The Man in the Arena Meets the Man in the Diaper

Teddy Versus Donald, a colloquy in one act.

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This week, Donald Trump stood in the new Theodore Roosevelt Presidential Library in Medora, North Dakota, and spoke with a hologram. The AI ghost of TR, trained on his letters and speeches, gave Trump a gentle pep talk about how “the nation comes first,” and Trump, hearing words he has never once believed, called them “fantastic.”

The hologram was polite. It was programmed to be. It was built by a foundation, vetted by lawyers, and sanded down to museum-gift-shop smoothness.

The real Theodore Roosevelt was not smooth. The real TR was a human artillery barrage, a man who boxed in the White House until a punch detached his retina, who took a bullet to the chest in Milwaukee and finished the speech, who called crooked rich men “malefactors of great wealth” to their faces and dared them to do something about it.

A Word From Our Sponsor — Because The Hologram Is Only The Beginning

Quick pause before I open the curtain, because something about that hologram deserves a harder look.

Some foundation somewhere ingested every letter, speech, diary entry, and telegram Theodore Roosevelt ever wrote, ran the whole corpus through a neural network, and produced a polite museum-safe simulacrum you can chat with under a soft LED spotlight. That is the state of the art in 2026: enough data plus enough compute equals a functioning ghost.

Now ask yourself a question I never had to ask when I was a young ad man in the pre-Google era: what could someone build from what’s already sitting on the internet about YOU?

Someone just looked you up. You had no idea.

A researcher at Consumer Reports — someone whose job is online safety — typed her own name into a search engine. Her home address, age, and phone number were sitting there, on data broker sites she’d never heard of. No hack. No breach. Just her name in a search box.

Yours is there too. Right now. Available to an ex, a stranger, anyone who decides they want to find you.

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Every AI hologram, every deepfake, every targeted attack ad, every dead-of-night threat call to a poll worker gets sharper when it’s trained on cheap broker data. Cut the supply line before somebody builds a hologram of you and points it in a direction you don’t like.

Now, back to the show.

So let us conduct a small thought experiment. Suppose the machine glitched. Suppose that instead of the polite hologram, the actual man stepped out of history and into the gilded Oval Office, spectacles flashing, teeth bared in that famous grin that, this time, wasn’t a smile…

TRUMP: Teddy! Welcome back. A lot of people are saying this is the most beautiful Oval Office in history. The gold, the moldings, we did the ceiling, nobody’s ever seen anything like it. You had a nice office, but this, this is luxury.

TEDDY: Luxury. Yes. That is precisely the word, and precisely the problem. Luxury is an addiction of weak men who cannot meet the world as it is, cannot stand strong in wind, weather, and war.

Sir, I have seen this decor before in brothels that aspired to gentility. I saw it in the parlors of the railroad men I broke. I saw it in the townhouses of the beef trust and the sugar trust, men who believed that gilding a room could gild a soul. It cannot.

A man who needs this much gold around him is advertising naught but the poverty of his soul.

TRUMP: You should see the ballroom. Ninety thousand square feet. We took down the East Wing, which frankly was falling apart, total disaster, and we built the most incredible ballroom. Kings have called me about this ballroom.

TEDDY: You demolished a wing of the People’s House to build yourself a ballroom. By God, I put a boxing ring in this building. I brought judo masters and wrestlers, and I invited men to knock me down, because a president should be tested daily.

You built a room so that this era’s robber barons in evening clothes can tell you that you are tall and handsome. We are not the same kind of animal, you and I. I’d wager you’ve never taken nor delivered a punch, you weakling cockwollop.

TRUMP: With respect, Teddy, and I have great respect from the most handsome men, the strongest men, the most well-muscled men…I’ve done more than any president. Maybe Washington or Lincoln, they say, maybe. But probably me. The economy, the border, the canal. Speaking of which, I’m getting your canal back. The Democrats gave it away for a dollar. A dollar!

TEDDY: Do not speak to me of Lincoln, you gibbering fool. I watched Lincoln’s funeral procession from my grandfather’s window when I was six years old, and I spent the rest of my life trying to be worthy of the sight. Lincoln held this nation together with his bare hands while it tried to tear itself apart.

Washington surrendered power when he could have kept it forever, which is the single hardest thing any man in this office has ever done. Grant took Lee’s surrender and then spent his presidency trying to protect freedmen from terrorists while his own party abandoned him. These men bled for the office. You have bled from the ear from a mythical wound.

TRUMP: I’ve been shot at! In Butler. I said, “Fight, fight, fight!” Very famous moment. Iconic, they say. Maybe the most important speech in Presidential history.

TEDDY: I was shot, sir.

Not shot at or injured by flying glass. I was shot through the chest in Milwaukee in 1912. The bullet is still in me. I told the crowd it takes more than that to kill a bull moose, and then I spoke for another hour, because the speech mattered more than the wound. And here is the difference between us: I never once mentioned it again as a credential.

Courage that requires an audience is not courage. It is dinner theater.

TRUMP: People say I’m the toughest president. Strong. Very strong. So virile. The military loves me.

TEDDY: Do they?

I resigned my post as Assistant Secretary of the Navy to raise a regiment and charge up a Kettle Hill into Spanish rifle fire, because I did not believe a man should send others where he would not go himself.

You had a doctor invent a foot ailment so that other boys, poorer boys, boys from the Bronx and Appalachia and the Delta, would go to the jungle in your place. You speak of toughness the way a man who has never been in the water speaks of swimming. Strenuously, and from the shore.

TRUMP: OK, but the deals. Nobody makes deals like me. I ended seven wars. Maybe eight. They’re saying Nobel Prize, everyone’s saying it.

TEDDY: I have a Nobel Peace Prize. I won it for ending an actual war between two actual empires, Russia and Japan, by locking their diplomats in a room in New Hampshire until they made peace. I did not campaign for the medal. I did not whine for it. I did the work, and the work was the reward. Your war with the Persians is shaping up to be the worst debacle in history, even worse than the war you avoided fighting in Indochina.

You want the prize the way a child wants a prize. That is the whole of you, sir. What is it the children of your era call it? A participation trophy?

TRUMP: Look, we’re very similar, everybody says it. Doug Burgum says it constantly. Two transformative presidents. Two tough guys. Two...

TEDDY: Stop. I will grant you one similarity, and one only. We were both born rich in New York. There the resemblance ends, because I spent my life trying to prove that inherited money had not made me soft, and you spent yours proving that it had made you the weakest of men in every aspect of your character.

You have never kept a vow in marriage, business, politics, or life, sir, and a man who will not honor his word has no honor at all. You are a vulgar liar, a cheat, a small man in a big job, a petty thief serving nothing but your avarice.

You loathe your own family, except for your unnatural carnal desire for your daughter. I went to the Badlands and buried my grief in cattle work and grizzly country. You went to Studio 54 and paid women to indulge your low passions, when you didn’t stoop to outright rape.

I busted the trusts. You’ve broken American free enterprise and sold it for parts. I hunted predatory wealth. You practice it, from this desk, a billion dollars in snake oil, stealing more money than many can conceive from your “fans” in a single year.

From the seat where I signed the Pure Food and Drug Act to stop exactly your kind of man from poisoning this country, you’ve set loose plagues your science had defeated.

TRUMP: The environment, though. Cleanest air, cleanest water. I say it all the time.

TEDDY: And there it is. There is the thing I came to say, so hear it plainly. I set aside two hundred and thirty million acres of this country. Five national parks. A hundred and fifty national forests. Fifty-one bird sanctuaries. The Grand Canyon itself, which Congress would not protect, so I protected it anyway and dared them to undo it. I did this because I had seen the buffalo herds vanish in a single generation, and I understood that a nation which destroys its soil and squanders its forests destroys itself. It was the least Trump-like thing any president has ever done. I held that land away from mere commerce and rapine, sir. Held it as a gift to everyone. To those not yet born. To even your grandchildren, whose inheritance you are incinerating.

TRUMP: We’re unleashing American energy, Teddy. Drill, baby, drill. Very popular.

TEDDY: You have opened eighty-six million protected acres to the drillers. You have gutted the protections for the wild creatures of this continent. You even sold ninety acres of the national forest that bears my name to build the library where your hologram of me flatters you, and you brag that you ripped it from the federal government like a thief boasting of the lock he picked.

Every elk, every trout stream, every stand of ponderosa I saved, you regard as inventory. I called men like you the despoilers. I broke men like you for sport. The only reason you are not in one of my courtrooms or, if I may speak more truly, hammered into a pulp with my fists is an accident of the calendar that even this miracle of time travel cannot bridge.

TRUMP: You know, the hologram was much nicer.

TEDDY: The hologram was a machine built to please you.

So is every other low, gawping toady in this building. That is what you have never understood about this office, and why history will recoil in disgust when it says your name. The presidency is not a throneroom. It is a hill.

You charge up that hill under fire, working every day for people whom you will never know in service to this nation and our posterity. I said once that the credit belongs to the man in the arena, whose face is marred by dust and sweat and blood.

Your face is marred by garish whore’s makeup, sir, but it reflects your character perfectly; an utter lack of manly virtues, a fancy-boy’s prissy self-regard, a foppish, soft dilettante with a bully’s character.

TRUMP: Are you going to be at the ballroom opening? Black tie. Very exclusive.

ROOSEVELT: No. I am going back to the Badlands, where the land is honest. Bully for the country that produced Washington, Lincoln, and Grant, and the boys who took San Juan Hill.

It will outlast you. That is not a prediction. That is a promise. Good day.

TRUMP: You must never disrespect the President, Teddy. Bad things can happen when you do.

TEDDY: Summon me no more, you filthy rogue, for if you do, I will pray God or your technology gives me a corporeal form to administer the beating you more than richly deserve.

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