                                                                        FILED
                                                            United States Court of Appeals
                                                                    Tenth Circuit
                   UNITED STATES COURT OF APPEALS
                                                                  August 10, 2011
                                TENTH CIRCUIT                   Elisabeth A. Shumaker
                                                                    Clerk of Court


 UNITED STATES OF AMERICA,

              Plaintiff-Appellee,
                                                         No. 11-5021
 v.                                           (D.C. No. 4:10-CR-00135-CVE-1)
                                                       (N.D. of Okla.)
 OMAR GOMEZ-ALAMILLA, a/k/a
 Omar Almaya Renedomeo, a/k/a Omar
 Gomez Alamilla, a/k/a Rene Marshal
 Domeq, a/k/a Omar Gomez-Alamillo,
 a/k/a Rene Domeq, a/k/a Omar
 Alamellla Gomez, a/k/a Rene Dumeo,
 a/k/a Omar Almaya Gomez, a/k/a
 Omar Alamilla, a/k/a Omar Gomez,
 a/k/a Rene Marshal, a/k/a Rene
 Marshall Domeq, a/k/a Omar
 Alamilla Gomez, a/k/a Omar Alamillo,

              Defendant-Appellant.


                           ORDER AND JUDGMENT *


Before O’BRIEN, McKAY, and TYMKOVICH, Circuit Judges. **




      *
         This order and judgment is not binding precedent except under the
doctrines of law of the case, res judicata and collateral estoppel. It may be cited,
however, for its persuasive value consistent with Fed. R. App. P. 32.1 and 10th
Cir. R. 32.1.
      **
         After examining the briefs and the appellate record, this three-judge
panel has determined unanimously that oral argument would not be of material
assistance in the determination of this appeal. See Fed. R. App. P. 34(a); 10th
Cir. R. 34.1(G). The cause is therefore ordered submitted without oral argument.
      Omar Gomez-Alamilla, a federal prisoner, appeals his 46-month sentence

for illegally reentering the United States after deportation. He contends the

district court erred in applying a 16-level sentencing enhancement under United

States Sentencing Guidelines (USSG) § 2L1.2(b)(1)(A), and he challenges the

substantive reasonableness of his sentence. After a thorough review of the

record, we find both claims lack merit.

      Therefore, exercising jurisdiction under 28 U.S.C. § 1291, we AFFIRM

Gomez-Alamilla’s sentence.

                                  I. Background

      In 1988, Gomez-Alamilla was convicted of a felony drug crime and, as a

result, was deported to Mexico. Not long after being deported, he illegally

reentered the United States, where he was arrested and convicted for possession

of a controlled substance and receiving stolen property. Gomez-Alamilla was

again deported, and he again illegally reentered the United States. In 2001, he

was arrested and charged with multiple cocaine offenses and possession of a

firearm during a felony. After again being convicted of illegal reentry, he was

deported to Mexico for a third time. He returned to the United States once again.

Finally, in 2010, Gomez-Alamilla was arrested in Oklahoma for driving under the

influence.

      Gomez-Alamilla pleaded guilty to illegally reentering the United States

after having been previously deported, in violation of 8 U.S.C. §§ 1326(a) and

                                          -2-
1326(b)(2). The presentence investigation report (PSR), which the district court

adopted, detailed Gomez-Alamilla’s numerous prior convictions. Pursuant to the

report, the district court calculated that Gomez-Alamilla’s base offense level was

8, but because he had previously been deported after a conviction for a felony

drug trafficking offense, the court applied a 16-level enhancement pursuant to

USSG § 2L1.2(b)(1)(A). The court also granted Gomez-Alamilla a 3-level

reduction for acceptance of responsibility.

      Accordingly, based on his total offense level of 21 and criminal history

category of III, Gomez-Alamilla’s advisory sentencing range was 46 to 57

months’ imprisonment. Gomez-Alamilla objected to the 16-level enhancement

and filed a motion for a variance below the advisory guideline range. The district

court overruled the objection, denied Gomez-Alamilla’s motion for a variance,

and imposed a 46-month sentence.

                                  II. Discussion

      Gomez-Alamilla challenges (1) the district court’s application of a 16-level

enhancement under § 2L1.2(b)(1)(A), and (2) the substantive reasonableness of

his sentence. Neither argument is meritorious.

      A.     16-Level Enhancement

      The foundation for the enhancement traces back to Gomez-Alamilla’s first

relevant conviction. In 1988, he was sentenced to three years’ imprisonment for

violating California Health & Safety Code § 11351, which makes it a felony to

                                         -3-
“possess[] [a controlled substance] for sale or purchas[e] [a controlled substance]

for purposes of sale.” The district court determined this was a “drug trafficking

offense” under § 2L1.2(b)(1)(A), such that a 16-level enhancement was

appropriate. Gomez-Alamilla disputes this classification. Specifically, he

contends the California statute is ambiguous and, accordingly, that the district

court should have applied a modified categorical approach to determine whether

his conviction qualified as a drug trafficking offense.

      Before the district court, Gomez-Alamilla contested the 16-level

enhancement, but he did so only on the vague basis that “there [was] insufficient

information to ascertain whether or not his conviction was a drug trafficking

offense.” Aplt. Br., Ex. 4 at 1. Because Gomez-Alamilla now takes a

fundamentally different tack—challenging the clarity of the statute and the

district court’s interpretive approach—the district court did not have the

opportunity to consider his specific objections and, if necessary, correct its ruling.

Accordingly, we review only for plain error. See F ED . R. C RIM . P. 52(b); United

States v. Poe, 556 F.3d 1113, 1128 (10th Cir. 2009).

      Under plain error review, we may not reverse unless we find “(1) error, (2)

that is plain, and (3) that affects substantial rights. If all three conditions are met,

[we] may then exercise [] discretion to notice a forfeited error, but only if (4) the

error seriously affects the fairness, integrity, or public reputation of [the] judicial

proceedings.” United States v. Balderama-Iribe, 490 F.3d 1199, 1204 (10th Cir.

                                          -4-
2007) (quotation omitted). Under the third prong, the error affects substantial

rights only if it has affected the outcome of the district court proceedings.

Morales-Fernandez v. INS, 418 F.3d 1116, 1124 (10th Cir. 2005). Gomez-

Alamilla bears the burden of demonstrating plain error. Id.

      Defendants are subject to 16-level enhancements under § 2L1.2(b)(1)(A) of

the Guidelines if they have been previously deported for “a drug trafficking

offense for which the sentence imposed exceeded 13 months.” A drug trafficking

offense is defined as “an offense under federal, state, or local law that prohibits

the manufacture, import, export, distribution, or dispensing of a controlled

substance . . . or the possession of a controlled substance with intent to

manufacture, import, export, distribute, or dispense.” § 2L1.2 cmt. n.1(B)(iv). 1

Accordingly, the task for the district court was to decide whether this definition

encompasses Gomez-Alamilla’s 1988 felony for “possess[ing] [a controlled

substance] for sale or purchas[ing] [a controlled substance] for purposes of sale.”

Cal. Health & Safety Code § 11351.

      In deciding whether Gomez-Alamilla’s past conviction triggered an

enhancement under § 2L1.2(b)(1)(A), the district court was required to employ


      1
          In interpreting the Guidelines, we look “at the language in the guideline
itself, as well as the interpretive and explanatory commentary to the guideline
provided by the Sentencing Commission. Commentary to the Guidelines is
authoritative unless it violates the Constitution or a federal statute, or is
inconsistent with, or a plainly erroneous reading of, that guideline.” United
States v. McConnell, 605 F.3d 822, 824 (10th Cir. 2010) (quotations omitted).

                                          -5-
one of two analytical approaches: the “categorical approach” or the “modified

categorical approach.” The categorical approach is appropriate if the statute of

conviction encompasses only conduct triggering enhancements under

§ 2L1.2(b)(1)(A). Under the categorical approach, a sentencing court “looks to

the words of the statute and judicial interpretations of it, rather than to the

conduct of any particular defendant convicted of the crime.” United States v.

Armijo, — F.3d —, No. 09-1533, 2011 WL 2687274, at *2 (10th Cir. July 12,

2011) (quotation omitted); see also Taylor v. United States, 495 U.S. 575, 600–02

(1990). Thus, it is irrelevant “how an individual offender might have committed

[the crime] on a particular occasion.” Armijo, 2011 WL 2687274, at *2. “To

satisfy th[e] categorical approach, it is not necessary that every conceivable

factual offense covered by a statute fall within [the sentencing enhancement].”

United States v. Smith, — F.3d —, No. 10-6209, 2011 WL 2714083, at *1 (10th

Cir. July 13, 2011) (quotation omitted). Rather, we have held that “the proper

inquiry is whether conduct encompassed by the elements of the offense, in the

ordinary case, qualifies under the [enhancement].” Id. (quotation omitted).

      The modified categorical approach, on the other hand, is appropriate when

a criminal statute is ambiguous. Indeed, if the statute of conviction encompasses

a broad range of conduct—some of which would trigger the enhancement and

some of which would not—a court must employ the modified categorical

approach. Under the modified approach, a court resolves the statutory ambiguity

                                           -6-
by determining under which part of the statute the defendant was convicted; in so

doing, a court may “consult[] reliable judicial records, such as the charging

document, plea agreement or plea colloquy.” United States v. Martinez-

Hernandez, 422 F.3d 1084, 1086 (10th Cir. 2005). Review under the modified

categorical approach “does not involve a substantive inquiry into the facts of the

case, but rather its purpose is to determine which part of the statute was charged

against the defendant and, thus, which portion of the statute to examine on its

face.” Armijo, 2011 WL 2687274, at *2.

      At sentencing, the district court used the categorical approach to determine

that Gomez-Alamilla’s conviction under § 11351 was a drug trafficking offense.

Gomez-Alamilla contends this approach was improper, because a “purchase[] for

purposes of sale” may, under some circumstances, constitute neither actual nor

constructive possession. He argues that because possession is a prerequisite to

committing drug trafficking offense under § 2L1.2(b)(1)(a)’s definition, a

conviction under § 11351, which may or may not involve possession, must be

assessed using a modified categorical approach.

      Neither the Supreme Court nor the Tenth Circuit has decided whether the

categorical approach is the correct method for assessing convictions under

§ 11351. For this reason, we need not consider whether the district court’s

approach was erroneous, because any such error would not have been plain.

United States v. Story, 635 F.3d 1241, 1248 (10th Cir. 2011) (“[F]or an error to be

                                         -7-
contrary to well-settled law, either the Supreme Court or this court must have

addressed the issue.”); United States v. Goode, 483 F.3d 676, 681 (10th Cir.

2007) (to show plain error, a defendant must establish that an error, if it occurred,

was not “clear or obvious under current law”).

      Indeed, although we have not ruled on the issue, numerous courts have held

that a conviction under § 11351 is fundamentally a drug trafficking offense, such

that a court need not assess the specifics of a defendant’s charged conduct when

deciding whether to apply an enhancement under § 2L1.2(b)(1)(A). See, e.g.,

United States v. Morales-Perez, 467 F.3d 1219, 1223 (9th Cir. 2006); United

States v. Palacios-Quinonez, 431 F.3d 471, 474 (5th Cir. 2005). For example, the

Ninth Circuit decided that because the federal crime of attempted possession of a

controlled substance with intent to sell—unquestionably a drug trafficking offense

for the purposes of § 2L1.2(b)(1)(A)—encompasses all conduct criminalized by

§ 11351 (including purchasing narcotics for the purpose of sale), an assessment

under the modified categorical approach is unnecessary. Morales-Perez, 467 F.3d

at 1223. Accordingly, Gomez-Alamilla has failed to meet his burden of showing

that the purported error was plain.

      Moreover, even if the district court had applied the modified categorical

approach, as urged by Gomez-Alamilla, it still would have reached the conclusion

that his 1988 conviction qualified as a drug trafficking crime. In his 1988

declaration, Gomez-Alamilla admitted he “possessed heroin for sale on Sept. 15th

                                          -8-
1988. More than ½ oz.” Aplt. Br., Ex. 10. Because this document was a

“comparable judicial record” of “the factual basis for the plea [which] was

confirmed by the defendant,” it could have been considered by the district court

in assessing Gomez-Alamilla’s prior conviction under the modified categorical

approach. Shepard v. United States, 544 U.S. 13, 26 (2005). Therefore, it is

plain that Gomez-Alamilla was convicted under the “possession” prong of

§ 11351, rather than the “purchase for sale” prong. Because possession of

distribution quantities of heroin is unequivocally a drug trafficking offense under

§ 2L1.2(b)(1)(A), any error in employing the categorical approach was not

prejudicial.

      In sum, under any interpretive approach, there is no doubt that Gomez-

Alamilla’s 1988 conviction was for a drug trafficking crime. Accordingly, the

district court did not plainly err—and even if it did, its failure to apply the

modified categorical approach did not affect Gomez-Alamilla’s substantial rights.

      B.       Substantive Reasonableness

      Gomez-Alamilla also contends his 46-month sentence is substantively

unreasonable. He alleges the district court failed to account for: (1) time he

served in prison between his state DUI arrest and his federal indictment, (2) his

health, (3) the age of his 1988 drug trafficking conviction, (4) his age, and (5) his

likely deportation to Mexico after his incarceration. These contentions are belied

by the record, which shows Gomez-Alamilla received a sentence tailored to the

                                           -9-
facts of his crime, based on a conscientious consideration of the 18 U.S.C.

§ 3553(a) factors.

      We review the substantive reasonableness of a defendant’s sentence for

abuse of discretion. See United States v. Mancera-Perez, 505 F.3d 1054, 1058

(10th Cir. 2007). Under this deferential standard, we may overturn Gomez-

Alamilla’s sentence only if the district court’s decision was “arbitrary, capricious,

whimsical, or manifestly unreasonable.” United States v. Friedman, 554 F.3d

1301, 1307 (10th Cir. 2009) (quotation omitted). In this regard, we assess

whether his sentence is reasonable “given all the circumstances of the case in

light of the factors set forth in 18 U.S.C. § 3553(a).” Id. (quotation omitted).

Because Gomez-Alamilla’s sentence is within a properly calculated guidelines

range, we presume it to be reasonable. United States v. Verdin-Garcia, 516 F.3d

884, 898 (10th Cir. 2008).

      Gomez-Alamilla has not rebutted the presumption of reasonableness.

Notably, in addition to carefully weighing the § 3553(a) factors, the district court

expressly considered and rejected all the arguments Gomez-Alamilla makes here.

For example, before pronouncing a sentence, the court took into account the

dangers of deportation to Mexico and Gomez-Alamilla’s health concerns. In fact,

the court recommended that Gomez-Alamilla, in connection with serving his

sentence, “be initially designated to a medical facility for evaluation and

treatment of his medical conditions, including hepatitis C.” R., Vol. III at 18.

                                         -10-
Moreover, the court recognized the potential staleness of the 1988 conviction but

rejected Gomez-Alamilla’s argument because he had once before received a

downward departure based on the age of the conviction, but that departure “did

nothing to deter him from committing the same offense again,” given his

subsequent illegal reentry into the United States. Id. at 16. Finally, the district

court indicated that but for Gomez-Alamilla’s uncredited jail time, it would have

imposed a 48-month sentence; in reality, the court imposed a 46-month sentence

to account for Gomez-Alamilla’s time served.

      Furthermore, the district court carefully accounted for the § 3553(a)

factors, including the “nature of the offense, the defendant’s personal

characteristics, and his extensive criminal history which has been ongoing for

more than 30 years.” Id. at 16. The court also “afforded equal weight to the need

for the sentence to reflect the seriousness of the offense, to promote respect for

the law, and to provide for just punishment.” Id. The court concluded that a

bottom-of-the guidelines sentence was appropriate in light of the “nonviolent

nature of the [] offense, the significant amount of time afforded under the

sentencing guidelines . . . , and the fact that the defendant [would] likely be

deported following his term of imprisonment”—even though Gomez-Alamilla’s

“extensive criminal history and repeat unauthorized reentry” justified an above-

guidelines sentence. Id. at 17.

      Accordingly, Gomez-Alamilla’s sentence is substantively reasonable.

                                         -11-
                        III. Conclusion

For the reasons discussed above, we AFFIRM Gomez-Alamilla’s sentence.

                                     ENTERED FOR THE COURT

                                     Timothy M. Tymkovich
                                     Circuit Judge




                              -12-
