President Eisenhower’s National Security Advisor Robert “Bobby” Cutler shaped US Cold War strategy in far more consequential ways than previously understood. A lifelong Republican, Cutler also served three Democratic presidents. The life of any party, he was a tight-lipped loyalist who worked behind the scenes to get things done. While Cutler’s contributions to the public sphere may not have received, until now, the consideration they deserve, the story of his private life has never before been told.