[DO NOT PUBLISH]

IN THE UNITED STATES COURT OF APPEALS

FOR THE ELEVENTH CIRCUIT

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No. 15-14537

Non-Argument Calendar

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D.C. Docket No. 1:15-cr-20406-KMM-1

UNITED STATES OF AMERICA, 

 Plaintiff-Appellee,

 versus

ANDRES QUINTANILLA, 

 Defendant-Appellant.

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Appeal from the United States District Court

for the Southern District of Florida

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(August 19, 2016)

Before MARTIN, ROSENBAUM, and ANDERSON, Circuit Judges.

PER CURIAM: 

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Andres Quintanilla, a former sergeant with the Miami Springs Police 

Department, appeals his sentence of 108 months of imprisonment after pleading 

guilty, under a written plea agreement, to one count of Hobbs Act extortion under 

color of official right, 18 U.S.C. § 1951(a). Quintanilla raises two arguments on 

appeal: (1) the sentence appeal waiver in his plea agreement is unenforceable 

because the government breached the plea agreement by breaking a promise made 

during the plea colloquy; and (2) the district court erred in enhancing Quintanilla’s

offense level by two levels, per U.S.S.G. § 2B1.1, and refusing to reduce his 

offense level by two levels, per U.S.S.G. §§ 2D1.1(b)(17) and 5C1.2(a)(2),

1 after 

finding that Quintanilla possessed a firearm in connection with the offense. After 

careful review, we decline to enforce the appeal waiver and affirm Quintanilla’s 

sentence. 

I.

We review the validity of a sentence appeal waiver provision de novo. 

United States v. Johnson, 541 F.3d 1064, 1066 (11th Cir. 2008). Generally, we 

will enforce an appeal waiver that 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 

 1 All guidelines references are to the 2014 version of the Guidelines Manual. 

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the plea colloquy, or (2) “it is manifestly clear from the record that the defendant 

otherwise understood the full significance of the waiver.” Id. at 1351.

Here, we decline to enforce the appeal waiver. Putting aside the question of 

whether the government breached the plea agreement, the government has not 

shown that the waiver was made knowingly and voluntarily.2

 See id. While the 

magistrate judge who conducted Quintanilla’s plea colloquy read out loud the 

terms of the waiver during the colloquy, she did not specifically question 

Quintanilla about the waiver or confirm that he understood what those terms 

meant. Moreover, Quintanilla’s response to the magistrate judge’s explanation of 

the waiver, “Okay,” does not clearly show that he understood the magistrate 

judge’s explanation, and the government has not identified parts of the record that 

make “manifestly clear” his understanding of the full significance of the waiver. 

Therefore, the government has not shown either of the two routes under Bushert 

for establishing the validity of the waiver. See id.

And because the government has briefed Quintanilla’s guidelines challenges, 

we neither burden nor prejudice the government by enforcing the waiver. Cf.

United States v. Bascomb, 451 F.3d 1292, 1294 (11th Cir. 2006) (“[R]equiring the 

 2 The government notes that Quintanilla challenged the appeal waiver on only the ground

that the plea agreement was breached, and it limits its arguments to the breach issue. But it is the 

government’s burden to show that the appeal waiver was made knowingly and voluntarily, and it 

has not done so here, no matter what Quintanilla argued. See Bushert, 997 F.2d at 1351. 

Because the only remedy Quintanilla requested for the government’s alleged breach was 

invalidation of the waiver and we decline to enforce the waiver here, we need not and do not 

decide whether the government breached the plea agreement. 

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government to file a brief where there has been a valid appeal waiver undermines 

the interests of both the government and defendants generally.”). We therefore do 

not enforce the sentence appeal waiver in Quintanilla’s plea agreement.

II.

Turning to the merits, Quintanilla argues that no evidence supports the 

district court’s finding that he possessed a firearm in connection with the offense. 

As a result, he asserts, the court erred in applying the two-level enhancement for 

possession of a firearm, per U.S.S.G. § 2D1.1(b)(1), and in refusing to apply a twolevel reduction for meeting the safety-valve criteria, per U.S.S.G. § 2D1.1(b)(17) 

(providing for a two-level reduction if the defendant meets the five requirements 

set forth in U.S.S.G. § 5C1.2(a)). One of the five requirements under § 5C1.2(a) is 

that the defendant not have “possess[ed] a firearm . . . in connection with the 

offense.” U.S.S.G. § 5C1.2(a)(2).

A.

Quintanilla was a sergeant with the Miami Springs Police Department. Near 

the end of 2014, he began having conversations with a confidential source working 

with the Federal Bureau of Investigation. The source told Quintanilla that he was a 

drug trafficker who imported cocaine shipments through the Miami International 

Airport. Quintanilla agreed to help.

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In November 2014, the source told Quintanilla about an upcoming shipment 

of ten kilograms of cocaine that the source planned to sell in the City of Miami 

Springs. Quintanilla helped choose a date and location for the planned drug deal. 

On December 5, 2014, Quintanilla, while on duty, met the source at the agreedupon location, a grocery store parking lot, where the source showed Quintanilla

fake cocaine and indicated that it was being sold for $250,000. Quintanilla then 

left the parking lot for a brief period while the sale was completed. Later, 

Quintanilla told the source that he left the parking lot to distract a police detective 

he had seen in the area. After the sale, Quintanilla, in his patrol car, followed the 

source’s car to a shipping facility, where the source said the drug proceeds would 

be dropped off in order to be laundered elsewhere. Quintanilla was paid $2,500 for 

his assistance.

Before sentencing, Quintanilla’s revised presentence investigation report 

(“PSR”) calculated his offense level using the drug-trafficking guideline, § 2D1.1, 

because Quintanilla committed his extortion offense for the purpose of facilitating 

a drug offense. U.S.S.G. § 2C1.1(c)(1). Under the drug-trafficking guideline, a 

two-level enhancement was added because “a dangerous weapon (a firearm) was 

possessed.” U.S.S.G. § 2D1.1(b)(1). In his objections to the PSR, Quintanilla did 

not dispute that he possessed a firearm, but he asked for a two-level reduction 

under §§ 2D1.1(b)(17) and § 5C1.2(a)(2) because, he contended, his possession of 

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a firearm was not in connection with the offense. In a second addendum to the 

PSR, the probation officer disagreed with Quintanilla that a two-level reduction 

was applicable “because the defendant, while armed, provided protection for and 

escorted drug proceeds.” 

Quintanilla pressed his § 5C1.2(a)(2) argument at sentencing, contending 

that his service firearm, though possessed, had no connection to the offense. 

Sentencing Hr’g Tr. at 4 (Doc. 37) (stating that “the firearm was not used in 

furtherance of any of the crime and that it does not preclude him from the benefits 

of § 5C1.2(a)(2)”); id. at 5 (“The firearm happened to be present on him, but there 

is no evidence that it was used in furtherance of the crime.”); id. (“There was never 

any circumstance in which that weapon was ever involved in any way or took part 

in the case itself. He was in a vehicle. There was never any circumstance where it 

was [employed] or used in furtherance of the crime. Again, my client pled to a 

bribery case.”). Over Quintanilla’s objections, the district court agreed with the 

probation officer and found that Quintanilla possessed the firearm in connection 

with the drug offense. The court applied the § 2D1.1(b)(1) enhancement but did 

not apply the § 2D1.1(b)(17) reduction. The district court sentenced Quintanilla to 

108 months of imprisonment, at the low end of his guideline range. 

B.

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We review a district court’s factual findings, including a finding that a 

defendant possessed a firearm, for clear error. United States v. Carillo-Ayala, 

713 F.3d 82, 87 (11th Cir. 2013); United States v. Stallings, 463 F.3d 1218, 1220 

(11th Cir. 2006). The district court’s legal interpretations of the Sentencing 

Guidelines are reviewed de novo. Carillo-Ayala, 713 F.3d at 87. While we review 

de novo the legal standard that the district court applies, we generally review for 

clear error the court’s application of the standard to a detailed fact pattern. Id. at 

87–88. We will not find clear error unless we are left with a definite and firm 

conviction that a mistake has been made. United States v. White, 335 F.3d 1314, 

1319 (11th Cir. 2003).3

 

Under § 2D1.1(b)(1), a defendant’s offense level is increased by two levels 

“[i]f a dangerous weapon (including a firearm) was possessed.” To prove that the 

enhancement applies, the government bears the burden of showing, by a 

preponderance of the evidence, either “that the firearm was present at the site of 

the charged conduct or . . . that the defendant possessed a firearm during conduct 

associated with the offense of conviction.” Stallings, 463 F.3d at 1220; United 

States v. Hunter, 172 F.3d 1307, 1309 (11th Cir. 1999). If the government meets 

its burden, “the evidentiary burden shifts to the defendant, who must demonstrate 

 3 Quintanilla did not object to the district court’s application of the § 2D1.1(b)(1) firearmpossession enhancement on the grounds he raises on appeal, so we would normally review for 

plain error only. In any case, he preserved his interrelated challenge under § 5C1.2(a)(2), and 

our inquiry into both guidelines is substantially the same. Accordingly, we do not apply plainerror review. 

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that a connection between the weapon and the offense was ‘clearly improbable.’” 

Stallings, 463 F.3d at 1220 (quoting United States v. Audain, 254 F.3d 1286, 1289 

(11th Cir. 2001)). 

Section § 2D1.1(b)(17) likewise implicates a defendant’s possession of a 

firearm, providing for a two-level decrease in the offense level if, among other 

criteria listed in § 5C1.2(a), the defendant “did not . . . possess a firearm or other 

dangerous weapon . . . in connection with the offense.” U.S.S.G. § 5C1.2(a)(2)

(emphasis added). We have held that possession “in connection with” means 

something more than possession, so a defendant may possess a firearm, for 

purposes of § 2D1.1(b)(1), without possessing the firearm “in connection with the 

offense,” for purposes of § 5C1.2(a)(2). Carillo-Ayala, 713 F.3d at 89–91. 

Where a defendant who possessed a firearm seeks the protection of the 

safety valve, § 5C1.2(a) (in this case, by way of § 2D1.1(b)(17)), “the district court 

must determine whether the facts of the case show that a connection between the 

firearm and the offense, though possible, is not probable.” Id. at 91. The 

defendant may negate proof of a connection by a preponderance of the evidence, or 

the government may preclude relief by proving the fact of a connection by a 

preponderance of the evidence. Id. at 96.

A sufficient “connection” between the firearm and the offense may be 

shown if the firearm is in proximity to drugs or if the firearm facilitates or has the 

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potential to facilitate the drug offense. Id. at 91–96. Facilitation, in turn, includes 

“emboldening an actor who had the ability to display or discharge the weapon, . . . 

serving as an integral part of a drug transaction as in a barter situation, . . . 

instilling confidence in others who relied on the defendant, or serving as a ‘badge 

of office’ to help the defendant avoid detection.” Id. (citations omitted). For 

example, we have concluded that an INS agent’s possession of a firearm while 

escorting a drug courier through an airport facilitated the offense because the 

firearm’s presence increased the chances for successful drug trafficking, both by 

instilling confidence in the drug courier and “diminish[ing] the likelihood that 

someone [would] look at him suspiciously.” Id. at 94–95 (discussing the facts of 

Audain, 254 F.3d at 1289). 

We analyze the provisions of § 2D1.1(b)(1) and § 5C1.2(a)(2) by reference 

to the defendant’s relevant conduct. See Stallings, 463 F.3d at 1220; U.S.S.G. 

§ 5C1.2 cmt. n.3 (the term “offense” for § 5C1.2(a)(2) means “the offense of 

conviction and all relevant conduct”). So although Quintanilla’s offense of 

conviction was Hobbs Act extortion, we evaluate the application of the two 

guideline provisions based on his relevant conduct, which includes his facilitation 

of what he believed to be a transaction involving ten kilograms of cocaine. 

Here, the district court did not err in applying § 2D1.1(b)(1) or in refusing to 

apply § 2D1.1(b)(17). First, the court did not clearly err in finding that Quintanilla 

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possessed a firearm during conduct relevant to the offense. See Stallings, 463 F.3d 

at 1220. Quintanilla was an on-duty police officer during relevant conduct. He 

also did not dispute factual statements in the second addendum to the PSR stating 

that he was “armed” during conduct related to the December 5, 2014, cocaine 

transaction, so he is deemed to have admitted those facts for purposes of 

sentencing. See United States v. Bennett, 472 F.3d 825, 832 (11th Cir. 2006) (“A 

sentencing court’s findings of fact may be based on undisputed statements in the 

[PSR].”); id. at 833–34 (“Bennett failed to object to the facts of his prior 

convictions as contained in his [PSR] and addendum to the [PSR] despite several 

opportunities to do so; thus, he is deemed to have admitted those facts.”). Indeed, 

far from objecting to the fact of his possession of a firearm, Quintanilla, through 

counsel, admitted multiple times during the sentencing hearing, recounted above,

that he possessed a firearm during conduct relevant to the offense. Therefore, the 

facts adequately establish that Quintanilla possessed a firearm during the offense. 

Second, the district court did not clearly err in finding that Quintanilla’s 

possession of the firearm was in connection with the offense, because the firearm

facilitated or had the potential to facilitate the offense. See Carillo-Ayala, 713 

F.3d at 87–88, 95–96. The record shows that Quintanilla admitted that he had 

agreed to provide cover and protection for a drug trafficker transporting ten 

kilograms of cocaine. In particular, during the plea colloquy, Quintanilla agreed 

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with the prosecutor’s statement that he had “agreed he would watch over the drug 

transaction in the City of Miami Springs and protect the confidential information 

source from something going wrong.” Plea Hr’g Tr. at 35 (Doc. 29). Acting on 

that agreement, Quintanilla, while armed, met with the source on the planned date 

of the drug sale and then followed the source as the source drove with the drug 

proceeds to another location.

Based on these facts, Quintanilla’s firearm facilitated or had the potential to 

facilitate the offense because it was available for use as a weapon in order to 

protect the confidential source “from something going wrong,” most notably while 

the source drove, purportedly, with a substantial amount of drug proceeds. See 

Carillo-Ayala, 713 F.3d at 95–96. For similar reasons, the firearm had the 

potential to facilitate the offense by instilling confidence in the person who hired 

Quintanilla for protection. See id. 

In sum, Quintanilla’s possession of a firearm while providing cover and 

protection for a drug transaction was sufficient to show both possession of a 

firearm, § 2D1.1(b)(1), and possession of a firearm in connection with the offense,

§ 5C1.2(a)(2). Accordingly, the district court did not err in calculating 

Quintanilla’s guideline range. We therefore affirm Quintanilla’s sentence.

AFFIRMED.

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