Affirming the Conclusive‐Record Standard for §2255 Ineffective Assistance Claims in Plea Agreements

Introduction

In Edward J. DiMaria v. United States, No. 22-11470 (11th Cir. Apr. 9, 2025), the Eleventh Circuit addressed the threshold for granting an evidentiary hearing in a collateral attack under 28 U.S.C. § 2255 when ineffective assistance of counsel is alleged in the context of a guilty plea. Edward DiMaria, former CFO of Bankrate, pleaded guilty to securities fraud and related counts based on a “cookie-jar” accounting scheme. He later sought to vacate his plea and sentence, asserting that trial counsel failed (1) to investigate potentially exculpatory internal reports and (2) to challenge the government’s loss calculation. The district court denied relief without an evidentiary hearing, and on appeal the Eleventh Circuit affirmed, reaffirming that conclusory allegations contradicted by the plea‐colloquy record warrant no hearing.

Summary of the Judgment

The Court of Appeals affirmed the district court’s denial of DiMaria’s § 2255 motion. Key holdings include:

The attorney‐investigation claim was conclusory: DiMaria identified no plausible way the Grant Thornton or Wachtell, Lipton reports would have altered counsel’s view of materiality or changed the plea recommendation.
The loss‐calculation claim failed because DiMaria had stipulated to a $25 million loss at his change-of-plea hearing after a detailed government explanation, and Stein (846 F.3d 1135) did not apply to plea stipulations.
No evidentiary hearing was required where the files and record “conclusively show” no entitlement to relief under Strickland v. Washington, Hill v. Lockhart, and related precedent.

Analysis

Precedents Cited

Strickland v. Washington (466 U.S. 668, 1984): Sets the two‐prong test for ineffective assistance—deficient performance and prejudice.
Hill v. Lockhart (474 U.S. 52, 1985): Applies Strickland in the guilty‐plea context; prejudice asks whether counsel’s errors would have led to rejection of plea.
Rosin v. United States (786 F.3d 873, 11th Cir. 2015): Holds district courts need not conduct hearings if § 2255 motion and record conclusively show no relief.
Lynn v. United States (365 F.3d 1225, 11th Cir. 2004): Clarifies standards of review in § 2255 proceedings (de novo legal, clear error factual).
United States v. Stein (846 F.3d 1135, 11th Cir. 2017): Requires proof of investor reliance for loss calculations under the Sentencing Guidelines—but applies to contested sentencing, not plea stipulations.
Gordon v. United States (518 F.3d 1291, 11th Cir. 2008): Confirms that reasonable strategic decisions by counsel foreclose IAC claims without hearing.
Padilla v. Kentucky (559 U.S. 356, 2010): Emphasizes rational‐choice analysis in plea advice and the importance of accurate counsel guidance on plea consequences.

Legal Reasoning

The panel’s reasoning unfolds in two segments:

Failure to Investigate Reports: DiMaria alleged counsel neglected two internal reports suggesting no material misstatements. The court found these allegations “conclusory” because DiMaria offered no explanation how counsel’s further investigation would have uncovered new exculpatory facts. Moreover, DiMaria had actively concealed audit entries from Grant Thornton, undermining any argument that the report carried independent weight. Under Strickland, counsel need not pursue meritless or speculative defenses.
Challenge to Loss Amount: DiMaria argued counsel should have realized—based on Stein—that his actual loss exposure was negligible. But parties had stipulated to a $25 million loss at the change‐of‐plea hearing after a detailed explanation by the government, and DiMaria affirmed under oath that the government could prove that amount beyond a reasonable doubt. A plea colloquy admitting loss forecloses later challenges unless counsel’s advice was affirmatively misinforming. Here, DiMaria offered no evidence counsel misadvised him or that the stipulated figure was irrational to accept.

Because both claims were “contradicted by the record,” the court found no abuse of discretion in denying a hearing under § 2255(b).

Impact on Future Cases

This decision reinforces several principles in the Eleventh Circuit:

Plea‐colloquy admissions and stipulations carry decisive weight in later collateral proceedings.
Conclusive records that contradict IAC allegations justify summary denial of § 2255 relief without a hearing.
Counsel’s duty to investigate does not extend to chasing speculative theories or nonexistent defenses.
Contested sentencing decisions (as in Stein) do not automatically apply to plea‐stipulated loss amounts.

Lower courts will look to DiMaria to limit evidentiary hearings where petitioners offer only bare or self-serving assertions that conflict with their plea‐colloquy record.

Complex Concepts Simplified

28 U.S.C. § 2255 Motion: A federal prisoner’s request to vacate or correct a sentence on grounds like constitutional error (including IAC).
Ineffective Assistance of Counsel (IAC): A two‐part test under Strickland: (1) counsel’s performance fell below an objective standard of reasonableness, and (2) the deficiency prejudiced the defense (in pleas, would counsel’s errors make it irrational to plead?).
Evidentiary Hearing: A live proceeding where the court receives sworn testimony. Under § 2255(b), courts need not hold such hearings if the motion and record “conclusively” refute the petitioner’s claims.
"Cookie-Jar" Accounting: Shifting expenses or revenues across reporting periods to smooth reported earnings—deceptive when undisclosed.
Sentencing Loss Calculation: Under U.S.S.G. § 2B1.1, the amount of financial harm (loss) influences the offense level; “but for” causation requires showing investors relied on false statements.

Conclusion

Edward DiMaria v. United States crystallizes the Eleventh Circuit’s rule that when § 2255 petitioners challenge the effectiveness of counsel in plea bargaining, their § 2255 motion and the underlying record must present more than conclusory or self-contradictory assertions to warrant an evidentiary hearing. By affirming the district court, the appellate panel reaffirmed that sound plea colloquies and stipulations, together with strategic counsel decisions not to pursue meritless theories, will bar collateral relitigation of plea terms. This ruling strengthens the finality of guilty pleas and guides both defense counsel and district courts when navigating post-conviction claims of counsel malpractice.