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1981 Trump talks on a car phone in a limo in New York City. “It looks like he’s running for President in there,” Benson said. “There’s a bit of control there ... People walking about but he’s in the limo.”Harry Benson
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1987 Trump and his first wife, Ivana, in their bedroom at Trump Tower in New York City. Benson chose the location—“it tells you a lot about the people”—and wanted them to dance. “She could dance,” he joked, “but he was a bit slow.”Harry Benson
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1987 Trump and his father Fred and mother Mary Ann and Ivana, at a dinner in New York City.Harry Benson
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1986 Trump celebrates after the completion of repairs to Wollman Rink in Central Park. He got the contract from the city, finishing early and well under budget.Harry Benson
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1996 Trump and his second wife, Marla Maples, at Trump International Hotel & Tower in New York City.Harry Benson
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1987 Trump reflected in a mirror during a portrait session.Harry Benson
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1987 Trump gesticulates during a helicopter ride to Atlantic City. Benson, who prides himself on spontaneity and closeness, said he likes “to get people moving.”Harry Benson
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1990 “Donald, I’ve never seen a million dollars in my life,” Benson told Trump at the Trump Taj Mahal in Atlantic City.Harry Benson
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1990 Trump and Michael Jackson, his guest, at the grand opening of the Trump Taj Mahal casino resort in Atlantic City.Harry Benson
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1987 Trump stands on top of Trump Tower on Fifth Avenue in New York City.Harry Benson
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2014 Trump and his wife, Melania, in their apartment at Trump Tower in New York City. “Donald was very proud of her,” Benson said.Harry Benson
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Republican presidential candidate Donald Trump with his children, from left: Donald John “Don” Trump Jr., Ivanka Trump and Eric Trump at Trump Tower in New York City on July 6, 2016.Harry Benson for TIME
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Eric Trump in his office at Trump Tower in New York City on July 6, 2016.Harry Benson for TIME
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Donald Trump Jr. in his office at Trump Tower in New York City on July 6, 2016.Harry Benson for TIME
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Ivanka Trump in her office at Trump Tower in New York City on July 6, 2016.Harry Benson for TIME
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2016 Trump and his wife, Melania, at the Mar-a-Lago Club in Palm Beach Florida.Harry Benson
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Donald Trump in a conference room, where he's storing his archive of press and memorabilia, on July 11, 2016.Harry Benson for TIME
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Republican presidential candidate Donald Trump with his grandson Theodore James in Trump’s office in New York City on July 11, 2016.Harry Benson for TIME
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Republican presidential candidate Donald Trump with his grandson Theodore James in Trump’s office in New York City on July 11, 2016.Harry Benson for TIME
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Republican presidential candidate Donald Trump in his office at Trump Tower in New York City on July 11, 2016.Harry Benson for TIME
The first time legendary photographer Harry Benson saw a million dollars, in cash, it was in Donald Trump’s arms. “It was always on the spur of the moment,” says Benson. It was 1990 and he was in Atlantic City for the grand opening of the now-shuttered Trump Taj Mahal casino resort.
“You know, I can go over there and get a million dollars,” Benson recalled Trump saying. Benson replied, “Donald, I’ve never seen a million dollars in my life.” Trump said, “You’ve got it.”
That’s how it’s always been between these two: the famed Scottish photographer who chronicled the Beatles on their inaugural trip to America in 1964 and has turned his lens to every U.S. president since Dwight Eisenhower, and the camera-ready real estate mogul who found his way into politics. Benson has photographed Trump over nearly 40 years, and his portfolio provides perhaps the clearest look at Trump’s rise and reality.

Ahead of the GOP convention in Cleveland, held from July 18 to 21, TIME revisited Benson’s archive. It shows the transformation from businessman during the stock market boomtimes to celebrity to, now, presumptive Republican presidential nominee.
After a recent shoot, Benson sat down with TIME to talk about his decades around Trump. “The man I met the other day there, that was him from the beginning,” Benson said. “And if you come up with an idea, he jumps on it right away … like going in and getting the money.”
That’s a key theme throughout Benson’s photography. There’s spontaneity and honesty. “I hate studio pictures because they’re not real,” he adds. “I want people to be what they think they are, not what I think they are.” He lets his subjects do what they want, and Trump always has: he’s chosen to show off his wives and his rides, his buildings and his gold.
Benson remembers photographing Trump with each of his wives. The first time he met and photographed Ivana, he wanted them in their bedroom and asked them to dance. And they did. “She could dance,” Benson recalls, “but he was a bit slow.” With Marla, Trump’s second wife, Benson photographed the two in robes at the Trump International Hotel & Tower in Manhattan. In 2014, Trump and Melania are at home on a gold table. Her legs are across him. “Donald was very proud of her,” he says.
Recalling these moments and more, Benson said, “I must say, Donald Trump, it’s always been fun.”
Harry Benson is an award-winning photographer known for chronicling the world’s most fascinating figures. This fall the documentary Harry Benson: Shoot First will be released by Magnolia Pictures. You can see more of his work here.
Paul Moakley, who edited this photo essay, is TIME’s Deputy Director of Photography and Visual Enterprise. Follow him on Instagram @paulmoakley.
Andrew Katz is TIME’s International Multimedia Editor. Follow him on Instagram @katzandrew.
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