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Trump is offended by a painting of himself. For once, I get where he’s coming from | Dave Schilling

While his friends are getting messy in the group chat, Donald Trump simply has more important things on his mind. Namely, himself. The United States’ war plans are being divulged to journalists like gossip on a second-rate Real Housewives spinoff, but the focus of the American president is squarely on a painting of himself that he doesn’t care for. Trump posted on Truth Social, his personal squawk box for various grievances, that he takes umbrage with a depiction of his face in the Colorado state capitol.

The painting depicts Trump as full-faced, cherubic and without wrinkles. He almost looks younger, like a large baby in a suit. A boss baby, if you will. You might assume that at 78, Trump would jump at the chance to shave a few years off his face, but sadly, it seems he’d prefer to look like he was lit by the director of photography from Nosferatu.

If I had to put my art critic hat on, I’d say Trump almost looks regal in the Colorado painting. Squint, and he resembles Henry VIII after a shave. You’d think he’d be flattered by that association. After all, Henry VIII had twice the number of wives Trump has. So far.

But no, the ire of Trump came down fully on Sunday – and the painting was swiftly removed. “Nobody likes a bad picture or painting of themselves, but the one in Colorado, in the State Capitol, put up by the Governor, along with all other Presidents, was purposefully distorted to a level that even I, perhaps, have never seen before,” Trump said in his social media post.

The state of Colorado is an easy target for Trump. He lost it by 11 points in 2024. The governor, Jared Polis, is a Democrat. The painting was actually crowdfunded in large part by Republicans, but even then, for Trump, it was a perceived insult. And Trump is the kind of person to perceive insults around every corner.

“The artist also did President Obama, and he looks wonderful, but the one on me is truly the worst,” he continued. I’m sure that compliment for Obama was one he typed with stubby-fingered frustration. No one should be getting the royal treatment but him. In a sense, that’s the most relatable thing about the man.

Take a photo of me without my consent and chances are I will be horrified by the finished product – angles that make me look heavier, show off my ever-expanding bald spot or generally remind me of what I actually look like. The worst pictures are the ones that capture you in some gruesome motion – chewing your food, preparing to launch into a conversation or scratching some intimate area on your body. We’re used to our reversed image in a mirror, our own personal fantasyland where we can pick and choose how we see our flip-flopped face to ensure we leave the house with some semblance of self-esteem intact. Photos reveal what people – strangers and familiars alike – actually see when they look at us: the facial tics, the gestures, the lumps and bumps and frown lines.

Worse yet is a painting or drawing. That anyone submits to one of those exaggerated drawings from carnivals or the beach is beyond me. Why would you want a caricature of you drawn by someone you’ve never met, giving you a giant head and a pair of rollerblades or a large pencil? Maybe someone should get one of these for Trump and see if he prefers it to the Henry VIII boss baby painting. “Sir, we thought you’d like this drawing of you surfing while wearing a backwards baseball hat and carrying a puppy in one hand.”

There’s a caricature drawing of me on the wall of a bar in Los Angeles called Capri Club, if you ever find your way out here. My drawing sits among those of other regular patrons and luminaries of the neighborhood. It’s based off of a photo of me in front of said bar, having a martini. The moment captured is a lovely memory for me of a summer night well spent with friends and cocktails. The drawing, on the other hand, gives me deep anxiety. I look puffy, for starters. My substantial, jowly cheeks seem to grow every time I look at it, as though I have Dorian Gray-ed myself inside this bar. It’s very clearly me up there, but it’s not who I see myself to be. Granted, if I drew myself, I’d just be a wobbly stick with a circle for a head. So perhaps I shouldn’t be giving notes to artists.

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The very act of existing is to perceive and to be perceived, often without you even knowing it. I am pained when I think about how other people look at me. I know I’m not alone in that self-conscious whinging and navel-gazing. I wish I could blithely ignore the cacophony of doubt, but I can’t manage it, and countless people in the world feel the same way.

Perhaps that’s why I’m mildly shocked Trump is so concerned with how he looks in a painting in Colorado. This is a man who tells the world he never doubts himself, that he is resolute in his decision-making and is always in control. The first few months of his second term in office have been almost exclusively about proving how strong he is and that anyone who wrongs him will be punished.

So why be so worried about a painting? Perhaps it’s that the painting exposes him, casts him as soft, childlike and ill-prepared to wear the clothes of an adult. His preferred image of himself is a backlit Batman villain rather than the backwards-aging Benjamin Button in Colorado. In that case, maybe the painting did its job.

  • Dave Schilling is a Los Angeles-based writer and humorist

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