo. Rev. Stat. § 571.015,

is not a “crime of violence” under the Guidelines—with

the court of appeals concluding the Guidelines miscalculation constituted plain error, even though the defendant

failed to raise the objection before the district court.

United States v. Miranda-Zarco, 836 F.3d 899, 901–903

(2016); see also United States v. Brown, No. 20-2847, 2021

WL 3732369, at *1 (8th Cir. Aug. 24, 2021) (concluding

that this offense is not a “crime of violence”). On remand,

the defendant in Miranda-Zarco prevailed in his objection, and had his sentence shortened by twenty months.

But despite timely raising the same objection, petitioner is worse off than the defendant in Miranda-Zarco,

who did not. That cannot be right.

*****

Sentencing courts in a few jurisdictions are routinely

relying on boilerplate assertions that the Guidelines did

not affect their sentencing decision to insulate their

sentences from appellate scrutiny. Courts in the Eighth

and Eleventh Circuits are reflexively deferring to such

blanket findings instead of doing the important work

Congress and this Court have mandated must be done

before any defendant is sentenced, and before any

sentence is affirmed on appeal. That must not be allowed

to stand.

24

CONCLUSION

The petition for a writ of certiorari should be granted.

Respectfully submitted.

JOHN P. ELWOOD

ARNOLD & PORTER

KAYE SCHOLER LLP

601 Massachusetts Ave., NW

Washington, DC 20001

(202) 942-5000

SEPTEMBER 2022

LAINE CARDARELLA

Federal Public Defender

Daniel P. Goldberg

Assistant Federal Public

Defender

Counsel of Record

OFFICE OF THE FEDERAL

PUBLIC DEFENDER

WESTERN DISTRICT OF

MISSOURI

1000 Walnut St., Suite 600

Kansas City, MO 64106

(816) 471-8282

Dan_Goldberg@fd.org