Monday, November 15th, 2021

On appeal, a preserved challenge to a Rule 11 error at the guilty plea is reviewed for harmless error, and it’s the government’s burden to prove that the Rule 11 error was harmless. United States v. Freeman, No. 19-2432, __F.4th__ , 2021 WL 5114918 (2d Cir. Nov. 4, 2021) (C.J.J. Sullivan, Park, and Nardini).

During a guilty plea allocution to a drug conspiracy, the district court erroneously stated that the mandatory minimum term of supervised release term was 5 years, when it actually was 10 years, thereby violating Fed.R.Crim.P. 11(b)(1)(I)’s requirement the defendant be accurately informed about punishment, including “any mandatory minimum penalty.” Freeman preserved his challenge to the Rule 11 error by moving to withdraw his guilty plea before sentencing. The district court denied the motion. And the Circuit affirmed, saying the error was harmless (under Fed.R.Crim.P. 11(h)). But the Opinion’s stated purpose is to “clarify” that “a preserved challenge to a Rule 11 error is subject to harmless error review on appeal and that the government bears the burden of showing that the error had no effect on the defendant’s substantial rights.” Op at 3.


The grand jury returned a one-count  indictment charging Freeman with a drug conspiracy in violation of 21 U.S.C.  §§ 841(a), 841(b)(1)(A), and 846 (offense involving 5 or more kilograms. of cocaine or 280 or more grams of cocaine base). The government then filed an information, under  21 U.S.C. § 851 (because of Freeman’s prior felony drug conviction), raising Freeman’s mandatory minimum term of imprisonment from 10 to 20 years and his mandatory minimum term of supervised release from 5 to 10 years.

In May 2018, Freeman pleaded guilty to the indictment under a plea agreement that accurately reflected the prison term he faced (10 years to life) and accurately reflected “that he faced a maximum term of supervised  release of life.” Op at 4. But the agreement incorrectly stated that Freeman was subject to a mandatory minimum term of supervised release of 5 years, when it was actually 10, years. Id. “The error in the agreement carried over to Freeman’s plea allocution.” Op at 5. And the district court wrongly stated that the mandatory minimum term of supervised release was five years, although it correctly said the ‘maximum” term of supervision was life. Id.

Before sentencing (and after the filing of the Presentence Report), the court recognized the error and informed the defense. Freeman moved to withdraw the guilty plea. The motion was denied. And “[o]n June 14, 2019, the district court sentenced Freeman to 15 years’ imprisonment and 10 years’ supervised release, the minimum total sentence allowed by law.” Op at 5-10.


The Circuit affirmed the district court’s order, denying the motion to withdraw the guilty plea. But it stated it would “first clarify the applicable framework and standard of review on appeal where a defendant asserts a Rule 11 error.” Op at 10.

It said: “Because both parties wrongly assume that Freeman, as the defendant, bears the ultimate burden of persuasion to show that the Rule 11 error affected his substantial rights, we clarify that where a defendant moved to withdraw a guilty plea before sentencing based on a Rule 11 error, it is the government’s burden on appeal to show that such error was harmless.” Op. at 3.

But it added: “While this framework is more defendant-friendly than what the parties argue in their briefs, we nevertheless find that Freeman’s substantial rights were not violated by the Rule 11 error in his plea agreement and colloquy and therefore conclude that the error was harmless.” Op at 3; see Op at 15-23 (discussing why, in this case, the Rule 11 error about the mandatory minimum term of supervised release was harmless).

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Categories: guilty plea, Rule 11
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