               Case: 16-15164       Date Filed: 07/17/2017      Page: 1 of 14


                                                                                 [PUBLISH]

                 IN THE UNITED STATES COURT OF APPEALS

                           FOR THE ELEVENTH CIRCUIT
                             ________________________

                                    No. 16-15164
                              ________________________

                         D.C. Docket No. 5:16-cr-00006-RH-1



UNITED STATES OF AMERICA,

                                                                        Plaintiff - Appellee,

                                           versus

ARTHUR KYLE LANGE,

                                                                    Defendant - Appellant.

                              ________________________

                      Appeal from the United States District Court
                          for the Northern District of Florida
                            ________________________

                                      (July 17, 2017)

Before ED CARNES, Chief Judge, WILLIAM PRYOR, Circuit Judge, and
MOORE, * District Judge.

WILLIAM PRYOR, Circuit Judge:




*
 Honorable K. Michael Moore, United States District Chief Judge for the Southern District of
Florida, sitting by designation.
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      This appeal requires us to decide whether a Florida conviction of principal to

attempted manufacture of a controlled substance, see Fla. Stat. § 777.011, qualifies

as a “controlled substance offense,” United States Sentencing Guidelines Manual

§ 4B1.2(b) (Aug. 2016). We must also decide whether the government engaged in

sentencing factor manipulation when it arranged multiple transactions in a sting

operation. Arthur Kyle Lange sold guns and drugs to a confidential informant in

five separate transactions. After Lange pleaded guilty to various firearm and drug

offenses, the district court sentenced him to a term of 130 months of imprisonment,

at the low end of his advisory guideline range. Lange objected to receiving a higher

base offense level for his prior Florida conviction of principal to attempted

manufacture of methamphetamine, but the district court overruled his objection.

Lange argues that because the Florida statute for principal liability makes an

individual liable if he aids and abets an attempted crime without requiring a

completed offense, the Florida statute is too broad to be a “controlled substance

offense” under the Guidelines. But the definition of “controlled substance offense”

and the authoritative commentary make clear that the crime of aiding an attempt to

manufacture is “an offense . . . that prohibits . . . manufacture,” U.S.S.G.

§ 4B1.2(b). Because a conviction of principal to attempted manufacture of a

controlled substance qualifies as a “controlled substance offense,” and because


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Lange cannot prove that the government engaged in sentencing factor

manipulation when it arranged multiple transactions, we affirm.

                                I. BACKGROUND

      With the help of a confidential informant, federal agents facilitated a total of

five controlled purchases from Arthur Kyle Lange. In the first transaction, Lange

agreed to sell the informant Xanax and a firearm and discussed future purchases.

Over a few months, Lange sold the informant more drugs and firearms, including a

gun with an obliterated serial number. After he was arrested, Lange pleaded guilty

to five counts of unlawful possession of a firearm, 18 U.S.C. §§ 922(g)(1),

924(a)(2), three counts of distributing alprazolam, 21 U.S.C. § 841(a)(2), (b)(2),

and two counts of distributing methamphetamine and alprazolam, id. § 841(a)(1),

b(2), (b)(1)(C). The district court accepted Lange’s guilty plea and, with the

parties’ consent, applied the amended Sentencing Guidelines that were to take

effect on August 1, 2016.

      Lange’s criminal history included a 2011 conviction for the Florida offense

“Principal to Attempted Manufacture of Controlled Substance.” Lange objected to

the factual description of the offense in the presentence investigation report but

agreed that he had the prior conviction. For the purpose of determining Lange’s




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sentence, the district court counted this prior conviction as a “controlled substance

offense,” U.S.S.G. § 4B1.2(b).

      Lange’s sentencing range was a function of his prior conviction of a

controlled substance offense as well as the specific facts surrounding his crimes.

Under the firearm guideline, U.S.S.G. § 2K2.1, unlawful possession of a firearm

after committing a controlled substance offense provided a base offense level of

20. Id. § 2K2.1(a)(4)(A). Because the offense involved five firearms, the district

court added two levels. Id. § 2K2.1(b)(1)(A). Because the offense involved a

firearm with an obliterated serial number, the district court added four levels. Id.

§ 2K2.1(b)(4)(B). Because Lange possessed the firearm in connection with another

felony offense—the sale of drugs along with the firearms—the district court added

an additional four levels. Id. § 2K2.1(b)(6)(B). Because Lange accepted

responsibility and assisted authorities, the district court subtracted three levels. Id.

§ 3E1.1(a), (b). That calculation provided a total offense level of 27. Combined

with Lange’s criminal history category of VI, the Guidelines provided a sentencing

range of 130–162 months of imprisonment. After considering the statutory

sentencing factors, 18 U.S.C. § 3553(a), the district court imposed concurrent

sentences of 130, 120, and 60 months, three years of supervised release, and

$1,000 in a special monetary assessment.


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                           II. STANDARDS OF REVIEW

       This Court reviews de novo whether a prior conviction is a “controlled

substance offense” under Section 4B1.2(b). See United States v. Frazier, 89 F.3d

1501, 1505 (11th Cir. 1996). When a party raises an argument for the first time on

appeal, this Court reviews for plain error. United States v. Chafin, 808 F.3d 1263,

1268 (11th Cir. 2015). We may not correct an error that the defendant failed to

raise in the district court unless the error is plain, affects substantial rights, and

seriously affects the fairness, integrity, or public reputation of judicial proceedings.

United States v. Rodriguez, 398 F.3d 1291, 1298 (11th Cir. 2005); Fed. R. Crim. P.

52.

                                   III. DISCUSSION

       We divide our discussion in two parts. First, we explain that Lange’s prior

conviction qualifies as a “controlled substance offense” under the Guidelines.

Second, we explain that the government did not engage in sentencing factor

manipulation.

                         A.     Controlled Substance Offense

       The district court determined that Lange’s prior conviction for “Principal to

Attempted Manufacture of Controlled Substance” was a “controlled substance

offense” as defined by the Guidelines, U.S.S.G. § 4B1.2(b). The parties do not


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contest that the Florida crime of “Manufacture of Controlled Substance” is a

controlled substance offense. They instead dispute whether Florida principal

liability as applied to a controlled substance offense reaches conduct beyond the

scope of the inchoate liability covered by the Guidelines.

      We apply the categorical approach to determine what constitutes a

controlled substance offense, which means that we compare the definition in the

Guidelines with the statutory offense, “not the conduct underlying the conviction.”

United States v. Lipsey, 40 F.3d 1200, 1201 (11th Cir. 1994). “We look to the plain

language of the definitions to determine their elements,” and we “need not search

for the elements of ‘generic’ definitions of . . . ‘controlled substance offense’

because the[] term[] [is] defined by . . . the Sentencing Guidelines.” United States

v. Smith, 775 F.3d 1262, 1267 (11th Cir. 2014).

      The Guidelines define a “controlled substance offense” as including any

state or federal offense punishable by a year or more for the manufacturing or

trafficking of a controlled substance:

      The term “controlled substance offense” means an offense under
      federal or state law, punishable by imprisonment for a term exceeding
      one year, that prohibits the manufacture, import, export, distribution,
      or dispensing of a controlled substance (or a counterfeit substance) or
      the possession of a controlled substance (or a counterfeit substance)
      with intent to manufacture, import, export, distribute, or dispense.



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U.S.S.G. § 4B1.2(b). The commentary in Application Note 1 further states that this

definition includes inchoate crimes: “‘Crime of violence’ and ‘controlled substance

offense’ include the offenses of aiding and abetting, conspiring, and attempting to

commit such offenses.” Id. § 4B1.2(a) cmt. n.1 (emphasis omitted). “[T]h[is]

commentary constitutes ‘a binding interpretation’ of the term ‘controlled substance

offense.’” United States v. Smith, 54 F.3d 690, 693 (11th Cir. 1995) (citation

omitted).

      “[O]ur interpretation of the Sentencing Guidelines is governed by traditional

rules of statutory construction,” United States v. Shannon, 631 F.3d 1187, 1189

(11th Cir. 2011), and “[d]efinition sections and interpretation clauses are to be

carefully followed,” Antonin Scalia & Bryan A. Garner, Reading Law: The

Interpretation of Legal Texts 225 (2012). We give an application note “its most

natural reading” even if “it actually enlarges, rather than limits, the applicability of

the enhancement.” United States v. Probel, 214 F.3d 1285, 1288 (11th Cir. 2000).

We presume that the Sentencing Commission “said what it meant and meant what

it said.” Shannon, 631 F.3d at 1190 (quoting United States v. Browne, 505 F.3d

1229, 1250 (11th Cir. 2007)).

      Lange’s prior conviction is not for “aiding and abetting” or “attempting” a

controlled substance offense; instead, Lange was convicted under a Florida statute


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that defines principal liability. Florida law creates principal liability for aiding and

abetting an attempted crime:

      Principal in first degree. – Whoever commits any criminal offense
      against the state, whether felony or misdemeanor, or aids, abets,
      counsels, hires, or otherwise procures such offense to be committed,
      and such offense is committed or is attempted to be committed, is a
      principal in the first degree and may be charged, convicted, and
      punished as such, whether he or she is or is not actually or
      constructively present at the commission of such offense.

Fla. Stat. § 777.011 (emphasis added). We must decide whether the definition of

“controlled substance offense,” as informed by Application Note 1, is broad

enough to encompass liability as a principal in the first degree under Florida law.

      Lange relies on our opinion in Young v. United States, 936 F.2d 533 (11th

Cir. 1991), to argue that we must construe the Guidelines narrowly, but we

disagree. Young explained that when applying a previous version of the Guideline

that included offenses “substantially equivalent to the offenses listed,” we

considered as “similar” only other drug trafficking convictions. Id. at 536–37.

Young did not create a general principle of reading the Guidelines narrowly, but

instead interpreted a general phrase to “apply only to . . . things of the same general

kind or class specifically mentioned,” Scalia & Garner, supra, at 199.

      Although Application Note 1 states that the term “‘controlled substance

offense’ include[s] the offenses of aiding and abetting, conspiring, and attempting


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to commit such offenses,” this list is not exhaustive. Lange argues that the word

“includes” expands the definition of “controlled substance offense” to reach the

three listed examples and nothing else. But in discussing its general principles, the

Guidelines explain that “[t]he term ‘includes’ is not exhaustive.” U.S.S.G. § 1B1.1

cmt. n.2 (emphasis omitted). We have applied this principle across the Guidelines.

See, e.g., Probel, 214 F.3d at 1288. And the “traditional rules of statutory

construction,” Shannon, 631 F.3d at 1189, provide that “the word include does not

ordinarily introduce an exhaustive list.” Scalia & Garner, supra, at 132, 226; see

also Chickasaw Nation v. United States, 534 U.S. 84, 89 (2001); Campbell v.

Acuff-Rose Music, Inc., 510 U.S. 569, 577 (1994). The definition of “controlled

substance offense” is not necessarily limited to aiding and abetting, conspiring, and

attempting.

      The definition of “controlled substance offense” in Section 4B1.2(b)

“require[s] only that the predicate offense . . . ‘prohibit[s]’ certain activities related

to controlled substances.” Smith, 775 F.3d at 1267 (third alteration in original)

(internal citations omitted). Application Note 1 informs how we should interpret

this definition. “Prohibit” can mean “[t]o forbid . . . by a command, statute, law, or

other authority” or “[t]o ban or exclude . . . from an action or place; to prevent,

hinder.” Prohibit, Oxford English Dictionary (online ed. 2017); see also Prohibit,


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Webster’s Second International Dictionary 1978 (1961) (“1. To forbid by authority

or command; to interdict; . . . 2. To stop or prevent (a person); to render impossible

(an action); to hinder; debar.”). Because Application Note 1 tells us that an offense

prohibits the manufacture of a controlled substance when it prohibits aiding and

abetting, conspiring, and attempting that manufacture, U.S.S.G. § 4B1.2(a) cmt.

n.1, we must not construe “prohibit” too narrowly. “[C]ontrolled substance

offense” cannot mean only offenses that forbid conduct outright, but must also

include related inchoate offenses that aim toward that conduct. A ban on

attempting manufacture will bar some unsuccessful attempts, but it will also make

it practically impossible to manufacture without violating the law. So too a ban on

conspiring to manufacture drugs hinders manufacture even though it will ban

conduct that is not itself manufacturing. In precisely the same way, a ban on aiding

and abetting manufacture, whether or not the offense is completed, prevents and

hinders manufacture. Because a statute that forbids aiding and abetting an attempt

essentially forbids manufacture itself, the crime of aiding an attempt to

manufacture is “an offense . . . that prohibits . . . manufacture,” id. § 4B1.2(b).

      This conclusion is bolstered by the substantial similarity between the Florida

statute for principal liability and the offenses listed in Application Note 1—aiding

and abetting, attempt, and conspiracy. The Supreme Court of Florida refers to


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section 777.011 as the “aider-abettor statute[,] which makes all participants in a

crime principals in the first degree.” Potts v. State, 430 So. 2d 900, 901 (Fla.

1982). “The Supreme Court of Florida has held that to be guilty as a principal for a

crime committed by another, the defendant ‘must intend that the crime be

committed and do some act to assist the other person in actually committing the

crime.’” Jamerson v. Sec’y for Dep’t of Corr., 410 F.3d 682, 689 (11th Cir. 2005)

(quoting Staten v. State, 519 So.2d 622, 624 (Fla. 1988)). The federal law of aiding

and abetting, 18 U.S.C. § 2, also requires that the defendant have the intent to aid

the commission of a crime and do some act that contributed to the offense. United

State v. DePace, 120 F.3d 233, 238 (11th Cir. 1997). And although Florida law

does not require there be a completed offense, the examples of attempt and

conspiracy in the application note make clear that to “prohibit” an offense does not

require a state to prohibit the completed offense. The text of the application note

covers “prohibit[ing]” manufacture of controlled substances by prohibiting those

who aid and abet the attempt to do so.

      The district court did not err. Interpreting the Guideline in the light of the

authoritative interpretation provided in Application Note 1, Florida prohibits a

controlled substance offense when it prohibits principal liability for a controlled

substance offense. Lange’s Florida conviction for “Principal to Attempted


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Manufacture of Controlled Substance” qualifies as a “controlled substance

offense” under the Guidelines.

                       B.     Sentencing Factor Manipulation

      Because Lange did not raise the argument that the government engaged in

sentencing factor manipulation before the district court, we review for plain error.

Lange argues that he is due relief because the government wrongfully manipulated

his sentence by encouraging the commission of five separate criminal transactions

instead of arresting him after the first sale. We disagree.

      The doctrine of sentencing factor manipulation asks “whether the

manipulation inherent in a sting operation, even if insufficiently oppressive to

support an entrapment defense, or due process claim, must sometimes be filtered

out of the sentencing calculus.” United States v. Sanchez, 138 F.3d 1410, 1414

(11th Cir. 1998) (alterations adopted) (citation omitted). “[T]o bring sting

operations within the ambit of sentencing factor manipulation, the government

must engage in extraordinary misconduct.” United States v. Ciszkowski, 492 F.3d

1264, 1271 (11th Cir. 2007). “Government-created reverse sting operations are

recognized and useful methods of law enforcement investigation,” so “[t]he

standard for sentencing factor manipulation is high.” Id. This Court has never

reduced a sentence on the basis of sentencing factor manipulation, see United


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States v. Docampo, 573 F.3d 1091, 1097–98 (11th Cir. 2009), so no binding

precedent requires this Court to countenance sentencing factor manipulation as a

legitimate defense.

      Even if a sentence can be reduced based on sentencing factor manipulation,

Lange cannot prove error, let alone plain error in the failure of the district court to

determine sua sponte that the government engaged in extraordinary misconduct.

“A plain error is an error that is ‘obvious’ and is ‘clear under current law.’” United

States v. Humphrey, 164 F.3d 585, 588 (11th Cir. 1999) (citing United States v.

Olano, 507 U.S. 725, 734 (1993)). And “there can be no plain error where there is

no precedent from the Supreme Court or this Court directly resolving it.” United

States v. Lejarde-Rada, 319 F.3d 1288, 1291 (11th Cir. 2003). Lange fails to

identify any precedent that establishes that law-enforcement officers have a duty to

arrest as soon as a single illegal transaction has occurred or that a sting operation

that engages in multiple transactions is extraordinary misconduct. To the contrary,

this Court has held that the government’s decision to make “four purchases instead

of just one . . . is no more manipulative than . . . setting in motion a fictitious sting

operation involving a large quantity of drugs instead of a small one.” United States

v. Govan, 293 F.3d 1248, 1251 (11th Cir. 2002); see also Sanchez, 138 F.3d at

1414 (“The fact that the government’s . . . operation involved a large quantity of


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drugs does not amount to the type of manipulative governmental conduct

warranting a downward departure in sentencing.”). Even when multiple

transactions are intended to “make[] it easier to obtain a conviction, . . . there is

nothing wrong with the government attempting to strengthen its case for

conviction.” Govan, 293 F.3d at 1251. And as the government argues, “conducting

five transactions was not outrageous” in the light of a legitimate government

interest in “remov[ing] firearms from the streets, especially those accessible to a

convicted felon dealing drugs.” Lange “has not met his burden of establishing that

the government’s conduct is sufficiently reprehensible to constitute sentencing

factor manipulation,” Ciszkowski, 492 F.3d at 1271. “Because [Lange] is unable to

meet his burden to show plain error, his argument fails.” United States v. Castro,

455 F.3d 1249, 1253 (11th Cir. 2006).

                                 IV. CONCLUSION
      We AFFIRM Lange’s sentence.




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