Winston Frederick Churchill Guest (May 20, 1906 – October 25, 1982) was an Anglo-American polo champion and a member of the Guest family of Britain.

Winston Frederick Churchill Guest was born on May 20, 1906, to Frederick Guest (1875–1937),^[1] a British politician, and Amy Phipps. His mother was the daughter of Henry Phipps, Jr., an American businessman and philanthropist. His paternal grandfather was Ivor Guest, 1st Baron Wimborne (1835–1914), a Welsh industrialist. His great-grandfather was John Spencer-Churchill, 7th Duke of Marlborough, making him a first cousin once removed of British Prime Minister Winston Churchill.^[2]

His brother, Raymond R. Guest (1907–1991), was the United States Ambassador to Ireland from 1965 to 1968,^[3] who married three times.^[4][5]

In 1918, during World War I, his mother turned over their London home, Alford House on Park Lane, to be used by the American Red Cross as a hospital for the American Navy.^[6] In 1919, his parents entered into a separation agreement and his mother received custody of him, thereafter living in the United States.^[7][8] He graduated from Yale University in 1927 and received a law degree from Columbia University in 1942.^[9]

After graduating from Columbia University Law School, he was appointed law secretary for Joseph C. Baldwin III, minority leader of the Board of Alderman.^[9] He, along with Alexander Hamilton, a descendant of Alexander Hamilton, the first Treasury Secretary, was paid $1 a year for his work.^[10]

In 1934, Guest married Helena Woolworth McCann, daughter of Charles E. F. McCann and Helena Maud Woolworth McCann (1878–1938). Her maternal grandfather was F. W. Woolworth, the American business magnate. She attended Miss Hewitt's School, Miss Chapin's School, and graduated from Miss Porter's School in Farmington, Connecticut.^[9][13] They subsequently divorced in 1944. With her, his two sons:

• Winston Alexander Guest (b. 1936),^[14] who married Helen Mane Elizabeth Shields in 1967.^[15]
• Frederick Edward Guest II (1938-2021), who married Stephanie Wanger (b. 1943), daughter of Walter Wanger and Joan Bennett, in 1963.^[16] They divorced and he married Carole Baldoff in 1988.^[17]

In 1947, Guest married Lucy Douglas Cochrane (1920-2003), later known as C. Z. Guest. With her, he had a son and a daughter:

• Alexander Michael Douglas Cochrane Guest (b. 1954), who married Elizabeth Geacintov, a daughter of Dr. Cyril Geacintov (a former president of Russian Nobility Association in America), in 1986.^[18]
• Cornelia Cochrane Churchill Guest (b. 1963), a debutante.^[19]

In 1947 Guest leased historic Gardiners Island from its 15th owner, Sarah Diodati Gardiner.^[20] Guest used it to host hunting parties, inviting high profile guests, like Ernest Hemingway and Dag Hammarskjöld. On January 24, 1947, Van Campen Heilner was staying in the mansion, when a fire swept through the island's 1774 Georgian mansion. Heilner survived by jumping out a window. The mansion was a complete loss.

Winston Guest died on October 25, 1982, at Nassau Hospital in Mineola, New York.^[21]

• Guest family
• Phipps family
• Bror von Blixen-Finecke