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Decided: April 8, 2014

The Fourth Circuit held that Whiteside could use 28 U.S.C. § 2255 to challenge his erroneous “career offender enhancement” prison sentence under the United States Sentencing Guidelines (U.S.S.G.).  The Court also held that Whiteside did not waive his right to collaterally attack the sentence in his plea agreement, and the Court tolled the one-year limitations period normally allowed for Whiteside’s motion to vacate the sentence.  Ultimately, the Court vacated the sentence and remanded for resentencing.

Whiteside was indicted on a charge of Possession With Intent to Distribute (PWID) cocaine.  Based on an earlier felony drug conviction he received, the Government sought a career offender enhancement prison sentence under the U.S.S.G.  The U.S.S.G. defines a career offender as a person with “a prior state conviction for an offense punishable by imprisonment for a term exceeding one year . . . .”  Whiteside entered into his plea agreement with the Government under the assumption that he qualified as a career offender because of his prior conviction, and he received a prison sentence based on the U.S.S.G.’s recommended range for a career offender.  His prison sentence was eight years longer than it would have been had he not qualified as a career offender.  After Whiteside’s sentencing, a Fourth Circuit decision changed the law that applied to his prior offense so that he would not have been punished by more than one year in prison.  Thus, Whiteside should not have qualified as a career offender, nor be subject to a longer prison sentence.  Whiteside moved to set aside his sentence in the plea agreement as “in violation of the Constitution or Laws of the United States” under 28 U.S.C. § 2255, because he lacked the necessary predicate offense.

The Court reasoned that Whiteside could use 28 U.S.C. § 2255 to vacate his prison sentence under the plea agreement because the application of the erroneous career offender enhancement had a “significant impact” on his sentence, and refusal to allow Whiteside to appeal would amount to a “miscarriage of justice.”  This erroneous enhancement amounted to a miscarriage of justice even though Whiteside’s sentence in the plea agreement fell below the applicable range recommended in the U.S.S.G.  Furthermore, although technically “advisory” in nature, the U.S.S.G. significantly influenced Whiteside’s sentence.

The Court also reasoned that Whiteside’s waiver in the plea agreement did not bar an appeal of his prison sentence because the waiver was ambiguous.  Additionally, the Court tolled the limitations period for Whiteside’s motion to vacate his prison sentence because the erroneous application of the career offender enhancement “worked a gross miscarriage of justice[,]” Whiteside pursued his motion “diligently[,]” and “extraordinary circumstances” caused the delay in filing.

Full Opinion

– James Bull Sterling