During World War II, he saw service in the Philippines at the Battle of Bataan and was taken prisoner by Japanese armed forces after the Battle of Corregidor. Initially sent to a prison camp on Luzon, he was later transferred to another prison camp on Mindanao where conditions were somewhat better. The new prison camp was actually a pre-war convict facility on a plantation. Eventually, he and two other POWs, one of whom was William Dyess, planned an escape. However, the need for additional expertise in their post-escape plans brought the total number of Americans in the group to ten, including Samuel Grashio and Austin Shofner. Then they enlisted the help of two Filipinos who had been imprisoned before the war as convicts to serve as guides. The escape was successful and the two Filipinos eventually received pardons for their assistance. The group moved through dangerous swamps for several days and eventually stumbled upon a guerrilla unit. This unit passed the Americans on to other bands until the escapees eventually were led to Colonel Wendell Fertig, who commanded the American-Filipino guerrillas on Mindanao. Hawkins served with the guerrillas for seven months. He led raiding parties in attacks against Japanese forces, before traveling to Australia via submarine in November 1943. Hawkins received the Distinguished Service Cross for his actions in the Philippines during the period 4 April - 15 November 1943. In 1961, Hawkins authored a book, Never Say Die, on his POW and guerrilla experiences. In 1945, Hawkins was involved in the planning of the U.S. invasion of Japanese-held territory in the Battle of Okinawa. Author Don Bohning states that Hawkins was not involved in planning for the Battle of Iwo Jima.
On the recommendation of Marine Corps Commandant General David M. Shoup, Colonel Hawkins was recruited by the CIA which wanted a Marine officer with background in amphibious warfare to help with a project to land some exile troops in Cuba. He was assigned to the Cuba task force on Sept 1, 1960, when CIA Deputy Director of Plans Richard M. Bissell Jr. began to expand the planned operation from a guerrilla infiltration to an amphibious assault. At the CIA, Hawkins was appointed Chief of Paramilitary Operations Western Hemisphere Division Branch 4, reporting to Jacob Esterline, Chief of Western Hemisphere Branch 4. He was already fluent in Spanish, and under his command were Grayston Lynch and William "Rip" Robertson as the CIA representatives in the amphibious landings.. From his base in Miami, he instructed the combatants via radio links relayed via US Navy ships, aiming to defeat Cuban government forces in the conflict. He retired from the Marines in 1965.
