The Telling Emptiness of Trump’s Doodles

I agree with Donald Trump on one thing: He doesn’t “draw pictures.” Right. He doesn’t. He makes Sharpie skylines — coloring-book stuff. Generic buildings. Little boxes for windows. Undulating lines for streets. Objects that might be cars. These images are stiff, symmetrical, totally vacant. Declarative but dead. They tell you nothing, and loudly.

Buildings are supposed to be his trade, his bread and butter, his life’s work. But most of these buildings are old, Deco, prewar — historically “New York,” but anonymously so. They read like borrowed dreams: half-postcard, half-projection. He doesn’t draw to design or to express some vision of the city. He draws to claim, as if history owes him the skyline.

The drawings — often sold at auction for charity — are small and rigid, clenched like a fist. The lines are thick and joyless. The people are often missing or reduced to stick figures. The weather doesn’t show up. There’s no scale, no depth, no light, no curiosity. Each one a closed loop. A thing to be framed and sold. Like the man himself.

And then, always: the name. The signature is the main event, much more so than his forgettable depictions of Trump Tower. Large, screaming, sharp-toothed. Not a flourish, not a caption — more a hot brand seared into the paper. The drawing’s only job is to give it a place to land. “I did this,” it says. “This is mine.” It’s the same message every Trump building gives off. Not shelter. Ownership.

These aren’t even doodles. A doodle — by Cocteau, Lennon, Prince — is a squiggle with soul. A little poem in ink. Doodles entertain and surprise. Trump’s sketches march along and insist. They rehearse the same claim, again and again, afraid to express anything about the man who made them. In fact, what’s interesting is how hard these drawings work to reveal nothing. You can feel him trying.

Compared to George W. Bush’s paintings — bizarre, awkward, sometimes accidentally moving — Trump’s drawings are in full armor. Bush paints his feet in the tub. Trump draws empty towers. Bush’s bathtub, somehow, becomes art. Trump’s cityscape is a business card blown up. These are monuments to repetition, rendered in black marker, glazed in emptiness. They don’t house anything — not people, not thought, not time.

The exception, maybe, is one reported drawing.

This drawing, reportedly made for Jeffrey Epstein, doesn’t follow the script. A stylized naked woman, crudely outlined, reportedly featuring his signature as pubic hair. It’s gross, Playboy, bro art. But it’s not framed or for sale. It wasn’t made to hide. It was made to coyly reveal, to hint at a secret, to titillate and delight.

And because it’s unguarded, it might be the only one that’s real.

Which is to say: It might be the only one he actually drew.