Charged in federal court with drug trafficking, Fred Dowell decided to enter into a plea agreement with the government. The deal included various stipulations as to his sentence, but reserved for Dowell the right to challenge the government’s contention that he should be sentenced as a career offender under the federal sentencing guidelines. Assuming the stipulations were accepted by the sentencing judge, Dowell waived his right to appeal the sentence, except that he expressly reserved the right to appeal an adverse career offender determination. Dowell also surrendered his right to mount a collateral attack on the sentence under 28 U.S.C. §2255.
Dowell was, in fact, sentenced as a career offender. By his account, he instructed his lawyer to appeal this decision, as he had reserved the right to do. No appeal was filed. By the time Dowell realized this, it was already too late for an appeal to be taken. Accordingly, he tried a §2255 motion in the district court, contending that his lawyer’s failure to appeal constituted ineffective assistance of counsel in violation of the Sixth Amendment. Sorry, said the district court, but you waived your rights under §2255 in the plea agreement.