FILED

U.S. COURT OF APPEALS

ELEVENTH CIRCUIT

May 31, 2006

THOMAS K. KAHN

CLERK

The Honorable Alfred T. Goodwin, United States Circuit Judge for the Ninth Circuit,

*

sitting by designation.

[PUBLISH]

IN THE UNITED STATES COURT OF APPEALS

FOR THE ELEVENTH CIRCUIT

________________________

No. 05-12591

Non-Argument Calendar

________________________

D. C. Docket No. 05-00006-CR-T-26MAP

UNITED STATES OF AMERICA, 

Plaintiff-Appellee, 

versus 

ALEJANDRO AGUILAR-ORTIZ, 

a.k.a. Alejandro Ortiz, 

Defendant-Appellant. 

________________________

Appeal from the United States District Court

for the Middle District of Florida

_________________________

(May 31, 2006)

Before TJOFLAT, BARKETT and GOODWIN , Circuit Judges. *
With a 3-level reduction for acceptance of responsibility, Ortiz’s adjusted offense level

1

was 17, which, combined with his criminal history category III, resulted in an advisory

guidelines range of 30 to 37 months imprisonment. The court imposed a sentence of 30 months’

imprisonment.

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BARKETT, Circuit Judge:

Alejandro Aguilar-Ortiz appeals his sentence of thirty months imprisonment,

imposed following a guilty plea, for being found in the United States after

deportation, in violation of 8 U.S.C. § 1326. Over Aguilar-Ortiz’s objection, the

district court applied a 12-level enhancement under U.S. Sentencing Guidelines

§ 2L1.2(b)(1)(B) for a prior conviction of a “drug trafficking offense.” The prior

conviction enhancement was based on a conviction in Florida state court for

solicitation to deliver cocaine. Aguilar-Ortiz appeals his sentence, arguing that the 1

district court erred in treating solicitation as a drug trafficking offense and that his

sentence is unreasonable.

We review questions of law with respect to the district court’s application of

the Sentencing Guidelines de novo. See United States v. Crawford, 407 F.3d 1174,

1178 (11th Cir. 2005). Where the district court incorrectly calculates a defendant’s

Guidelines range because of legal error, we remand for resentencing because the

Supreme Court’s decision in Booker “at a minimum, obliges the District Court to

calculate correctly the sentencing range prescribed by the Guidelines.” Id. 

Whether solicitation constitutes a drug trafficking offense for purposes of
3

U.S. Sentencing Guidelines § 2L1.2(b)(1)(B) is a question of first impression in

our Circuit. Section 2L1.2(b)(1)(B) provides that if a defendant previously was

deported, or unlawfully remained in the United States, after conviction for a

“felony drug trafficking offense” for which the sentence imposed was 13 months

or less, the offense level should be increased by 12 levels. The Guidelines do not

themselves define the term “drug trafficking offense” in regard to the

enhancement. However, the application notes define a “drug trafficking offense”

as “an offense under federal, state, or local law 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.” 

U.S.S.G. § 2L1.2 cmt. n.1(B)(iv). The notes also provide that “[p]rior convictions

of offenses counted under subsection (b)(1) include the offenses of aiding and

abetting, conspiring, and attempting, to commit such offenses.” The Notes do not

mention whether solicitation should be counted under subsection (b)(1). Id. cmt.

n.5.

The facts regarding Ortiz’s prior conviction for solicitation to deliver

cocaine as set forth in the PSI were admitted by Ortiz at sentencing and are

undisputed. According to the PSI, Ortiz solicited an undercover police officer to
In Taylor, the Supreme Court was faced with determining whether Congress intended a 2

defendant’s prior conviction for second-degree burglary under Missouri law to qualify as a

4

sell him $30 worth of crack cocaine. He was arrested after the officer sold him

said amount of counterfeit crack cocaine. Aguilar-Ortiz was convicted of

solicitation of the delivery of drugs, in violation of Fla. Stat. § 777.04(2), which

states that “[a] person who solicits another to commit an offense prohibited by law

and in the course of such solicitation commands, encourages, hires, or requests

another person to engage in specific conduct which would constitute such offense

or an attempt to commit such offense commits the offense of criminal solicitation,”

and § 893.13(1)(a), which makes it “unlawful for any person to sell, manufacture,

or deliver, or possess with intent to sell, manufacture, or deliver, a controlled

substance.” The question presented is whether this offense constituted a drug

trafficking offense for purposes of the Sentencing Guidelines. We conclude that,

under these facts, the district court erred in applying the enhancement for a prior

drug trafficking offense.

Generally, in determining whether a prior conviction is a qualifying offense

for enhancement purposes, we apply a “categorical” approach, which means that

we look no farther than the judgment of conviction. See United States v. Spell, 44

F.3d 936, 939 (11th Cir. 1995); Taylor v. United States, 495 U.S. 575, 602

(1990). However, where the judgment of conviction and statute are ambiguous, 2
“violent felony” for purposes of enhancing his sentence under the Armed Career Criminal Act

(“ACCA”). The government had successfully argued before the Eighth Circuit that by listing

“burglary” as a “violent felony” in the ACCA, Congress intended “burglary” to be defined

however a state chose. Taylor, 495 U.S. at 579 (citations omitted). In reversing, the Court

concluded that the ACCA’s use of “burglary” was not intended by Congress to encompass any

crime labeled a “burglary” under state law. Rather, “burglary” under the ACCA encompassed

only crimes fitting the generic or contemporary meaning of burglary, to wit: “an unlawful or

unprivileged entry into, or remaining in, a building or other structure, with intent to commit a

crime.” Id. at 598.

Having reached this conclusion, the Court recognized that it was then faced with “the

problem of applying this conclusion to cases in which the state statute under which a defendant

is convicted varies from the generic definition of ‘burglary.’” Id. at 599. Recognizing the

“practical difficulties and potential unfairness of a factual approach” in which mini-trials might

have to be conducted to determine whether the defendant indeed had been convicted of the

requisite prior crime, the Court held that “an offense constitutes ‘burglary’ for purposes of a §

924(e) sentence enhancement if either its statutory definition substantially corresponds to

‘generic’ burglary, or the charging paper and jury instructions actually required the jury to find

all the elements of generic burglary in order to convict the defendant.” Id. at 602.

Although Taylor was an ACCA case, this court applied and followed it in Spell, 44 F.3d 3

at 939-40. In Spell, the ambiguity of the conviction and the statute under which Spell was

prosecuted required the sentencing court to look behind the judgment of conviction. 44 F.3d at

939. The judgment of conviction entered into through a plea agreement stated the offense as a

“burglary of a structure,” yet the statute under which he was convicted encompassed three

different burglary scenarios, all of which could be a burglary of a structure. Id. at 939-40. The

sentencing court could not determine from the conviction and statute whether Spell burglarized a

dwelling, which would subject him to a guidelines enhancement, or unaggravated burglary of a

structure, which would not. Accordingly, we remanded for the district court to examine “ easily

produced and evaluated court documents, including the judgment of conviction, charging papers,

plea agreement, presentence report adopted by the court, and the findings of a sentencing judge.” 

Id. 

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i.e., the determination whether a prior conviction is a qualifying offense from the

face of the judgment itself is impossible, we remand for the district judge to look at

the facts underlying a state conviction. See United States v. Krawczak, 331 F.3d

1302, 1306 (11th Cir. 2003) (citing United States v. Spell, 44 F.3d 936 (11th Cir.

1995)). In examining the facts underlying a prior conviction to determine whether 3
We are not concerned here with Shepard’s applicability to an advisory guidelines 4

scheme. We have held that there is no constitutional error when a district court applies the

Sentencing Guidelines in an advisory manner. See United States v. Chau, 426 F.3d 1318 (11th

Cir. 2005). On the other hand, we view Shepard as applying and refining the evidentiary analysis

of Taylor. Under the Taylor line of cases in this Court, evidentiary limitations on the district

court’s application of sentencing enhancements apply in both ACCA and non-ACCA cases. See,

e.g., Spell, 44 F.3d at 939 (holding that the reasoning in Taylor “applies with equal force to

| decisions under §§ 4B1.1 and 4B1.2”); see also United States v. Krawczak, 331 F.3d 1302, 1306

(11th Cir. 2003) (applying reasoning in Taylor to the sentencing guidelines); United States v.

Gay, 251 F.3d 950, 952 (11th Cir. 2001) (same and holding that the ability to look behind a state

conviction in federal sentencing is “very limited”); United States v. Richardson, 230 F.3d 1297,

1300 (11th Cir. 2000) (applying reasoning in Taylor to the sentencing guidelines). We see no

meaningful distinction between the level of reliability in an analysis of a fact of a prior

conviction for purposes of the ACCA and for purpose of the sentencing guidelines, as both

require the same or similar factual analysis and raise similar concerns of reliability. We note that

our sister circuits have applied Shepard to the Sentencing Guidelines notwithstanding their

advisory nature after Booker. See United States v. Gutierrez-Ramirez, 405 F.3d 352 (5th Cir.

2005) (holding that Shepard’s discussion should be used to determine whether a prior conviction

is a “drug trafficking offense” under § 2L1.2 of the Sentencing Guidelines); see also United

States v. Galloway, 439 F.3d 320, 323-24 (6th Cir. 2006) (“While Shepard involves the

definition of a violent felony under the ACCA, we conclude that Shepard’s holding is fully

applicable to Sentencing Guideline cases that require a court to determine the nature of a prior

conviction when the defendant has a prior conviction under a generic statute that may or may not

serve as a predicate for a sentencing enhancement.”); United States v. Kendrick, 423 F.3d 803,

808-09 (8th Cir. 2005); United States v. Lewis, 405 F.3d 511, 513-15 (7th Cir. 2005); United

States v. Delaney, 427 F.3d 1224, 1226 (9th Cir. 2005); United States v. Washington, 157 Fed.

Appx. 43 (10th Cir. 2005); United States v. Estevez, 419 F.3d 77 (1st Cir. 2005); United States

v. Washington, 404 F.3d 834, 841 (4th Cir. 2005) (applying Shepard to the guidelines based on

the Sixth Amendment). 

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it qualifies for a sentencing enhancement, our cases, relying on Taylor, have held

that sentencing courts may rely only on a limited set of materials. In Shepard v.

United States, 544 U.S. 13, 125 S. Ct. 1254 (2005), the Supreme Court clarified

Taylor, holding that a court may rely only on the “charging document, written plea

agreement, transcript of plea colloquy, and any explicit factual finding by the trial

judge to which the defendant assented.” Shepard, 125 S. Ct. at 1257.4
7

Ortiz argues that solicitation of the delivery of drugs does not constitute a

drug trafficking offense because in cases like his, where the defendant solicits the

delivery of a “personal quantity amount” of drugs, there is no intent for the

defendant to “to manufacture, import, export, distribute, or dispense” a controlled

substance (or counterfeit substance). Ortiz further argues that because the

Application Notes provide explicitly that eligible prior convictions include aiding

and abetting, conspiracy, and attempt, we should infer from the omission of

solicitation offenses that such offenses were not intended to be used to enhance

under § 2L1.2(b). 

In response, the government argues that the district court properly applied

the enhancement because solicitation is sufficiently similar to the offenses of

aiding and abetting, conspiracy, and attempt that solicitation should fall within the

intended offenses covered by § 2L1.2, even if it is not mentioned explicitly. 

Although no Circuit has held that solicitation constitutes a drug trafficking offense,

the Tenth Circuit recently held that solicitation is sufficiently similar to aiding and

abetting, conspiracy, and attempt that “solicitation of an offense that otherwise

meets the definition of ‘crime of violence’ is also a crime of violence” for purposes

of the enhancement for crimes of violence under U.S. Sentencing Guidelines

§ 2L1.2(b)(1)(A). See United States v. Cornelio-Pena, 435 F.3d 1279, 1288 (10th
Although the use of the term “drug trafficking” in the U.S. Sentencing Guidelines is 5

what we must apply, we find persuasive support in the Florida statute defining a “trafficking”

offense under Florida law, which limits trafficking offenses to those involving 28 grams or more

of cocaine. See Fla. Stat. § 893.135(1)(b) (2005). Aguilar-Ortiz solicited only $30 worth of

cocaine, which would not qualify as a “drug trafficking offense” under Florida law.

8

Cir. 2006). 

We begin our analysis by evaluating the judgment of conviction and statute

to determine whether the Florida statute under which Aguilar-Ortiz was convicted

comports fully with the definition provided in the Application Notes. See

Krawczak, 331 F.3d at 1306. We first note that defendants may be found guilty of

the crime of solicitation in Florida on the basis of a wide range of conduct. A

conviction could be based on the solicitation of the delivery of enormous quantities

of narcotics for redistribution. However, a conviction could also be based on the

solicitation of the smallest amount of drugs solely for personal use. Thus the crime

of solicitation cannot be considered as providing a categorical, or per se, basis for

this enhancement. Accordingly, whether a solicitation offense under Florida law

qualifies as a drug trafficking offense under the enhancement depends on the facts

of the case. 

5

In this case, the only conduct Ortiz has committed is the solicitation of a

personal quantity amount of drugs – in essence, attempted possession without

intent to distribute. Cf. Hutchinson v. State, 315 So. 2d 546 (Fla. 2d DCA 1975)
9

(explaining that Florida law does not recognize a crime of “attempted conspiracy,”

but rather prohibits such conduct as “solicitation”). Possession, both actual and

attempted, fails to qualify as a drug trafficking offense under the Guidelines. See

U.S. Sentencing Guidelines § 2L1.2. Solicitation of the delivery of a personal

quantity amount of drugs is not different in kind from attempted possession, thus

we should not treat them as such for purposes of the enhancement under § 2L1.2. 

Furthermore, we find that solicitation of a personal quantity amount of drugs

is different in kind from the other inchoate offenses listed in the Guidelines

Application Notes. Solicitation of a personal quantity amount of drugs results

solely in the distribution of drugs to the defendant. In such a case, the defendant

has not himself engaged in the trafficking of drugs to others. In contrast, when a

defendant commits the crime of attempted distribution, conspiracy to distribute

drugs, or aiding and abetting the distribution of drugs, it is the defendant whose

conduct may be characterized as the trafficking of drugs to another. These three

offenses included within the Application Notes are thus quite different from the

solicitation of a personal quantity amount. See United States v. Dolt, 27 F.3d 235

(6th Cir. 1994) (holding that solicitation is not a “controlled substance” offense

under § 4B1.2 of the Guidelines because “[s]olicitation is not enumerated as a

predicate offense in the Guidelines and Florida’s solicitation statute is not
10

sufficiently similar to aiding and abetting, conspiracy or attempt to serve as a

predicate ‘controlled substance offense’ as defined by § 4B1.2 of the Sentencing

Guidelines”); cf. Salinas v. United States, --- S.Ct. ----, No. 05-8400, 2006 WL

1059408, at *1 (Apr. 24, 2006) (holding that Fifth Circuit erred in treating

defendant's prior conviction for simple possession of a controlled substance as a

“controlled substance offense” within meaning of career offender Sentencing

Guideline).

Ultimately, we cannot say as a categorical matter that all solicitation

offenses under Florida law either do or do not qualify as drug trafficking offenses.

There may be some solicitation cases where a defendant has been convicted for

soliciting a sufficiently large quantity of drugs that the sentencing court may infer a

defendant’s intent to distribute the drugs. In those cases, the district court may

determine that the defendant’s prior conviction for solicitation of the delivery of

drugs constituted a drug trafficking offense so long as the court permissibly finds

substantial evidence, on the basis of the “charging document, written plea

agreement, transcript of plea colloquy, and any explicit factual finding by the trial

judge to which the defendant assented,” Shepard, 125 S. Ct. at 1257, that the

defendant manufactured, imported, exported, distributed, or dispensed of a

controlled (or counterfeit) substance, or possessed a substance with the intent to
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manufacture, import, export, distribute, or dispense it. See U.S. Sentencing

Guidelines § 2L1.2 cmt. n.1(B)(iv). This is not such a case.

Accordingly, we vacate the sentence imposed on the basis of the

enhancement and remand for resentencing.

VACATED AND REMANDED.