You may have thought Harry Benson had seen it all. His camera front-loaded the pillow-fighting Beatles into the 1960s, hitting the tarmac with them in New York, and closed the decade by capturing Robert F. Kennedy’s assassination, Ethel Kennedy’s hand taking up much of a frame, as if to stop the tragedy cold. The civil rights movement, the Ku Klux Klan, Truman Capote’s Black and White Ball, Muhammad Ali and other assignments from the magazines Look, Life and Time, along with seemingly every lethal crisis and celebrity hideaway in the world.
In the 1970s, Mr. Benson shot a hard-driving, show-offy young real estate heir named Donald J. Trump shadowboxing as if with his future on the roof of Mr. Trump’s Fifth Avenue tower. Some 20 years later, Mr. Benson posed Mr. Trump in the money cage of his casino, the Taj Mahal in Atlantic City, with a million dollars in cash in his arms. “He was trying to hold on to it,” Mr. Benson said. “It was against gaming commission rulings for him to even be there.”