Of the United States District Court for the Northern District



of Indiana, sitting by designation.

In the

United States Court of Appeals

For the Seventh Circuit

No. 10-2912

FRED E. DOWELL,

Petitioner-Appellant,

v.

UNITED STATES OF AMERICA,

Respondent-Appellee.

Appeal from the United States District Court 

for the Southern District of Indiana, Evansville Division.

No. 09 CV 00063—Richard L. Young, Chief Judge.

ARGUED OCTOBER 31, 2011—DECIDED SEPTEMBER 17, 2012

Before KANNE and WILLIAMS, Circuit Judges, and

DEGUILIO, District Judge.

WILLIAMS, Circuit Judge. 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
2 No. 10-2912

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 assistance of counsel which can be corrected in a § 2255 proceeding. We remand to the district court to make a determination as to whether Dowell told his attorney to

file the appeal.

I. BACKGROUND

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 government agreed to withdraw the section 851 information.

Without that withdrawal, Dowell would have faced a

mandatory minimum sentence of twenty years’ imprisonment.

The parties prepared and signed a written plea agreement. In addition to memorializing the government’s
No. 10-2912 3

withdrawal of the 21 U.S.C. § 851 information, the agreement also provided, among other things, that the base

offense level for Dowell’s crime was 32. But, the agreement said, if the court determined Dowell to be a career

offender under section 4B1.1 of the United States Sentencing 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 Guidelines Stipulations set forth herein and sentences

Dowell to a term of imprisonment with the guidelines 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 agreement stated:

Additionally, Dowell expressly agrees not to contest,

or seek to modify, his conviction or sentence or the
4 No. 10-2912

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 commented, “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’ imprisonment. 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 information, 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
No. 10-2912 5

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. The district court later

denied Dowell’s other motions; pursuant to Federal

Rule of Appellate Procedure 4(a)(b)(4), the request for

enlargement of time had come too late. We dismissed

the appeal for lack of jurisdiction. United States v. Dowell,

No. 08-3920 (Order Jan. 27, 2009) (unpublished).

On May 5, 2009, Dowell filed a pro se motion for postconviction relief pursuant to 28 U.S.C. § 2255, asserting

in it that his defense counsel failed to file a timely

notice of appeal after Dowell had requested that he do

so. He also submitted a sworn statement stating that

he instructed his trial attorney to appeal the career

offender finding and that counsel failed to do so. The

district court agreed with the government that the

waiver provisions in the plea agreement precluded any

relief. Dowell, now represented by appointed counsel,

appeals.

II. ANALYSIS

The Sixth Amendment to the United States Constitution guarantees criminal defendants the assistance of
6 No. 10-2912

counsel. The Supreme Court has stated that “a lawyer

who disregards specific instructions from the defendant to file a notice of appeal acts in a manner that

is professionally unreasonable.” Roe v. Flores-Ortega,

528 U.S. 470, 476-77 (2000). And “[w]hen counsel fails to

file a requested appeal, a defendant is entitled to . . . an

appeal without showing that his appeal would likely

have merit.” Peguero v. United States, 526 U.S. 23, 28 (1999).

In other words, “[w]hen a defendant asks his attorney

to pursue a direct appeal and the attorney does not do

so, it is per se ineffective assistance of counsel.” Gant

v. United States, 627 F.3d 677, 681 (7th Cir. 2010).

Dowell maintains that he received constitutionally

ineffective assistance of counsel because his counsel did

not follow his directive to file a notice of appeal of an

issue specifically reserved for appeal in the plea agreement. The government, however, maintains that

Dowell’s agreement in his plea not to contest his

sentence in a collateral attack precludes any relief here.

It argues that the plea agreement only reserved the

right to appeal the career offender determination in

a direct appeal. Because the § 2255 proceeding is a collateral attack, not a direct appeal, the government

says Dowell waived the ability to get any relief here.

We review de novo the enforceability of a plea agreement’s waiver of direct or collateral review. See United

States v. Quintero, 618 F.3d 746, 750 (7th Cir. 2010).

A defendant may certainly waive the right to appeal

his conviction and sentence, as well as the ability to

challenge either in a collateral attack. United States v.
No. 10-2912 7

Alcala, 678 F.3d 574, 577 (7th Cir. 2012); Keller v. United

States, 657 F.3d 675, 681 (7th Cir. 2011). We have

repeatedly held “that a voluntary and knowing waiver

of an appeal is valid and must be enforced.” See, e.g.,

United States v. Sakellarion, 649 F.3d 634, 638 (7th Cir.

2011). There are only limited instances when we will

not enforce a knowing and voluntary waiver of direct

appeal or collateral review, including when the

sentence exceeds the statutory maximum, when the plea

or court relies on a constitutionally impermissible

factor like race, or when counsel is ineffective in the

negotiation of the plea agreement. Keller v. United

States, 657 F.3d 675, 681 (7th Cir. 2011). Dowell signed the

agreement voluntarily, and none of the other aforementioned circumstances are present, so the government

contends we must enforce the collateral attack waiver.

But for a waiver to apply, the disputed appeal or collateral attack must fall within the waiver’s scope. Id.

A plea agreement is a contract. Quintero, 618 F.3d at 751.

As with any contract, “[w]e interpret the terms of the

agreement according to the parties’ reasonable expectations” and construe any ambiguities in the light most

favorable to Dowell. Id. (citations omitted).

The parties’ reasonable expectations could not have

extended as far as the government presses here. 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
8 No. 10-2912

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.

The fact that Dowell specifically reserved the right to

appeal the career offender determination distinguishes

this case from our decision in Nunez v. United States,

546 F.3d 450 (7th Cir. 2008). There we considered a § 2255

ineffective assistance of counsel claim asserting that an

attorney had not followed his client’s request to file a

notice of direct appeal. The plea agreement waived

the right to appeal and to pursue collateral attack, and

the only exceptions were to contest the voluntariness

of the plea and to challenge a sentence above the

statutory maximum. The plea there was voluntary and

the sentence well below the maximum allowed by statute. We said in those circumstances that “[a] lawyer who

respects his client’s formal waiver of appeal does

not render objectively deficient service” by failing to file

a notice of appeal. See id. at 453. (That position put us

at odds with other circuits who have held that the

lawyer must always file a notice of appeal upon request.

See id. at 453-54 (collecting cases)). But, speaking to circumstances like ours, we said:

One important caveat bears attention. Our analysis

supposes the defendant really has waived his en-
No. 10-2912 9

titlement to direct appeal. If it turns out that the

waiver does not cover an issue that the defendant

told counsel he wanted to present on direct appeal,

then counsel’s failure to file a notice of appeal is

within the scope of Roe and will lead to collateral

relief without regard to prejudice. Our conclusion

that Strickland applies is limited to situations in

which the waiver actually governs the proposed

appeal.

Id. at 456.

That important caveat describes our case. Dowell’s

waiver did not waive his ability to appeal the issue that

he told counsel he wanted to present on direct appeal;

rather, the plea specifically reserved it. Therefore, counsel’s failure to file a notice of appeal means collateral

relief without inquiring into prejudice.

The government seems to acknowledge that the

prejudice inquiry does not matter here, as it says that

Dowell’s sworn statement, “if truthful, would have required the filing of an appeal, no matter how futile, on

Dowell’s behalf.” That statement is correct. See Roe, 528

U.S. at 476-77. But several of the arguments the government makes sound of prejudice. The government argues

that we should deny Dowell relief because his sentence

is “reasonable,” but that is an inquiry into the merits of

an appeal. We also note that while it is true that the

district court imposed a below-guidelines sentence,

it might have imposed an even lower one if Dowell

were not a career offender. Without career offender
10 No. 10-2912

status, Dowell’s criminal history category would have

been no higher than III. The resulting guidelines range

would have been 108-135 months, far less than the 180-

month sentence he received. Similarly, the government’s position that we should rule in its favor on the

basis that there was no error in the career offender determination incorrectly assumes that we should inquire

into the merits of the appeal at this stage. The Supreme

Court has made clear that we should not. See Peguero,

526 U.S. at 28-29.

So if Dowell instructed his trial attorney to file a notice

of appeal so that he could appeal the career offender

determination and counsel failed to do so, Dowell

received ineffective assistance of counsel. Before Dowell

can be afforded any relief, however, that “if” must be

resolved in his favor. The government’s final argument

is that we should rule against Dowell on the basis that

Dowell did not in fact make this request to his attorney. But because the district court decided this case on

the basis of waiver, no determination has yet been made

on this question of fact. We are not the proper court

to do so.

Dowell submitted a sworn statement saying that he

requested that his attorney appeal the career offender

determination and that counsel failed to do so, and

this statement clearly alleged a constitutional violation.

He had personal knowledge of that allegation, and there

is nothing “palpably incredible” about it. See Ryan v.

United States, 657 F.3d 604, 606 (7th Cir. 2011). The

request was consistent with Dowell’s insistence on the
No. 10-2912 11

carve-out for such an appeal in his plea agreement. It

also makes sense that Dowell would have wanted to

appeal the career offender finding in light of the

much lower guidelines range that would have resulted.

Dowell’s allegations are therefore sufficient to warrant

further proceedings. See id. at 607.

They are not, however, conclusive. As the government highlights, Dowell’s former trial counsel stated

in his motion to withdraw that Dowell had filed “a

letter with the District Court which was subsequently

treated as a Notice of Appeal. In that letter Appellant

states that he directed Counsel to file a notice of appeal

and that he failed to do so . . . . Counsel states that

the statements of Appellant set forth in his letter dated

November 11, 2008 or his motion of January 7, 2009, are

inaccurate as to alleged conversations with Counsel

concerning the notice of appeal.” Counsel also stated in

his motion to withdraw that “[b]ased on a number of

discussions with Appellant following sentencing

Counsel for Appellant did not file a Notice of Appeal.”

In light of the conflicting accounts, whether Dowell

asked his counsel to file a notice of appeal is a factual

question for the district court to resolve on remand, and

we remand for it to do so. See id. at 608.

III. CONCLUSION

The judgment of the district court is VACATED, and

this case is REMANDED for further proceedings.

9-17-12