In the
United States Court of Appeals
For the Seventh Circuit
No. 10-2912
F RED E. D OWELL,
Petitioner-Appellant,
v.
U NITED S TATES OF A MERICA,
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.
A RGUED O CTOBER 31, 2011—D ECIDED S EPTEMBER 17, 2012
Before K ANNE and W ILLIAMS, Circuit Judges, and
D EG UILIO , District Judge.
W ILLIAMS, 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
Of the United States District Court for the Northern District
of Indiana, sitting by designation.
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 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.
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 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
No. 10-2912 3
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 agree-
ment’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
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, Sec-
tion 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
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 post-
conviction 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 Constitu-
tion 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 de-
fendant 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 agree-
ment. 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 collat-
eral 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 agree-
ment’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 aforemen-
tioned circumstances are present, so the government
contends we must enforce the collateral attack waiver.
But for a waiver to apply, the disputed appeal or col-
lateral 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 expecta-
tions” 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 reserva-
tion of that right necessarily includes a meaningful op-
portunity 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, espe-
cially 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 stat-
ute. 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 cir-
cumstances 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, coun-
sel’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 re-
quired 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 govern-
ment 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 govern-
ment’s position that we should rule in its favor on the
basis that there was no error in the career offender deter-
mination 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 attor-
ney. 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 govern-
ment 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 V ACATED , and
this case is R EMANDED for further proceedings.
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