[DO NOT PUBLISH]

IN THE UNITED STATES COURT OF APPEALS

FOR THE ELEVENTH CIRCUIT

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No. 15-13594

Non-Argument Calendar

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D.C. Docket No. 1:14-cr-00199-WS-7

UNITED STATES OF AMERICA, 

 Plaintiff-Appellee,

versus

JUSTIN RYAN BOLES, 

 Defendant-Appellant.

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Appeal from the United States District Court

for the Southern District of Alabama

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(November 17, 2016)

Before TJOFLAT, MARCUS and WILLIAM PRYOR, Circuit Judges.

PER CURIAM: 

Justin Ryan Boles appeals his convictions and sentences for conspiracy to 

manufacture methamphetamine with intent to distribute and conspiracy to possess 

pseudoephedrine with knowledge that it will be used to manufacture a controlled 

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substance. On appeal, Boles argues that: (1) the district court plainly erred in 

convicting and sentencing him for both conspiracy counts because doing so 

violates the Fifth Amendment’s protection against double jeopardy; (2) the district 

court erred by imposing a six-level enhancement for creating a substantial risk of 

harm to a minor because there was no evidence of risk of harm to a minor; and (3) 

the district court plainly erred by imposing one criminal history point for a 2003 

theft conviction because the conviction occurred more than 10 years before the 

instant offenses commenced. The government moved to dismiss Boles’s appeal 

based on a conviction-and-sentence appeal waiver contained in his plea agreement, 

but we carried that motion with the case and address it now. After careful review, 

we dismiss the appeal in part, and affirm it in part.

We review the validity of an appeal waiver de novo. United States v. 

Johnson, 541 F.3d 1064, 1066 (11th Cir. 2008). Where, as here, the defendant fails 

to raise a double jeopardy challenge before the district court, we review for plain 

error. United States v. Smith, 532 F.3d 1125, 1126 (11th Cir. 2008). To show 

plain error, the defendant must show (1) an error, (2) that is plain, and (3) that 

affected his substantial rights. United States v. Turner, 474 F.3d 1265, 1275-76 

(11th Cir. 2007). If the defendant satisfies the three conditions, we may exercise 

our discretion to recognize the error if it seriously affects the fairness, integrity, or 

public reputation of judicial proceedings. Id. at 1276. To be plain, the error must 

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be clear under the current law, either by precedent directly on point, or by the 

explicit language of a statute or rule. United States v. Chau, 426 F.3d 1318, 1322 

(11th Cir. 2005). 

First, we dismiss the portion of Boles’s appeal challenging his sentence, due 

to the appeal waiver he signed. An appeal waiver will be enforced if it was made 

knowingly and voluntarily. United States v. Bushert, 997 F.2d 1343, 1350-51 

(11th Cir. 1993). To establish that the waiver was made knowingly and 

voluntarily, the government must show either that (1) the district court specifically 

questioned the defendant about the waiver during the plea colloquy, or (2) the 

record is manifestly clear “that the defendant otherwise understood the full 

significance of the waiver.” Id. at 1351. The government cannot show that an 

appeal waiver was knowing and voluntary from an examination of the plea 

agreement’s text alone. Id. at 1352. 

“An appeal waiver includes the waiver of the right to appeal difficult or 

debatable legal issues or even blatant error.” United States v. Grinard-Henry, 399 

F.3d 1294, 1296 (11th Cir. 2005). An appeal waiver is enforceable despite the fact 

that particular sentencing issues have been disputed on the merits. United States v. 

Bascomb, 451 F.3d 1292, 1295-96 (11th Cir. 2006). We’ve held that a guilty plea 

does not waive a double jeopardy challenge when, based on the record that existed 

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at the time the guilty plea was entered, the second crime is one that the government 

“may not constitutionally prosecute.” Smith, 532 F.3d at 1127 (quotation omitted). 

Here, the appeal waiver concerning Boles’s sentence was entered into 

knowingly and voluntarily. As the record shows, the district court specifically 

discussed at the plea colloquy Boles’s waiver of the right to appeal any sentence, 

the effect of the sentence-appeal waiver, and the relevant exceptions. Boles 

affirmed that he understood. In addition, the narrow exceptions to Boles’s appeal 

waiver do not encompass his sentencing claims. For instance, Boles’s total 

sentence does not exceed the statutory maximum, nor does it constitute an upward 

variance or departure from the guidelines range as determined by the district court 

at sentencing. Boles presents no ineffective assistance of counsel claim and the 

government has not appealed his case. And despite Boles’s argument that the riskof-harm enhancement and criminal history point were, in effect, upward variances, 

they in fact are alleged guideline calculation errors, which do not fall outside the 

appeal waiver. Bascomb, 451 F.3d at 1295-96. Accordingly, we grant the 

government’s motion to dismiss Boles’s sentencing claims.

Unlike the sentencing claims, however, Boles’s double jeopardy claim is not 

barred by a knowing and voluntary waiver because the government has not met its 

burden of establishing that the conviction part of the waiver was entered into 

knowingly and voluntarily. Rather, the record indicates that the district court’s 

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questioning about the appeal waiver at the guilty plea hearing was limited to the 

sentencing part of the waiver. Bushert, 997 F.2d at 1351. The only portion of the 

colloquy that addressed an appeal of his conviction discussed the waiver effect of 

the plea itself, not the appeal waiver. Otherwise, nothing in the record manifestly 

shows that Boles understood the full significance of his conviction appeal waiver. 

Thus, the conviction appeal waiver is only expressly discussed in the waiver 

provision itself, but the text of the waiver alone is not sufficient to establish a 

knowing and voluntary waiver. Id. at 1352. 

Nor is Boles’s double jeopardy challenge barred by the plea itself, 

independently of the appeal waiver. Boles seeks to challenge his convictions based 

on the record as it existed at the time the guilty plea was entered, and we have 

allowed these kinds of challenges. Smith, at 532 F.3d 1127. As a result, we deny 

the government’s motion to dismiss Boles’s double jeopardy claim and address it 

on the merits. 

Nevertheless, we are unpersuaded by Boles’s claim that the district court 

plainly violated his double jeopardy rights. The Fifth Amendment’s Double 

Jeopardy Clause protects against, in part, multiple punishments for the same 

offense. United States v. Bobb, 577 F.3d 1366, 1371 (11th Cir. 2009). If the same 

conduct violates two statutory provisions, courts must first determine whether the 

legislature intended each violation to be a separate offense, with separate 

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punishments. Garrett v. United States, 471 U.S. 773, 778 (1985). When 

legislative intent is unclear, two crimes are treated as the “same offense” unless 

each crime requires proof of an additional element that the other does not require. 

Blockburger v. United States, 284 U.S. 299, 304 (1932). 

The Double Jeopardy Clause protects a defendant from being convicted 

under two statutes where one act is a lesser-included offense of the other. Bobb, 

577 F.3d at 1371-72. A lesser-included offense is one where it is “impossible to 

commit the greater without having first committed the lesser.” Theriault v. United 

States, 434 F.2d 212, 214 (5th Cir. 1970) (quotation omitted).

1

 When a defendant 

suffers a double jeopardy violation, the proper remedy is to vacate one of the 

underlying convictions, even when sentences run concurrently, because 

“unlawfully multiplicitous convictions” can have serious consequences. Bobb, 577 

F.3d at 1372. For example, they could affect a defendant’s eligibility for parole, an 

increased sentence for a future offense, and an additional societal stigma for an 

additional criminal conviction. Id.

Section 841(a) provides, in part, that it is unlawful to knowingly or 

intentionally “manufacture, distribute, or dispense, or possess with intent to 

manufacture, distribute, or dispense, a controlled substance.” 21 U.S.C. § 841(a). 

Section 841(b)(1)(C) provides that the punishment for violating Section 841(a) 

 1 In Bonner v. City of Prichard, 661 F.2d 1206, 1209 (11th Cir.1981) (en banc), we adopted as 

binding precedent all Fifth Circuit decisions issued before October 1, 1981.

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with methamphetamine is a term of imprisonment of not more than 20 years, a fine 

of not more than $1,000,000, and a term of supervised release of at least 3 years. 

21 U.S.C. § 841(b)(1)(C). Section 841(c)(2) provides that any person who 

knowingly or intentionally “possesses . . . a listed chemical knowing . . . that the 

listed chemical will be used to manufacture a controlled substance . . . shall be 

fined in accordance with [Title 18], or imprisoned not more than 20 years.” 21 

U.S.C. § 841(c)(2). 

Relevant here, we have not published a decision, nor has the Supreme Court, 

addressing whether convictions for both conspiracy to manufacture 

methamphetamine and conspiracy to possess pseudoephedrine with knowledge it 

would be used to make methamphetamine violate the Double Jeopardy Clause. 

Moreover, the penalty provisions at issue do not clearly indicate whether Congress 

intended them to be separate offenses because both provide for a 20-year 

maximum term of imprisonment, but the methamphetamine count carries 

additional penalties. Garrett, 471 U.S. at 778. Thus, even if there was an error, it 

was not plain because there is no case or statute directly on point that resolves 

whether Count 8 would be considered a lesser included offense of Count 1. Chau, 

426 F.3d at 1322. We therefore affirm Boles’s convictions. 

AFFIRMED IN PART; APPEAL DISMISSED IN PART. 

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