In Padilla v. Kentucky, 130 S. Ct. 1473 (2010), the Supreme Court held that a lawyer provides ineffective assistance of counsel by failing to inform a client of the deportation risks that result from a guilty plea. However, the Court did not clearly indicate whether its holding must be applied retroactively to cases on collateral review, leaving the lower courts to sort out the mess. A handful of district courts have already split on this issue. Now, with the Seventh Circuit’s ruling last week in Chaidez v. United States (No. 10-3623), the circuits are also split. A divided panel in Chaidez rejected both retroactivity and the Third Circuit’s reasoning to the contrary in United States v. Orocio, 645 F.3d 630 (3d Cir. 2011).
As the Chaidez majority observed, the key legal issue is whether Padilla announced a new rule, or merely provided an application of the established principles of ineffective assistance from Strickland v. Washington, 466 U.S. 668 (1984). Under Teague v. Lane, 489 U.S. 288 (1989), a new rule may not be applied retroactively unless it falls into one of two exceptions that plainly do not encompass the Padilla holding.
Teague and least some of its progeny suggest what seems effectively a strong presumption in favor of a “new rule” finding (and hence against retroactivity). Here is how the Chaidez majority characterized the law:






After pleading guilty in federal court to various drug-trafficking offenses, Isaiah Gregory received an eye-popping sentence of 327 months in prison — more than 27 years behind bars. Driving this extraordinary sentence was the district court’s finding that Gregory was a “career offender” under the federal sentencing guidelines. It was the career offender guideline that raised Gregory’s guidelines range from either 120-135 months (as he calculated it) or 121-151 months (as the government calculated it) to 262-327 months. Thus, the career-offender finding likely added more than fourteen years to Gregory’s sentence.
Police found marijuana hidden in a car that Maurice Crowder and a colleague tried to ship from Arizona to Illinois. Crowder was then charged with, convicted of, and sentenced for two crimes: attempted possession with intent to distribute and conspiracy, both in violation of 21 U.S.C. § 846. Sounds like double-dipping, right? After all, both crimes of conviction arose from the same underlying criminal plot. Crowder appealed to the Seventh Circuit on this basis, arguing that he could not be punished for both crimes.
Under 21 U.S.C. § 841(b)(1)(A), certain drug offenders face a mandatory sentence of life imprisonment if they have two prior drug felony convictions. As befits such a draconian statute, special procedural protections have been adopted to ensure that the mandatory minimum does not take defendants by suprise at sentencing. Thus, 21 U.S.C. § 851(a)(1) requires that “before trial . . . the United States attorney [must] . . . serve[] a copy of [an] information on the [defendant] . . . stating in writing the previous convictions to be relied upon.” But the statute does not specify under what circumstances, if any, a failure to comply with the rule precludes imposition of the mandatory minimum.
If Congress makes an obvious error in drafting a statute, can a court correct that error by effectively adding something to the statute that is not there? Such was the interesting jurisprudential question the Seventh Circuit confronted last January in United States v. Head, 552 F.3d 640 (2009). Because of a mix-up with statutory cross-references, the statute that lists permissible conditions of supervised release in the federal system does not include assignment to a halfway house. However, the first seven circuits to consider the question held that sentencing judges could indeed order placement in a halfway house, reasoning that a literal interpretation of the statute would produce an absurdity. In Head, the Seventh Circuit bucked the trend and rejected the government’s absurdity argument. (My post on Head is
The Seventh Circuit continues to struggle with the question of what it means for the federal sentencing guidelines to be “advisory.” In United States v. Booker, 543 U.S. 220 (2005), the Supreme Court held that the then-mandatory guidelines system violated the Sixth Amendment. The Court corrected the constitutional problem by converting the guidelines from mandatory to advisory. Then, in Kimbrough v. United States, 128 S. Ct. 558 (2007), the Court confirmed what even the government had recognized and conceded: “advisory” means that a district court judge may impose a sentence outside the recommended guidelines range on the basis of a policy disagreement with the guidelines.
