Fitzgerald worked for six years at a New York law firm. At the outbreak of World War II Fitzgerald was "a 31-year-old attorney with a wife and a child" yet he enlisted as a private in the Army. He soon transferred to
Officer Candidate School and was commissioned as an officer. His assignment was as liaison to the
Republic of China Army operating in the China-Burma-India theater, where he was promoted to the rank of major and awarded the
Bronze Star. After the war, Fitzgerald returned to New York City, where he worked at a Wall Street law firm. He enjoyed connections with the city's elite social circles.
CIA Fitzgerald was recruited to the CIA's
Office of Policy Coordination by
Frank Wisner in 1950. In January 1961, Fitzgerald approved
James William Lair's proposal for arming
Hmong guerrillas to fight in the
Laotian Civil War. In February 1964, Fitzgerald became chief of Western Hemisphere (WH) Division responsible for clandestine operations in Central America, South America, Caribbean and Cuba. In 1964 Fitzgerald came into conflict with Secretary of Defense
Robert McNamara over McNamara's
demand for quantified information from Vietnam. In June 1965, Fitzgerald was selected as
Deputy Director of Plans, responsible for worldwide collection of foreign intelligence. Fitzgerald supervised the increase in personnel assigned to
South Vietnam to support military operations. In one instance he asked Edgar Applewhite to attack
Ramparts magazine as part of the CIA's Cold War strategy. Applewhite claimed he used "dirty tricks" and blackmail to harm the magazine's business. Later, Fitzgerald worked on the CIA's accurate prediction of the outbreak of the
Six-Day War in the Middle East between Egypt and Israel. He was regarded highly by many, including
Allen Dulles, who became director of the agency. Dulles described Fitzgerald as "an officer of imagination and sense of daring, backed by his credentials as a fellow Wall Street lawyer and his impeccable social connections, coupled with his ability to get things done."
John Kenneth Galbraith, an economist and diplomat who was influential in the Kennedy administration, also admired him, although also describing Fitzgerald as reckless. == Personal life ==