A recidivist illegal re-enterer tends to get little sympathy from a sentencing court (to paraphrase Oscar Wilde, to come back once may be regarded as a misfortune; to come back twice “looks like carelessness”). But Milton Gonzalez explained that he returned to the United States to see his girlfriend and two young children when he thought he would lose his battle with cancer. At his sentencing following his guilty plea to one count of illegal re-entry after a drug felony conviction, his defense counsel sought a below-Guidelines sentence on two grounds – a mitigating narrative, and a structural challenge to the applicable guideline. First, defense counsel argued that Gonzalez deserved leniency because of his health problems and family circumstances. Second, defense counsel challenged the applicable guideline of 46 to 57 months, arguing that the 16-level enhancement based on the prior felony conviction lacked “a nexus to sound policy and empirical support.” Notably, while a structural challenge is rarely successful, it can trigger a greater departure based on other mitigating factors. Here, the district court departed downward to 36 months. The Eighth Circuit affirmed in United States . Gonzalez, issued on February 4, 2014 (published), noting that the district court was empowered but was not required to reject and vary categorically from the Guidelines based on a policy disagreement, and that the court articulated a reasoned basis for its sentence, which was not substantively unreasonable.