In 1992, at a ceremony to commemorate the 50th anniversary of the Office of Strategic Services (OSS) and dedicate a memorial to members who lost their lives during World War II, CIA director Robert M. Gates singled out one individual for special comment: Roderick Stephen Goodspeed Hall. Hall’s proposal to “drop a man by parachute” behind enemy lines in northeastern Italy with the plan to obstruct the Brenner Pass and thereby hasten the war’s end, and his eventual death in a Nazi prison camp, have been the subject of a biography by combat historian Patrick K. O’Donnell, who calls the episode “the most daring spy mission” of the war. Donna Hennessee Bryan, whose mother-in-law was Hall’s non-genetically-related first cousin and also his first sweetheart, reveals how family dynamics helped motivate Hall to dream up and try to execute such a daring plan.