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United States v. Zambrano-Reyes

United States Court of Appeals, Seventh Circuit

July 29, 2013

United States of America, Plaintiff-Appellee,
Jose Manuel Zambrano-Reyes, Defendant-Appellant.

Argued February 15, 2013.

Appeal from the United States District Court for the Northern District of Illinois, Western Division. No. 11 cr 50046—Philip G. Reinhard, Judge.

Before Flaum, Wood, and Hamilton, Circuit Judges.

WOOD, Circuit Judge.

Jose Manuel Zambrano-Reyes, then a lawful permanent resident, was removed from the United States on November 13, 2000. A decade later, immigration agents discovered that he was back in the country, and he was charged with illegal reentry. 8 U.S.C. § 1326. Zambrano pleaded guilty in October 2011, but on the eve of his February 2012 sentencing, he moved to withdraw his plea. The reason he offered for this eleventh-hour move was that the Supreme Court's recent decision in Judulang v. Holder, 132 S.Ct. 476 (2011), coupled with its earlier ruling in I.N.S. v. St. Cyr, 533 U.S. 289 (2001), provided a new basis for him to mount a collateral attack on his original removal. The illegal reentry statute authorizes such challenges, provided the alien can establish three points: "(1) [he] exhausted any administrative remedies that may have been available to seek relief against the order; (2) the deportation proceedings . . . improperly deprived [him] of the opportunity for judicial review; and (3) the entry of the order was fundamentally unfair." 8 U.S.C. § 1326(d). The district court refused to permit the withdrawal of Zambrano's plea and sentenced him to 12 months and one day. We affirm.


Zambrano pleaded guilty in 1993 to two counts of aggravated sexual abuse of a minor, an aggravated felony that rendered him deportable, see 8 U.S.C. § 1227(a)(2)(A)(iii), and served four years of probation. Until 1996, many permanent resident aliens facing deportation were entitled to apply for a discretionary waiver, known as Section 212(c) relief. St. Cyr, 533 U.S. at 295-97. There is no dispute that Zambrano, who had been in the United States since 1979 and did not serve any jail time for his felony offenses, would have been eligible to apply for a Section 212(c) waiver had his deportation order been entered before 1996. And there is some reason to think that such discretionary relief would have been granted: between 1989 and 1995, immigration judges granted waivers to over 10, 000 aliens, approving over 42% of all Section 212(c) applications filed. Julie K. Rannik, Comment: The Anti-Terrorism and Effective Death Penalty Act of 1996: A Death Sentence for the 212(c) Waiver, 28 U. Miami Inter-A m. L. Rev. 123, 137 n.80 (1996).

Zambrano's removal proceedings did not begin until 1998, however, and in the interim, Congress significantly curtailed the availability of discretionary relief for aliens facing removal (the new term for deportation). With the passage of the Antiterrorism and Effective Death Penalty Act of 1996 (AEDPA), enacted on April 24, 1996, Pub. L. No. 104-132, and the Illegal Immigration Reform and Immigrant Responsibility Act of 1996 (IIRIRA), enacted on September 30, 1996, Pub. L. No. 104-208, Congress repealed Section 212(c) and replaced it with a much narrower form of discretionary relief known as "cancellation of removal." See St. Cyr, 533 U.S. at 297. Under the new regime, the Attorney General may still cancel removal for certain lawful permanent residents, but not for those convicted of aggravated felonies. 8 U.S.C. § 1229b(a)(3).

Following the passage of AEDPA and IIRIRA, it was unclear whether these amendments applied retroactively to bar the possibility of Section 212(c) relief for aliens who committed deportable offenses under the pre-1996 statutory scheme. The Attorney General adopted the position that AEDPA, and to a small degree IIRIRA, eliminated the Attorney General's discretionary power to grant Section 212(c) waivers altogether, regardless of when the alien's criminal wrongdoing occurred. See In re Soriano, 21 I. & N. Dec. 516 (Op. Atty Gen. Feb. 21, 1997). In 2001, however, the Supreme Court held otherwise. At least for persons "whose convictions were obtained through plea agreements and who, notwithstanding those convictions, would have been eligible for § 212(c) relief at the time of their plea under the law then in effect, " Section 212(c) relief remains available. St. Cyr, 533 U.S. at 326.

Despite the promise of St. Cyr, aliens facing removal for certain criminal offenses continued to encounter obstacles when seeking discretionary relief. One reason for this was an odd quirk in the way the Board of Immigration Appeals evaluated applications for Section 212(c) relief. Although we have spoken thus far of Section 212(c) as a form of relief from deportation of an alien already in the country, by its terms, the provision only applied to aliens facing exclusion from entry. See Judulang, 132 S.Ct. at 479-82. This created some "peculiar asymmetr[ies], " since "[d]eportable aliens who had traveled abroad and returned could receive § 212(c) relief, while those who had never left could not." Id. at 480. The Board resolved this problem by adopting the policy that Section 212(c) gave the Attorney General the authority to grant discretionary relief to aliens facing exclusion and deportation alike. Id. at 480; see Matter of S—, 6 I. & N. Dec. 392, 394-96 (BIA 1954); Matter of Silva, 16 I. & N. Dec. 26 (BIA 1976). Not every alien facing deportation was automatically eligible for a waiver, however, since the list of grounds that rendered an alien excludable, see § 1182(a), was not perfectly congruent with the list of grounds that rendered an alien deportable, see § 1227(a). To determine whether Section 212(c) relief might be available in particular deportation proceedings, some form of comparison between the bases for deportation and exclusion was necessary.

The Board vacillated between two ways of making this comparison. One approach, perhaps the more intuitive, was to consider how the alien facing deportation would fare in an exclusion proceeding. Judulang, 132 S.Ct. at 481. If the specific offense that rendered the alien deportable fell within a statutory ground for exclusion, and no other bars would have applied in the exclusion context, that person could apply for a Section 212(c) waiver. Id. (citing Matter of Tanori, 15 I. & N. Dec. 566, 567-68 (1976)). The alternative approach, known as the "comparable-grounds" rule, undertook a comparison of the more general grounds for exclusion and removal. Only if the charged deportation ground consisted of a set of offenses "substantially equivalent" to the set of offenses comprising a particular exclusion ground could the alien be eligible for Section 212(c) relief. This result obtained even if the particular offense that made the alien deportable would also have made the alien excludable (and eligible for Section 212(c) relief in that context). The Board "definitively adopted" the "comparable-grounds" rule in 2005. Id.; In re Blake, 23 I. & N. Dec. 722 (BIA 2005).

To illustrate the difference between these two approaches, the Judulang Court posited a defendant convicted of first-degree sexual abuse of a child, a particularly fortuitous hypothetical for our purposes. Id. at 482. Like Zambrano, this man could face deportation on the ground that he committed an aggravated felony involving sexual abuse of a minor. 8 U.S.C. § 1101(a)(43)(A). The conviction would also make him excludable, but on a different basis: the offense would qualify, along with many others, as a "crime involving moral turpitude." 8 U.S.C. § 1182(a)(2)(A). Applying the first approach, the same person would be eligible for a Section 212(c) waiver in the deportation context, because someone convicted of the same sexual abuse crime would be eligible to seek such relief in the exclusion context. The comparable-grounds rule produces a different result because the "moral turpitude" exclusion ground "addresses a distinctly different and much broader category of offenses" than the "'aggravated felony' involving 'sexual abuse of a minor'" deportation ground. Judulang, 132 S.Ct. at 482 (quoting Blake, 23 I. & N. Dec. at 728). The divergence is fatal: using "comparable-grounds, " an alien like Zambrano would have been categorically barred from seeking discretionary relief when facing deportation, not because his aggravated felony was particularly grievous, but because of the coincidental breadth of the corresponding exclusion ground. In Judulang, the Court held that this approach, which hinges eligibility for relief "on the chance correspondence between statutory categories [rather than] the alien's fitness to reside in this country, " was arbitrary and capricious. Id. at 484.


In moving to withdraw his guilty plea, Zambrano argued that he met the criteria for a collateral attack on the underlying removal order that provided the predicate for his charge of unlawful reentry. See 8 U.S.C. ยง 1326(d). His alleged ability to set that order aside, he asserted, constituted a "fair and just reason[] for requesting the withdrawal" of his plea. Fed. R. Crim. P. 11(d)(2)(B). The district court was willing to accept that Zambrano had exhausted his administrative remedies, but it concluded that he could not show either that the deportation proceedings improperly deprived him of the ...

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