U.S. v. Harrington, Docket No. 01-1505.

• Decision Date: 06 January 2004
• Docket Number: Docket No. 01-1505.
• Parties: UNITED STATES of America, Appellee, v. Gary HARRINGTON, Craig Whitman, Mark Vince, and Michael Crawford, Defendants, Christopher MAIN, Defendant-Appellant.
• Court: U.S. Court of Appeals — Second Circuit

354 F.3d 178

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.

Darrell B. Fields, Legal Aid Society, Federal Defender Division, New York, N.Y., for Defendant-Appellant.

David V. Kirby, First Assistant United States Attorney for the District of Vermont, Burlington, VT (John P. Tavana, Assistant United States Attorney for the District of Vermont, of counsel, Peter W. Hall, United States Attorney for the District of Vermont, on the brief), for Appellee.

Before: MESKILL, MINER and STRAUB, Circuit Judges.

MINER, Circuit Judge.

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 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

BACKGROUND

Main, an individual with an extensive history of drug use and felonious conduct, and several other individuals living in Vermont were involved in a conspiracy (the "Conspiracy") to import various drugs — including cocaine, heroin, and crack — from New York City for distribution in Vermont. Main and his co-conspirators were indicted as a result of an investigation that was launched by the Government when one user of the Conspiracy's drugs turned up dead and another nearly so. During the investigation, it was also revealed that Main had hired one of his co-conspirators, Gary Harrington, to burn down a building that was owned by Main. Harrington owed Main a substantial amount of money for drugs and had agreed to commit the arson in exchange for Main's forgiveness of the debt after the insurance proceeds from the building were collected. On June 10, 1998, Main and four others were charged in a sixty-one-count indictment with various controlled-substance offenses and the forfeiture of certain pieces of real estate.

In August 1998, a Vermont federal grand jury returned a superseding indictment charging Main with conspiracy to distribute and possess with intent to distribute controlled substances, in violation of 21 U.S.C. §§ 841(a)(1) and 846; violation of the Travel Act, 18 U.S.C. § 1952(a)(3); eighteen separate counts of distributing controlled substances, some involving users under the age of twenty-one, in violation of 21 U.S.C. §§ 841(a)(1) and 859; and various forfeitures of real property and cash, pursuant to 21 U.S.C. § 853. Notably, the indictment did not charge specific quantities of any of the drugs Main was charged with distributing and conspiring to possess and distribute.

After Main's indictment and arrest, his attorney at the time, Cindy Ellen Hill, negotiated a plea agreement with the Government. In exchange for Main's cooperation with the Government in its case against Harrington and the other conspirators, the Government agreed to permit Main to (i) plead guilty to the counts in the superseding indictment charging him with conspiracy to possess and distribute drugs in violation of 21 U.S.C. §§ 841(a)(1) and 846, and the forfeiture of certain property and (ii) waive indictment and plead guilty to an information charging him with mail fraud, in violation of 18 U.S.C. § 1341. The plea agreement set out the penalties for the offenses. It provided that the drug count carried a mandatory minimum penalty of twenty years' imprisonment and a maximum penalty of life imprisonment and that the maximum penalty for the mail fraud count was five years' imprisonment and a $250,000 fine. Notably, the plea agreement did not mention restitution.

On July 8, 1999, in a lengthy plea proceeding, Main accepted the plea and allocuted in open court to the elements of the crimes. The District Court described the elements of the charges to which Main was pleading, and Main confirmed his understanding of what the court told him. The prosecutor, at the District Court's direction, described the facts that the Government would prove at trial to establish the drug conspiracy and mail fraud charges. Chief Judge Murtha then asked Main if the charges were true, to which he replied, "Yes, sir."

The District Court then directed Main's attention to the Government's proffer that it would "show that throughout the course of th[e] 3-year conspiracy the quantity of drugs that were brought back were [sic] sufficient to meet the[] levels described in [21 U.S.C. §] 841(b)(1)(A)" — specifically, a quantity of "5 kilos or more of a ... mixture or substance containing cocaine... [or] 50 grams or more of a mixture or substance containing cocaine base." The District Court then addressed Main as follows:

What I will be asking you shortly, Mr. Main, is the potential — if you understand the potential penalties here. And the reason we're discussing the quantities is that the [G]overnment is saying [it] would prove that the amounts involved meet the requirements of the statute as to those penalties, that I will shortly ask you about.

Do you understand that?

Main replied, "Yes." It is unclear from the record, however, whether Main actually was agreeing to the quantities stated by the Government or simply acknowledging the Government's proffer. In any event, the District Court did not ask Main to provide an independent estimate of the quantities of the drugs that were the object of the conspiracy. Thus, although Main admitted to possessing, distributing, and conspiring to possess and distribute drugs, he never allocated to any specific quantity. Nor, as noted above, did the superseding indictment attribute any specific quantities of drugs to the Conspiracy. In addition, no mention was made of restitution during the colloquy.

Following the plea, Main's relationship with attorney Hill soured, and on November 2, 1999, Main wrote to the District Court asking that a new lawyer be assigned to his case. Hill did not object; indeed, on the same date, she filed her own motion to be relieved as Main's counsel. The District Court granted the motions and, on November 4, appointed Public Defender Elizabeth Mann to represent Main. That relationship continued until December 2000, when Mann disclosed to Main a disqualifying conflict of interest. At Mann's and Main's mutual request, the District Court relieved Mann as counsel and, on March 29, 2001, appointed federal public defender Amy Seidman to represent Main.

Notably, in Mann's motion to be relieved as Main's counsel, dated December 6, 2000, Mann mentioned that Main had expressed a desire to withdraw his guilty plea. Main made no formal motion in this regard, however, until June 15, 2001 — two weeks after Amy Seidman had taken over Main's case, and four days before Main was to be sentenced. In that motion, Main claimed that his first attorney in this case, Ms. Hill, had lied to Main about his sentencing options and, thereby, manipulated him into accepting the plea.

In a four-page, unpublished opinion and order dated July 26, 2001, the District Court denied without a hearing Main's motion to withdraw his guilty plea. Chief Judge Murtha found that Main had submitted no credible evidence in support of his allegations that attorney Hill had "lied to [Main], manipulated him, and coerced him into pleading [g]uilty."² The court recited several excerpts from the transcript of Main's allocution, including passages recording Main's express (i) admission to the crimes, (ii) confirmation that no threats or promises had been made inducing him to waive the superseding indictment, and (iii) acknowledgment of the finality and irrevocability of his guilty plea. The District Court concluded that these facts, along with the almost two-year delay in the filing of Main's motion to withdraw his plea, tended to show that the motion was nothing more than an opportunistic attempt by Main to...