Sarah Boardman, President D.J. Trump, oil on canvas (Courtesy of the artist)

Trump is the master of the image. I know—I’m not the only one to point it out. LA Review of Books’ Gideon Jacobs did it before, whose perfectly titled essay “Trump l’Oeil” grabbed me, up until he used the word “ontology” in an essay about Donald Trump. But at this point, isn’t it a cliché to even proclaim Trump the master of the image? I mean, obviously. This is the man who took a mugshot so memorable—his menacing, defiant, Never-Surrender-While-Surrendering Kubrick stare and the characteristically cartoonish clash between his shock of bronzer-stained skin and gold hair, that not only is it hanging in the hallway outside of the Oval Office like some delinquency trophy, but I stare at it every night while drinking my peppermint tea out of my Never Surrender mug. He also nailed the mugshot in unfavorable circumstances. YOU try posing while blinking into the garish glare of a Georgia police station’s fluorescent lights. This is the man who turned his own attempted assassination into a photo op, rising after screaming for his shoes to punch his fist dramatically into the air, yelling, “Fight, Fight, Fight!” The photos of which were so unbelievably cinematic that numerous people I know instantly became BlueAnon wackos, telling me with a feverish look in their eyes that he must have staged his own assassination to get the perfect shot. Hoooo-K. Having a bullet whizz by your head, only inches from bursting your noggin like a grape, seems a bit risky for a stunt, even for Donald Trump. This is the photographic subject who made working the McDonald’s drive-thru a warped Norman Rockwell painting and harnessed the cheesy transformation of the White House into a Tesla dealership for at least one Bond-like badass print ad suitable for a Clio. Even more recently, while attending the NCAA wrestling championships, Trump was photographed embracing the winner Wyatt Hendrickson, wrapped in an American flag, looking like a benevolent Father America comforting the common man, an image straight out of one of “Trump court artist” Jon McNaughton’s syrupy repertoire.

And these are just examples from the 2024 campaign and the beginning (yes, we still are at the beginning) of his 2025 “Art of the Comeback” presidency. The photos are so good that you almost, almost forget that this second go-around isn’t going so well between unnecessary trade wars, Elon’s Ketamine-inspired fork sculptures, winging-it deportations of protesters from the “free speech” set, adding reporters to classified and sassy National Security group chats, and Trump’s reimagining of the Kennedy Center as his own Andrew Lloyd Webber fan club.

For those who want proof that this posing prowess did not start recently, look no further than the unchanging walls of Trump’s own bar, 45 Wine and Whiskey, that still feature the same old black-and-white photos of Trump since my first visit: Trump with Un, Trump signing something with a Sharpie, Trump in front of a gaggle of fake news, etc. Fuck, at least add the mugshot for a tourist stop-and-repeat! Not to mention change the name to 45-47 Wine and Whiskey. Come on!

Yes. I visited Planet Donnywood, the airport lounge without a destination, a musty cigar bar without the stench, yet again for a $21 Negroni (ok, two) as I was in the neighborhood to watch German expressionist-inspired, puppets and a giant needle menacing Dame Darcy in Lisa Hammer’s short Empire of Ache and a righteous and violent queer body horror battle against goo-spewing transphobe brain worms, alongside drag queen Etcetera Ecetera channelling Elvira as a framing device, in Alice Maio Mackay’s lo-budge romp, T-Blockers at MoMA. Yes, I realize the cognitive dissonance between my aperitif and evening’s feature. Regardless, given my previous writing on Trump Tower, I had to do my due diligence for you, dearest Filthy Dreams readers. And it brings me no, ok some, pleasure to report that: Donald Trump made Trump Tower Great Again! What was once an empty pink marble shell of winding hallways and stopped escalators is now stuffed with tourists yet again, taking photos in front of his 45 seal, gawking at the gaudy glamour, and mostly meandering aimlessly, mouths agape. Hell, there were so many people that my stall in Trump Tower’s women’s room was all out of toilet paper! There were so many people that some of them were even getting blasted with multiple rounds at 45 Wine and Whiskey rather than just splurging for a single “the 45”—a $45 mix of an Old Fashioned, two burger sliders, and, of course, a Diet Coke. One tipsy fellow came over and started trying to…it’s hard to say…flirt with my cousin and me? Later, the bartender approached and asked if he was bothering us. No, we answered. What was she going to do—deport him to El Salvador? Or switch him to that nonalcoholic Trump classic, Diet Coke?

Speaking of Diet Coke, when labeling Trump as the master of the image, I don’t just mean photography. So much of his trademark aesthetics become weirdly removed from their original context, only to orbit around him much like both the Republican and Democrat political platforms (It’s always about Donnie, not the rest of us). Take that aspartame-tainted soda, which is so linked with the Donald that he includes a small bottle in his tacky Donnyworld memorabilia case at 45 Wine and Whiskey, alongside two Trump-branded Sharpies (another product irrevocably tied to the man). His image is so tightly curated that even mega-corps like Coca-Cola lose their grasp on their own products.

Diet Coke display at 45 (photo by moi)

The moving image, too, bends to his will. In addition to my Trumpy tourism, I also rewatched Season 1 of The Apprentice. The Apprentice is a fascinating and perplexing archive for many reasons, especially as a time capsule of the golden age of early aughts trash reality TV. So early that nobody involved, from the contestants to Trump himself, has any idea what they’re doing. Every so often, you see Trump’s eyes slide to the side as he singsong reads off his cue cards. The show also reveals how little the man has changed in over 20 years. Trump in the boardroom is Trump in the Oval Office, only here he’s dismissing Omarosa’s feigned days-long concussion after being beaned by plaster at a construction site, which required her to have a relaxing two-hour lunch rather than grab a bodega sandwich, with an “All my life I’ve been hit in the head by little pieces of plaster.” Does that explain it?

Even with the Season 1 jitters, The Apprentice most intriguingly captures Trump and Mark Burnett as they construct his mythology in real time, as the aspirational New York businessman, not the guy who desperately needed a gig after his latest bankruptcy. And it’s so flawlessly manufactured that it’s even hard for me not to fall for it as he flies around Manhattan in his Trump-branded helicopter, doles out “Art of the Deal” tips like “You cannot be successful without passion,” and saunters around the nicotine-stained carpeted floors of the Trump Taj Mahal like the people’s billionaire to cries of “Donald!!” Even the appearance of a truck emblazoned with Trump Ice, his failed bottled water company, with his big tawny mug as its logo, set to blaring pageantry horns, is as hilarious as it is effective in building the image.

All of which is to say, Donald Trump would be King of All Media if not for one lone hitch: Donald Trump really blows as a painting subject. Portraits of the man, unlike all the many phenomenal photographs, almost universally suck in gratifyingly hilarious ways. I’ve been thinking about Trump’s egregious failure as a portrait subject after laughing all last week about his moaning and groaning directed at one portrait in particular: Sarah A. Boardman’s painting formerly hanging in the Colorado State Capitol Building’s Gallery of Presidents. Granted, this portrait could have just sightlessly gazed dull-eyed and gathered dust for eternity if Trump hadn’t randomly decided to pluck it out of obscurity. His likeness had already been languishing there since 2019. Why is he just miffed now? Time, though, did not temper his ire, leading to this hysterically bitchy Truth Social truth:

Is the portrait all that bad? Well, kinda. Ok, yes. Rendered with a muted fuzziness that reminds me of the bleary-eyed experience of spring allergies, Trump stands in a brown abyss as if he chose the worst backdrop at the Sears Portrait Studio. There’s no Trump-branded golden tacky opulence here. No money, money, money. Just bland nothing. Trump’s physicality too, is just as subdued. Gone is the trademark Trump glower. No more dominating Kubrick stare downs. There’s not even his rictus white veneered grin alongside his go-to smiling photo pose: a thumbs-up. Boardman traded these for a placid little smirk barely perceptible on his round, jowly face that is so heavy, he might be melting. He looks almost serene. He also looks like he’s chewing. It reminds me of both one of those amusingly dour 19th-century American folk art portraits in the American Wing at the Met and a portrait of a kindly lesbian gym teacher hanging in a high school. It’s almost feminine. I love it. I love it so much.

But, I also see why Trump hates it. Although not all of his criticisms land. His observation about Boardman’s Obama portrait being masterful isn’t quite right. In it, Obama’s face is so far forward on his head that it looks like his facial features are trying to escape his skull. Is Obama significantly more attractive in his portrait? Sure, but Donnie, I don’t know how to tell you this, she’s not a magician. Still. Even though I would tinkle a little bit in my trousers with joy at spotting Boardman’s painting at a flea market, it’s objectively not a good painting.

Yet, how much worse is that bad Trump painting than THIS bad Trump painting, which hangs in a prominent and privileged place, the bar at Mar-a-Lago?:

Ralph Wolfe Cowan, The Visionary (Donald Trump), 1989, at Mar-A-Lago (via lacmaonfire.blogspot.com)

Ralph Wolfe Cowan’s The Visionary is a different type of bad, sure, but it’s still bad, a fawning, absurd, and cloying overreach that belongs on the cover of a romance novel plucked out of one of those squeaky rotating displays at Dollar General. Though Cowan describes his process in Town and Country Magazine as making his subjects appear “healthy,” Trump’s skin is so flushed he may want to check his temperature, and his eyes look a tad glassy, too. Not to mention, when the hell has Trump EVER worn a tennis sweater? Or played tennis at all?

Even so, it’s not that hard to see why Trump likes The Visionary, depicted as a preppy Adonis vamping in a Hudson River School heavenly sunburst. But the painting is so over-the-top, it cannot be taken seriously. Notably, Cowan has also painted Trump’s playlist standard and (imagined) twin: Elvis. However, Elvis at one point DID look like the figure in his painting. Trump, not quite. Even though The Visionary Trump may make come-hither bedroom eyes, so intense even in online photos that I fear they’re going to shoot lasers or weep blood, at Trumpettes and other assorted barflies at Mar-a-Lago, Donnie, a wannabe art critic, wasn’t always all that fond of Cowan’s artistic flourishes. Reportedly, he was miffed about Cowan leaving one hand partially sketchily unfinished. This was a purposeful stylistic choice. Trump, however, did not get it, repeatedly badgering the artist, “When are you going to finish my painting?” Eventually, Cowan gave in after Trump tossed in a couple thou for a hand.

Money, as Trump well knows, can change everything. It can give you a hand. It can also make a terrible painting into one worth scamming charity money to buy at auction. Hey! If Sarah Boardman wants Trump to change his tune on her Colorado state house portrait instantly, just put it up for auction with no other prospective buyers. A Trump fixer will certainly emerge from the ether to funnel money from the Trump Foundation to purchase the now-spectacular, must-have portrait, suddenly no longer relegated to “best left abandoned in the bin.” That’s exactly what happened to three laughably wretched paintings. Let’s take a look at where all that money went, starting with the best of the worst (I think): this golden-hued portrait by Havi Schanz that appears to be done on floor plans and business record cast-offs:

Havi Schanz, Donald Trump (Courtesy of the artist)

Because I picked it as the best does not make it good. I can imagine it hanging in a Thomas Kinkade store at the mall alongside a painting of Kramer. But it does capture that smarmy je ne sais quoi about Trump. Yet, it’s fucking tacky as hell and I’m not sure it lives up to Schanz’s own gushing description to Trump: “I paint souls, and when I had to paint you, I asked your soul to allow me.” Trump’s soul looks like an ad for Trump Ice was mistakenly printed on a pile of paper intended for the shredder. This painting is also the cheapest of the scammed lot, possibly because Havi really half-assed that tie. According to New York attorney general Letitia James when she was investigating the various tentacles of Trump’s financial schemes, Trump bid $10,000 of his charity’s funds on his own painting at his own auction at Mar-a-Lago in 2014. Supposedly, as reported in The Guardian, Trump’s lawyer claimed he was only hoping to start the bidding with a high price, but as no one else bid, he ended up paying for it. Huh. Why wouldn’t you want this giant Trump leering at you in your apartment, reminding you of the taxes you still need to file and the mortgage you’ll never afford? Spotted by Univision, Schanz’s painting is hanging out at Doral, though I’m sure it’ll soon be given prominent placement in one of the various Smithsonian Institutions under Trump’s new nutty anti-anti-American executive order.

The better of the worst will unquestionably need a warning label in the Smithsonian’s upcoming Trump Wing (I’m sure that’s the next executive order). Imagine turning the corner with the fam and having to confront this monster:

AAHHH!!! (via tampabay.com)

Like Schnaz’s portrait, artist Michael Israel, who completed this speed painting at a 2007 charity action, went with the same orange color scheme but decided to scrimp on the eyeballs. The painting looks like it’s about to rotate its head 360 degrees and spew projectile mushy peas puke onto a priest. Trumpy Bear needs an exorcism ASAP! And if the possessed rendering wasn’t enough, this thing is six feet tall. Good fucking god! A perfect prop for a scary movie—or Melania’s upcoming Nightmare in Santaland White House Christmas décor. Melania had to have some use for it in mind, as she’s the one who bid on it, naturally with Trump Foundation money, for double the price of Schantz’s at a whopping $20,000.

Yet even that freaky portrayal doesn’t touch the most heinous (and expensive) of the bunch. What the fuck is this gloppy mess?

William Quigley’s Trump painting (Courtesy of the artist)

Trump’s sickly skin has the consistency of moldy bathtub caulking and flung mud with shocks of bright orange psoriasis, and his hair is two different colors of gastrointestinal distress. His eyes are an eerie shade of red that screams out for an emergency optometrist appointment. His face is also so thinned out that he resembles a rat in a Trump wig. William Quigley’s painting is such an appalling crime against aesthetics that I can’t believe Trump would waste $60k to get former fixer and current hangdog Michael Cohen to save face at an ArtHamptons auction (then act surprised and honored about the number on Twitter). I mean, come on…

I should note that there are Trump portraits that I wouldn’t put in the category of bad, so much as completely unhinged. I’m not even sure it’s fair to list them along with the rest. Of course, I’m talking about MAGA Master Jon McNaughton, whose kitschy paintings aren’t good per se as their overblown, effusive style belongs in an outlet mall kiosk. However, McNaughton’s imaginative scenarios are so deranged and funny that I really don’t care, such as Trump and Melania zooming through the D.C. streets on a Harley, Trump and Melania in a monster truck, and Trump praying in the Oval Office alongside JFK, Ronald Reagan, and…is that Harriett Tubman? This is cheesy Americana romanticism at its most sincere, and you have to at least appreciate it for what it is: pure schlock. Yet, if I had to be honest, something is still lacking. Painted Trump rumbling down the road in an American flag monster truck has nothing on the documentation of him in a Trump campaign garbage truck.

Jon McNaughton’s Keep on Trumpin’ (Courtesy of the artist)

Which raises questions: Why are paintings of Trump so goddamn bad? SO goddamn bad? Is it because the artists who actually want to paint Trump have crappy skills and taste? Is it because to paint Trump at all belies some shaky decision-making? Is it because Trump’s singularly bizarro look is so exaggerated that it does not translate to paint? Is it because these paintings simply cannot live up to the surrealism of Trump himself? Or capture his deeply strange charisma? Is it that Trump’s image is already so manufactured that it renders painting completely useless? That he has such a stranglehold on his own image that to put it in the hands of another just doesn’t work? Why do they just never quite cut it? Unlike photography, Trump cannot dominate the image in painting. Giving up that control, his image mastery fails. He’s just a shitty portrait subject. Hell, even the National Portrait Gallery, when I last visited in 2023, had a photograph of the man in the presidential portraits.

Cumwizard69420, Diva Down, watercolor on paper (Courtesy of the artist)

If the curators need a recommendation, I have one. The only artist whose Trump portraits I can say are good (yes, anti-Trump Trump art also sucks shit) is Cumwizard69420, whose renderings of the president may be the only ones that capture the soul of the man with his butthole eyes, goofball expressions, and general ridiculousness. My absolute favorite portrait—and maybe the only Trump masterpiece in existence—barely features him, sidestepping the issue of representing Trump at all. Instead, Trump is just two bare feet sticking out of a pile of Secret Service agents as he demands his golden, American flag-emblazoned, self-branded, limited editioned Trump shoes at his doomed Butler, PA rally. The title? Diva Down. You cannot possibly get better than that—and as far as I’m concerned, nobody has.