Kevin Sharp, a retired federal judge who presided in the Middle District of Tennessee, spends a lot of time thinking about the mandatory minimum sentencing laws that forced him to mete out punishments he felt were too harsh. And Sharp’s mind often goes right to Chris Young, who he sentenced in 2014 to life in prison.

Young was twice convicted, at ages 18 and 19, in state court on drug charges, the second time for possessing an amount of cocaine weighing about as much as a quarter, Sharp said in an interview.