Adorable Story #76: Jimmy Donahue

The Prince of High Society

American socialites James Paul Donahue, III (1915 - 1966) and C.Z. Guest (Mrs Winston F.C. Guest, 1920 - 2003) at a party given by the Duke and Duchess of Windsor at the Waldorf Astoria on Park Avenue, New York City, 1953 — Photo © by Slim Aarons / Getty Images

Jimmy Donahue was a heir of the Woolworth fortune and a prominent New York socialite in the 30s and 40s. Exceptionally handsome, Jimmy was openly homosexual, spoke several languages, could fly a plane, and became first the closest man to his cousin Barbara Hutton and later part of a bizarre love triangle with the Duke and Duchess of Windsor.

Table of Contents: Early Years and Education / Chorus Boy / Relationship with Barbara Hutton / “Viva Ethiopia!” Incident / World War II / Homosexuality / Philanthropy / A Royal Connection: the Duke and Duchess of Windsor / Later years and Passing

---

If you aren’t subscribed yet, hit the subscribe button below to receive the Adorable Stories every weekend, directly in your inbox:

---

Early years and Education

James Paul (“Jimmy”) Donahue Jr. was born on June 11th, 1915 in Greenwich, Connecticut.

Jimmy was the second son of James Paul Donahue Sr. and Jessie Woolworth Donahue (the first son was his brother Woolworth “Wooly” Donahue): his father was a successful businessman and financier who by marrying into the Woolworth family, gained access to one of the largest retail fortunes of the time.

Jessie Woolworth Donahue, Jimmy’s mother, was a socialite and the daughter of Frank W. Woolworth, the founder of the Woolworth retail empire.

Her marriage to James Paul Donahue Sr. solidified the union of two powerful New York families.

The couple lived in a luxurious mansion on Fifth Avenue in New York City and also maintained Winfield Hall, a sprawling estate in Glen Cove on Long Island.

Winfield Hall, Glen Cove, Long Island

Their lifestyle was one of opulence and high society engagements, which deeply influenced Jimmy’s upbringing: Jessie was known for her philanthropy and lavish parties, traits that Jimmy would also inherit.

Jimmy was a child of exceptional beauty and spent his early years in New York City, basking in the splendor of the family’s opulent lifestyle. He initially attended the Hun School in Princeton, New Jersey. However, after his parents were advised to remove him from the school for disciplinary reasons, he was shifted to the prestigious Choate School in Connecticut.

At Choate, Jimmy refused to abide to any restrictions whatsoever: among his many transgressions there was an unauthorized escape from his dorm to go to New York City on a whim, in order to take dance lessons from the sensational black dancer Mr. Bojangles.

After this incident, his time at Choate was short-lived, as he was expelled at the age of 17 and did not finish high school.

Chorus Boy

In his youth Jimmy had ambitions to be an actor, and appeared as a chorus boy in the 1933 Broadway “Hot and Bothered.”

The show closed after 10 days and following that experience Jimmy confined his theatrical efforts to financing and assisting in producing a few occasional shows.

The press started noticing him though, as he was frequently photographed escorting some of the most attractive showgirls around New York. In those early years, theatrical personalities — whom he called “all the beautiful people” — were among his closest friends.