No Exception for Prosecutorial Eavesdropping: Guilty-Plea Challenges Must Proceed via Ineffective Assistance (United States v. Jordan, 10th Cir. 2025)

Introduction

In United States v. Jordan, the United States Court of Appeals for the Tenth Circuit affirmed the denial of a § 2255 motion by Gary Jordan, who sought to vacate his guilty plea based on the government’s pre-plea intrusion into his confidential attorney-client meetings. The decision clarifies and consolidates two important strands of federal criminal procedure in the Tenth Circuit:

Under Tollett v. Henderson, a defendant who has pleaded guilty may attack the plea’s constitutional validity as “knowing and voluntary” only through an ineffective assistance of counsel (IAC) claim, absent narrow exceptions rooted in Brady v. United States (threats, misrepresentations, or improper prosecutorial promises).
Following the Tenth Circuit’s recent en banc decision in United States v. Hohn, government intrusion into attorney-client communications is not a structural error with presumed prejudice; a Sixth Amendment violation requires an actual showing of prejudice.

The case arises from the District of Kansas’s acknowledged, now-ceased practice of obtaining recordings of detainees’ calls with counsel, a practice that has generated multiple appeals. Judge Carson, writing for a unanimous panel (Judges Eid, Kelly, and Carson), held that Jordan’s challenge could not proceed because he did not frame it as an IAC claim and relied exclusively on a structural-error theory that the court has since repudiated.

Summary of the Opinion

Jordan pleaded guilty to armed bank robbery and related offenses and received a 30-year sentence. He later learned that the prosecution had obtained silent recordings of his strategy meetings with counsel before the plea. Although prosecutors denied reviewing the recordings, Jordan moved under 28 U.S.C. § 2255(a) to vacate his plea, arguing that the intrusion rendered the plea unknowing and involuntary.

The district court denied relief, holding that under Tollett, challenges to a plea’s voluntariness based on pre-plea events must be raised as ineffective-assistance claims. Jordan sought and obtained a certificate of appealability limited to whether a defendant “could challenge the constitutionality of his guilty plea only via an ineffective-assistance-of-counsel claim.”

The Tenth Circuit affirmed. It held that:

Tollett channels post-plea constitutional challenges of voluntariness into the IAC framework, absent the limited Brady exceptions (threats, misrepresentations, or improper promises).
Prosecutorial intrusion into attorney-client communications is not an exception to Tollett (reaffirming its earlier decision in United States v. Spaeth).
Because Jordan did not assert IAC and relied solely on the overruled structural-error approach from Shillinger v. Haworth, his claim necessarily failed under Hohn, which requires a showing of prejudice.

The court reviewed the legal question de novo and rejected the government’s argument for plain-error review, noting that Jordan had, in substance, challenged the voluntariness of his plea.

Analysis

Precedents Cited and Their Role

Tollett v. Henderson, 411 U.S. 258 (1973):
The Supreme Court established the “break in the chain” principle: a valid guilty plea forecloses most antecedent constitutional claims. After a plea, a defendant “may only attack the voluntary and intelligent character of the guilty plea by showing that the advice he received from counsel” was constitutionally deficient (now measured by Strickland). In Jordan, this is the controlling framework. The panel reads Tollett to mean that pre-plea constitutional violations cannot, by themselves, invalidate a plea as unknowing or involuntary unless channeled through an IAC claim.
Brady v. United States, 397 U.S. 742 (1970):
Brady identifies the limited, non-IAC grounds on which a plea can be involuntary: if it is induced by threats, misrepresentations, or promises not properly related to the prosecutor’s business. The Jordan panel underscores that these are the only recognized non-IAC voluntariness exceptions relevant here; prosecutorial eavesdropping is not among them.
Strickland v. Washington, 466 U.S. 668 (1984):
The modern standard for IAC claims requires showing deficient performance and prejudice. In the plea context, prejudice typically means a reasonable probability that, but for counsel’s errors, the defendant would not have pleaded guilty (see Hill v. Lockhart, 474 U.S. 52 (1985)). Although Jordan did not bring an IAC claim, the panel highlights Strickland as the requisite vehicle for a voluntariness challenge post-plea.
United States v. Spaeth, 69 F.4th 1190 (10th Cir. 2023):
The Tenth Circuit declined to create a prosecutorial-intrusion exception to Tollett, emphasizing that a guilty plea “breaks the causal effect of any unconstitutional conduct on a defendant’s conviction” and that “no reason exists to hold that a sunken pre-plea constitutional violation somehow resurfaces on the other side of a guilty plea.” Jordan expressly relies on Spaeth to reject a new carve-out for attorney-client intrusions.
Shillinger v. Haworth, 70 F.3d 1132 (10th Cir. 1995), overruled by United States v. Hohn, 123 F.4th 1084 (10th Cir. 2024) (en banc):
Shillinger had held that intentional government intrusion into the attorney-client relationship, absent a legitimate law-enforcement purpose, was a structural error with presumed prejudice. In Hohn, the Tenth Circuit sitting en banc overruled Shillinger and held that a Sixth Amendment violation based on intrusion requires an actual showing of prejudice. Jordan relied exclusively on Shillinger’s now-defunct presumption and therefore failed under Hohn.
English v. Cody, 241 F.3d 1279 (10th Cir. 2001) and Ross v. Ward, 165 F.3d 793 (10th Cir. 1999):
These decisions support de novo review of legal questions in the certificate-of-appealability context. The court applied de novo review to the question at hand.
Context cases from the Kansas recordings litigation:
The opinion refers to other appeals arising from the U.S. Attorney’s Office for the District of Kansas’s former practice of obtaining detainee–attorney communications, e.g., United States v. Carter, 995 F.3d 1214 (10th Cir. 2021), and United States v. Spaeth, 69 F.4th 1190 (10th Cir. 2023). Jordan fits within that line.

Legal Reasoning

The panel’s reasoning proceeds in two interlocking steps:

Tollett channels voluntariness challenges to pleas through IAC, with narrow Brady-based exceptions.
The court emphasizes that once a defendant “has solemnly admitted in open court” guilt, he cannot “raise independent claims” about pre-plea constitutional deprivations. He may attack only the “voluntary and intelligent character” of the plea, and he may do so generally by showing that counsel’s advice fell below Strickland standards or (within the narrow ambit of Brady) that the plea was induced by threats, misrepresentations, or improper promises. Prosecutorial intrusion, the panel reiterates, is not one of these exceptions.
No prosecutorial-intrusion exception; no structural-error presumption.
Citing Spaeth, the panel declines to treat attorney-client eavesdropping as a special exception to Tollett. And under Hohn, the structural-error presumption of prejudice from Shillinger is no longer valid. Thus, Jordan’s decision to rely exclusively on Shillinger doomed his claim: he neither alleged IAC nor attempted to show actual prejudice from the intrusion.

The government sought plain-error review, arguing Jordan had not preserved an involuntariness argument, but the panel rejected that contention, noting the district court itself characterized his submission as a challenge to the plea’s voluntariness. The court then reviewed the legal question de novo and affirmed.

Impact

Consolidation of the Tenth Circuit’s guilty-plea framework.
Jordan cements two constraints on post-plea challenges within the Tenth Circuit: first, the Tollett channeling principle that voluntariness challenges must proceed via IAC (absent the limited Brady exceptions); second, Hohn’s elimination of the structural-error presumption for attorney-client intrusions and its insistence on proof of prejudice.
Narrow path for detainees affected by the Kansas recordings practice.
Defendants seeking to set aside guilty pleas based on government access to attorney-client communications must now:
- Plead and prove an IAC claim under Strickland/Hill, connecting the intrusion to counsel’s deficient advice and a reasonable probability the defendant would not have pleaded guilty;
- Or fit within the tight Brady exceptions (threats, misrepresentations, improper promises).
Mere proof of intrusion, without prejudice, will not suffice.
Prosecutorial-intrusion claims are not self-executing in plea cases.
Even serious governmental misconduct occurring pre-plea does not, by itself, invalidate a subsequently entered guilty plea. The causal chain is broken by the plea unless the defendant demonstrates that counsel’s advice was constitutionally inadequate or a recognized Brady defect tainted the plea.
Guidance for district courts and counsel.
District courts evaluating § 2255 motions should look for properly pleaded IAC claims when a petitioner asserts plea involuntariness based on pre-plea events. Defense counsel must gather evidence linking the intrusion to deficient advice and to the decision to plead. Prosecutors should recognize that while intrusion alone no longer triggers automatic relief, any proven prejudice tied to counsel’s advice may still upend a plea.
Scope note.
Jordan is about attacking the “knowing and voluntary” character of a plea. Some claims survive a guilty plea by their nature (e.g., certain double jeopardy or constitutional challenges to the statute of conviction), but those are different categories and not at issue here. For voluntariness-based challenges, Tollett and Brady govern the routes available.

Complex Concepts Simplified

“Knowing and voluntary” plea: A plea is valid only if the defendant understands the nature of the charges and consequences and chooses to plead without coercion or improper inducements.
Tollett’s “break in the chain”: After a valid guilty plea, most complaints about earlier constitutional violations are no longer relevant. The defendant can generally challenge only whether the plea itself was valid.
Ineffective assistance of counsel (IAC): Under Strickland, a defendant must show (1) deficient performance by counsel and (2) prejudice. For guilty pleas, prejudice usually means a reasonable probability that, but for counsel’s errors, the defendant would have gone to trial (Hill standard).
Brady voluntariness exceptions: A plea is involuntary if induced by threats, misrepresentations, or promises unrelated to legitimate prosecutorial objectives.
Structural error vs. showing prejudice: Structural errors require automatic reversal without showing harm; trial errors require a showing of prejudice. The Tenth Circuit’s en banc decision in Hohn holds that attorney-client intrusion is not structural; a defendant must show prejudice.
Certificate of appealability (COA): A federal prisoner may appeal the denial of § 2255 relief only if a COA issues on specific questions where “jurists of reason” could debate the district court’s disposition. Jordan’s COA addressed whether he could challenge his plea’s constitutionality only via an IAC claim.
Pre-plea versus post-plea conduct: Misconduct occurring before a guilty plea may not invalidate the plea unless it affected counsel’s advice (IAC) or falls within narrow Brady exceptions. Post-plea conduct can raise different issues not governed by Tollett.

Conclusion

United States v. Jordan reinforces a clear, disciplined approach to post-plea litigation in the Tenth Circuit. When a defendant seeks to invalidate a guilty plea as unknowing or involuntary based on pre-plea events—including serious prosecutorial misconduct such as attorney-client eavesdropping—the claim must be framed and proven as ineffective assistance of counsel under Strickland (and Hill), unless the narrow Brady exceptions apply. The court expressly declines to create a special exception for prosecutorial intrusion and, in light of Hohn, rejects any presumption of prejudice.

The upshot is twofold: defendants bear the burden to connect pre-plea violations to deficient legal advice and to a different plea decision; and courts will not vacate pleas based on pre-plea constitutional violations alone. Jordan therefore serves as a pivotal marker in the Tenth Circuit’s jurisprudence, aligning plea-collateral-attack doctrine with the en banc shift in Sixth Amendment intrusion law and providing concrete guidance for the many cases arising from the Kansas recordings episode and beyond.