United States v. Orduno-Ramirez

61 F.4th 1263

• Court: Court of Appeals for the Tenth Circuit
• Decided: March 10, 2023
• Docket: 22-3019
• Status: Published

Opinion

Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 1 FILED United States Court of Appeals PUBLISH Tenth Circuit

UNITED STATES COURT OF APPEALS March 10, 2023

Christopher M. Wolpert FOR THE TENTH CIRCUIT Clerk of Court _________________________________

UNITED STATES OF AMERICA,

Plaintiff - Appellee,

v. No. 22-3019

OMAR FRANCISCO ORDUNO- RAMIREZ,

Defendant - Appellant. _________________________________

Appeal from the United States District Court for the District of Kansas (D.C. Nos. 2:19-CV-02491-JAR-JPO, 2:19-CV-02166-JAR-JPO & 2:14-CR-20096-JAR-7) _________________________________

Paige A. Nichols, Assistant Federal Public Defender (Melody Brannon, Federal Public Defender, with her on the briefs), Topeka, Kansas, for Defendant-Appellant.

Bryan C. Clark, Assistant United States Attorney (Duston J. Slinkard, United States Attorney; Carrie N. Capwell, and James A. Brown, Assistant United States Attorneys, with him on the briefs), Kansas City, Kansas, for Plaintiff-Appellee. _________________________________

Before MATHESON, KELLY, and PHILLIPS, Circuit Judges. _________________________________

MATHESON, Circuit Judge. _________________________________

Omar Francisco Orduno-Ramirez pled guilty to a conspiracy drug offense. He

received a below-Guidelines-range prison sentence of 144 months, which we affirmed on Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 2

direct appeal. After he pled guilty, but before he was sentenced, the Kansas United States

Attorney’s Office (“USAO”) obtained soundless video recordings of five meetings

between Mr. Orduno-Ramirez and his attorney.

Mr. Orduno-Ramirez sought postconviction relief under 28 U.S.C. § 2255, arguing

the Government violated the Sixth Amendment by intruding on his meetings with

counsel. The district court denied relief. It said that Shillinger v. Haworth, 70 F.3d 1132

(10th Cir. 1995)—which held that a pre-plea or pre-conviction (“pretrial”) intrusion is a

per se Sixth Amendment violation—does not apply to post-plea intrusions. Instead, the

court determined that Mr. Orduno-Ramirez was required to show prejudice and found he

had not done so.

We granted a certificate of appealability (“COA”) on the following issue:

[W]hether the district court erred in concluding that the United States’ purposeful sentencing-phase intrusion into a defendant’s confidential attorney-client communications is not a per se Sixth Amendment violation.

Doc. 10920619, at 2.

Exercising jurisdiction under 28 U.S.C. §§ 1291 and 2253(a), we affirm the

denial of Mr. Orduno-Ramirez’s § 2255 motion. We agree with the district court that

the Shillinger per se rule does not apply. We affirm because the Government has

shown the intrusion did not prejudice Mr. Orduno-Ramirez’s sentencing, and

Mr. Orduno-Ramirez does not argue he suffered any prejudice.

2 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 3

I. BACKGROUND – USAO INTRUSIONS

A. Attorney-Client Intrusions

CoreCivic (“CCA”) is a private detention facility in Leavenworth, Kansas.

See United States v. Carter, 429 F. Supp. 3d 788, 798 n.5 (D. Kan. 2019).1 In 2016,

the USAO suspected that certain inmates at CCA were engaged in a drug-smuggling

conspiracy. Id. The USAO initiated an investigation. Id. It obtained and served a

broad grand jury subpoena asking for all video and still images from all surveillance

cameras at CCA, including footage from attorney visitation rooms. The subpoena

also requested recordings of inmates’ telephone calls, including calls with their

attorneys. Id. at 846-48. The subpoena garnered information on “potentially

hundreds of CCA detainees.” Id. at 869. The investigation led to the indictment of

Karl Carter and five others for conspiracy to distribute controlled substances in the

CCA. Id. at 801. At a discovery conference, the government “discussed having

obtained voluminous video-surveillance footage from video cameras stationed

throughout the CCA facility.” Id.

1 Much of our discussion of the factual background derives from the district court’s August 13, 2019 order in United States v. Carter, which includes the district court’s findings about the USAO’s intrusions into attorney-client communications at CCA. 429 F. Supp. 3d at 788. Both parties here use facts from Carter, see Aplt. Br. at 4; Aplee. Br. at 47, and neither argues Carter’s factual findings were clearly erroneous. See United States v. Craine, 995 F.3d 1139, 1153 (10th Cir. 2021) (we review a district court’s factual findings for clear error).

3 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 4

B. The District Court’s Investigation and Findings

When the Federal Public Defender for the District of Kansas (“FPD”) learned

about the foregoing, it was allowed to “intervene . . . in [the Carter] case on behalf of

its many clients detained at CCA.” Id. at 799. The FPD “filed a motion for return of

property under Fed. R. Crim. P. 41(g)” in “dozens of . . . active cases” to divest the

USAO of the recordings. Id. at 801, 802 n.13. The district court held several

evidentiary hearings to “find out from the Government the scope of its discovery

efforts that potentially intruded on confidential in-person and telephonic attorney-

client meetings, but the Government evaded the Court’s questions, and denied that its

practices implicated the Sixth Amendment.” Id. at 799.

In October 2016, the district court appointed a special master to investigate.

Id. at 802. It instructed the USAO to cooperate with the special master, return

privileged material it had obtained unlawfully, and preserve documents relevant to

the investigation. Id. at 808-10. But according to the court, the USAO defied these

instructions by (1) deleting files from its computer system and refusing to preserve

computer hard drives, id. at 814-18; (2) delaying implementation of a litigation hold

on relevant files, id. at 818-23; (3) failing to make personnel available to the special

master, id. at 827; (4) failing to produce documents the special master requested,

id. at 828-29; and (5) misrepresenting to the court whether specific USAO attorneys

reviewed certain attorney-client communications, id. at 831.

Based on the special master’s findings, the district court found that USAO

attorneys intentionally intruded on attorney-client communications because they

4 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 5

knew the subpoena would sweep in video footage and phone calls but took no

reasonable steps to filter out privileged material. Id. at 835-36; 848; 864-65; 898.

The court also found there was “no legitimate law-enforcement purpose” for the

breadth of the USAO’s collection of attorney-client communications. Id. at 899.

And the court documented at least one occasion on which USAO attorneys used

information they gained from the defendant’s attorney-client communications to

influence plea negotiations with that defendant. Id. at 853.

In sum, the district court found that the USAO intruded into a large number of

defendants’ communications with their attorneys, with no legitimate law-enforcement

purpose, and later tried to conceal these actions. As the district court put it, the

USAO committed “systemic prosecutorial misconduct” with “far reaching

implications in scores of pending [] cases,” and exacerbated the harm by “delay[ing]

and obfuscat[ing] th[e] investigation” into its misconduct. Id. at 903.

By the time of the Carter opinion in 2019, many defendants affected by the

USAO intrusions, including Mr. Orduno-Ramirez, ROA, Vol. II at 293, had filed

motions for post-conviction relief under § 2255. Carter, 429 F. Supp. 3d at 903. The

district court reassigned all of those cases to itself, id. at 904, and later aggregated

them into one “consolidated master case.” See ROA, Vol. I at 444; see also In re

CCA Recordings 2255 Litig., No. 19-2491 (D. Kan.) (the “consolidated master

case”).

5 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 6

C. Legal Background

The Sixth Amendment Right to Counsel

The Sixth Amendment guarantees criminal defendants the right to effective

assistance of counsel “at all ‘critical’ stages of the criminal proceedings.” Missouri

v. Frye, 566 U.S. 134, 140 (2012) (quotations omitted). Sentencing is one of the

“critical stages.” See, e.g., Strickland v. Washington, 466 U.S. 668, 686 (1984).

Because the primary purpose of the right to counsel is “to secure the

fundamental right to a fair trial,” the “‘benchmark’ of a Sixth Amendment claim is

‘the fairness of the adversary proceeding.’” Shillinger v. Haworth, 70 F.3d 1132,

1141 (10th Cir. 1995) (quoting Nix v. Whiteside, 475 U.S. 157, 175 (1986)). Thus, to

prove a Sixth Amendment violation, a defendant must normally demonstrate “some

effect of [the] challenged conduct on the reliability of the trial process”—prejudice.

Shillinger, 70 F.3d at 1141 (quotations omitted). To establish prejudice, a defendant

must normally show “that there is a realistic possibility of injury to defendants or

benefit to the [government].” Id. at 1140 (quoting United States v. Mastroianni,

749 F.2d 900, 907 (1st Cir. 1984) (quotations omitted)).

But “[i]n certain Sixth Amendment contexts, prejudice is presumed.”

Id. at 1141 (alterations in original) (quoting Strickland, 466 U.S. at 692). These

include “various kinds of state interference with counsel’s assistance.” Strickland,

466 U.S. at 692. For example, the Supreme Court has found per se Sixth Amendment

violations when the government prevented the defendant from “consult[ing] his

attorney” before testifying, Geders v. United States, 425 U.S. 80, 81 (1986), or barred

6 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 7

direct examination of the defendant, Ferguson v. Georgia, 365 U.S. 570 (1961). See

also United States v. Lustyik, 833 F.3d 1263, 1269-70 (10th Cir. 2016) (listing types

of per se Sixth Amendment violations). “[P]rejudice in these circumstances is so

likely that case-by-case inquiry into prejudice is not worth the cost.” Strickland,

466 U.S. at 692.

In United States v. Cronic, 466 U.S. 648 (1984), when discussing ineffective-

assistance-of-counsel claims, the Supreme Court identified three circumstances when

a per se rule is appropriate: (1) the defendant suffers “the complete denial of counsel

. . . at a critical stage” of the criminal justice process; (2) “counsel entirely fails to

subject the prosecution’s case to meaningful adversarial testing”; and (3) when “the

likelihood that any lawyer, even a fully competent one, could provide effective

assistance is so small that a presumption of prejudice is appropriate.” Id. at 659-60.

These examples illustrate that a per se Sixth Amendment rule is appropriate only for

extreme situations. See Florida v. Nixon, 543 U.S. 175, 190 (2004) (Cronic

“illustrated just how infrequently the surrounding circumstances will justify a

presumption of ineffectiveness” (quotation and citation omitted)).

The Court’s caution about per se rules also extends to cases where the

defendant alleges government interference in an attorney-client relationship. For

instance, in Weatherford v. Bursey, 429 U.S. 545 (1977), the Court struck down a

Sixth Amendment per se rule that bypassed the prejudice question. There, an

undercover officer participated in the defendant’s trial strategy meetings with defense

counsel. Id. at 547-48. The court of appeals reversed the defendant’s conviction,

7 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 8

adopting a “per se right-to-counsel rule” under which any time an undercover officer

intruded on attorney-client conversations, “a violation of the defendant's

constitutional rights has occurred . . . whether or not any specific prejudice to the

defendant’s preparation for or conduct of the trial is demonstrated or otherwise

threatened.” Id. at 550. The Court held that this “per se rule cut[] much too

broadly.” Id. at 557. Instead, it said the defendant should be required to demonstrate

some likelihood of prejudice due to the intrusion—which was lacking because “at no

time did [the officer] discuss with or pass on to . . . the prosecuting attorney . . . any

details or information regarding [the defendant’s] trial plans.” Id. at 548 (quotations

omitted); see also id. at 557-58.

In United States v. Morrison, 449 U.S. 361 (1981), the Court again reversed a

per se Sixth Amendment ruling. Id. at 363-64. The Third Circuit had “concluded

that [the defendant’s] Sixth Amendment right to counsel had been violated” by law

enforcement agents who spoke to her outside her attorney’s presence, “and that

whether or not any tangible effect upon [the defendant’s] representation had been

demonstrated or alleged, the appropriate remedy was dismissal of the indictment with

prejudice.” Id. at 363. The Court disagreed, writing that finding a per se violation

was inappropriate, and that any Sixth Amendment remedy must be tailored to address

the prejudice the defendant suffered. Id. at 365 (“Our approach [to putative Sixth

Amendment violations] has thus been to identify and then neutralize the taint by

tailoring relief appropriate in the circumstances to assure the defendant the effective

8 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 9

assistance of counsel and a fair trial . . . . Absent such impact on the criminal

proceeding, [] there is no basis for imposing a remedy in that proceeding . . . .”).2

Shillinger v. Haworth

In Shillinger, the defendant and his attorney conducted several “trial

preparation sessions.” 70 F.3d at 1134. Because the defendant was in custody, a

sheriff’s deputy was required to be present. Id. The defense attorney “paid the

deputy overtime wages for his services,” “instructed the deputy to consider himself

an employee of defense counsel during the [] sessions,” and said that “none of this

goes out of this room.” Id. But the deputy spoke with the prosecuting attorney, who

obtained damaging information about the defense and attempted to use it at trial.

Id. at 1134-36. After a jury convicted the defendant, he sought post-conviction relief,

arguing the deputy’s actions violated his Sixth Amendment right to counsel.

Id. at 1136.

We agreed and adopted a per se rule,3 holding that “a prosecutor’s intentional

intrusion into the attorney-client relationship constitutes a direct interference with the

2 The Court has occasionally upheld per se Sixth Amendment rules in government-interference cases. But as the Court wrote in Strickland, most of these rules apply to situations where the government “interferes in certain ways with the ability of counsel to make independent decisions about how to conduct the defense,” such as a “bar on summation at [a] bench trial,” a “requirement that [the] defendant be [the] first defense witness,” or a “bar on direct examination of [the] defendant.” 466 U.S. at 686 (collecting cases; citations omitted). 3 When we decided Shillinger, there was a circuit split on whether “intentional intrusions by the prosecution [on a defendant’s attorney-client relationship] constitute per se violations of the Sixth Amendment.” 70 F.3d at 1140. Some courts held that such an intrusion automatically entitled a defendant to a new trial; others held that 9 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 10

Sixth Amendment rights of a defendant . . . . [A]bsent a countervailing state interest,

such an intrusion must constitute a per se violation of the Sixth Amendment.”

Id. at 1142. Put differently, “when the [government] becomes privy to confidential

communications because of its purposeful intrusion into the attorney-client

relationship and lacks a legitimate justification for doing so, a prejudicial effect . . .

must be presumed.” Id. This presumption is conclusive—the court must accept that

the defendant suffered prejudice even if the government presents evidence to the

contrary.4

In Shillinger, we provided two justifications for presuming prejudice: (1) the

inherent harmful effect of such intrusions on adversarial proceedings, especially the

trial; and (2) the need to deter government misconduct. Id.

First, we said intrusions into the attorney-client relationship are a “state-

created procedure[] [to] impair the accused’s enjoyment of the Sixth Amendment

guarantee by disabling his counsel from fully assisting and representing him.”

the defendant needed to show prejudice; and others imposed a rebuttable presumption of prejudice on the government. Id. at 1140-41. 4 Courts use the phrase “conclusive presumption” as synonymous with irrebuttable presumption. See, e.g., Halliburton Co. v. Erica P. John Fund, Inc., 573 U.S. 258, 268-69 (2014). A “rebuttable presumption” is one that may be disproved. Id. (discussing the difference between conclusive and rebuttable presumptions). Instead of using the phrase “conclusive presumption,” Shillinger said that a pretrial intrusion is a “per se violation of the Sixth Amendment. In other words . . . a prejudicial effect on the reliability of the trial process must be presumed.” 70 F.3d at 1142. We use “conclusive presumption” to denote the Shillinger rule.

10 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 11

Id. at 1141 (quoting United States v. Decoster, 624 F.2d 196, 201 (D.C. Cir. 1979)).

These intrusions inherently harm “the reliability of the trial process,” meaning

“[p]rejudice in these circumstances is so likely that case-by-case inquiry” about

prejudice is unnecessary. Id. at 1142 (alterations in original) (quoting Strickland,

466 U.S. at 692).

Second, we said “direct state interference” with attorney-client

communications is “susceptible to easy correction by prophylactic rules.” Id. at 1142

(quoting Decoster, 624 F.2d at 201). We concluded that “no other standard [than a

per se rule] can adequately deter this sort of misconduct.” Id. at 1142.

D. The District Court’s Generally Applicable Orders

After the district court discovered the USAO’s intrusions into attorney-client

communications, it issued a standing order appointing the FPD to represent

defendants with claims that the USAO violated their Sixth Amendment rights by

collecting privileged communications. The FPD filed separate motions under

28 U.S.C. § 2255 on behalf of multiple defendants, including Mr. Orduno-Ramirez,

and argued that they were entitled to a conclusive presumption of prejudice under

Shillinger. ROA, Vol. I at 638-51.

The district court aggregated these post-conviction proceedings into one

consolidated master case, In re CCA Recordings 2255 Litig., No. 19-2491. It then

divided over 100 consolidated petitioners’ alleged intentional-intrusion Sixth

Amendment claims into violations that occurred (1) before the plea or conviction,

11 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 12

(2) after the plea or conviction but before sentencing, and (3) after sentencing.

ROA, Vol. I at 641-42.

In December 2021, the district court issued a memorandum and order stating

general principles it would apply to the second category of claims—alleged Sixth

Amendment violations that occurred “post-plea or conviction but prior to

sentencing.” Id. at 653. For ease of reference, we refer to these situations as “post-

plea intrusions.” The court held that for such intrusions, Shillinger’s conclusive

presumption does not apply, and the defendant must show actual prejudice to be

entitled to relief. Id. at 652.5

The district court noted that “when the alleged intrusion occurs after the

petitioner entered a guilty plea or was convicted at trial, it eliminates the possibility

that the intrusion could have tainted the petitioner’s plea or conviction.” Id. Instead,

“[t]he only tainted proceeding could be sentencing.” Id. at 655. The court said the

justifications for Shillinger’s conclusive presumption do not support extending the

presumption to post-plea intrusions. Id. at 652. First, it found that Shillinger’s

likelihood-of-prejudice rationale applies with less force for a post-plea intrusion

5 The district court also held that under Tollett v. Henderson, 411 U.S. 258 (1973), defendants who suffered pretrial intrusions and later pled guilty waived any later challenge to those intrusions. Tollett held that “[w]hen a criminal defendant has [pled guilty], he may not thereafter raise independent claims relating to the deprivation of constitutional rights that occurred prior to the entry of the guilty plea,” except to the extent the deprivation rendered his plea involuntary. 411 U.S. at 267. The Tollett rule applies only to pre-plea constitutional violations. It does not foreclose relief for Mr. Orduno-Ramirez because his alleged Sixth Amendment violation occurred after he pled guilty.

12 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 13

violation because it does not “pervade the entire criminal proceeding . . . the way it

does at trial,” and “does not implicate the same potential for prejudice.” Id. at 655.

Second, as to Shillinger’s deterrence rationale, the district court said the USAO’s

misconduct was serious, but “[d]eterrence of such misconduct alone is not enough to

justify presumptive relief” absent “the fairness or reliability concerns identified” in

Shillinger. Id. at 657.

II. BACKGROUND – MR. ORDUNO-RAMIREZ’S CASE

Mr. Orduno-Ramirez’s case became enmeshed in the USAO intrusions

outlined above.

A. Indictment and Guilty Plea

In October 2014, Mr. Orduno-Ramirez was indicted in the District of Kansas

for conspiracy to distribute and possess with intent to distribute more than 50 grams

of methamphetamine in violation of 21 U.S.C. §§ 841(a)(1) and 841(b)(1)(A)(viii).

The district court appointed Kevin Babbitt to represent him. Mr. Orduno-Ramirez

was incarcerated at CCA pending trial. On April 13, 2016, he pled guilty under a

plea agreement.

B. Government Intrusion

Between March 11 and April 11, 2016—before Mr. Orduno-Ramirez pled

guilty—he met four times with Mr. Babbitt in an attorney visitation room at CCA.

ROA, Vol. I at 258-59. On May 6—after he pled guilty—Mr. Orduno-Ramirez and

Mr. Babbitt met to discuss his case in advance of sentencing. Id. at 259-60. The

visitation room surveillance camera captured video footage, but not sound, from

13 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 14

these meetings. Id. at 258-59. On May 17, the USAO obtained copies of these five

soundless video recordings. Id. at 603.

Mr. Orduno-Ramirez does not argue that CCA’s choice to keep a video camera

in the attorney meeting room was itself an intrusion. Rather, he asserts that the

intrusion occurred when the USAO obtained the footage on May 17. See Aplt. Br.

at 3. The parties thus agree that the USAO intruded on Mr. Orduno-Ramirez’s

communications with his attorney only after he pled guilty. See also Aplee. Br.

at 65.6

The recordings reveal little about Mr. Orduno-Ramirez’s interactions with

Mr. Babbitt because they contain no sound. In each recording, Mr. Babbitt and

Mr. Orduno-Ramirez appear to speak, make gestures, and examine documents and

legal materials. See ROA, Vol. I at 258-60.7

C. Sentencing and Direct Appeal

In November 2017, the district court sentenced Mr. Orduno-Ramirez to

144 months in prison, a below-Guidelines-range sentence reflecting a 44-month

6 Even though some of the video footage depicted pre-plea meetings between Mr. Orduno-Ramirez and Mr. Babbitt, the intrusion here was post-plea because the Government acquired the footage after Mr. Orduno-Ramirez pled guilty. See Aplt. Br. at 19 (describing the issue in this case as “whether a prosecutor who intentionally intrudes upon the defendant’s attorney-client communications after a trial or guilty plea, but before sentencing, commits a per se Sixth Amendment violation”); Aplee. Br. at 5. 7 This description of the videos derives from a summary of their contents by Mr. Orduno-Ramirez’s counsel, prepared at the direction of the district court. See ROA, Vol. I at 257-60.

14 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 15

downward variance. Mr. Orduno-Ramirez appealed his sentence, arguing it should

have been lower because he was a minor participant in the conspiracy. We affirmed.

United States v. Orduno-Ramirez, 719 F. App’x 830, 830-31 (10th Cir. 2017)

(unpublished).

D. Post-Conviction § 2255 Proceedings

In March 2019, the FPD moved on behalf of Mr. Orduno-Ramirez for

postconviction relief under 28 U.S.C. § 2255, alleging that the Government violated

his Sixth Amendment right to counsel by intruding on his attorney-client

communications. ROA, Vol. II at 293-328. Mr. Orduno-Ramirez argued that

Shillinger’s presumption should extend to post-plea intrusions, and he therefore did

not need show prejudice to succeed on his Sixth Amendment claim. Id. at 314-15.

The Government opposed the motion, arguing that Shillinger’s conclusive

presumption should not extend to the sentencing phase. And it contended that Mr.

Orduno-Ramirez had not shown any actual prejudice. ROA, Vol. II 360-63. To

support this contention, the Government submitted an affidavit from the lead

prosecutor in Mr. Orduno-Ramirez’s case stating that “[a]t no time during my

involvement in this case did I view or was privy to any video recordings of the

defendant at CCA” and “[a]t no time prior to the defendant’s sentencing . . . was

I aware that video recordings existed of the defendant’s meetings at CCA with his

defense counsel.” See ROA, Vol. II at 385-86. At one point, another prosecutor

entered an appearance in Mr. Orduno-Ramirez’s case, but she withdrew from the case

in 2016—well before Mr. Orduno-Ramirez’s sentencing. Id. at 385. Thus, the only

15 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 16

prosecutor involved in Mr. Orduno-Ramirez’s sentencing did not view the soundless

video recordings.8

The Government also pointed out that Mr. Orduno-Ramirez had not identified

“any snippet on any video in his case where the substance of discussions relating to

legal advice or strategy is discernible or ascertainable by any viewer of the video.”

Id. at 360. The Government further observed that prejudice was unlikely because Mr.

Orduno-Ramirez received a favorable sentence. Id. at 362.

Mr. Orduno-Ramirez’s § 2255 motion became part of the consolidated master

case, In re CCA Recordings 2255 Litig., No. 19-2491, along with the other post-

conviction proceedings. As noted, the district court’s December 2021 order in the

consolidated case held that the Shillinger conclusive presumption does not apply to

post-plea intrusions. The court then applied this holding to Mr. Orduno-Ramirez’s

§ 2255 motion. ROA, Vol. II at 539-53. It rejected his claim that the Government’s

intrusion into his communications with his attorney constituted a per se Sixth

Amendment violation. The court also found there was no “realistic possibility that

[Mr. Orduno-Ramirez] was prejudiced as a result of the government’s alleged

intrusion” because (1) the Government received the video recordings after he pled

8 At oral argument, the FPD noted that the other prosecutor did not withdraw from Mr. Orduno-Ramirez’s case until after the USAO obtained the video recordings, suggesting that she could have communicated the content of those recordings to the lead prosecutor before Mr. Orduno-Ramirez’s sentencing. Oral Arg. at 30:00-30:45. But this suggestion is speculative and does not warrant disregarding the lead prosecutor’s sworn statement that he was not aware of the videos at the time of sentencing.

16 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 17

guilty, so the intrusion did not affect the plea negotiations; and (2) his “sentencing

bears no indicia of a tainted proceeding.” Id. at 551-52. The court thus denied

Mr. Orduno-Ramirez’s § 2255 motion and declined to grant a COA. We granted a

COA, and this appeal followed.

III. DISCUSSION

In evaluating the denial of Mr. Orduno-Ramirez’s § 2255 motion, “we review

the district court’s findings of fact for clear error and its conclusions of law de novo.”

United States v. Rushin, 642 F.3d 1299, 1302 (10th Cir. 2011).

On appeal, 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. See Aplee. Br.

at 28, 47. Mr. Orduno-Ramirez does not contend that he suffered any actual

prejudice from the intrusion. Aplt. Br. at 12. The only disputed question is whether

Shillinger’s conclusive presumption should extend to post-plea government

intrusions.

A. No Conclusive Presumption of Prejudice

Mr. Orduno-Ramirez urges us to reverse the district court and hold that

Shillinger’s conclusive presumption categorically extends to sentencing. We are not

persuaded this is the proper course.

A Sixth Amendment per se rule of prejudice is a blunt legal instrument.

Lustyik, 833 F.3d at 1268 (“[A] rigid, per se rule is, by its nature, too blunt an instrument

to account for the legitimate demands of the adversarial system.”) (citation and

17 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 18

quotations omitted). The Supreme Court has cautioned against sweeping Sixth

Amendment rules that “cut[] much too broadly.” Weatherford, 429 U.S. at 557;

see 3 Wayne R. LaFave & Jerold H. Israel, Criminal Procedure § 2.9(g) (4th ed.)

(explaining that in the Sixth Amendment context, a “per se standard is either

overinclusive or underinclusive as compared to the application of that function to all

relevant circumstances on a case-by-case basis”).

The case to create a Sixth Amendment conclusive presumption must therefore

be especially strong. The record must demonstrate a high likelihood of prejudice.

See Strickland, 466 U.S. at 692. In deciding whether there should be a per se

prejudice rule for post-plea intrusions, we consider the rationales underlying the

Shillinger conclusive presumption for pretrial intrusions.

Likelihood of Prejudice

In Shillinger, we concluded that a pretrial government intrusion into attorney-

defendant communications is so likely to cause prejudice at trial that “case-by-case

inquiry into prejudice is not worth the cost.” 70 F.3d at 1142 (quoting Strickland,

466 U.S. at 692). We repeatedly referred to the high risk that such an intrusion will

prejudice the trial process. Id.9 In Cronic, the Supreme Court said that the “Sixth

Amendment guarantee is generally not implicated” without “some effect . . . on the

9 We concluded that “a prejudicial effect on the reliability of the trial process must be presumed” in cases of intentional intrusion, and observed that “groundless prosecutorial intrusions are never harmless because they necessarily render a trial fundamentally unfair.” Shillinger, 70 F.3d at 1142.

18 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 19

reliability of the trial process.” 466 U.S. at 658. Neither Shillinger nor Cronic said

anything about the likelihood of prejudice extending to sentencing.

A post-plea intrusion is less likely to cause prejudice than a pretrial intrusion

because the latter can taint any part of a criminal prosecution—trial, sentencing, or

both—and greatly expand the task of ascertaining prejudice as compared to a post-

plea intrusion.10 As the district court said in its December 2021 order, “when the

alleged intrusion occurs after the petitioner entered a guilty plea or was convicted at

trial, it eliminates the possibility that the intrusion could have tainted the petitioner’s

plea or conviction,” ROA, Vol. I at 652, and thus “does not implicate the same

potential for prejudice,” id. at 655. In short, Shillinger’s primary concern—that a

pretrial intrusion will prejudice the trial—is absent when the intrusion is post-plea.

Another way to assess the likelihood of prejudice is to compare the risk at trial

and sentencing. Commonly understood features of sentencing suggest the risk of

prejudice is lower at sentencing because the opportunity for a prosecutor to use

information from attorney-defendant communications is narrower.11 Judges and

10 A district court evaluating a pretrial intrusion “face[s] the virtually impossible task of reexamining the entire proceeding to determine whether the disclosed information influenced the government’s investigation or presentation of its case or harmed the defense in any other way.” United States v. Levy, 577 F.2d 200, 208 (3d Cir. 1978). 11 The following general observations briefly touch on only a few aspects of sentencing and are made with appreciation for the variety of trials and sentencings. They are, of course, subject to exceptions and debate. But, along with the other points made here about likelihood of prejudice, they support the norm of needing to establish prejudice for a Sixth Amendment violation.

19 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 20

prosecutors can and do play significant roles in both proceedings. But at sentencing,

the judge finds facts12 and imposes punishment,13 largely in reliance on the Probation

Office’s presentence investigation report.14 If the defendant pled guilty—which

occurs in nearly 90 percent of federal cases15—the court may also rely on factual

stipulations in the plea agreement.16 As a result, the prosecutor plays a lesser role

relative to the judge at sentencing than at trial, especially when a plea agreement

limits prosecutorial discretion.17 The prosecutor thus has less opportunity to

influence sentencing than at trial with information gleaned from a post-plea

12 The district judge “may accept any undisputed portion of the presentence report as a finding of fact” and “must—for any disputed portion of the presentence report or other controverted matter—rule on the dispute or determine that a ruling is unnecessary . . . .” Fed. R. Crim. P. 32(i)(3)(A), (B). See United States v. Lozano, 921 F.3d 942, 946 (10th Cir. 2019) (district court is factfinder at sentencing). 13 “The court shall determine the kinds of sentence and the guideline range . . . .” United States Sentencing Guideline § 1B1.1(a). See United States v. Smart, 518 F.3d 800 (10th Cir. 2008) (district court makes ultimate determination of a defendant’s sentence). 14 A “probation officer shall make a presentence investigation of [the] defendant . . . and shall . . . report the results of the investigation to the court.” 18 U.S.C. § 3552(a). See United States v. Harrison, 743 F.3d 760, 763 (10th Cir. 2014) (explaining how the district court can use the facts in the presentence report to inform its sentencing). 15 “Nearly ninety percent of all federal criminal cases involve guilty pleas and many of these cases involve some form of plea agreement.” U.S. Sent’g Guidelines Manual at 8 (U.S. Sent’g Comm’n 2021). 16 See United States v. Richardson, 901 F.2d 867, 869 (10th Cir. 1990) (district court can, but is not required to, rely on stipulated facts in plea agreement). 17 See United States v. Scott, 469 F.3d 1335, 1340 (10th Cir. 2006) (the government cannot argue for a higher sentence than agreed to in plea agreement).

20 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 21

intrusion.18 Further, judges can protect against the risk of prejudice to defendants at

sentencing because they are often better situated than juries to screen improperly

gained information.19

One further consideration cuts against creating a per se prejudice rule here

based on likelihood of prejudice—a comparison between the facts underlying

Shillinger and this case. In Shillinger, a law enforcement official disclosed

confidential attorney-client trial-preparation communications to the prosecution.

70 F.3d at 1137-38. Here, the USAO obtained, after the guilty plea and before

sentencing, soundless video footage of Mr. Orduno-Ramirez meeting with counsel.

We viewed the likelihood of prejudice to be so great in Shillinger that we not only

found a per se violation but also announced a broad per se rule for all pretrial

intrusions. The facts in this case present no comparable likelihood.

18 Much of a prosecutor’s influence over sentencing occurs before a plea or conviction through the charging decision, plea negotiations, and plea agreements— which occur before a post-plea intrusion. See Arthur W. Campbell, Law of Sentencing § 12.1 (Sept. 2022 update). 19 See Douglas A. Berman & Stephanos Bibas, Making Sentencing Sensible, 4 Ohio St. J. Crim. L. 37, 55 (2006) (In contrast to juries, “[j]udges . . . are repeat players with more information about criminal justice purposes and practicalities. Thus, they necessarily have broader insights about punishment options and how to sentence effectively . . . . In short, judges are more flexible, expert, can better apply complex rules, and can try to equalize outcomes across a range of cases.”); see also Tosco Corp. v. Koch Indus., Inc., 216 F.3d 886, 896 (10th Cir. 2000) (“[I]n bench trials, questions raised relative to the admission or exclusion of evidence become relatively unimportant, because the rules of evidence are intended primarily for the purpose of withdrawing from the jury matter which might improperly sway the verdict,” whereas judges can “consider[] only competent evidence and disregard[] any incompetent evidence.” (quotations and alterations omitted)).

21 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 22

Mr. Orduno-Ramirez advances various arguments about how the prosecutors

can use “ill-gotten attorney-client communications” to prejudice a defendant at

sentencing. Aplt. Reply Br. at 7-8; see also Aplt. Br. at 33-40. We agree that this is

possible. For example, he contends that prosecutors could advocate for fact-intensive

upward adjustments at sentencing, possibly based on improperly obtained

information. Aplt. Reply Br. at 7-8. But the possibility of prejudice is not enough to

warrant a per se rule. Instead, Strickland and Cronic admonish that “prejudice is

presumed” only when “[p]rejudice . . . is so likely that case-by-case inquiry into

prejudice is not worth the cost.” Strickland, 466 U.S. at 692 (emphasis added). And

for the reasons discussed above, post-plea intrusions do not meet that standard.

Mr. Orduno-Ramirez thus has not made the strong case needed for a

conclusive presumption of prejudice based on a post-plea intrusion. He has given us

no reason to expect a risk of prejudice at sentencing from a post-plea intrusion that

rises to the level of what the Shillinger panel feared would occur at trial from a

pretrial intrusion.20 And he has not shown why we should disregard the Supreme

Court’s caution against Sixth Amendment per se prejudice rules.

20 Indeed, the district court said in its December 2021 order that all § 2255 movants in the consolidated cases, including Mr. Orduno-Ramirez, who were seeking relief based on post-plea/pre-sentencing intrusions, “acknowledge that they cannot demonstrate the possibility of prejudice on their Sixth Amendment claims, but instead allege presumptive prejudice under the rule in Shillinger.” ROA, Vol. I at 652. This alone shows that creating a per se prejudice rule would be “overinclusive . . . compared to” determining prejudice “on a case-by-case basis.” 3 Wayne R. LaFave & Jerold H. Israel, Criminal Procedure § 2.9(g) (4th ed.).

22 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 23

We intend none of the foregoing to suggest that post-plea government

intrusions into attorney-defendant communications pose no significant risk to

sentencing proceedings. They may do so, and should be taken seriously, but not

through an overinclusive per se prejudice rule.

Deterrence

In Shillinger, this court also relied on deterrence to create a per se prejudice

rule. We said “no other standard can adequately deter this sort of misconduct.”

70 F.3d at 1142. Despite the district court’s deep concern about the USAO’s

systemic intrusions into many attorney-defendant communications at the CCA, a

concern that we share, it determined that deterrence was not sufficient to extend a

conclusive presumption of prejudice to post-plea intrusions without “the fairness or

reliability concerns identified” in Shillinger. ROA, Vol. I at 657.

Like the district court, we read Shillinger as weighing the likelihood of

prejudice and the need for deterrence together as complementary factors. Although

the USAO’s systemic conduct may point to the need for a “prophylactic rule[],”

Shillinger, 70 F.3d at 1142 (quotations and citations omitted), we are mindful of the

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

obviate consideration of prejudice in every instance. We find insufficient reason here

to adopt a per se rule.

* * * *

The “‘benchmark’ of a Sixth Amendment claim is ‘the fairness of the

adversary proceeding.’” Shillinger, 70 F.3d at 1141 (quoting Nix, 475 U.S. at 175).

23 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 24

At sentencing, a government intrusion into attorney-client communications does not

render prejudice “so likely that case-by-case inquiry into prejudice is not worth the

cost.” Id. at 1142 (quoting Strickland, 466 U.S. at 692). Nor does the need to deter

government misconduct warrant a conclusive presumption of prejudice. We

therefore affirm the district court’s determination that Shillinger’s conclusive

presumption does not extend to post-plea intrusions.

B. Actual Prejudice

Without a conclusive presumption, a defendant must suffer prejudice from a

post-plea intrusion into attorney-client communications to obtain relief under the

Sixth Amendment. The district court said the defendant must show prejudice, but we

need not decide which party bears the burden because the Government has shown

that Mr. Orduno-Ramirez has not been prejudiced, and he does not contend

otherwise. We therefore leave open whether the defendant must show prejudice or

the government must show lack of prejudice.21 Because Mr. Orduno-Ramirez has not

21 As the district court pointed out in its January 2021 and December 2021 orders, the Supreme Court has not resolved “the issue of who bears the burden of persuasion for establishing prejudice or lack thereof when the Sixth Amendment violation involves the transmission of confidential defense strategy information.” ROA, Vol. I at 451; 645; 653 (quotations and citations omitted); see Cutillo v. Cinelli, 485 U.S. 1037, 1037-38 (1988) (White, J., dissenting from denial of cert.) (noting circuit split on who bears the burden to prove prejudice). In most cases, a defendant alleging a Sixth Amendment violation must show prejudice. See Strickland, 466 U.S. at 658. But courts may shift the burden on an issue “when the true facts relating to a disputed issue lie peculiarly within the knowledge of” the party opposing relief, making it difficult for the party seeking relief to bear the burden of proof. Hennessey v. Univ. of Kansas Hosp. Auth., 53 F.4th 516, 530 (10th Cir. 2022) (quotations and citation omitted); see also Lima v. United States, 708 F.2d 502, 509 24 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 25

been prejudiced, there is no Sixth Amendment violation and no ground for § 2255

relief.

In the district court, the judge and the Government assumed that Mr. Orduno-

Ramirez bore the burden to show prejudice. Nonetheless, the Government introduced

affirmative evidence and arguments demonstrating that Mr. Orduno-Ramirez suffered

no prejudice. The Government showed:

(1) The lead prosecutor did not view the videos, and the other prosecutor withdrew from the case before Mr. Orduno-Ramirez’s sentencing. ROA, Vol. II at 385-86. Thus, no prosecutor involved in the sentencing was aware of the contents of the recordings.

(2) The soundless video recordings provided no strategic value to the prosecution. Aplee. Br. at 52-53; ROA, Vol. II at 359-60.22

(10th Cir. 1983) (noting the merit of “redistribut[ing] the burden [of proof] to those who have superior knowledge of the truth and better access to evidence”). In fact, the First Circuit uses a burden-shifting approach for government intrusions on attorney-client communications. United States v. DelCologero, 530 F.3d 36, 64 (1st Cir. 2008) (“[W]e only require defendants to make a prima facie showing of prejudice by proving that confidential communications were conveyed as a result of the government intrusion into the attorney-client relationship. The burden then shifts to the government to show that the defendant was not prejudiced; that burden is a demanding one.” (quotations, citations, and alterations omitted)). 22 The recordings depict only Mr. Orduno-Ramirez and his attorney talking without revealing their conversation. ROA, Vol. I at 258-60. Mr. Orduno-Ramirez says a viewer could “observe non-verbal communications” like “body language,” or “use [] viewing software to zoom in, for instance, on a document.” Aplt. Br. at 4 (quotations omitted). While this may be true in some cases, nothing in the record suggests that the Government could gain usable information from the videos in this case.

25 Appellate Case: 22-3019 Document: 010110824546 Date Filed: 03/10/2023 Page: 26

(3) The record reveals no irregularity in Mr. Orduno-Ramirez’s sentencing.23

The Government therefore showed the intrusion did not cause prejudice, and

Mr. Orduno-Ramirez does not contend he was prejudiced. We agree with the district

court that Mr. Orduno-Ramirez’s “sentencing bears no indicia of a tainted

proceeding.” ROA, Vol. II at 552.

IV. CONCLUSION

We affirm the district court’s denial of Mr. Orduno-Ramirez’s § 2255

motion.24

23 Mr. Orduno-Ramirez objected to a number of factual findings in his presentence investigation report. In response, the Government cited extensive evidence from the investigation into Mr. Orduno-Ramirez, including statements by his alleged co-conspirators. None of the information the Government relied on for sentencing could have come from the soundless video recordings. Mr. Orduno- Ramirez’s 144-months prison sentence fell below the Guidelines range. 24 On February 14, 2023, Mr. Orduno-Ramirez filed a motion asking us to order supplemental briefing on whether we should adopt a rebuttable presumption of prejudice when, between a plea and sentencing, the prosecution intrudes on defense attorney/client communications. We denied the motion because we do not decide that issue here. Mr. Orduno-Ramirez, nonetheless, submitted his arguments in a letter filed under Federal Rule of Appellate Procedure 28(j), and the Government filed a response.