Appeal from the United States District Court for the Southern District of Indiana, Evansville Division. No. 09 CV 00063--Richard L. Young, Chief Judge.
The opinion of the court was delivered by: Williams, Circuit Judge.
ARGUED OCTOBER 31, 2011--
Before KANNE and WILLIAMS, Circuit Judges, and DEGUILIO, District Judge.*fn1
Fred Dowell signed a plea agreement that specifically reserved his right to appeal "career offender" designation if the district court found him to be one at sentencing. After the court made this designation, Dowell claims that he then directed his attorney to file a notice of appeal to contest whether he was a career offender. However, his counsel did not file the notice of appeal. So Dowell filed a 28 U.S.C. § 2255 motion asserting that his counsel's failure to file the directed appeal constituted ineffective assistance of counsel. The government opposed the motion, arguing that Dowell's agreement in his plea not to challenge his sentence on collateral attack precluded relief. We agree with Dowell that if he told his attorney to appeal the issue specifically reserved in his plea for appeal and counsel did not do so, he received ineffective assis- tance of counsel which can be corrected in a § 2255 pro- ceeding. We remand to the district court to make a de- termination as to whether Dowell told his attorney to file the appeal.
The federal government charged Fred Dowell with possessing with the intent to distribute 50 grams or more of a substance containing cocaine base in violation of 21 U.S.C. § 841(a)(1) and later filed an information pursuant to 21 U.S.C. § 851 alleging that Dowell had previously been convicted of a felony drug offense. Dowell decided to plead guilty, and in return the gov- ernment agreed to withdraw the section 851 information. Without that withdrawal, Dowell would have faced a mandatory minimum sentence of twenty years' imprison- ment.
The parties prepared and signed a written plea agree- ment. In addition to memorializing the government's withdrawal of the 21 U.S.C. § 851 information, the agree- ment also provided, among other things, that the base offense level for Dowell's crime was 32. But, the agree- ment said, if the court determined Dowell to be a career offender under section 4B1.1 of the United States Sen- tencing Guidelines, the offense level would be 37.
The agreement also specified a three-level reduction for acceptance of responsibility if Dowell continued to cooperate with the government.
Dowell did not agree that he was a career offender, and the plea agreement specifically reserved his ability to appeal a determination that he had career offender status. He waived the right to appeal his conviction and sentence on any other ground. The plea agreement's exact language provided:
In the event the Court adopts the Sentencing Guide- lines Stipulations set forth herein and sentences Dowell to a term of imprisonment with the guide- lines range determined in accordance therewith, or lower, regardless of how the sentence is calculated by the Court, Dowell expressly waives his right to appeal the conviction and sentence imposed in this case on any grounds . . . with the exception of the "career offender" status issue.
Like many plea agreements, this one also contained a provision noting Dowell's agreement not to contest his conviction or sentence in a collateral attack. The agree- ment stated:
Additionally, Dowell expressly agrees not to contest, or seek to modify, his conviction or sentence or the manner in which it was determined in any collateral attack, including, but not limited to, any action brought under Title 28, United States Code, Section 2255.
At the sentencing hearing, Dowell's counsel argued that Dowell was not a career offender because his two prior convictions were relevant conduct to the instant offense. The district court disagreed, although it com- mented, "Be an interesting bar [exam] question, wouldn't it?" The district court concluded that Dowell had two prior qualifying felony drug convictions that made him a career offender under U.S.S.G. § 4B1.1. The resulting guidelines range was 262-327 months' imprison- ment. After considering the factors in 18 U.S.C. § 3553(a) and noting that some of Dowell's offenses occurred before he turned eighteen, as well as the fact that the government had agreed to drop the section 851 infor- mation, the court imposed a sentence of 180 months' imprisonment.
The district court entered judgment on June 12, 2008. A notice of appeal was not filed within the ten days that followed, which was required for timely filing. See Fed. R. App. P. 4(b)(1)(A) (2008). (A 2009 amendment to Federal Rule of Appellate Procedure 4 changed the time to file a notice of appeal in a criminal case to fourteen days.) On November 11, 2008, Dowell sent a letter to the district court asking that it allow the letter to serve as notice to request an appeal. The letter stated that Dowell had previously instructed his attorney to request an appeal, but that he had only recently learned that the attorney had failed to act on his request. Dowell later requested an enlargement of time to file a notice of appeal on the basis that he had been in transit in the weeks following judgment, was unable to reach his attorney, and was not aware that the notice of appeal had not been filed. He also asked that the court appoint counsel to represent him going forward. Before the district court ruled on those motions, Dowell's counsel filed a motion with this court to withdraw as counsel, asserting a conflict of interest, and the motion was granted. ...