                       NOT RECOMMENDED FOR PUBLICATION
                               File Name: 14a0375n.06

                                          No. 12-5118
                                                                                       FILED
                          UNITED STATES COURT OF APPEALS                         May 20, 2014
                               FOR THE SIXTH CIRCUIT                         DEBORAH S. HUNT, Clerk

                                                        )
ADRIAN HAMILTON,                                        )
                                                        )
       Petitioner-Appellant,                            )
                                                                ON APPEAL FROM THE
                                                        )
                                                                UNITED STATES DISTRICT
               v.                                       )
                                                                COURT FOR THE WESTERN
                                                        )
                                                                DISTRICT OF KENTUCKY
UNITED STATES OF AMERICA,                               )
                                                        )
       Respondent-Appellee.                             )
                                                        )


BEFORE: DAUGHTREY, McKEAGUE, and GRIFFIN, Circuit Judges.

       GRIFFIN, Circuit Judge.

       Adrian Hamilton appeals the district court’s dismissal of his motion to vacate his

sentence filed pursuant to 28 U.S.C. § 2255. Hamilton pled guilty to certain drug-related crimes

under a written plea agreement, reserving the right to appeal whatever sentence the district court

imposed but waiving his right to “contest or collaterally attack his conviction and the resulting

sentence pursuant to 28 U.S.C. § 2255 or otherwise, including but not limited to, claims of

ineffective assistance of counsel.” After the district court sentenced Hamilton to 120 months’

imprisonment, he allegedly directed his attorney to appeal his sentence but counsel never did.

Once Hamilton learned that an appeal had not been taken, he brought a motion to vacate his

sentence under § 2255 for the limited purpose of reinstating his opportunity to file a delayed

appeal, arguing that his attorney provided ineffective assistance of counsel in violation of the

Sixth Amendment by ignoring his instructions to file an appeal. The district court dismissed the
No. 12-5118, Hamilton v. United States


motion, concluding that the collateral-review waiver barred the claim. For the reasons that

follow, we reverse and remand for an evidentiary hearing on the merits of Hamilton’s

ineffective-assistance claim.

                                                 I.

       On January 5, 2009, a federal grand jury indicted Hamilton on charges of possession with

intent to distribute 50 grams or more of cocaine base, possession with intent to distribute

cocaine, and possession with intent to distribute marijuana. Hamilton retained counsel and pled

guilty to all three counts under a Rule 11(c)(1)(C) plea agreement. The parties agreed that the

mandatory minimum sentence of 120 months’ imprisonment was appropriate and that the

government would not seek an enhancement under 21 U.S.C. § 851, which would have doubled

Hamilton’s sentence to 240 months because of his prior record.

       The agreement also contained a waiver clause regarding Hamilton’s rights to appeal and

to collaterally attack his conviction and sentence:

       11. Defendant is aware of his right to appeal his conviction and that 18 U.S.C.
       § 3742 affords a defendant the right to appeal the sentence imposed. The
       Defendant knowingly and voluntarily waives the right (a) to directly appeal his
       conviction and the resulting sentence pursuant to Fed. R. App. P. 4(b) and 18
       U.S.C. § 3742, and (b) to contest or collaterally attack his conviction and the
       resulting sentence pursuant to 28 U.S.C. § 2255 or otherwise, including but not
       limited to, claims of ineffective assistance of counsel. Defendant understands and
       agrees that nothing in this plea agreement should be construed as a waiver by the
       United States of its right to appeal the sentence under 18 U.S.C. § 3742.

Although the agreement originally contained a waiver of appeal and collateral attack, the parties

struck out the waiver of appeal by placing their initials beside the lined-out portion of the second

sentence, leaving the waiver of collateral attack in place.1 Hamilton explained that he did not

want to waive his right to appeal because counsel advised him that if the then-pending Fair

       1
         We note that Hamilton does not contend that the striking out of the language preceding
clause (a) nullifies the waiver of the rights in clause (b).
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No. 12-5118, Hamilton v. United States


Sentencing Act (“FSA”) became law while his direct appeal was unresolved, he would benefit

from the FSA’s lower mandatory minimum sentences.

       At Hamilton’s guilty plea hearing, the district court found him competent, that he desired

to waive his constitutional rights, and that there was a factual basis for the plea. The government

outlined the terms of the plea agreement, including the provision that Hamilton “is waiving any

collateral attack at a later time based upon issues, not the least of which might be ineffective

assistance of counsel.” Hamilton acknowledged that he read, reviewed, and understood the

agreement.

       During the sentencing hearing, the parties again discussed the collateral-review waiver in

the plea agreement. Addressing Hamilton directly, the district court advised: “Mr. Hamilton,

you waived your right to collaterally attack your sentence, but you did not waive your right to

appeal. And if you want to appeal this case, you need to file a notice of appeal within ten days

after I enter an order setting your sentence.” The court then sentenced Hamilton to 120 months’

imprisonment. Contrary to Hamilton’s alleged instruction otherwise, his counsel did not file a

notice of appeal challenging the sentence.

       Proceeding pro se, Hamilton filed a timely motion to vacate sentence under 28 U.S.C. §

2255, alleging one claim of ineffective assistance of counsel for his lawyer’s failure to file a

notice of appeal. Hamilton requested only that he be afforded the opportunity to file a delayed

appeal of his sentence. The government filed a motion to dismiss based on the collateral-attack

waiver in the plea agreement.

       The court referred the motion to a magistrate judge, who recommended that the court

deny the government’s motion without prejudice and hold an evidentiary hearing to determine

the merits of the ineffective-assistance claim before ruling on the effect of the collateral-attack


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No. 12-5118, Hamilton v. United States


waiver.       The court rejected the recommendation, granted the government’s motion, and

dismissed Hamilton’s motion, holding that the collateral-attack waiver was knowing and

voluntary, and that it barred the instant claim. Hamilton timely appealed and has been appointed

counsel.

                                                 II.

                                                 A.

          Whether a defendant has waived a right under a plea agreement and, if so, whether that

waiver is enforceable are questions of law that we review de novo. United States v. McGilvery,

403 F.3d 361, 362 (6th Cir. 2005); Davila v. United States, 258 F.3d 448, 450 (6th Cir. 2001).

“[A] defendant’s informed and voluntary waiver of the right to collaterally attack a conviction

and sentence is enforceable.” In re Acosta, 480 F.3d 421, 422 (6th Cir. 2007).

                                                 B.

          Under the collateral-attack waiver in Hamilton’s plea agreement, he has waived the right

“to contest or collaterally attack his conviction and the resulting sentence pursuant to 28 U.S.C.

§ 2255 or otherwise, including but not limited to, claims of ineffective assistance of counsel.”

The parties dispute whether this provision bars the instant § 2255 motion, which presents a post-

sentencing, ineffective-assistance-of-counsel claim based on counsel’s alleged failure to file a

notice of appeal.2




          2
         A lawyer’s failure to appeal when expressly instructed by the client to do so is
objectively unreasonable conduct per se under Strickland v. Washington, 466 U.S. 668 (1984).
See Roe v. Flores-Ortega, 528 U.S. 470, 477 (2000). Further, because depriving a defendant of
his right to appeal is presumptively prejudicial, it is irrelevant whether the appeal is likely to
succeed. Id. at 483; see also Ludwig v. United States, 162 F.3d 456, 459 (6th Cir. 1998) (holding
that “the failure to perfect a direct appeal, in derogation of a defendant’s actual request, is a per
se violation of the Sixth Amendment”).
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No. 12-5118, Hamilton v. United States


       Hamilton argues that the waiver does not apply here because he does not “contest or

collaterally attack” his “sentence,” nor does he raise a claim that his sentence is the product of

ineffective assistance of counsel. Hamilton only challenges his lawyer’s ineffective assistance in

failing to file an appeal of his sentence. And, unlike most § 2255 movants, Hamilton does not

seek to have his sentence permanently vacated or lowered; he seeks instead to have his sentence

vacated only for the limited purpose of reinstating it so that he has a fresh opportunity to appeal.

The government responds that the plain language of the waiver expressly precludes ineffective

assistance claims, and, as the district court found, Hamilton’s claim that his waiver was based on

his expectation that an appeal would be filed does not take his ineffectiveness allegation outside

the scope of his waiver.

       We “use traditional contract law principles in interpreting and enforcing” plea

agreements because they are contractual in nature. United States v. Bowman, 634 F.3d 357, 360

(6th Cir. 2011). In determining whether a plea agreement has been breached, this court examines

what the defendant “reasonably understood” when he entered into the agreement. United States

v. Phibbs, 999 F.2d 1053, 1081 (6th Cir. 1993). “[T]he most persuasive evidence of what a

defendant reasonably appreciated as his bargain is found in the plain language of the court-

approved agreement.”       Id.   Moreover, plea agreements are to be interpreted strictly, with

ambiguities construed against the government “because the government can take steps in drafting

a plea agreement to avoid imprecision.” Bowman, 634 F.3d at 360–61.

       Hamilton has the better argument. Because the ineffective-assistance claim does not

challenge his sentence, but instead only challenges his lawyer’s alleged failure to appeal his

sentence, it does not fall within the plain language of the collateral-attack waiver.           The

government’s contrary interpretation is not persuasive because the government offers no analysis


                                                -5-
No. 12-5118, Hamilton v. United States


to support its conclusion that the instant claim is “expressly included” under the waiver; it simply

states the proposition without textual support. Comparatively, and by identifying the controlling

language that limits the scope of the waiver, Hamilton maintains that he does not “contest or

collaterally attack” his “resulting sentence” with an ineffective-assistance claim. Instead, he

challenges counsel’s post-sentencing failure to file an appeal, a claim temporally unrelated to his

“resulting sentence” as it accrued only after Hamilton was sentenced. Hamilton only asks that

his sentence be vacated and immediately reentered—on the same exact terms—so that he may

file a delayed direct appeal of his sentence with this court, a right he expressly reserved in the

plea agreement. Thus, Hamilton is not “contesting” or “attacking” his sentence within the

ordinary meaning of those words because the redressable harm arises from counsel’s alleged

post-sentencing misconduct, not the sentence itself. Hamilton’s request for relief in his § 2255

motion confirms that he is not using this proceeding to attack or contest the merits of his

sentence; it is the only procedural vehicle through which he can enforce his right to a direct

appeal. Therefore, although it is true that the collateral-attack waiver bars ineffective-assistance

claims challenging the sentence, Hamilton does not actually present such a claim in his motion.

       Case law supports Hamilton’s position. The dispositive distinction that he asks the court

to accept is that the instant § 2255 claim based on counsel’s alleged failure to file an appeal is

not a challenge to his sentence. Case law on this issue is marginally helpful because the precise

language of a collateral-attack waiver provision differs from case-to-case. However, in at least

four cases, circuit courts have allowed analogous ineffective-assistance claims to proceed on

collateral review notwithstanding a defendant’s waiver of his right to collaterally attack his

“sentence” as part of his plea agreement. See United States v. Tapp, 491 F.3d 263, 265–66 (5th

Cir. 2007); Campusano v. United States, 442 F.3d 770, 772 n.1 (2d Cir. 2006); Gomez-Diaz v.


                                                -6-
No. 12-5118, Hamilton v. United States


United States, 433 F.3d 788, 790 (11th Cir. 2005); United States v. Garrett, 402 F.3d 1262, 1263

n.2 (10th Cir. 2005). In Campusano and Gomez-Diaz, the courts described, but did not analyze,

the collateral-attack waiver, which in both cases was expressly limited to a collateral attack on

the “sentence.” See Campusano, 442 F.3d at 772 n.1; Gomez-Diaz, 433 F.3d at 790. In Tapp,

the court separately addressed the collateral-attack waiver and concluded that waiver was also

limited to an attack on the “sentence.” 491 F.3d at 264, 265–266. And in Garrett, the court

noted that “the plain language of the waiver,” which was limited to “sentence” challenges, “does

not address the type of claim [that the § 2255 movant] has raised.” 402 F.3d at 1266 n.5.

Although these courts did not interpret the same waiver language presented in this case, they

stand for the sound proposition that Hamilton asks us to accept: a § 2255 ineffective-assistance

claim based on an attorney’s failure to file an appeal is not tantamount to a “contest or

collateral[] attack” on his “resulting sentence.”

       Further, Hamilton could not have reasonably understood that a waiver precluding a

“contest” or “attack” on his “resulting sentence” would also bar a challenge to his attorney’s

alleged post-sentencing failure to file a notice of appeal upon direction, especially in this case

where Hamilton negotiated to preserve the right to appeal his sentence given the pendency of the

FSA. See Phibbs, 999 F.2d at 1081. Any ambiguity on the question of whether the waiver

precludes the subject claim is resolved in favor of securing Hamilton’s appellate rights. See

Bowman, 634 F.3d at 360. Accordingly, the collateral-attack waiver is no bar to the ineffective

assistance claim presented in Hamilton’s § 2255 motion, and we reverse the district court’s

holding otherwise.

       We must next consider the appropriate course of action to be taken on remand. Although

nothing in the record contradicts Hamilton’s assertion in his affidavit that he affirmatively


                                                    -7-
No. 12-5118, Hamilton v. United States


expressed to counsel his desire for an appeal, at oral argument the parties agreed that there is a

fact question on this point. Because the resolution of this factual issue is pivotal to Hamilton’s

claim for relief, the district court should conduct an evidentiary hearing to determine if Hamilton

in fact expressed the desire for an appeal as he now asserts. After the evidentiary hearing, if the

district court finds that Hamilton instructed counsel to file an appeal, his attorney’s failure to file

an appeal constituted ineffective assistance of counsel, and Hamilton is entitled to file a delayed

direct appeal of his sentence. If, on the other hand, the district court determines that Hamilton

provided no such instruction, he is not entitled to any further relief.3

                                                 III.

       For these reasons, we reverse and remand for an evidentiary hearing consistent with this

opinion.




       3
        We have taken this prudent course of action in a factually similar case, see Campbell v.
United States, 686 F.3d 353 (6th Cir. 2012), and our approach recognizes that the district court
granted Hamilton a certificate of appealability only on its procedural ruling that the collateral-
attack waiver bars the ineffective-assistance claim presented in the subject motion.
                                                  -8-
