Deficient Sentencing Advocacy and the Prejudice Requirement: Clarifying Strickland and Cronic in Baker v. Conway

Introduction

Baker v. Conway is a 2025 decision of the United States Court of Appeals for the Second Circuit in which the court considered whether an inmate’s Sixth Amendment right to effective assistance of counsel was violated at his sentencing hearing. Petitioner‐appellant Sean Baker, convicted of second‐degree murder under New York’s felony‐murder statute, challenged his 20-to-life sentence on habeas review under 28 U.S.C. § 2254. He argued that his court-appointed attorney, Patrick Bruno, provided no meaningful advocacy at sentencing—failing to review the presentence report, investigate mitigating evidence, or advise Baker to address the court—and that prejudice should either be presumed under United States v. Cronic or, in the alternative, found under Strickland v. Washington. The Second Circuit affirmed the denial of relief, recognizing counsel’s performance as deficient but holding that Baker could not show a reasonable probability of a more favorable outcome.

Summary of the Judgment

The court first assumed familiarity with the underlying facts: at age 17, Baker participated in a robbery that led to Ramiro Ramos Luna’s fatal fall down a flight of stairs. After a jury conviction, at sentencing Bruno made only a three‐sentence statement and Baker declined to address the judge. On post‐conviction review the New York courts applied Strickland, found no deficiency or prejudice, and denied Baker’s CPL § 440.10 motion. On federal habeas review, Baker urged a Cronic presumption of prejudice; the magistrate judge and district court rejected that, applied Strickland, and denied relief. The Second Circuit affirmed, holding (1) counsel’s performance at sentencing was deficient, but (2) Baker failed to show “a substantial, not just conceivable, likelihood” of a different sentence and therefore could not satisfy Strickland’s prejudice prong, and (3) Cronic’s presumption did not apply because counsel’s shortcomings did not deprive Baker of meaningful adversarial testing of the prosecution’s case.

Analysis

Precedents Cited

Strickland v. Washington, 466 U.S. 668 (1984): Established the two‐prong test for ineffective assistance: (1) deficient performance, and (2) resulting prejudice.
United States v. Cronic, 466 U.S. 648 (1984): Holds that in exceptional circumstances—such as total denial of counsel or failure to challenge the prosecution—prejudice is presumed.
Glover v. United States, 531 U.S. 198 (2001): Confirms Sixth Amendment protection extends to sentencing.
Gonzalez v. United States, 722 F.3d 118 (2d Cir. 2013): Recognizes that failure to prepare for sentencing may constitute deficient performance.
Pinholster, Burt, Harrington: AEDPA standards of deference to state‐court decisions and counsel’s strategic judgments.

Legal Reasoning

1. Deficient Performance: The court held that “no fairminded jurist” could conclude that an attorney who neither reviewed the presentence report with his client nor advanced any argument for leniency rendered objectively reasonable assistance. Bruno’s minimal three‐sentence statement and his post‐hoc rationales—avoiding “backfiring” by sharing childhood trauma and preserving issues for appeal—did not withstand Strickland’s requirement of reasonable investigation and advocacy.

2. Prejudice: Even assuming deficiency, Baker could not show a “reasonable probability” of a reduced sentence. The sentencing judge, who denied the post-conviction motion, made clear that mitigating evidence would not have altered the indeterminate term imposed below the statutory maximum. The record—Baker’s refusal to speak at sentencing, his maintained innocence, and the court’s decision to impose 20-to-life (below the 25-to-life request)—undermined any likelihood of a more lenient outcome.

3. Cronic’s Presumption: The court rejected the application of Cronic because, although counsel performed poorly, he did not entirely fail to challenge the prosecution’s case at sentencing nor was counsel absent at a critical stage. Prejudice therefore had to be proven under Strickland.

4. AEDPA Deference: Applying the “doubly deferential” standard, the court concluded that the state courts did not unreasonably apply Strickland or Cronic. Moreover, Baker’s Cronic argument was not fairly presented below as a standalone ground for relief and thus was not entitled to de novo application.

Impact

Baker v. Conway reinforces that:

Counsel must meaningfully prepare for and conduct sentencing advocacy, including reviewing the presentence report, investigating mitigating circumstances, and advising the client.
Even clear deficiencies in sentencing representation do not entitle a defendant to relief absent a strong showing of prejudice under Strickland.
Cronic’s presumption of prejudice remains a narrow exception, reserved for total breakdowns of adversarial testing.
Habeas petitioners face a high bar under AEDPA’s deference regimes when challenging state‐court Strickland applications.

Complex Concepts Simplified

Strickland Two-Prong Test: (1) Was counsel’s performance objectively unreasonable? (2) Did any unreasonable errors undermine confidence in the outcome?
Cronic Presumption: In extreme cases—like no counsel at a critical stage or total abandonment by counsel—courts assume prejudice without specific proof.
AEDPA Deference: Federal courts must defer to state‐court decisions unless those decisions are “contrary to” or an “unreasonable application” of clearly established Supreme Court law.
Presumptive vs. Actual Prejudice: Strickland requires a showing that deficient performance probably changed the result, whereas Cronic allows a presumption without that showing—but only in rare circumstances.

Conclusion

Baker v. Conway makes clear that while sentencing hearings are a critical stage deserving of effective counsel, proving prejudice under Strickland remains a formidable challenge. The Second Circuit recognized that withholding preparation and advocacy at sentencing is deficient—but affirmed the requirement that defendants demonstrate a substantial likelihood of a different outcome. Cronic’s presumption of prejudice is confined to only the most extreme breakdowns in representation. For trial and appellate practitioners, this decision emphasizes thorough sentencing preparation, candid client advisement, and diligent record-building to meet both Strickland’s and AEDPA’s exacting standards.