How the Photo on Barack Obama's New Memoir Almost Didn't Happen: A Wife's Special Request Went Awry

When the former president chose a 2016 portrait for his upcoming A Promised Land, it was a happy — and ironic — ending to the story of how that picture came to be

Dan Winters (right) photographing President Barack Obama at the White House for New York magazine on Aug. 25, 2016. Photo: Courtesy Dan Winters

It took the famously contemplative and cerebral Barack Obama almost four years (and 768 pages) to produce just volume one of his post-presidential memoir, the upcoming A Promised Land.

But when it came to producing the photograph for the back of the book jacket — revealed exclusively here — Obama's well-known impatience in front of a camera made for a precision-timed mad dash for photographer Dan Winters.

Shooting at the White House on Aug. 25, 2016, for New York magazine, Winters was given five minutes of President Obama's time ("I think I stretched it to 10," admits the photographer whose portfolio includes everyone from George W. Bush to Nicole Kidman) in order to take several pages' worth of images for a cover story on Obama's eight years in office.

In an interview with PEOPLE, Winters recalls how he spent at least five hours carefully pre-setting each shot before the president arrived in the Blue Room: "Each of the setups was lit and dialed in. Each setup had its own camera and tripod, so I could just jump from setup to setup to setup to setup and work really quickly, 45 seconds on one setup."

Once it was go time, "I had someone behind me the whole time, calling out the time and it was lightning fast," Winters says. "It was an ambitious shoot and I was not wasting time. I was like, boom, boom, boom, eyes here, chin down, turn left, blah, blah. Good. Move. Okay, sit here. Cross your arms. Boom, boom, boom. Move."

"The magazine's photo director actually called my wife while the shoot was going on and said, 'Your husband is bossing around the president of the United States!' And I can do it fast."

Until, that is, Winters got to the final shot — where the president was instructed to gaze out the Blue Room window.

President Barack Obama photographed at the White House on Aug. 25, 2016, for New York magazine. Dan Winters. President Barack Obama, photographed at the White House on August 25, 2016 for New York Magazine

There, Winters discovered in a panic the one thing he had not prepared for: that his wife Kathryn had separately called his first assistant and asked him to take some souvenir shots of Winters at work with Obama.

"So the camera that I had left at that position to get that photograph of him at the window — the aperture was set, shutter speed was set, exposure," Winters says. "Everything was ready for me to pick the camera up, hold it to my eye and get the shot."

Except that the assistant had changed all the camera settings when he dashed off the shots that Winters' wife wanted and "casually put the camera back without restoring my settings."

With Obama at the window, Winters took his final frame, checked the camera's monitor and found the image over-exposed — almost completely white — from the light through the window.

"While I was lamenting the predicament and trying to guess the exposure, the president was like, 'I don't hear any clicking, Dan. I don't hear any clicking.' He said it twice. And I'm like, 'I'm on it. Hang on a second.' And everybody was on me, his handlers were giving me the stinkeye," the Austin, Texas-based Winters recalls. "But I think I nailed that shot on my second frame."

A Promised Land
Pari Dukovic/Penguin Random House

Riding to the airport afterward, Winters was suddenly nervous that the shot had been a bad idea. "I love the picture so much, but I didn't know if people would recognize who it was," he says.

So he tried it out at the airport ticket counter, on the woman checking him in for his flight. "I said to the ticket-counter lady, I go, 'I'm going to show you a picture. Tell me who it is. Ready, set, go.' And I held my phone in front of her then took it away really quickly. And she goes, 'Obama.' And I'm like, 'Okay. Cool. It worked.'"

So well, in fact, that five years later, Obama himself selected the photo to be a prominent part of the historical record that A Promised Land will become when it is released on Nov. 17. Winters' portrait, which was printed in black and white for the Oct. 3, 2016, issue of New York, appears in full color for the first time on Obama's memoir.

"A lot of this stuff is just kind of for consumption and it goes away, except for being part of our own archives and legacy. To have an image live in this place of honor on a historical document for all time is a personal and professional achievement that I never could have dreamed of," Winters says. "That book is going to sell many, many millions of copies. And I think it's kind of a cool thing."

He also sees a symmetry between the "very reflective" vibe of the photograph and what he expects to find on the pages of the former president's memoir.

Plus, says Winters, having Obama resurrect the photograph all these years later is "100 percent a happy ending to that harrowing photo shoot."

A Promised Land will be published on Nov. 17.

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