Jimmy Donahue was the second son of James Paul Donahue (1887–1931), the scion of an
Irish American family which had made a fortune in the
fat rendering business (Retail Butchers' Fat Rendering Company), by his wife Jessie ( Woolworth) Donahue (1886–1971), one of the three daughters of
Frank Winfield "F. W." Woolworth, founder of the
Woolworth retail chain. His older brother was Woolworth Donahue (1913–1972) who brought a cheetah to Cannes following a safari. Donahue was a nephew of Edna Woolworth (1883–1917), a wealthy socialite and a nephew by marriage of
Franklyn Laws Hutton (1877–1940), a co-founder of the brokerage firm
E. F. Hutton & Co. He was also the
first cousin and confidant of the American
socialite Barbara Hutton (1912–1979). Donahue was a high school dropout. He initially attended the
Hun School in
Princeton, New Jersey, and after his parents were advised to remove him from there, he was shifted to the
Choate School in
Connecticut. However, he was expelled from that school at age 17. Following his expulsion from Choate he took tap dance lessons with the tap dance master
Bill "Bojangles" Robinson. Despite his mother's opposition, he made a brief debut as a dancer in a Broadway musical production that closed ten days after its opening in September 1933. He fought reporting to New York but the
draft board denied his request. Thereafter, he returned to New York where he was sworn into the
U.S. Army ==Career==