United States v. Boliero, 923 F. Supp. 2d 319

Bolieiro, a Brazil-born permanent resident, was deported in 1999 following a 1992 removal order predicated on a drug conviction.
Her 1991 cocaine-sale conviction was later vacated in 2011 as constitutionally infirm, affecting related deportability.
From 1995–1999 she served as a confidential informant for immigration authorities.
She learned of the 1992 deportation order only around 1999, when detained for removal, and promptly sought to reopen.
Her 1999 motion to reopen was denied for noncompliance with filing requirements; she later pursued VAWA relief and a BIA appeal.
She was indicted in 2011 for illegal reentry after the vacatur of the underlying conviction, which this court now considers invalid.

Issue	Plaintiff's Argument	Defendant's Argument	Held
Whether 8 U.S.C. § 1326(d) exhaustion is satisfied.	Bolieiro argues due process excused exhaustion due to notice/counsel failures.	GOV asserts exhaustion required appeal to BIA absent exceptions.	Exhaustion excused due to due process violations; motion granted.
Whether deprivation of judicial review occurred.	Due process violations prevented merits review of deportation order.	GOV contends no merits review due to lack of exhaustion.	Judicial review deprived; merits review not reached.
Whether entry of the deportation order was fundamentally unfair (prejudice).	Ineffective counsel and notice failures prejudiced outcome; relief likely merited.	No prejudice shown; normal procedures followed.	Fundamental unfairness shown; a reasonable likelihood of merit relief under §212(c).
Whether the deportation order based on a vacated conviction invalidates the criminal prosecution for illegal reentry.	Vacatur ab initio undermines the element of deportability.	Prosecution remains valid notwithstanding vacatur.	Order invalid; dismissal granted under due process and §1326(d).
Whether dismissal is required by due process considerations given Padilla-based vacatur.	Padilla-led vacatur undermines legitimacy of enforcement.	Enforcement choice belongs to prosecutorial discretion.	Dismissal warranted; proceeding constitutes ongoing consequence of vacated conviction.

Mendoza-Lopez v. United States, 481 U.S. 828 (U.S. 1987) (deportation order as element; need for judicial review when administrative review defective)
Luna v. United States, 436 F.3d 312 (1st Cir. 2006) (exhaustion exceptions when due process violated; prejudice analysis)
United States v. Perez, 330 F.3d 97 (2d Cir. 2003) (motion to reopen can satisfy exhaustion for due process claims)
Copeland v. United States, 376 F.3d 61 (2d Cir. 2004) (due process right to seek 212(c) relief; prejudice analysis)
Penar-Muriel v. Gonzales, 489 F.3d 438 (1st Cir. 2007) (vacatur/appeal; due process distinctions in reopening/removal)
Padilla v. Kentucky, 559 U.S. 356 (2010) (counsel must inform client of deportation risks of plea)
De Leon v. Ashcroft, 444 F.3d 41 (1st Cir. 2006) (exhaustion and administrative remedies within INA proceedings)
Cerna v. United States, 603 F.3d 32 (2d Cir. 2010) (motion to reopen; due process implications; waiver considerations)