United States v. Orduno-Ramirez

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.
26