The Second Circuit (Leval, Lynch, Droney) issued a decision reversing a mandatory life sentence, finding  plain error because the district court failed to apply the categorical approach when considering whether the defendant’s prior conviction qualified for a sentencing enhancement.  The case, United States of America v. Jay Kroll, 16-4310-cr, is another example of the Second Circuit applying the categorical approach, this time to 18 U.S.C. § 3559(e) rather than to the Armed Career Criminal Act.  Section 3559(e) provides for mandatory life imprisonment when the defendant is a convicted of a child exploitation offense and has a prior sex conviction.

In 2015, Kroll, proceeding pro se, pled guilty to four counts of various sex offenses involving children.  Count One and Count Two were for sexual exploitation of a child in violation of 18 U.S.C. § 2251(a) and § 2251(e), each requiring the imposition of a mandatory life sentence when the defendant has a prior sex conviction under 18 U.S.C. § 3559(e).  Kroll has a 1993 New York state conviction under New York Penal Law § 130.45 which, in 1993, applied to “deviate sexual intercourse with another person less than fourteen years old.”  Before allowing Kroll to proceed pro se, the district judge asked Kroll if he knew that the court “‘must impose life imprisonment’ if Kroll were found guilty on either [c]ount” based upon this prior conviction, and Kroll responded in the affirmative.  Kroll was then sentenced to two concurrent life sentences on Counts One and Two, to twenty years on Count Three, and to ten years on Count Four. 

Kroll appealed his sentence on the ground that the district court erred in determining that his 1993 conviction was  a “prior sex condition” under 18 U.S.C. § 3559(e)(1) “because the New York statute under which he was convicted in 1993 punishes a broader range of conduct than the most comparable federal sex offense.”  Applying the categorical approach, which requires a court to compare the elements of the state offense to the elements of a comparable federal offense to determine if the offenses are compatible such that the state offense can be considered a prior conviction for sentencing purposes, the Second Circuit agreed.  The Court noted that in 1993, New York Penal Law § 130.45 prohibited conduct that the comparable federal statute, 18 U.S.C. § 2241(c), does not.  Despite the fact that Kroll’s actual conduct that led to his 1993 conviction would have violated either statute, the Court held that his 1993 conviction cannot be considered a “prior sex offense” for sentencing purposes because the statutes are not comparable when the categorical approach is applied.  

Because the district court plainly erred in considering Kroll’s 1993 a “prior sex conviction” and in determining that it was required to impose two mandatory life sentences—both when engaging in a colloquy with Kroll concerning his desire to proceed pro se, and when imposing sentence—the Court vacated the sentence and remanded for further proceedings.  The Court noted that the district court “retains full discretion to take account of all relevant factors, including the abhorrent circumstances underlying the four counts of conviction in this case, as well as those underlying the 1993 state-court conviction,” when determining the appropriate sentence.  The Court’s comments imply that the reversal was not based on a view that a life sentence or the functional equivalent (“decades in prison”) would necessarily be substantively unreasonable for this defendant, given his extremely dangerous and abhorrent conduct, only that the mandatory life sentence enhancement could not be applied and the district court has discretion to select the sentence.

In recent years, the Court has applied the categorical approach when reviewing criminal sentences, including in United States v. Rood, Mathis v. United States, and United States v. Barrett.  Its decision in Kroll is another such instance, and a clear indication that the Court will continue to apply that approach in the wake of the Supreme Court’s 2015 decision in Johnson v. United States, even where the conduct is of the most reprehensible kind and where the decision may not result in a significant reduction of the defendant’s sentence.