Petition for Writ of Certiorari — Omar Francisco Orduno-Ramirez, Petitioner v. United States

Supreme Court briefJun 30, 2023

Ask Donna

What actually matters in this document.

Text

No. ______________________

IN THE

Supreme Court of the United States

OMAR FRANCISCO ORDUNO-RAMIREZ

Petitioners,

UNITED STATES OF AMERICA,

Respondent.

On Petition for Writ of Certiorari

To The United States Court of Appeals for The Tenth Circuit

Petition for a Writ of Certiorari

MELODY BRANNON

Federal Public Defender

DANIEL T. HANSMEIER

Appellate Chief

PAIGE A. NICHOLS

Assistant Federal Public Defender

Counsel of Record

KANSAS FEDERAL PUBLIC DEFENDER

117 SW 6th Avenue, Suite 200

Topeka, Kansas 66603

Tel: (785) 232-9828

Email: paige_nichols@fd.org

QUESTION PRESENTED

In Weatherford v. Bursey, this Court held that an undercover agent did not cause

structural (“per se”) Sixth Amendment error when he sat in on a defendant’s attorneyclient meetings but did not convey the details of the meetings to the prosecution. 429

U.S. 545 (1977). This Court nonetheless cautioned that “had the prosecution learned”

the details of the meetings, the defendant “would have a much stronger case.” Id. at

554. This is that “much stronger case.” For years, prosecutors in the Kansas United

States Attorney’s Office secretly engaged in a “systematic practice of purposeful

collection, retention, and exploitation of” recorded communications between defense

counsel and their detained clients. United States v. Carter, 429 F.Supp.3d 788, 900

(D. Kan. 2019). And yet the Tenth Circuit has now held that when such intrusions

into attorney-client communications occur between a guilty plea and sentencing, they

do not violate the Sixth Amendment unless the defendant is prejudiced. Pet. App.

24a-25a. The question presented is:

When prosecutors intentionally and without any legitimate law-enforcement

justification access confidential attorney-client communications before sentencing, do

the prosecutors thereby commit structural Sixth Amendment error?

RELATED PROCEEDINGS

United States v. Orduno-Ramirez

D.Kan. No. 2:14-cr-20096-JAR-7 (criminal proceeding; judgment filed

01/12/2017)

D.Kan. No. 2:19-cv-2166-JAR-JPO (28 U.S.C. § 2255 proceeding; judgment

denying § 2255 relief filed 01/03/2022)

10th Cir. No. 15-3195 (affirming detention order 11/12/2015)

10th Cir. No. 17-3010 (affirming sentence on direct appeal 12/28/2017)

10th Cir. No. 22-3019 (affirming denial of § 2255 relief 03/10/2023)

In re CCA Recordings 2255 Litigation

D.Kan. No. 2:19-cv-02491-JAR-JPO (consolidated 28 U.S.C. § 2255

proceeding; consolidated order predicating judgment in petitioner’s individual

§ 2255 case filed 12/10/2021)

United States v. Carter

D.Kan. No. 2:16-cr-20032-JAR (criminal proceeding in which Special Master

investigation took place; order predicating petitioner’s 28 U.S.C. § 2255 filed

08/13/2019)

TABLE OF CONTENTS

Question Presented......................................................................................................... i

Related Proceedings....................................................................................................... ii

Table of Contents .......................................................................................................... iii

Index to Appendix ......................................................................................................... iv

Table of Authorities ...................................................................................................... v

Petition for Writ of Certiorari ....................................................................................... 1

Opinions Below .............................................................................................................. 1

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

Constitutional Provision Involved ................................................................................ 2

Statement of the Case ................................................................................................... 3

1. District Court Proceedings ................................................................................. 5

2. Tenth Circuit Proceedings ................................................................................ 11

Reasons for Granting the Writ .................................................................................... 12

1. Deliberate and systemic prosecutorial intrusions into the defense camp

undermine the legitimacy of our adversarial system and cry out for

this Court’s attention. ....................................................................................... 12

2. How to identify structural constitutional error is a question of

exceptional importance to both federal and state courts. ............................... 15

3. The Tenth Circuit’s decision undervalues a core Sixth Amendment

right; the critical nature of sentencing proceedings; and the role of

legitimacy and deterrence interests in structural-error analyses. ................. 20

4. No vehicle problems stand in the way of this Court’s review. ........................ 25

Conclusion .................................................................................................................... 25

iii

INDEX TO APPENDIX

Appendix A: Tenth Circuit Decision ........................................................................... 1a

Appendix B: Memorandum and Order regarding Shillinger ................................... 27a

Appendix C: Memorandum and Order Denying § 2255 Motion............................... 51a

Appendix D: Tenth Circuit Order Denying Petition for Rehearing ......................... 66a

TABLE OF AUTHORITIES

Cases

Ballard v. United States, 329 U.S. 187 (1946) ............................................................ 17

Bank of Nova Scotia v. United States, 487 U.S. 250 (1988) ....................................... 13

Brecht v. Abrahamson, 507 U.S. 619 (1993) ............................................................... 13

Chapman v. California, 386 U.S. 18 (1967) ................................................................ 15

Coplon v. United States, 191 F.2d 749 (D.C. Cir. 1951) ............................................. 20

Faretta v. California, 422 U.S. 806 (1975) .................................................................. 17

Gideon v. Wainwright, 372 U.S. 335 (1963)................................................................ 17

Gray v. Mississippi, 481 U.S. 648 (1987) .................................................................... 17

Greer v. United States, 141 S.Ct. 2090 (2021) ............................................................ 19

Hoffa v. United States, 385 U.S. 293 (1966) ......................................................... 12, 14

In re CCA Recordings 2255 Litigation, No. 2:19-cv-2166-JAR-JPO, Doc. 1033 (D.

Kan. Dec. 9, 2021) .................................................................................................... 10

In re Rider, 195 P. 965 (Cal. App. 1920) ..................................................................... 20

In re United States, No. 18-3007 (10th Cir. Feb. 26, 2018) .......................................... 5

McCoy v. Louisiana, 138 S.Ct. 1500 (2018) ................................................................ 17

McKaskle v. Wiggins, 465 U.S. 168 (1984).................................................................. 18

Neder v. United States, 527 U.S. 1 (1999) ................................................................... 18

Nordstrom v. Ryan, 762 F.3d 903 (9th Cir. 2014) ...................................................... 21

Powell v. Alabama, 287 U.S. 45 (1932) ....................................................................... 21

Rita v. United States, 551 U.S. 338 (2007) ................................................................. 22

Rose v. Clark, 478 U.S. 570 (1986) .............................................................................. 19

Shillinger v. Haworth, 70 F.3d 1132 (10th Cir. 1995) ...................................... 4, 14, 23

State v. Davis, 130 P. 962 (Okla. Ct. Crim. App. 1913) .............................................. 20

State v. Paumier, 288 P.3d 1126 (Wash. 2012) ..................................................... 16, 17

Strickland v. Washington, 466 U.S. 668 (1984) .......................................................... 15

Sullivan v. Louisiana, 508 U.S. 275 (1993) ................................................................ 17

Tumy v. Ohio, 273 U.S. 510 (1927) ............................................................................. 17

United States v. Antonelli Fireworks Co., 155 F.2d 631 (2d Cir. 1946) ..................... 15

United States v. Carter, 429 F.Supp.3d 788 (D. Kan. 2019) .............................. passim

United States v. Carter, D. Kan. 16-cr-20032, Doc.560 (Aug. 2, 2018) ........................ 4

United States v. Davila, 569 U.S. 597 (2013) ....................................................... 19, 20

United States v. Gonzalez-Lopez, 548 U.S. 140 (2006) ......................................... 17, 21

United States v. Jackson, 32 F.3d 1101 (7th Cir. 1994) ............................................. 22

United States v. Levy, 577 F.2d 200 (3d Cir. 1978) .................................................... 21

United States v. Marcus, 560 U.S. 258 (2010) ...................................................... 19, 20

United States v. McDonald, 43 F.4th 1090 (10th Cir. 2022) ...................................... 23

United States v. Morrison, 449 U.S. 361 (1981) ................................................... 12, 19

United States v. Orduno-Ramirez, 61 F.4th 1263 (10th Cir. 2023) ............................. 1

United States v. Orduno-Ramirez, 719 Fed.Appx. 830 (10th Cir. 2017) ..................... 5

United States v. Orduno-Ramirez, No. 22-3018 (10th Cir. Order filed June 16, 2022)

................................................................................................................................... 11

United States v. Orduno-Ramirez, No. 22-3018 (10th Cir. Order filed March 10,

2022) ......................................................................................................................... 11

United States v. Ruiz-Rodriguez, 277 F.3d 1281 (11th Cir. 2002) ............................. 22

United States v. Russell, 411 U.S. 423 (1973)............................................................. 13

United States v. Spaeth, 69 F.4th 1190, 2023 WL 3940537 (10th Cir. 2023) ............ 14

Vasquez v. Hillery, 474 U.S. 254 (1986) ...................................................................... 17

Waller v. Georgia, 467 U.S. 39 (1984) ................................................................... 17, 19

Weatherford v. Bursey, 429 U.S. 545 (1977) ........................................................ i, 4, 20

Weaver v. Massachusetts, 582 U.S. 286 (2017) ........................................................... 18

Williams v. Pennsylvania, 579 U.S. 1 (2016) .................................................. 13, 17, 18

Wolff v. McDonnell, 418 U.S. 539 (1974) .................................................................... 21

Statutes

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

28 U.S.C. § 2253(c)(1)(B) ............................................................................................... 1

28 U.S.C. § 2255 ................................................................................................... passim

Other Authorities

3 CRIM. PRAC. MANUAL § 102:2 (March 2023) ............................................................. 22

David McCord, The “Trial”/”Structural” Error Dichotomy: Erroneous, and Not

Harmless, 45 U. KAN. L. REV. 1401 (1997) .............................................................. 16

Department of Justice Manual 9-27.710 cmt. ............................................................ 22

Department of Justice Manual 9-27.720(1) ................................................................ 23

Department of Justice Manual 9-27.720(1) cmt. ........................................................ 23

vii

Department of Justice Manual 9-27.720(2) cmt. ........................................................ 23

Department of Justice Manual 9-27.720(5) cmt. ........................................................ 23

Department of Justice Manual 9-27.720(6) cmt. ........................................................ 23

Department of Justice Manual 9-27.730 .................................................................... 23

Fed. R. Crim. P. 32(i)(3)(B) .......................................................................................... 23

Justin Murray, Policing Procedural Error in the Lower Criminal Courts, 89

FORDHAM L. REV. 1411 (2021) ............................................................................ 16, 24

Nancy Fox Kaden, Sentencing, 73 GEO. L. J. 671 (Dec. 1984) ................................... 22

Paul H. Robinson, Criminal Law’s Core Principles, 14 Wash. U. Jurisprudence Rev.

153 (2021) ................................................................................................................. 13

U.S. Const. amend. VI ......................................................................................... passim

Wayne R. LaFave, et al., 7 CRIM. PROC. § 27.6(d) (4th ed. Nov. 2022) ...................... 16

Zachary L. Henderson, A Comprehensive Consideration of the Structural-Error

Doctrine, 85 Mo. L. Rev. 965 (2020)......................................................................... 16

viii

PETITION FOR WRIT OF CERTIORARI

Petitioner Omar Francisco Orduno-Ramirez respectfully petitions for a writ of

certiorari to review the judgment of the United States Court of Appeals for the Tenth

Circuit.

OPINIONS BELOW

The Tenth Circuit’s panel opinion was published as United States v. OrdunoRamirez, 61 F.4th 1263 (10th Cir. 2023); it is included as Appendix A. The Tenth

Circuit’s unpublished order denying rehearing en banc is included as Appendix D.

The district court orders appealed from are included as Appendix B and Appendix C.

JURISDICTION

The United States District Court for the District of Kansas had jurisdiction over

the petitioner’s motion to vacate his sentence under 28 U.S.C. § 2255. The petitioner

timely appealed the district court’s denial of his motion to the United States Court of

Appeals for the Tenth Circuit, which granted a certificate of appealability (thereby

establishing jurisdiction for the appeal) under 28 U.S.C. § 2253(c)(1)(B). The Tenth

Circuit affirmed in a published decision. The Tenth Circuit denied the petitioner’s

petition for rehearing on April 3, 2023. This Court has jurisdiction under 28 U.S.C.

§ 1254(1).

CONSTITUTIONAL PROVISION INVOLVED

The Sixth Amendment provides: “In all criminal prosecutions, the accused shall

enjoy the right . . . to have the Assistance of Counsel for his defence.”

STATEMENT OF THE CASE

For untold years, the United States Attorney’s Office for the District of Kansas

engaged in a secret and “systematic practice of purposeful collection, retention, and

exploitation of calls from . . . detainees to their attorneys.” United States v. Carter,

429 F.Supp.3d 788, 849-54, 900 (D. Kan. 2019). This practice was so entrenched and

longstanding that it has been “impossible . . . to identify or even quantify the number

of calls obtained in . . . cases investigated or prosecuted by the USAO.” Id. at 847.

This practice culminated in the USAO’s collection, through broad records requests in

a single conspiracy investigation, of at least 74 audio recordings of attorney-client

phone calls and over 700 soundless video recordings of attorney-client meetings at a

local detention center. Id. at 835, 849.1

This practice only came to light because prosecutors tried to exploit the videos to

bully a defense attorney into withdrawing from a case, and failed to remove the phone

calls from a massive discovery dump distributed to multiple counsel. Id. at 810, 83742. When the district court investigated, the USAO resisted, engaging in a “wholesale

strategy to delay, diffuse, and deflect” the court’s inquiry. Id. at 800. The USAO’s

conduct caused the public to wonder “how this could be”; it “outraged” the defense

bar; and it devastated the already-precarious trust our clients had in their lawyers,

not to mention the system at large. United States v. Carter, D. Kan. 16-cr-20032,

1 The district court found that these videos, despite being soundless, “visually captured meaningful

communication between attorneys and clients.” 429 F.Supp.3d at 833. A viewer “could easily observe

non-verbal communications, including the communicants’ use of their hands, fingers, and other body

language.” Id. And a viewer could use the viewing software to zoom in, for instance, on a document.

Id. at 834.

Doc.560 at 68-69 (Aug. 2, 2018). And yet the government has refused to concede in

any case that any of its prosecutors ever violated the Sixth Amendment with this

practice. See, e.g., Carter, 429 F.Supp.3d at 800 (district court noting, three years into

its inquiry, that government continued to assert that the communications it collected

were fair game and that prosecutors could unilaterally decide to access them).

Against this egregious backdrop, the Tenth Circuit has now held that a prosecutor

who intentionally and without a legitimate law-enforcement justification accesses

confidential attorney-client communications between a defendant’s guilty plea and

sentencing does not violate the Sixth Amendment unless the intrusion prejudices the

defendant. Pet. App. 24a-25a. This elevation of individual case outcomes over

institutional legitimacy and deterrence interests destabilizes a core constitutional

right and harms the rule of law itself.

This Court should grant certiorari and put some teeth into the Sixth Amendment

right to confidential attorney-client communications. When prosecutors intentionally

and without any legitimate law-enforcement justification access confidential

attorney-client communications before sentencing, those prosecutors commit

structural Sixth Amendment error, justifying a remedy regardless of prejudice.2

2 We use the “structural error” label here to mean constitutional error not subject to any prejudice (or

harmless-error) inquiry. Below, the courts and the parties sometimes used that label, but more often

conveyed the same meaning by speaking of conclusive presumptions of prejudice and “per se” Sixth

Amendment violations, following Shillinger v. Haworth, 70 F.3d 1132 (10th Cir. 1995) (conclusively

presuming prejudice and finding “a per se violation of the Sixth Amendment” where prosecutor

intentionally and unjustifiably became privy to attorney-client communications before trial), and

Weatherford, 429 U.S. at 552 (rejecting “per se rule” requiring reversal based on undercover agent’s

attendance at attorney-client meeting where agent did not convey details of meeting to prosecutor).

See, e.g., Pet. App. 10a. & n.4.

1. District Court Proceedings

a. In 2016, Mr. Orduno-Ramirez pleaded guilty as charged to a drug conspiracy.

R2.43, 68. After he pleaded guilty, but six months before he was sentenced, the

Kansas USAO secretly collected detention-center video footage (during an unrelated

investigation in a case called Carter) that included soundless videos of five of Mr.

Orduno-Ramirez’s attorney-client meetings. R1.596, 603; Carter, 429 F.Supp.3d at

835. Mr. Orduno-Ramirez was ultimately sentenced after a contested evidentiary

hearing to 144 months’ imprisonment followed by 5 years of supervised release.

R2.62-63, 92. Mr. Orduno-Ramirez appealed his sentence, and the Tenth Circuit

affirmed. United States v. Orduno-Ramirez, 719 Fed.Appx. 830 (10th Cir. 2017).

b. While Mr. Orduno-Ramirez was appealing his sentence, a Special Master

appointed by the district court in the Carter case was investigating the USAO’s

collection of attorney-client communications. This investigation would ultimately

comprise over three years of litigation, one mandamus action, and a protracted

evidentiary hearing during which over a dozen federal prosecutors testified. 429

F.Supp.3d at 805; In re United States, No. 18-3007 (10th Cir. Feb. 26, 2018) (denying

government’s petition for mandamus requesting termination of Special Master

investigation; limiting scope of investigation in part).

At one point, the local United States Attorney and the Federal Public Defender

negotiated an end to the litigation by agreeing to sentence reductions for stillincarcerated defendants whose attorney-client communications the government had

collected. 429 F.Supp.3d at 805. But the DOJ abruptly reneged the settlement,

advising that the government would “either negotiate or litigate each claim

individually.” Id.

After the Special Master completed his investigation, the district court issued an

extensive written order making a number of disturbing findings. The district court

found that for years, the USAO had engaged in a “systematic practice of purposeful

collection, retention, and exploitation of calls from CCA detainees to their attorneys.”

429 F.Supp.3d at 849-54, 900. This practice culminated in the USAO’s collection in

the Carter case of tens of audio recordings of attorney-client phone calls and hundreds

of soundless video recordings of attorney-client meetings. Id. at 835, 849. When

caught, “the Government evaded the [district court’s] questions and denied that its

practices implicated the Sixth Amendment or the attorney-client privilege.” Id. at

799.

The prosecutors did not just collect these communications; they used them. Two

prosecutors exploited the USAO’s possession of videos of attorney-client visits in an

effort to disqualify an appointed lawyer in a criminal case. Id. at 837-38. And multiple

other prosecutors “unilaterally determined that recorded attorney-client calls were

available for review, without approval from the court or notice to the defense.” Id. at

858. The record was “clear” that “upon receiving recordings, prosecutors and their

agents reviewed the calls.” Id. at 848. In one particularly egregious case, a prosecutor

secretly exploited the contents of a defendant’s attorney-client communications to

induce the defendant to take a plea, and then later lied to a federal judge about

listening to the calls. Id. at 853.

The USAO kept this practice secret for years. Prosecutors “intentionally avoided

any judicial determination” of whether the calls they routinely collected were

protected by the Sixth Amendment “by not disclosing to defendants that they had

obtained their attorney-client calls.” Id. at 861. The USAO’s “regular practice was to

not disclose to defense counsel that they had acquired and/or accessed attorney-client

calls.” Id. at 862. For nearly a decade without detection, the USAO retained

“attorney-client calls[] during the duration of the case rather than returning or

destroying them.” Id. at 866.

The district court also found that the USAO went to great lengths to frustrate the

court’s investigation into possible Sixth Amendment violations. For instance, the

prosecutor who collected the videos, Special Assistant United States Attorney Erin

Tomasic, “did not respond with candor” to the district court’s initial questions “about

whether there were video recordings of the attorney visitation rooms.” Id. at 836.

Tomasic and another prosecutor, Assistant United States Attorney Kim Flannigan,

along with a law-enforcement agent who was working with them, all denied using the

videos. Id. at 839. The district court found none of their testimony credible. Id.

Tomasic also lied about listening to calls in another criminal case. Id. at 851-52. And

the USAO knew about her lie for over a month before alerting the district court. Id.

at 852. Lead counsel in that case, (Assistant United States Attorney David Zabel, who

also prosecuted Petitioner Orduno-Ramirez), later denied knowing that Tomasic had

listened to the calls, but the district court also found his credibility “lacking.” Id. at

852. n.355. Yet another prosecutor, Assistant United States Attorney Tanya

Treadway, “lied about listening to . . . calls in a court proceeding” before a different

district court judge. Id. at 853. Her lie did not surface in that case, but rather in the

Special Master investigation. Id. at 854. Treadway retired, id. at 852, and Tomasic

was ultimately terminated, id. at 827, but they were not the only ones covering their

tracks.

For instance, after assuring the district court that the USAO had “locked down”

its office’s computer hard drives, the USAO violated its duty to preserve the one hard

drive necessary to determine whether any USAO staff had viewed the videos before

the district court impounded them. Id. at 870-74. Instead, the USAO allowed that

drive to be reformatted during a cyclical upgrade. Id. at 871. But the district court

found no reason for the upgrade “unless the objective was to destroy the data.” Id.

The USAO refused to preserve other evidence as well, eventually revealing that it

had delayed imposing a formal litigation hold to preserve emails, documents, and

other data until late 2018, despite its awareness that “we are losing some stuff in the

interim.” Id. at 822. Tomasic later testified that she “knew people were recording

[internal USAO] phone calls [and] . . . people were printing out e-mails every night

and taking them home in binders because they did not trust the people they worked

with.” Id.; id. at 847 (district court noting that prosecutors who collected calls often

left “no paper trail”). The district court found that the USAO’s “misrepresentations,

delays, and lack of transparency about the state of its preservation efforts in this

matter ma[d]e it impossible to conclude with certainty what information has been

lost and cannot be restored.” Id. at 873. The district court “easily” found that the

USAO “willfully violated myriad Court orders and Special Master directives,” and

concluded “that the Government acted with intent to deprive the Special Master and

the FPD of evidence in this investigation.” Id. at 799, 874.

c. In the wake of the Special Master investigation, Petitioner Orduno-Ramirez

joined over a hundred 28 U.S.C. § 2255 movants who challenged their convictions and

sentences based on the USAO’s collection of their attorney-client communications.

R1.114, 116-18, 366. Mr. Orduno-Ramirez alleged that the government’s post-plea,

pre-sentencing intrusion upon his confidential attorney-client communications

violated the Sixth Amendment. R2.297, 310-312. He argued that once he established

that the government had intentionally and without a legitimate law-enforcement

justification become privy to his confidential attorney-client communications, he had

established a Sixth Amendment violation and was entitled to a remedy regardless of

the presence or absence of prejudice. R2.312, 387. And he asked the district court to

remedy this Sixth Amendment violation by vacating his sentence and imposing a

reduced term of imprisonment. R2.290.

The district court consolidated the § 2255 cases for discovery and other casemanagement purposes. R1.114. After much litigation over the petitioners’ discovery

requests, the government notified the district court that, notwithstanding the district

court’s discovery orders, the government, upon a directive from the DOJ, refused to

provide further discovery. R1.365. The district court found that this blatant violation

of its orders “prejudiced petitioners’ ability to meaningfully develop their motions for

evidentiary hearing without any valid justification.” R1.377. And the district court

held in all of the § 2255 cases that, because the government had intentionally violated

orders designed to discover whether prosecutors had accessed communications that

the USAO had collected, the court would adopt an adverse-inference finding that they

had, “either by watching or listening to them or by directly or indirectly obtaining

information about them from someone who did.” R1.365, 377. Noting that “proof of

this element rests almost entirely within the government’s control,” the district court

stated that it would enter this finding in all of the § 2255 cases. R1.377-78.

As it turned out, the district court did not need to rely on any adverse inference in

the first § 2255 case to proceed to an evidentiary hearing. In that case, the district

court independently found that Assistant United States Attorney Terra Morehead

had collected and intentionally listened to a recorded attorney-client call and then

taken “steps to conceal that tactical advantage”—facts that Morehead later tried to

“minimize, deflect, and obfuscate.” In re CCA Recordings 2255 Litigation, No. 2:19cv-2166-JAR-JPO, Doc. 1033 at 49-50 (D. Kan. Dec. 9, 2021). The district court found

that Morehead’s conduct was “consistent with the litigation philosophy of USAO

prosecutors” who believed it was permissible to listen to recordings of attorney-client

phone calls from the detention center when they came across them. Id. And the

district court found that Morehead’s conduct was consistent with “the official

litigating position” of the USAO that it could unilaterally decide whether or not an

attorney-client communication was fair game. Id.

Just how many prosecutors sought this tactical advantage in how many cases

remains unknown because most of the § 2255 cases never made it to an evidentiary

hearing. Instead, the district court held in a consolidated order that—even assuming

that the government had intentionally and without a legitimate law-enforcement

justification

become

privy

the

movants’

confidential

attorney-client

communications—movants whose communications were collected between their

guilty pleas and their sentencing hearings (as opposed to before trial) would have to

show prejudice to establish a Sixth Amendment violation and justify a remedy.

R1.658-60.

Applying this new rule in Mr. Orduno-Ramirez’s case, the district court

denied relief without an evidentiary hearing, on grounds that Mr. Orduno-Ramirez

would be unable to show prejudice. R2.266, 550.

2. Tenth Circuit Proceedings

Mr. Orduno-Ramirez appealed, along with nine other § 2255 movants whose Sixth

Amendment claims were based on post-plea, pre-sentencing intrusions and had been

dismissed for lack of prejudice. The Tenth Circuit partially consolidated the appeals

and then abated all but Mr. Orduno-Ramirez’s. United States v. Orduno-Ramirez, No.

22-3018 (10th Cir. Order filed March 10, 2022). The Tenth Circuit then granted Mr.

Orduno-Ramirez a certificate of appealability to address whether the district court

erred in holding that post-plea, pre-sentencing intrusions—even if intentional and

unjustified—do not violate the Sixth Amendment unless they prejudice the

defendant. United States v. Orduno-Ramirez, No. 22-3018 (10th Cir. Order filed June

16, 2022).

The Tenth Circuit affirmed. Pet. App. 26a. The Tenth Circuit acknowledged that

“the Government does not dispute the district court’s findings that (1) its acquisition

of the video footage intruded on attorney-client communications or (2) the intrusion

lacked a legitimate law-enforcement purpose.” Pet. App. 17a. And the Tenth Circuit

shared the district court’s “deep concern about the USAO’s systemic intrusions into

many attorney-defendant communications at the CCA,” recognizing that “the USAO’s

systemic conduct may point to the need for a ‘prophylactic rule.’” Pet. App. 23a

(citation omitted). But the Tenth Circuit concluded that when prosecutors engage in

these intrusions between a defendant’s guilty plea and sentencing, they do not violate

the Sixth Amendment unless they succeeded in prejudicing the defendant. Pet. App.

23a-24a.3

Mr. Orduno-Ramirez petitioned for both panel rehearing and rehearing en banc.

The Tenth Circuit denied both petitions. Pet. App. 66a.

REASONS FOR GRANTING THE WRIT

1. Deliberate and systemic prosecutorial intrusions into the defense camp

undermine the legitimacy of our adversarial system and cry out for this

Court’s attention.

This Court has called deliberate prosecutorial interceptions of attorney-client

communications “government intrusion of the grossest kind upon the confidential

relationship between the defendant and his counsel.” Hoffa v. United States, 385 U.S.

293, 306 (1966). And this Court has warned prosecutors that particularly egregious

or repeated misconduct might justify a remedy even absent prejudice. See, e.g., United

States v. Morrison, 449 U.S. 361, 365 n.2 (1981) (holding that agents’ interference

3 The Tenth Circuit also found that the government had affirmatively shown that its intrusion did

not prejudice Mr. Orduno-Ramirez at sentencing. Pet. App. 24a-26a. This finding is irrelevant to the

question presented, which asks solely whether prejudice in individual cases ought to be on the table

in the first place.

with defendant’s attorney-client relationship did not justify dismissing indictment

absent prejudice, but noting that “a pattern of recurring violations . . . might warrant

the imposition of a more extreme remedy in order to deter further lawlessness”); Bank

of Nova Scotia v. United States, 487 U.S. 250, 259 (1988) (holding that, “as a general

matter,” prosecutorial misconduct before the grand jury must be prejudicial to justify

dismissing indictment, but distinguishing cases “with a history of prosecutorial

misconduct, spanning several cases, that is so systematic and pervasive as to raise a

substantial and serious question about the fundamental fairness of the process”);

Brecht v. Abrahamson, 507 U.S. 619, 638 n.9 (1993) (noting that habeas relief might

be warranted absent prejudice for “deliberate and especially egregious” trial

misconduct or “a pattern of prosecutorial misconduct”); cf. United States v. Russell,

411 U.S. 423, 432-33 (1973) (“we may some day be presented with a situation in which

the conduct of law enforcement agents is so outrageous that due process principles

would absolutely bar the government from invoking judicial processes to obtain a

conviction”).

It’s time for this Court to put some teeth into these warnings. A criminal-justice

system can only earn the public’s deference and assistance through its own moral

credibility. Paul H. Robinson, Criminal Law’s Core Principles, 14 Wash. U.

Jurisprudence Rev. 153 (2021); Cf. Williams v. Pennsylvania, 579 U.S. 1, 15-16 (2016)

(holding that appellate judge’s failure to recuse was structural error in part because

“[b]oth the appearance and reality of impartial justice are necessary to the public

legitimacy of judicial pronouncements and thus to the rule of law itself”). Cheating is

wrong, especially by those who wield the significant power of prosecutors. Prosecutors

who cheat undermine the credibility of the system, which presupposes two equal

opponents acting within a clear set of rules. And prosecutors who cheat by spying on

the defense camp commit the “grossest kind” of intrusion, Hoffa, 385 U.S. at 306,

“strik[ing] at the center of the protections afforded by the Sixth Amendment.”

Shillinger, 70 F.3d at 1141.

This Court’s intervention is critical given the Kansas USAO’s years-long

“systematic practice of purposeful collection, retention, and exploitation of calls,” 429

F.Supp.3d at 849-54, 900; its full-bore grab of video and audio recordings in Carter,

id. at 835, 848-49; its “intent to deprive the Special Master and the FPD of evidence”

during the ensuing investigation, id. at 874, and its blatant violation of discovery

orders in the consolidated § 2255 cases, R1.377. To this day, the Kansas USAO denies

any Sixth Amendment violations. The legal implications of the Kansas USAO’s

misconduct matter not only to the Kansas defendants whose communications were

collected, but also to the courts, the bar, and the public as a whole.

The Tenth Circuit has now twice announced that it “condemn[s] the conduct of the

Kansas U.S. Attorney’s Office.” United States v. Spaeth, 69 F.4th 1190, 2023 WL

3940537 at *1 (10th Cir. 2023); accord Pet. App. 23a (stating that “we share” the

district court’s “deep concern about the USAO’s systemic intrusions”). But

condemnation without consequences is an empty gesture. As the venerable Judge

Frank once warned: “Government counsel, employing such tactics, are the kind who,

eager to win victories, will gladly pay the small price of a ritualistic verbal spanking.

The practice of [denouncing prosecutors without reversing their victories]—recalling

the bitter tear shed by the Walrus as he ate the oysters—breeds a deplorably cynical

attitude towards the judiciary.” United States v. Antonelli Fireworks Co., 155 F.2d

631, 661 (2d Cir. 1946) (Frank, J., dissenting).

This Court and only this Court can correct that cynical attitude by granting

certiorari and holding that when prosecutors access confidential attorney-client

communications before a defendant is sentenced, and do so intentionally and without

any legitimate law-enforcement justification, those intrusions are structural Sixth

Amendment violations justifying a remedy regardless of prejudice. Such a rule would

not be unfair to the government—after all, it is completely within every prosecutor’s

control to avoid such intrusions. Cf. Strickland v. Washington, 466 U.S. 668, 692

(1984) (“In certain Sixth Amendment contexts, prejudice is presumed,” including

“various kinds of state interference with counsel’s assistance” that, “because the

prosecution is directly responsible,” are “easy for the government to prevent”). Review

is necessary for institutional reasons and to protect the rule of law.

2. How to identify structural constitutional error is a question of

exceptional importance to both federal and state courts.

In Chapman v. California, 386 U.S. 18 (1967), this Court held that most

constitutional errors are subject to harmless-error analysis; that is, they will not

justify a remedy unless they prejudiced the defendant. This Court nonetheless

recognized that some constitutional errors can never be treated as harmless. Id. at

23. Ever since Chapman, courts have struggled to identify which errors fall into

which category. See Justin Murray, Policing Procedural Error in the Lower Criminal

Courts, 89 FORDHAM L. REV. 1411, n.98 (2021) (“These labels are not helpful.”);

Zachary L. Henderson, A Comprehensive Consideration of the Structural-Error

Doctrine, 85 Mo. L. Rev. 965 (2020) (canvassing cases); David McCord, The

“Trial”/”Structural” Error Dichotomy: Erroneous, and Not Harmless, 45 U. KAN. L.

REV. 1401 (1997) (discussing “rampant confusion” over how to identify structural

errors).

One criminal-procedure treatise attributes this struggle to the fact that even this

Court’s own members “continue to disagree about the appropriate analysis for

distinguishing between those errors that may be harmless and those that may not be

harmless.” Wayne R. LaFave, et al., 7 CRIM. PROC. § 27.6(d) (4th ed. Nov. 2022).

Another commentator, in contrast, finds this Court’s cases “both conservative and

cohesive,” while “the ‘structural’ errors identified by the circuit courts are anything

but—exposing the need for a clearer and more accurate prescriptive definition of

structural error.” Henderson, A Comprehensive Consideration of the Structural-Error

Doctrine, 85 Mo. L. Rev. at 982.

Either way, how to identify structural constitutional error is a question of

exceptional importance to both federal and state courts. It is a question that

frequently reflects tension between concerns about the outcome in a particular case

(courts are loath to grant what they view as a “windfall” to criminal defendants) and

concerns about systemic interests beyond the case at hand. Compare, e.g., State v.

Paumier, 288 P.3d 1126, 1130 (Wash. 2012) (en banc) (finding violation of public-trialright procedural rule structural error justifying reversal regardless of prejudice, in

part because of right’s unique importance to the public), with id. at 1133 (Madsen,

C.J., dissenting on grounds that treating violation as structural error resulted in

“defendant automatically obtaining the windfall of reversal of his conviction and a

new trial”).

This Court has sometimes resolved this tension by prioritizing core constitutional

rights over individual case outcomes when those rights are not just derived from our

general interest in fair judicial proceedings, but are, rather, part of the essential

framework in which those proceedings are constitutionally required to take place.

United States v. Gonzalez-Lopez, 548 U.S. 140, 148-49 (2006) (denial of right to

counsel of choice is “structural defect” affecting “the framework within which the trial

proceeds,” rather than “simply an error in the trial process itself”). And thus

considerations of prejudice in an individual case are off the table when it comes to

enforcing the constitutional framework for a discrimination-free judicial system,

Vasquez v. Hillery, 474 U.S. 254 (1986); Ballard v. United States, 329 U.S. 187 (1946);

unbiased judges and juries, Williams v. Pennsylvania, 579 U.S. 1 (2016); Gray v.

Mississippi, 481 U.S. 648 (1987); Tumy v. Ohio, 273 U.S. 510 (1927); public trials,

Waller v. Georgia, 467 U.S. 39 (1984); counsel in criminal cases, Gonzalez-Lopez,

548 U.S. 140; Gideon v. Wainwright, 372 U.S. 335 (1963); defendant autonomy,

McCoy v. Louisiana, 138 S.Ct. 1500 (2018); Faretta v. California, 422 U.S. 806 (1975);

and jury verdicts, Sullivan v. Louisiana, 508 U.S. 275 (1993).

Despite these many examples, it remains difficult to identify which rights are

structural (“framework”-related) and which rights are not. This Court has relied on

one or more of three “broad” but “not rigid” rationales when deeming rights

structural: (1) when the “right at issue is not designed to protect the defendant from

erroneous conviction but instead protects some other interest”; (2) “if the effects of

the error are simply too hard to measure”; and (3) “if the error always results in

fundamental unfairness.” Weaver v. Massachusetts, 582 U.S. 286, 294-96 (2017).

This Court illustrated the “other interest” rationale in Williams when it held that

“an unconstitutional failure to recuse constitutes structural error” justifying a

remedy regardless of prejudice and “even if the judge in question did not cast a

deciding vote.” 579 U.S. at 14. As this Court explained, “[b]oth the appearance and

reality of impartial justice are necessary to the public legitimacy of judicial

pronouncements and thus to the rule of law itself.” Id. at 16. Framework-related

interests are so much stronger than individual outcomes in the defendant-autonomy

context that this Court enforces autonomy rights without regard to prejudice even

while recognizing that doing so “usually increases the likelihood of a trial outcome

unfavorable to the defendant.” McKaskle v. Wiggins, 465 U.S. 168, 177 n.8 (1984)

(emphasis added). In sum, “[t]he very premise of structural-error review is that even

convictions reflecting the ‘right’ result are reversed for the sake of protecting a basic

right.” Neder v. United States, 527 U.S. 1, 34 (1999) (Scalia, J., dissenting in part).

This means that sometimes individual defendants will get a second crack at things

(a trial, a sentencing, an appeal), not because their personal interests were harmed

the first time around, but because a court or prosecutor has blundered in a way that

disrupts the very framework of our constitutional system.4

When an entire United States Attorney’s Office has not merely blundered, but has

intentionally, secretly, and repeatedly disrupted that framework in countless cases,

it seems like an easy case for declaring structural error. But then again, this Court

has adopted a “strong presumption” that constitutional errors are subject to

harmless-error analysis, Rose v. Clark, 478 U.S. 570 (1986), and described structural

errors as “a very limited class of errors,” United States v. Marcus, 560 U.S. 258, 263

(2010) (citation omitted) that are “highly exceptional,” United States v. Davila, 569

U.S. 597, 611 (2013). These cautionary flags are understandable, and yet they leave

courts erring on the side of right results over basic rights. Here, for instance, the

Tenth Circuit recognized that “the USAO’s systemic conduct may point to the need

for a ‘prophylactic rule[ ],’” but the Tenth Circuit was sufficiently worried about this

Court’s “caution against per se or sweeping Sixth Amendment rules that obviate

consideration of prejudice in every instance” that it found “insufficient reason here to

adopt a per se rule.” Pet. App. 18a, 23a. Which raises the question: if not here, where?

This Court has previously granted certiorari to review and correct erroneous

adoptions of structural-error rules. See, e.g., Greer v. United States, 141 S.Ct. 2090,

2099-2100 (2021) (reversing Fourth Circuit decision vacating conviction without

4 It is usually not the case that recognizing error to be structural frees the defendants who benefit

from that recognition. Structural error justifies a remedy regardless of prejudice, but what remedy is

a separate question (a question that is not presented here). See Waller v. Georgia, 467 U.S. 39, 49-50

(1984) (discussing distinction between recognizing error and choosing a remedy “appropriate to the

violation”); United States v. Morrison, 449 U.S. 361, 364-66 & n.2 (1981) (assuming Sixth

Amendment error and discussing how remedies “should be tailored to the injury”).

regard to prejudice due to error in plea colloquy); Davila, 569 U.S. at 608-13

(reversing Eleventh Circuit decision vacating conviction without regard to prejudice

where magistrate judge improperly participated in plea discussions); Marcus, 560

U.S. at 262-67 (reversing Second Circuit decision vacating conviction on ex post facto

grounds without regard to prejudice); Weatherford, 429 U.S. at 557-58 (reversing

Fourth Circuit decision vacating conviction without regard to prejudice where

undercover agent attended defendant’s attorney-client meetings but did not convey

details of conversation to the prosecution).

This Court should grant certiorari to review and correct the Tenth Circuit’s

erroneous rejection of a structural-error rule here.

3. The Tenth Circuit’s decision undervalues a core Sixth Amendment right;

the critical nature of sentencing proceedings; and the role of legitimacy

and deterrence interests in structural-error analyses.

The Tenth Circuit’s decision here undervalues the Sixth Amendment’s core

requirement of confidentiality; the critical nature of sentencing proceedings; and the

role of legitimacy and deterrence interests in structural-error analyses.

a. State and federal courts have long recognized that the right to private

communications with counsel is at the core of the right to counsel. Coplon v. United

States, 191 F.2d 749, 758 (D.C. Cir. 1951) (“The sanctity of the constitutional right of

an accused privately to consult with counsel is generally recognized and zealously

enforced by state as well as federal courts.”); In re Rider, 195 P. 965, 966 (Cal. App.

1920) (“it is the absolute right of parties charged with crime to consult privately with

their attorneys”); State v. Davis, 130 P. 962, 964 (Okla. Ct. Crim. App. 1913) (same;

“if parties in prison and charged with crime are compelled to consult their attorneys

in the presence of an officer or officers of the law, the very object and purpose of the

Constitution and of the statute would be defeated . . . [t]his alone would render such

consultations a miserable and contemptible farce”).

This core value of confidentiality plays a critical role in the adversarial process.

The defendant “requires the guiding hand of counsel at every step in the proceedings

against him.” Powell v. Alabama, 287 U.S. 45, 61 (1932). To benefit from that guiding

hand, “[a] criminal defendant’s ability to communicate candidly and confidentially

with his lawyer is essential.” Nordstrom v. Ryan, 762 F.3d 903, 910 (9th Cir. 2014).

Indeed, “those necessary conferences between counsel and accused” are nearly

sacrosanct, “sometimes partak[ing] of the inviolable character of the confessional.”

Powell, 287 U.S. at 69; accord Nordstrom, 762 F.3d at 910 (“In American criminal

law, the right to privately confer with counsel is nearly sacrosanct.”). Given the value

and sensitivity of information exchanged during attorney-client conferences, that

information “must be insulated from the government” “[i]n order for the adversary

system to function properly.” United States v. Levy, 577 F.2d 200, 209 (3d Cir. 1978).

The

Sixth

Amendment

thus

necessarily

“protect[s]

the

attorney-client

relationship from intrusion in the criminal setting.” Wolff v. McDonnell, 418 U.S. 539,

576 (1974). In other words, the right to confidentiality of communications with

counsel is—like the right to counsel of choice—part of the Sixth Amendment

framework in which criminal proceedings are constitutionally required to take place.

See Gonzalez-Lopez, 548 U.S. at 148-49. The Tenth Circuit undervalued the core

value of this right when it refused to enforce it here absent prejudice.

b. Courts and commentators alike have recognized that “[t]he sentencing phase of

a criminal stage is one of the most critical stages of the judicial process.” Nancy Fox

Kaden, Sentencing, 73 GEO. L. J. 671, 671 (Dec. 1984). Indeed, given the fact that

“[t]he vast majority of [criminal] cases not dismissed ultimately result in conviction,

either after a trial or as a result of a negotiated plea,” sentencing is usually not just

“one of,” but “the most critical stage of a criminal prosecution, and the proceeding

having the greatest personal impact on the defendant.” 3 CRIM. PRAC. MANUAL § 102:2

(March 2023) (emphasis added); accord United States v. Ruiz-Rodriguez, 277 F.3d

1281, 1291 (11th Cir. 2002) (initial sentencing in a felony case is “often the most

critical stage when a defendant pleads guilty”); United States v. Jackson, 32 F.3d

1101, 1109 (7th Cir. 1994) (“sentencing is the most critical stage of criminal

proceedings, and is, in effect, the ‘bottom-line’ for the defendant” (marks and citations

omitted)).

Federal sentencing proceedings in particular are dizzyingly complex proceedings

during which the district court is required to “subject[ ] the defendant’s sentence to

the thorough adversarial testing contemplated by the federal sentencing procedure.”

Rita v. United States, 551 U.S. 338, 351 (2007). And prosecutors play an

“indispensable role” in these proceedings. Department of Justice Manual (JM) 927.710 cmt. (emphasis added).5 For instance, prosecutors provide the Probation Office

with detailed facts to include in the PSR, some of which are “obtainable only from

prosecutorial or investigative files to which probation officers do not have access.” JM

5 Available at https://www.justice.gov/jm/justice-manual.

9-27.720(1) & cmt.; see, e.g., R3.17-18 (PSR allegations derived from FBI reports).

And prosecutors routinely recruit and rely on cooperating witnesses for material

aspects of those facts. See, e.g., R3.18-19 (PSR allegations derived from proffer

statements). If a defendant objects to a fact that will affect sentencing, the prosecutor

then bears the burden of proving that fact at the sentencing hearing by a

preponderance of the evidence. United States v. McDonald, 43 F.4th 1090, 1095 (10th

Cir. 2022); Fed. R. Crim. P. 32(i)(3)(B); JM 9-27.720(5) cmt. (“the government should

be prepared to substantiate significant factual allegations disputed by the defense”).

Prosecutors also advocate for fact-sensitive adjustments that “can have a profound

effect on the defendant’s sentence.” JM 9-27.720(2) cmt. They gather and present

victim-impact statements at sentencing. Manual 9-27.720(6) cmt. (prosecutors should

“notify victims” of their statutory right to allocution and “notify the court of any

victims wishing to make a statement”). They advocate for upward variances, respond

to defense requests for leniency, and decide when to recommend sentence reductions

for substantial assistance. JM 9-27.730. With so many factual and legal issues in

play, prosecutors have many opportunities at sentencing to take strategic advantage

of the content of a defendant’s confidential communications with counsel.

The Tenth Circuit has previously recognized the unacceptable risk that

intentional, unjustified pre-trial intrusions pose, and has adopted a structural-error

rule regarding those intrusions. See Shillinger v. Haworth, 70 F.3d 1132 (10th Cir.

1995) (prosecutor per se violated Sixth Amendment where prosecutor intentionally

and unjustifiably became privy to attorney-client communications before trial;

harmless-error rule did not apply). But here the Tenth Circuit found “no reason to

expect a risk of prejudice at sentencing from a post-plea intrusion” that rises to the

level of what might occur at trial from a pre-trial intrusion. Pet. App. 19a-21a. In

finding that post-plea, pre-sentencing intrusions do not violate the Sixth Amendment,

the Tenth Circuit undervalued and understated the critical nature of sentencing

proceedings.

c. Perhaps more importantly, the Tenth Circuit’s focus on the likelihood of

prejudice at sentencing distracted it from any genuine inquiry into legitimacy and

deterrence interests as valid reasons to adopt a structural-error rule here. The Tenth

Circuit touched on these latter concerns only long enough to reject them on grounds

that such rules are “blunt legal instrument[s]” that this Court has “caution[ed]

against.” Pet. App. 7a, 17a-18a.

By defaulting to this presumption against structural-error rules without giving

legitimacy and deterrence interests their due, the Tenth Circuit liberated prosecutors

to carry on collecting and exploiting attorney-client communications “with a fair

assurance of impunity.” Justin Murray, Policing Procedural Error in the Lower

Criminal Courts, 89 FORDHAM L. REV. at 1432-36 (2021). Harm to the system matters

to the courts, the bar, and the public as a whole. But as long as courts like the Tenth

Circuit continue to believe “that outcome-determinative prejudice is the only kind of

harm that truly matters, deep reform will elude our grasp.” Id. at 1441. The Kansas

USAO broke the rules for years, concealed its misconduct, and then lied about it. The

Tenth Circuit erred when it held that the USAO’s intentional, secret, systemic, and

unjustified post-plea, pre-sentencing intrusions neither violated the Sixth

Amendment nor justified a remedy absent prejudice. Review is necessary.

4. No vehicle problems stand in the way of this Court’s review.

Finally, this case presents no procedural impediments to reviewing the question

presented. Mr. Orduno-Ramirez timely sought appellate review of the district court’s

order denying his § 2255 motion. The question presented was fully litigated in the

appellate briefs and at oral argument in the Tenth Circuit, and that court decided the

issue in a published decision. If this Court were to hold that post-plea, pre-sentencing

intrusions of the egregious type that occurred are structural Sixth Amendment

violations justifying a remedy regardless of prejudice, then Mr. Orduno-Ramirez and

several others whose appeals remain abated in the Tenth Circuit would be entitled

to return to the district court and pursue their § 2255 claims. No vehicle problems

stand in the way of this Court’s review.

CONCLUSION

For the above reasons, this Court should grant this petition for a writ of certiorari.

Respectfully submitted,