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Defendant-appellant Christopher Main appeals from a judgment entered in the United States District Court for the District of Vermont (Murtha, C.J.), following a plea of guilty, convicting Main of mail fraud and conspiracy to distribute and to possess with intent to distribute various controlled substances, sentencing him principally to 324 months' imprisonment, and ordering restitution of $29,211.50. Once again, we are faced with the complexities involved in striking a balance between enforcing strict adherence to the provisions of Fed.R.Crim.P. 11 and disregarding variances from the rule that do not affect defendants' substantial rights.

In July 1999, during Main's plea colloquy, the District Court told Main that he faced a mandatory minimum sentence of imprisonment for his crimes. Under the Supreme Court's subsequent decision in Apprendi v. New Jersey, 530 U.S. 466, 120 S.Ct. 2348, 147 L.Ed.2d 435 (2000), as applied by this Court in United States v. Thomas, 274 F.3d 655 (2d Cir.2001) (en banc), no such minimum could have applied without proof in the record of the precise quantities of the drugs that Main 180*180 pled guilty to conspiring to distribute and possess. At Main's August 2001 sentencing hearing, the District Court failed to rectify the situation, which it could have done by clarifying in the record the specific quantities of drugs at issue. In addition, Chief Judge Murtha ordered a not insubstantial amount of restitution for the mail fraud, despite the fact that no restitution was specified in Main's plea agreement or colloquy.

While in some circumstances a district court's error in overstating an applicable minimum sentence may be harmless, that is not the case before us. Here, that error, along with the issue of the improperly-imposed restitution and other circumstances, combine to create a "critical mass" of uncertainty regarding Main's state of mind in agreeing to the plea, and, consequently, we cannot be assured on the record before us that Main's guilty plea was knowing and voluntary. Because we cannot speculate on Main's state of mind, but rather must look solely to the record in determining whether Main's plea was knowing and voluntary, we vacate the conviction and remand to the District Court with instructions that Main be allowed to withdraw his guilty plea.[1]


354 F.3d 178 (2004)

UNITED STATES of America, Appellee, v. Gary HARRINGTON, Craig Whitman, Mark Vince, and Michael Crawford, Defendants, Christopher MAIN, Defendant-Appellant.

Docket No. 01-1505.

United States Court of Appeals, Second Circuit.

Argued: August 27, 2003.

Decided: January 6, 2004.

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