United States District Court, D. Massachusetts
OPINION AND ORDER
GEORGE A. O’TOOLE, JR. UNITED STATES DISTRICT JUDGE
On July 13, 2004, Kurt Roberson was convicted by a jury of possession with intent to distribute and distribution of fifty grams or more of a substance containing cocaine base in violation of 21 U.S.C. § 841(a)(1) and of using or carrying a firearm during and in relation to that drug trafficking crime in violation of 18 U.S.C. § 924(c)(1)(A). Both convictions carried statutory mandatory minimum sentences. This Court sentenced Roberson to a term of imprisonment of 300 months: the statutory minimum pursuant to 21 U.S.C. § 841(b)(1)(A) (twenty years) for the drug count in light of the government’s filing of a notice under 21 U.S.C. § 851 of a prior felony drug conviction, plus the statutory minimum pursuant to 18 U.S.C. § 924(c)(1)(A)(i) (five years) for the gun count, to be served consecutively. Roberson appealed, and the First Circuit affirmed. United States v. Roberson, 459 F.3d 39 (1st Cir. 2006).
While his direct appeal was pending, Roberson moved pro se to vacate the 1996 Stoughton District Court conviction that served as the § 851 predicate for his drug sentencing enhancement. The state court granted his motion to vacate the prior conviction on August 25, 2006, about two weeks after the issuance of the Circuit’s opinion in this case.
Roberson subsequently filed this motion pursuant to 28 U.S.C. § 2255 to vacate his federal sentence. The government opposed the motion and thereafter counsel was appointed for Roberson. After further briefing and oral argument, I denied the motion, concluding that a defendant whose sentence is enhanced because of the existence of a prior conviction under §§ 841 and 851 may not use a post-sentencing § 2255 motion to vacate the imposed sentence on the basis of a subsequent vacation of the prior conviction. United States v. Roberson, 684 F.Supp.2d 179 (D. Mass. 2010).
However, I granted Roberson’s motion to amend his § 2255 motion to add a claim that his trial counsel had been constitutionally ineffective in violation of the Sixth Amendment in failing to attack the state court conviction in state court prior to Roberson’s federal sentencing.
An evidentiary hearing on the ineffective assistance of counsel claim was held, and the parties then submitted memoranda in support of their arguments and were heard in oral argument.
I. The Ineffective Assistance Claim
To assert a claim of ineffective assistance of counsel under the Sixth Amendment, a petitioner must demonstrate that (1) his attorney rendered performance that fell below an objective standard of reasonableness, and (2) as a result of his attorney’s unreasonable performance, he suffered actual prejudice. Strickland v. Washington, 466 U.S. 668, 687 (1984). As to deficient performance, a reviewing court must determine “whether, in light of all circumstances, identified acts or omissions were outside the wide range of professional competent assistance.” Id. at 690. “Judicial scrutiny of counsel’s performance must be highly deferential, ” and “a court must indulge a strong presumption that counsel’s conduct falls within the wide range of reasonable professional assistance.” Id. at 689. As to prejudice, a defendant must show that “there is a reasonable probability that, but for counsel’s unprofessional errors, the result of the proceeding would have been different.” Id. at 694. “A reasonable probability is a probability sufficient to undermine confidence in the outcome.” Id. “[A]lthough the possibility of a different outcome must be substantial in order to establish prejudice, it may be less than fifty percent.” Ouber v. Guarino, 293 F.3d 19, 25-26 (1st Cir. 2002) (citing Strickland, 466 U.S. at 693).
In this case, the central issue is what Roberson’s counsel could or should have done to avoid the enhancement based on the 1996 state court conviction. Roberson argues that counsel was ineffective in the constitutional sense because he did not thoroughly investigate the state court proceedings and thus did not discover the grounds upon which the 1996 conviction might have been, and thereafter actually was, vacated.
A. Unreasonable Performance
As a general matter, the record reveals that Roberson was vigorously defended by his counsel, an attorney with substantial experience in criminal law, both as a prosecutor in the United States Attorney’s Office and the Middlesex County District Attorney’s Office and as a defense attorney in private practice. The evidence revealed that counsel spent 375 hours working on Roberson’s case, and the defense team as a whole spent over 700 hours.
According to his testimony at the evidentiary hearing, counsel initially pursued a plea agreement with the government in an effort to avoid the statutory mandatory minimum. When that was not successful, counsel diligently defended Roberson at trial, filing pre-trial motions related to jury voir dire and the exclusion of evidence, proposing jury instructions, and filing motions for acquittal under Rules 29(a) and 29(c) of the Federal Rules of Criminal Procedure. After trial, counsel focused on sentencing, lodging many objections to the presentence report and filing several sentencing memoranda. Although his legal arguments were unsuccessful, I imposed a sentence of twenty-five years, the lowest sentence possible given the mandatory minimums and significantly below the Sentencing Guideline range of thirty-five years to life. After sentencing, counsel pursued an appeal to the First Circuit, albeit unsuccessfully, and ultimately filed a petition for certiorari to the Supreme Court, which was denied.
However, although as a general matter counsel’s representation of Roberson was vigorous and skillful, Roberson contends that his counsel’s performance was constitutionally ineffective in the Strickland sense because he failed adequately to investigate the predicate 1996 conviction. In particular, Roberson argues that his counsel did not retrieve and review the full case file for the state court proceedings and consequently did not notice several irregularities in the paperwork that ultimately formed the basis for the later vacation of the conviction.
Roberson’s prior counsel testified at the evidentiary hearing that he requested and obtained through a document retrieval service a number of state court criminal records in order to consider challenging any convictions that might impact sentencing. He testified that he studied the file for the 1996 conviction in order to determine if there was something in it that would provide a good faith basis to challenge the underlying conviction. He understood that there was a presumption of regularity with regard to the conviction and that Roberson would have the burden of undermining ...