US v. Harrington, 354 F. 3d 178 - Court of Appeals, 2nd Circuit 2004

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\u27 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\u27 substantial rights. In July 1999, during Main\u27s plea colloquy, the District Court told Main that he faced a mandatory minimum sentence of imprisonment for his crimes. Under the Supreme Court\u27s 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\u27s 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\u27s plea agreement or colloquy. While in some circumstances a district court\u27s 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\u27s state of mind in agreeing to the plea, and, consequently, we cannot be assured on the record before us that Main\u27s guilty plea was knowing and voluntary. Because we cannot speculate on Main\u27s state of mind, but rather must look solely to the record in determining whether Main\u27s 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