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Collier’s magazine, January 26, 1901: A defiant Churchill stands apart from other prisoners of the Boers. “Before I had been an hour in captivity… I resolved to escape.”

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Well-known American politician and famed orator Bourke Cockran, c. 1900. “He inspired me when I was 19… he was my model,” said Churchill. Courtesy Granger.

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Bernard (“Bernie”) Mannes Baruch, c. 1920s. Financier, adviser to presidents, and one of America’s greatest stock-market speculators, he saved Churchill from financial ruin in the great stock market collapse of 1929. Courtesy Everett Collection/Alamy.

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London, July 1912: Brooklyn-born Jennie keeping an eye on her son. Courtesy Pictorial Press Ltd./Alamy.

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December 1900: Playbill for a lecture delivered at Gilmore’s Court Square Theatre, Springfield, Massachusetts: “his humor was worthy of Mark Twain,” wrote one reviewer.

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May 19, 1901: Churchill “who may some day be premier of England.” A Chicago Tribune prediction, realized thirty-nine years later.

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Planning for the peace, Versailles, France, January 1919. Right to left: Baruch, Prime Minster Lloyd George, French armaments minster Louis Loucheur, and Churchill (standing). Courtesy Baruch College Archives, Newman Library, New York.

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London, 1919: A British soldier (Churchill, age 44) from the trenches chats with an American general (Pershing, age 58). Both had seen military action in five wars. Courtesy Geopix/Alamy.

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MGM Studios, Hollywood, California, 1929: Churchill posing with Hearst (left) and Mayer (right), the moguls of two different media. Courtesy Everett Collection/Alamy.

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Hollywood, California, 1929: Churchill poses with Chaplin (in white) and to his right his son, Randolph, with his brother, Jack, slightly behind, and Jack’s son Johnny above the others, plus two unidentified men. Courtesy Popperfoto/Getty Images.

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Catalina Island, California, 1929: “People go for weeks & months without catching a swordfish…. I caught a monster in 20 minutes!” Courtesy Bettmann/Getty Images.

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Redwood State Park, California 1929: Churchill in the home of “a cathedral of trees,” wearing a ten-gallon Tom Mix cowboy hat. Courtesy PA Images/Alamy.

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Lenox Hill Hospital, New York City, December 1931: Churchill’s magnanimity in practice: “It was all my fault.” Courtesy Fremantle/Alamy.

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Collier’s magazine, December 17, 1932: Churchill, “the great star among Collier’s contributors of the thirties…”, urged his editors, “Always make me do it again if it is not right the first time. I am a journalist and a professional.”

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Hobcaw Barony, South Carolina, 1932: Baruch and his daughter, Belle, with Churchill and his eldest daughter, Diana, on a weekend “vacation.” The secretary who accompanied Churchill is not pictured. Courtesy The Belle W. Baruch Foundation, Hobcaw Barony.

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Life magazine, April 29, 1940. “The disillusioned cherub’s face on the cover is that of the driving brain behind the British fighting effort.”

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Punch magazine, November 1940. Roosevelt and Churchill as sailors dancing a jig. Cartoon by Bernard Partridge. Courtesy Punch Cartoon Library/TopFoto.

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London, 1940: Edward R. Murrow, who would soon broadcast news of the 56-day Nazi blitz on London, beginning with his famous catchphrase, “This… is London.” Courtesy CBS Photo Archive/Getty Images.

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Time magazine’s “Man of the Year,” January 6, 1941: “Blood, toil, tears and sweat—and untold courage.”

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A letter sent from Boston, January 2, 1942. Courtesy Churchill Archives Centre, The Papers of Sir John Martin.

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Little Hobcaw, Kingstree, South Carolina, 1960: Baruch wearing one gift from Churchill, a siren suit, while admiring another gift from him, a painting of Marrakech. Courtesy The Belle W. Baruch Foundation, Hobcaw Barony.

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New York City, April 1961: Churchill and Baruch, friends for half-century, through wars and peace, booms and busts, say goodbye. Courtesy New York World-Telegram and the Sun Newspaper Photograph Collection, Library of Congress, Washington, DC.

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Chicago Tribune, 1965: a cartoon by Joseph Lee Parrish.