James Carlyle “Jimmy” Dempsey, Jr.

Image Source: East Carolina Yearbooks, Tecoan, 1941. UA50-01. University Archives, East Carolina University, Greenville, NC.

James Carlyle Dempsey, Jr., was born in Wilson, N.C., on April 24, 1921, to Lt. Col. James C. Dempsey (1896-1970) and his wife Ada Bissette Dempsey (1894-1981). He studied at UNC, but it was at ECTC that he shined: in addition to starring in men’s basketball, he began flight instruction in early 1941 with the Civilian Pilot Training program coordinated through ECTC. In September, he enlisted in the Army Air Corps and soon completed further training at Fort Bragg and various Army flight instruction centers in the Southeast. In April of 1942, he received his commission as a second lieutenant and was assigned to the American Bomber Command in London.

In early 1943, Dempsey, 21, was given duty as personal pilot to the Allied leaders of the Mediterranean theatre – General Dwight D. Eisenhower (1890-1969), commander-in-chief of the Allied Forces in the Mediterranean, and General Andrew Spaatz (1891-1974), commander of the Air Forces in the Mediterranean. In that capacity, Dempsey met British prime minister Winston Churchill (1874-1965) and the British foreign secretary, Anthony Eden (1897-1977). Dempsey also met and piloted the troupe of actresses led by Kay Francis (1905-1968) on their tour of the African theatre.

Earlier, Dempsey had distinguished himself by safely returning his Flying Fortress and its crew from Nazi-occupied France to Africa after the B-17’s tail section broke away following a mid-air collision with another Allied aircraft. For his exceptional bravery as a pilot, he was awarded a Distinguished Flying Cross.

Dempsey successfully piloted 50 bombing missions in Europe and North Africa including 15 sorties over the Mediterranean island of Pantelleria in preparation for the Allied invasion of Fascist Italy. In July 1943, he also participated in the Allied bombing of Rome. For his exceptional service, Dempsey was awarded the Air Medal and eleven Oak Leaf Clusters. His 50 missions also earned him a leave of absence during which Dempsey returned to North Carolina to visit family and friends. In August of 1943, while in the state, Dempsey, gave a talk about his wartime experiences at UNC.

That fall, Dempsey was transferred to the air inspector’s office at the headquarters of the Second Bomber command in Washington state, training combat crews for heavy bombardment duty overseas. In 1944, he was promoted to major and named air inspector with the Second Air Command headquartered in Colorado.

After the war, Dempsey took a position as co-pilot with Pan American Airlines. In 1946, he went into business as the owner/manager of laundry facilities, including a dry-cleaning plant in Orlando, Florida, which eventually expanded to a chain of 17 coin-operated laundries in Florida. In 1948, Dempsey returned briefly to the air after signing a contract to fly commercial planes for a year with the Civil Air Transport Company of China, owned by Gen. Claire Chennault, former leader of the Flying Tiger fighter pilots who defended Nationalist China during WWII. A successful businessman, Dempsey also developed properties in Orlando, Melbourne Beach, and Cape Canaveral, Florida, as well as real estate interests in Wilson, Nash, and Edgecombe counties. Dempsey passed away on 30 Jun 1992 in his hometown, Wilson.

As a young B-17 Flying Fortress pilot in WWII and then later as a businessman, Dempsey proved himself to be one of East Carolina’s most successful and public-minded alumni, well exemplifying the school’s motto of service.

Sources:

• “22-Year-Old Wilson Boy Is Made Major.” News and Observer. February 15, 1944. P. 3.
• “Actress Takes Message From Dempsey To Wife.” News and Observer. March 16, 1943. P. 3.
• “Captain Jimmy Dempsey Stationed On West Coast.” Teco Echo. November 12, 1943. P. 4. https://digital.lib.ecu.edu/37928
• “Dempsey Has Post With Pan-American.” Rocky Mount Telegram. May 18, 1945. P. 4.
• Evans, Clifton. Untitled article on Civilian Pilot Training Course at ECTC. Teco Echo. March 28, 1941. P. 1. https://digital.lib.ecu.edu/37888
• Evans, Clifton. Untitled article on Civilian Pilot Training Course at ECTC. Teco Echo. April 25, 1941. P. 1. https://digital.lib.ecu.edu/37890
• Grey, Bill and Ned Handy. Grey Ghost: The Story of a Professional Soldier’s 3,000 Mile Epic Journey of Escape and Evasion in WWII Occupied Europe. Dog Ear Publishing, 2018. Pp. 22, 24.
• “James C. Dempsey, Jr.” News and Observer. July 1, 1992. P. 8.
• “James C. Dempsey, Jr. Manager Of New And Novel Cleaning Village Located Here On W. Thomas St.” Rocky Mount Telegram. April 4, 1961. P. 9.
• “Laundryman to Fly Again.” News and Observer. July 7, 1948. P. 6.
• “Lt. Vernon Tyson Home From War Front, Alumni in Various Branches of Service.” Teco Echo. August 23, 1944. Pp. 1, 4. https://digital.lib.ecu.edu/37925
• Orth, Bill. “Captain James Dempsey Leaves War Skies Over Rome and Sicily To Visit Carolina: Alumnus Gets DFC For Heroic Action.” Daily Tar Heel. August 4, 1943. P. 1.
• Taylor, Harold. “They’re In The Army Now, Also The Navy And Air Force.” Teco Echo. January 29, 1943. P. 1, 4.
• Thomas, John G. “Wilson Flier Comes Home After Helping Bomb Rome.” News and Observer. August 3, 1943. P. 10.
• “Wilson Man Is One Of Army’s Youngest Majors.” Durham Sun. February 15, 1944. P. 3.
• Wolk, Herman S. “Pantelleria, 1943.” Air Force Magazine. June 1, 2002. https://www.airforcemag.com/article/0602pantelleria/
• “Young Wilson Boy Pilots Eisenhower Over Africa: Lt. James C. Dempsey, Jr., Is Chose as Personal Pilot for General.” News and Observer. March 4, 1943. P. 3.
• “Young Wilson Pilot Flies In Air Raids: Lt. Dempsey Brought Heavily Damaged Plane Back to England from France.” News and Observer. November 12, 1942. P. 3.

Related Materials

James Carlyle “Jimmy” Dempsey, Jr. Image Source: East Carolina Yearbooks, Tecoan, 1943. UA50-01. University Archives, East Carolina University, Greenville, NC.

James Carlyle “Jimmy” Dempsey, Jr. (right) with unidentified male. Image Source: Evening Tribune (Cocoa, Florida). July 22, 1960. P. 5

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