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Hayward was born in Nebraska City, Nebraska, the grandson of Monroe Leland Hayward, a senator from Nebraska. His father, Colonel William Hayward, was a celebrated hero of the First World War who commanded the 369th Infantry Regiment, the "Harlem Hellfighters". Hayward's father and mother, Sarah Coe Ireland, divorced when he was nine. Hayward's father subsequently remarried, to Maisie Manwaring Plant, one of the wealthiest women in America at the time, who later traded her Fifth Avenue mansion to Cartier for a perfectly matched strand of pearls.
Hayward's forays into television were similarly notable. He produced The Ford 50th Anniversary Show on June 15, 1953, a live two-hour simulcast on CBS and NBC that looked back on the history of the United States and the world up to 1953. The program featuring a memorable extended duet by Ethel Merman and Mary Martin. In 1953, Hayward conceived Producers' Showcase (1954-1956), a series of 90-minute color spectaculars to be broadcast monthly on NBC. Illness forced Hayward to withdraw from the project shortly before the first broadcast, and production was assumed by his attorneys, Saul and Henry Jaffe. Hayward later produced That Was The Week That Was, a groundbreaking American adaptation of a British television show, from 1963-1965.
Hayward's interest in aviation led to his co-founding, in 1941,Southwest Airways, with financial help from his Hollywood friends.
Margaret Sullavan and Leland Hayward among the patrons of the Stork Club in New York City (November 1944)
Hayward was married five times.
In 1921, aged 19, Hayward married the debutante Lola Gibbs.
They divorced one year later, remarried and divorced again in 1934. They had no children.
On 15 November 1936, Hayward married the stage and screen actress Margaret Sullavan, who was pregnant with his child. He thus became the third of Sullavan's four husbands. Her previous husbands had been Henry Fonda and William Wyler, and after being divorced from Hayward in 1948, she would go on to marry British investment banker Kenneth Wagg. Hayward and Sullavan had three children, two of whom committed suicide. Margaret Sullavan herself died of an overdose of Barbiturates in 1960. Their children were:
Brooke, born 5 July 1937. She married twice, firstly to writer Michael Thomas and secondly to actor Dennis Hopper (1961-69). Her 1977 memoir, Haywire, recounts in detail the family's dysfunctional life. Her children were:
Bridget (1939-1960), who committed suicide by Barbiturate overdose in October 1960, aged 21, less than a year after her mother's death from exactly the same cause, and only a few months after her father's fourth marriage.
William, born 1941, who committed suicide on 20 March 2008, by shooting himself in the heart. By his marriage to Rita Marie Rosate, he had two children:
Leland William Hayward
Bridget Pamela Hayward
In 1950, Hayward married Slim Hawks. He had met her in Havana at a time when she was legally married to film director Howard Hawks but was staying with writer Ernest Hemingway and his latest wife Mary. Among her other previous relationships had been one with Clark Gable. Hayward and Slim divorced their respective spouses by 1949 and were married the following year; they had already been living together for some time. The marriage became strained after Slim had a one-night stand with Frank Sinatra and a longer affair with Peter Viertel. They were divorced in 1960.
In 1960, Hayward married for the fifth and last time. The bride was Pamela Churchill, former wife of Randolph Churchill. At the time when Hayward was introduced to her in 1958, Pamela was the mistress of Elie de Rothschild. On 4 May 1960, only hours after his divorce from Hawks was final, Hayward married Pamela Churchill in Carson City, Nevada. They remained nominally married until Hayward's death in 1971, but on the very day of his funeral, Pamela renewed her relationship with a former lover, W. Averell Harriman, and married him later the same year.
In her 1977 memoir, Haywire, Hayward's daughter Brooke recounts in detail the family's thoroughly dysfunctional dynamics. Hayward's great-grandchildren include William Leland Hayward V, Amelia James Hayward, Anna and Cooper Thomas, Violet Hayward Goldstone, Jack Munn, Cooper Hayward, and Ryan Hayward.