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.

Earlier today, the Seventh Circuit reversed in Dowell v. United States (No. 10-2912).  

To reach what seems the only fair result, Judge Williams had to engage in a bit of creative contract interpretation.  The question was whether Dowell’s §2255 motion fell within the scope of the waiver, as set forth in the plea agreement.  In holding that it did not, here was the court’s key analytical maneuver:

The plea agreement specifically reserves the right to appeal the career offender determination. The specific reservation of that right necessarily includes a meaningful opportunity to exercise it.  See United States v. Barnett, 415 F.3d 690, 692 (7th Cir. 2005) (stating that as contracts, plea bargains contain implicit as well as explicit terms, especially those implicit terms needed to avoid absurdities). A meaningful opportunity to appeal includes the effective assistance of counsel in filing the appeal. When counsel does not provide effective assistance by failing to file a notice of appeal of an issue specifically reserved for appeal in the plea, a petitioner must be able to use a collateral attack to save the appeal from being lost due to counsel’s failure to do what he was requested.  (7-8)

I could imagine other courts taking the view that Dowell’s express reservation of some appellate rights means that a failure to reserve  §2255 rights should be given greater interpretive significance than was done here.

On the other hand, the Seventh Circuit’s decision seems consistent with the established principle that courts should “interpret the terms of [a plea] agreement according to the parties’ reasonable expectations and construe any ambiguities in the light most favorable to [the defendant].”  (7)  It is regrettable that broad waivers of post-conviction remedies have become a routine part of federal criminal practice.  Narrow interpretations of these waivers based on principles of reasonableness, as in Dowell, can help to prevent some of the worst injustices.

Cross posted at Life Sentences.