At the dawn of World War II, Bulkeley was a lieutenant in command of Motor Torpedo Boat Squadron Three, a Philippine-based detachment of six motor torpedo boats. He hit his stride as a daring, resourceful and courageous leader. On 11 March 1942, he picked up General Douglas MacArthur, his family, and his immediate staff, who had been ordered to flee the Philippines, and took them aboard PT 41 and other motor torpedo boats through over of open ocean. On arriving at Mindanao, MacArthur said, "You have taken me out of the jaws of death. I shall never forget it." Bulkeley earned many of his array of decorations while in command of that squadron and a subsequent one. He was evacuated to Australia by a B-17 in the final days of the campaign.