As a litigation partner at Boies, Schiller & Flexner, Lee Wolosky is accustomed to pressure and to the spotlight. In his new post as the White House’s special envoy for Guantánamo closure, he’ll have both, in spades. Appointed June 30, Wolosky has just 14 months to find homes for detainees cleared for transfer. As of mid-October, there were 53 of them, although that number will rise as the administration speeds up review of previously uncleared detainees in an attempt to winnow down the population from its current 114 to a score or two.

It won’t be easy. The Pentagon has historically dragged its feet in signing off on approved transfers, and the administration is contending with election-year politics and a proposed defense appropriations bill that would further limit detainee transfers.