U.S. v. Medina-Almaguer

• Decision Date: 12 March 2009
• Docket Number: No. 07-4254.,07-4254.
• Citation: 559 F.3d 420
• Parties: UNITED STATES of America, Plaintiff-Appellee, v. Paulo Sergio MEDINA-ALMAGUER, Defendant-Appellant.
• Court: U.S. Court of Appeals — Sixth Circuit

559 F.3d 420

UNITED STATES of America, Plaintiff-Appellee, v. Paulo Sergio MEDINA-ALMAGUER, Defendant-Appellant.

No. 07-4254.

United States Court of Appeals, Sixth Circuit.

Argued: March 6, 2009.

Decided and Filed: March 12, 2009.

ARGUED: Thomas Patrick Ryan, Law Offices, Cleveland, Ohio, for Appellant. Phillip J. Tripi, Assistant United States Attorney, Cleveland, Ohio, for Appellee. ON BRIEF: Jaime P. Serrat, Cleveland, Ohio, for Appellant. Michael J. Rendon, Assistant United States Attorney, Cleveland, Ohio, for Appellee.

Before KEITH, SUTTON and GRIFFIN, Circuit Judges.

OPINION

SUTTON, Circuit Judge.

Paulo Sergio Medina-Almaguer appeals his 27-month sentence for illegal reentry after deportation. At stake is whether the district court properly characterized a 1989 state-court conviction as a "drug trafficking offense" under the sentencing guidelines.

I.

On September 19, 2007, Medina-Almaguer pleaded guilty to one count of illegal reentry following deportation. See 8 U.S.C. § 1326. In calculating his advisory guidelines range, the district court imposed a 16-level enhancement because Medina-Almaguer's deportation arose from a "drug trafficking offense." U.S.S.G. § 2L1.2(b)(1)(A). In 1989, he pleaded guilty to violating Cal. Health & Safety Code § 11352(a) (1989), which makes it a crime for any person to "transport, import . . ., sell, furnish, administer, or give away" a controlled substance or to "offer[]" to do those things.

Medina-Almaguer objected to the 16-level enhancement on the ground that the broad sweep of the California statute covers conduct that comes within § 2L1.2(b)(1)(A)'s definition of a "drug trafficking offense," as well as conduct that falls outside of it, and his guilty plea gave the district court no basis for determining whether his conduct amounted to a covered offense. The district court, however, did not just rely on the 1989 judgment in increasing Medina-Almaguer's sentence. It also looked to a preliminary-examination transcript from the 1989 state-court proceedings, which showed that he was arrested after selling heroin to an undercover police officer. Because a "drug trafficking offense" under the guidelines includes the "distribution ... or dispensing of a controlled substance," U.S.S.G. § 2L1.2(b)(1)(A), app. note 1(B)(iv) (2006), the court concluded that the conviction amounted to a "drug trafficking offense."

The 16-level enhancement together with a three-level reduction for acceptance of responsibility, see U.S.S.G. § 3E1.1, left Medina-Almaguer with a 37-46 month guidelines range. Opting to vary his sentence downward because the predicate offense for the 16-level enhancement occurred nearly 18 years earlier and because Medina-Almaguer had (for the most part) stayed out of trouble since, the district court imposed a 27-month sentence.

II.

Medina-Almaguer's appeal raises one issue: Does his 1989 state-court conviction qualify as a "drug trafficking offense" within the meaning of U.S.S.G. § 2L1.2(b)(1)(A)?

The Sixth Amendment, to start, does not bar this inquiry. Even though the question at hand is whether a sentencing court permissibly increased Medina-Almaguer's guidelines range based on a form of fact finding about his 1989 conviction, that kind of adjustment does not violate the Sixth Amendment because the Supreme Court has long exempted fact finding related to "prior conviction[s]," Almendarez-Torres v. United States, 523 U.S. 224, 243-44, 118 S.Ct. 1219, 140 L.Ed.2d 350 (1998), and because such adjustments at any rate now apply to an advisory guidelines system, United States v. Booker, 543 U.S. 220, 245, 125 S.Ct. 738, 160 L.Ed.2d 621 (2005).

In determining the nature of a prior offense, courts normally start—and stop—by looking at "the fact of conviction and the statutory definition of the prior offense." Taylor v. United States, 495 U.S. 575, 602, 110 S.Ct. 2143, 109 L.Ed.2d 607 (1990). That categorical approach to the problem provides no answer here, because the state statute under which Medina-Almaguer was convicted punishes conduct that qualifies as a "drug trafficking offense" and conduct that does not. The application note to § 2L1.2 defines a "drug trafficking offense" as one that targets "the manufacture, import, export, distribution, or dispensing of a controlled substance" or the possession of a controlled substance with the intent to do those things. U.S.S.G. § 2L1.2(b)(1)(A), app. note 1(B)(iv) (2006). And the California statute makes it a crime to "transport, import into [the] state, sell, furnish, administer, or give away" a controlled substance or to "offer[]" to do these things. Cal. Health & Safety Code § 11352(a). The California law thus proscribes conduct that § 2L1.2 does not—namely, the "transport[ation]" of controlled substances and "offers" to perform the proscribed activities. See, e.g., People v. Beyah, 170 Cal. App.4th 1241, 88 Cal.Rptr.3d 829, 832-33 (2009); People v. Encerti, 130 Cal.App.3d 791, 182 Cal.Rptr. 139, 140, 144-45 (1982); see also United States v. Crawford, 520 F.3d 1072, 1078 (9th Cir.2008); United States v. Gutierrez-Ramirez, 405 F.3d 352, 356 (5th Cir.2005). The "fact" of Medina-Almaguer's prior conviction under § 11352(a) together with "the statutory definition" of that offense, Taylor, 495 U.S. at 602, 110 S.Ct. 2143, do not by themselves show that he was convicted of a "drug trafficking offense."

That does not end the inquiry, however. If the state-law definition of a prior offense covers more ground than the conduct reached by the federal-sentencing enhancement, a sentencing court may consult a limited range of judicial documents to determine the nature of the prior conviction. See Shepard v. United States, 544 U.S. 13, 20-21, 125 S.Ct. 1254, 161 L.Ed.2d 205 (2005). In the context of a conviction stemming from a guilty plea—as Medina-Almaguer's predeportation conviction did—the question is whether the court documents establish that the defendant "necessarily admitted" the elements of a predicate offense through his plea. Id. at 16, 125 S.Ct. 1254; see also id. at 20-21, 26, 125 S.Ct. 1254; cf. Taylor, 495 U.S. at 602, 110 S.Ct. 2143. For that purpose, a sentencing court generally may consider the charging document, a written plea agreement, a plea-colloquy transcript in which the defendant confirmed the factual basis for the plea or some other "comparable judicial record," Shepard, 544 U.S. at 26, 125 S.Ct. 1254, so long as they establish what the defendant "necessarily admitted," id. at 16, 125 S.Ct. 1254. Otherwise, the sentencing court must stand by the fact of conviction and the definition of the offense—whether they establish the nature of the prior conviction or not. See, e.g., United States v. McGrattan, 504 F.3d 608, 615-616 (6th Cir.2007); United States v. Bernal-Aveja, 414 F.3d 625, 627-28 (6th Cir.2005).

In Medina-Almaguer's case, the 1989 information and abstract of judgment do not establish that he pleaded guilty to a "drug trafficking offense." Both documents merely restate the text of § 11352(a) and offer no information about the specific acts, if any, that he admitted committing. To its credit, the district court thus did not rely on the 1989 information and judgment in ratcheting up Medina-Almaguer's guidelines offense level.

The court, however, did believe that the transcript from his preliminary examination sufficed to support the enhancement. At the preliminary examination, a police officer testified about a controlled drug buy with Medina-Almaguer, in which the officer gave Medina-Almaguer $20 in exchange for heroin. Even granting for the sake of argument that a sentencing court may consult a preliminary-examination transcript in investigating the nature of a prior offense, this transcript does not show that Medina-Almaguer "necessarily admitted" to a "drug trafficking offense" when he pleaded guilty to violating § 11352(a). Much like a police report or a complaint application—upon which sentencing courts may not rely in determining the nature of a prior conviction, see Shepard, 544 U.S. at 16, 125 S.Ct. 1254—a preliminary examination deals with a gateway step in the criminal process: determining whether probable cause exists for detaining a suspect before a potential indictment or information. The examination takes place before the State has filed an information charging the defendant with a crime, see Cal.Penal Code §§ 738, 739, and its purpose is to determine "whether there exists probable cause to believe that the defendant has committed a felony," id. § 866(b); cf. Shepard, 544 U.S. at 21, 125 S.Ct. 1254.

No doubt, a police officer testified at the preliminary examination that Medina-Almaguer sold heroin to him. But that testimony showed only that the examining magistrate properly concluded that there was "sufficient cause" to believe that Medina-Almaguer violated § 11352(a). Medina-Almaguer did not admit that conduct during the examination, nor so far as the record shows did he admit that conduct when he pleaded guilty. The transcript at most provides a basis for establishing probable cause to hold him for violating the statute and perhaps for violating the statute in this way. But it does not follow that the transcript establishes the acts that he "necessarily admitted" when he later pleaded guilty.

United States v. Jones, 453 F.3d 777, 780 (6th Cir.2006), we realize, held that a sentencing court may determine the nature of a prior offense based on an "affidavit of complaint," which describes "the essential facts constituting the offense charged" and is used to obtain an arrest warrant, Tenn. R.Crim. P. 3(c); see also Tenn.Code Ann. § 40-6-203. An affidavit of complaint, we also realize, is similar to preliminary-examination testimony in at least one respect: It has "substantially greater indicia of reliability than mere police reports" because it is given "under oath and submitted in furtherance of formal prosecution." Jones, 453 F.3d at 780.

Although Jones provides...