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The Image That Will Live in Infamy

September 3, 2023 By David Hume Kennerly

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Former President Donald Trump’s police booking mugshot, to steal a quote from FDR, is an image that “will live in infamy.” It will end up being the most published photo ever taken. Unfortunately for him it will also be how he will be remembered for eternity. His short-term political gain will be a long-term disaster. A picture I took of him in 2016 is eerily similar (above right). He has unequivocally defined for the ages exactly who he is, and it’s not a pretty sight. Historian Mark Updegrove told me that he wished the photo hadn’t been taken, that it only feeds the Trump frenzy. Hard to disagree.

Photographs are powerful. They tell the story for good or bad. In the instance of Joe Rosenthal’s epic and unforgettable moment of U.S. Marines raising the flag over Iwo Jima in 1945, it was about patriotism and a heroic act. Eddie Adams’ shocking 1968 Saigon execution photo at the instant the South Vietnamese general placed his pistol to the head of a Viet Cong suspect and pulled the trigger was the exact opposite. It showed the brutality and reality of war. Rosenthal’s photo was used to help raise much needed money to support the final days of winning WWII. Adams’ picture was a significant factor in Americans turning against the Vietnam War. Both won Pulitzer Prizes. Both will be remembered and taken to heart as long as there are people to see them.

Eddie Adams, Saigon Execution, 1968 (AP)
Eddie Adams, Saigon Execution, 1968 (AP)
Joe Rosenthal, Marines raise flag on Iwo Jima, 1945 (AP)
Joe Rosenthal, Marines raise flag on Iwo Jima, 1945 (AP)

The harshly-lit vision of a former president mugging for the camera in jail will also be remembered forever. The snap is a propaganda poster advertising a bad Trump play. In this version he portrays the tough and intransigent tyrant who glares menacingly into the camera. He knows exactly how he will come off, after all he prepared for the moment. Trump also understands that his MAGA adherents will love and be riled up about the image. This one was for them and will be another fundraising bonanza. The guy, after all, is an actor and can drop an expression at a moment’s notice. Trump’s life could be a Twilight Zone episode where the central character morphs into the outlaw that he’s been playing on tv. Trump’s most famous acting line is, “You’re fired,” something he said on every show during the fourteen seasons he was on The Apprentice. That phrase made a career and a presidency. Trump’s mugshot pairs nicely with that look but reveals nothing about what is inside of his head.

Donald Trump on The Apprentice (NBC)
Donald Trump on The Apprentice (NBC)
Logo for The Apprentice (NBC)
Logo for The Apprentice (NBC)

On November 21, 2016, thirteen days after he was elected, I had a portrait session with the president-elect in his office at Trump Tower for the cover of CNN’s election book, “Unprecedented.” My photo would be used on the front of a special Inaugural imprint. Trump’s staff had asked for picture approval of my photos, but CNN and I said no. They gave us the greenlight anyway.

When Trump sat in the chair we got right down to it. In the first two frames he was smiling, but it didn’t seem natural. It felt too contrived and not genuine.

Trump smiles for the camera
Trump smiles for the camera

Figuring that I needed something more serious and honest, I asked him to give me his “You’re fired” look from The Apprentice. He immediately converted his face into an intimidating scowl. That one came naturally. That moment would reemerge when he sat for another portrait session, the one with the Fulton County Sheriff’s camera.

The “You’re fired” look
The “You’re fired” look

I thought his signature look was a tad too tough.  I asked him to try something in between. Trump relaxed a bit and produced a wry face. That worked. He asked me if he could see what I was doing. I showed him the last frame in the back of the camera. He said, “I look better here than I do in real life!” I thought OMG, a sense of humor.  The inbetweener became the cover, and anyone who watches CNN would have seen the portrait a thousand times. It became their branded Trump image. The scowling photo that I took wasn’t used but was a precursor to his big act at the Georgia jail.

CNN’s “Unprecedented” 2016 Inauguration edition
CNN’s “Unprecedented” 2016 Inauguration edition

When the Inaugural edition came out Trump tweeted, "@CNN just released a book called 'Unprecedented' which explores the 2016 race & victory. Hope it does well but used worst cover photo of me!"

In 1863, Scottish immigrant Alexander Gardner took a portrait of another president, Abraham Lincoln. He’s looking into the camera, quietly strong, confident, and relaxed. It’s photo that defines him for history. It is how the world will always imagine him. It’s how he was by all accounts.

Abraham Lincoln by Alexander Garner, 1863
Abraham Lincoln by Alexander Garner, 1863

A hundred and sixty years later down in Georgia, inside the grimy Fulton County Jail, a man who had once been President of the United States poses for the sheriff. Most people would find this situation embarrassing and humiliating. Not Trump. He produced a premeditated expression that seems at once angry, paranoid, and criminal. It was an acting tour de force and will be the visual legacy of Donald J. Trump. It is how he will be forever known.

The former president glowers for his booking photo. Rather than a painful moment as it would be for most normal people, he turned it into a fundraising opportunity. The grift goes on.
The former president glowers for his booking photo. Rather than a painful moment as it would be for most normal people, he turned it into a fundraising opportunity. The grift goes on.

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