Ineffective Assistance of Counsel Under Strickland: A Plain-English Guide for § 2255 Motions

by Richard Levitt

Levitt & Kaizer

(212) 480-4000

The Sixth Amendment guarantees more than a lawyer standing next to you. It guarantees a lawyer who actually does the job competently. If you were convicted in federal court and believe your lawyer let you down, the most common path to relief is a motion under 28 U.S.C. § 2255 claiming ineffective assistance of counsel (“IAC”) (By contrast, IAC claims by persons convicted in state court, and who have already lost their state court appeals, are brought in federal court under 28 U.S.C. § 2254).

IAC claims are also uniquely suited to § 2255. Most issues not raised on direct appeal are considered forfeited. IAC claims are the exception. In Massaro v. United States, 538 U.S. 500 (2003), the Supreme Court held that IAC claims may be brought for the first time in a § 2255 motion, because they usually depend on facts outside the trial record, such as what your lawyer told you privately or what they never bothered to investigate.

But “my lawyer was bad” is not enough. Every federal IAC claim is measured against a single test from Strickland v. Washington, 466 U.S. 668 (1984). Understanding that test, and how courts apply it, can mean the difference between a motion that gets traction and a hearing and one that is denied on the papers.

The Two-Prong Strickland Test: Deficiency and Prejudice

To win an IAC claim, you must prove two things. First, your lawyer’s performance was deficient. Second, that deficiency prejudiced you. You need both. A court can deny your claim by finding either of these two requirements missing, and many courts skip straight to prejudice because it is often the easier ground for denial.

Prong one: deficient performance

Under Strickland, performance is deficient when it falls “below an objective standard of reasonableness” measured by “prevailing professional norms.” In plain terms, the question is not whether your lawyer was the best available, or whether another lawyer would have done things differently. The question is whether what your lawyer did (or failed to do) was outside the range of what a competent criminal defense attorney would do in the same situation.

Courts start from a “strong presumption” that counsel acted reasonably. Judges are told to avoid “the distorting effects of hindsight” and to evaluate the lawyer’s conduct from their perspective at the time. That presumption is the main reason IAC claims fail. Your motion has to give the court concrete facts that overcome it.

Prong two: prejudice

Even a serious mistake does not entitle you to relief unless it mattered. Strickland requires a “reasonable probability that, but for counsel’s unprofessional errors, the result of the proceeding would have been different.” A reasonable probability is “a probability sufficient to undermine confidence in the outcome.”

Two points about this standard are often misunderstood:

•  You do not have to prove you would more likely than not have won. Strickland expressly rejected a preponderance standard. The question is whether confidence in the result is shaken.

•  The probability still has to be real. In Harrington v. Richter, 562 U.S. 86 (2011), the Court said the likelihood of a different result “must be substantial, not just conceivable.”

What counts as a “different result” depends on the stage where the error happened. After a trial, it usually means a reasonable probability of acquittal or conviction on a lesser charge. At sentencing, it means a lower sentence, and Glover v. United States, 531 U.S. 198 (2001), holds that any additional prison time counts. In the plea context the test changes, as discussed below.

In a few narrow situations prejudice is presumed. The most important is when a lawyer ignores your instruction to file a notice of appeal. Under Roe v. Flores-Ortega, 528 U.S. 470 (2000), and Garza v. Idaho, 586 U.S. 232 (2019), you need only show you would have appealed, even if you signed an appeal waiver.

What Courts Won’t Consider “Deficient”: Strategic Decisions vs. Actual Errors

The single most common reason IAC claims fail is that the court labels the lawyer’s decision “strategy.” Strickland says that “strategic choices made after thorough investigation of law and facts relevant to plausible options are virtually unchallengeable.” If your lawyer considered an option and made a reasoned choice, a court will almost never second-guess it, even if the choice backfired.

Decisions courts typically treat as strategic include:

• Which defense theory to present at trial

• Whether to cross-examine a witness aggressively or briefly

•  What to say in opening statements and closing arguments (see Yarborough v. Gentry, 540 U.S. 1 (2003))

• Whether to object to a particular question or exhibit

• Which of several plausible issues to raise on appeal (Jones v. Barnes, 463 U.S. 745 (1983))

Losing at trial does not make any of these choices unreasonable. Neither does a disagreement between you and your lawyer about tactics.

Where “strategy” stops protecting the lawyer

The protection for strategy has limits, and the best IAC claims are built around them.

Strategy requires investigation first. The same passage of Strickland quoted immediately above continues: choices “made after less than complete investigation are reasonable precisely to the extent that reasonable professional judgments support the limitations on investigation.” A lawyer cannot call it a strategic decision not to pursue a defense they never looked into. In Wiggins v. Smith, 539 U.S. 510 (2003), the Court found counsel deficient because their decision to stop investigating was itself unreasonable.

Ignorance of the law is not strategy. In Hinton v. Alabama, 571 U.S. 263 (2014), the lawyer failed to request funding for a qualified expert because he did not know the law allowed it. The Court called “an attorney’s ignorance of a point of law that is fundamental to his case combined with his failure to perform basic research on that point” a “quintessential example of unreasonable performance.”

Some decisions belong to you, not your lawyer. You alone decide whether to plead guilty, whether to waive a jury, whether to testify, and whether to appeal. A lawyer who overrides those choices has not made a strategic call. In McCoy v. Louisiana, 584 U.S. 414 (2018), conceding a client’s guilt over his express objection was a structural error requiring a new trial.

And so, when framing an IAC claim, focus on what the lawyer failed to learn, failed to know, or failed to let you decide, not on a tactical call you would have made differently.

The Most Viable IAC Claims in Federal § 2255 Motions

Some IAC theories succeed far more often than others. Three categories come up again and again because they involve facts outside the trial record and are hard to explain away as strategy.

1. Failed plea advice

As the Supreme Court noted in Missouri v. Frye, 566 U.S. 134 (2012), about 97 percent of federal convictions come from guilty pleas, so the plea stage is where many of the strongest claims arise. The Supreme Court has recognized several ways a lawyer can fail a client here:

• Not communicating a plea offer. Under Missouri v. Frye defense counsel must tell the client about formal plea offers from the prosecution.

• Bad advice that leads you to reject a deal. In Lafler v. Cooper, 566 U.S. 156 (2012), the defendant turned down a favorable offer based on his lawyer’s incorrect legal advice and received a much longer sentence after trial.

• Bad advice that leads you to accept a deal. This includes misstating your sentencing exposure or failing to warn you about deportation, which Padilla v. Kentucky, 559 U.S. 356 (2010), requires.

Prejudice works differently for plea claims. If you pleaded guilty, you must show a reasonable probability that, with proper advice, you would have gone to trial (Hill v. Lockhart, 474 U.S. 52 (1985)). In Lee v. United States, 582 U.S. 357 (2017), the Court held that this can be met even when the evidence against you was strong, if rejecting the plea would have been a rational choice given what mattered to you, like avoiding deportation. Courts want contemporaneous evidence, such as emails, letters, or notes, not just your say-so after the fact.

If you rejected a plea, Lafler and Frye require a reasonable probability that you would have accepted the offer, that the prosecution would not have withdrawn it, that the court would have accepted it, and that the result would have been less severe.

2. Uncalled witnesses

Failing to call a witness who could have helped the defense can be deficient, but courts approach these claims skeptically because choosing witnesses is usually strategy. To have a real chance, you generally need to show:

• Who the witness is and that your lawyer knew or should have known about them

• That the witness was available and willing to testify

• Exactly what they would have said, ideally in a sworn affidavit from the witness

•  Why that testimony creates a reasonable probability of a different outcome

A motion that says only “my lawyer should have called my cousin” will be denied. A motion attaching the cousin’s signed declaration describing an alibi, plus evidence that counsel never contacted them, is a different matter.

3. Uninvestigated defenses

This is often the strongest category, because the strategy defense collapses when the lawyer never did the groundwork. Common examples include failing to:

• Review discovery or interview key witnesses

• Hire a forensic, financial, or other expert where the government’s case depended on technical evidence

• File a meritorious motion to suppress evidence obtained through an illegal search

• Investigate mitigating facts for sentencing, or challenge an incorrect Guidelines calculation

For suppression claims, Kimmelman v. Morrison, 477 U.S. 365 (1986), requires showing both that the Fourth Amendment motion would have succeeded and that excluding the evidence would likely have changed the outcome. For sentencing errors, Glover means even a modest increase in your Guidelines range can satisfy prejudice.

Before You File: Deadlines and Evidence

A strong IAC claim can still be lost on procedure. Keep three points in mind.

•          The one-year deadline is strict. Under 28 U.S.C. § 2255(f), you generally have one year from the date your conviction became final. If you appealed and did not seek Supreme Court review, that is usually 90 days after the appellate court’s judgment (90 days being the time by which a cert petition must be filed). Clay v. United States, 537 U.S. 522 (2003). If you did not appeal, the clock typically starts when the 14-day window to appeal closed.

•          Facts win hearings. Under § 2255(b), the court must hold an evidentiary hearing unless the record “conclusively show[s]” you are not entitled to relief. Specific, sworn facts, such as your own declaration, witness affidavits, letters, and emails with your lawyer, are what earn that hearing.

•          Both prongs must be addressed. Every claim should explain what the lawyer did wrong and why it changed the outcome. Leaving out prejudice is one of the most common reasons motions are denied.

Summing Up

The Strickland standard is demanding, but it is not impossible. Claims built on concrete failures (an offer never conveyed, a witness never contacted, a defense never investigated) succeed far more often than complaints about trial tactics.

If you believe your lawyer’s mistakes denied you effective assistance of counsel, call us to discuss the possibility of bringing a § 2255 motion.

Richard Levitt

Levitt & Kaizer

(212) 480-4000