UNITED STATES DISTRICT COURT 

NORTHERN DISTRICT OF INDIANA 

SOUTH BEND DIVISION 

CLIFTON VALENTIUS HOLIDAY, 

Petitioner, 

 v. 

UNITED STATES OF AMERICA, 

Respondent. 

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Cause No. 3:16-cv-367 RLM

(Arising out of 3:14-cr-67)

OPINION AND ORDER 

Adam Holiday pleaded guilty to possessing a firearm as a convicted felon. 

18 U.S.C. § 922(g)(1). At sentencing, the court increased his base offense level 

based on its determination that his prior felony conviction for residential entry 

is a “crime of violence.” U.S.S.G. §§ 2K2.1(a)(2), 4B1.2(a). Mr. Holiday challenged 

the sentence in a motion to vacate under 28 U.S.C. § 2255 based on the Supreme 

Court’s holding in Johnson v. United States, 135 S. Ct. 2551 (2015) that parallel 

language in the Armed Career Criminal Act, 18 U.S.C. § 924(e)(2)(B), is 

unconstitutionally vague. The court held that the waiver in Mr. Holiday’s plea 

agreement barred his motion. He now requests a certificate of appealability 

under 28 U.S.C. § 2253(c)(2). 

Issuance of a certificate of appealability requires the court to find that Mr. 

Holiday has made “a substantial showing of the denial of a constitutional right.” 

28 U.S.C. § 2253(c)(2). He has done so. 

Mr. Holiday’s collateral attack failed under circuit precedent. He didn’t 

show that the appeal waiver was uninformed or involuntary, that a collateral 
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attack was outside of its scope, that sentencing relied on a constitutionally 

impermissible factor, that his sentence exceeded the statutory maximum, or that 

his counsel provided ineffective assistance in negotiating the plea agreement. See

Keller v. United States, 657 F.3d 675, 681 (7th Cir. 2011) (listing exceptions to 

an otherwise-valid appeal waiver). In United States v. Worthen, No. 15-3521 (7th 

Cir. Nov. 28, 2016), our court of appeals showed that it was willing to enforce an 

appeal waiver even in Johnson-based challenges to the constitutionality of a 

conviction. 

Reasonable jurists might disagree. Even though United States v. Bownes, 

405 F.3d 634 (7th Cir. 2005) enforced the appeal waiver of a defendant given a 

within-guideline sentence before United States v. Booker, 543 U.S. 220 (2005), 

Bownes doesn’t address whether a waiver is enforced if the guidelines that 

anchor the sentence are themselves invalid.1 Outside developments in the law 

might encourage the appeals court to revise its interpretation of whether a 

defendant can ever waive rights unknown at the time of the waiver. See United 

States v. McBride, 826 F.3d 293, 294-295 (6th Cir. 2016) (holding that defendant 

agreeing to career offender designation didn’t waive a Johnson-based challenge 

                                                            

1 The court disagrees with Mr. Holiday’s interpretation that Bownes allows flexible exceptions for 

later-determined due process violations because, as Mr. Holiday says, the listed exceptions are 

“all firmly rooted in the due process clause.” Bownes explains that broad waivers “are effective 

even if the law changes in favor of the defendant after sentencing,” Bownes, 405 F.3d at 636; see

Keller, 657 F.3d at 681 (explaining that waivers are upheld unless one of the “limited exceptions” 

applies), and isn’t based on the theory that appeal waivers can be circumvented for due process 

violations but not for other kinds of constitutional violations. The kind of exception that Bownes 

rejected was for a sentence imposed under the regime of binding sentencing guidelines that the 

Supreme Court rejected in Booker. The Court rejected this approach not just because it violated 

the Sixth Amendment but because due process requires “proof beyond a reasonable doubt of 

every fact necessary to constitute the crime with which [the defendant] is charged.” Booker, 543 

U.S. at 230 (quoting In re Winship, 397 U.S. 358, 364 (1970)). 
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because “a defendant can abandon only known rights,” so he “could not have 

intentionally relinquished a claim based on Johnson, which was decided after 

his sentencing”). Mr. Holiday points to district court decisions discarding appeal 

waivers within circuits that recognize exceptions for a “miscarriage of justice,” 

see, e.g., United States v. Swerdon, No. 3:16cv313, 2016 WL 4988065 (M.D. Pa. 

Sept. 19, 2016), or constitutional challenge, see, e.g., United States v. Hoopes, 

No. 3:11-cr-425-HZ, 2016 WL 3638114 (D. Or. July 5, 2016). 

Based on the foregoing, the court GRANTS Mr. Holiday’s motion for a 

certificate of appealability [Doc. No. 66] and issues a certificate of appealability 

with respect to the issue of whether a waiver of collateral attack in the plea 

agreement bars a challenge under Johnson v. United States, 135 S. Ct. 2551 

(2015). 

 SO ORDERED. 

 ENTERED: November 30, 2016 

 /s/ Robert L. Miller, Jr. 

 Judge 

 United States District Court