Donald Trump is set to take over Washington, with the Freedom 250 Grand Prix, another shiny new obsession.
It is the latest sports spectacle after Trump’s damaging UFC Freedom 250 on the White House South Lawn in June.
Trump is turning the capital into another stage for his grandiose political and sporting spectacle.
The Department of Education’s AI Grand Prix post backfired after viewers zoomed in on the background and spotted some controversial familiar faces. (Photo: Allison Robbert / For The Washington Post via Getty Images)
The actual Freedom 250 is a first-of-its-kind IndyCar street race around the National Mall, part of America’s 250th birthday celebration.
On Sunday, drivers will complete 147 laps of a 1.7-mile circuit past some of Washington’s biggest landmarks. Trump is expected to take an honorary lap in the Beast before Sunday’s race, according to the New York Post.
But on Aug. 19, the U.S. Department of Education got ahead of themselves, posting an AI-generated meme promoting the race without examining the optics.
The Grok Imagine-generated cartoon showed Trump leading a Mario Kart-style race through Washington.
A woman in pink rode beside him. Another man followed in a blue kart bearing a prominent Mercedes logo.
Freedom REVS.
Stay tuned for the Freedom 250 Grand Prix THIS WEEKEND! pic.twitter.com/NTw3zQvx0f
— U.S. Department of Education (@usedgov) August 19, 2026
But no one was worried about the race. The internet wanted the passenger list of those in the meme.
“Who’s that in the back?” one person asked. Another asked, “Is that seriously Jeffrey Epstein?” as someone else wondered, “Why is Jeffrey Epstein a racer?”
The new MAGA Superhero…PedoRacer!
— bradvegas (@bradvegas) August 20, 2026
Someone else guessed, “Jeffrey Epstein and Natalie Harp?” Along the same line, someone wrote, “Is that an old version of Natalie? Hanging out with old men, even in AI ages you.”
None of the names floated by people on the internet was of the people in the cartoon.
The Department of Education told The Independent that the figures represented Education Secretary Linda McMahon and Transportation Secretary Sean Duffy.
Unfortunately, social media thought the caricatures were way off. When it came to the woman in the kart, some viewers thought the rider looked like Hillary Clinton instead.
That produced another question: “Why is trump racing Hillary Clinton and Jeffery Epstein.”
The agency most certainly did not intend for the cartoons to resemble those hot-button individuals who have stirred up negative headlines for the president.
The Department of Justice largely has quieted the furor over its continued refusal to release all of its Epstein files, but Trump cannot escape the specter of his years-long friendship with the disgraced financier who died seven years ago in a Manhattan jail as he awaited trial on federal trafficking charges.
But for the caricature to be a smiling Clinton, a woman who spent years as one of Trump’s favorite political punching bags, would just seem unlikely.
Then there was Harp, the fiercely loyal Trump executive assistant. The woman in the meme has darker hair, but that hardly mattered to social media trolls. Connecting her to him was just funnier, especially this week.
Reports have also surfaced about unusually personal letters she wrote to Trump. Her estranged brother added fuel to the fire, saying she has an “unhealthy obsession” with the president. That level of “infatuation” has fed tabloid speculation about their relationship, speculation that also extends to why she is always by his side, even when his wife Melania is not.
The comments about the digitally-generated art only got nastier and directed to the Education Department.
One person wrote, “Nothing says we need to improve and fund education more like the official Dept of Education account tweeting a picture of Donald Trump with his best friend Jeffrey Epstein right behind him.”
“The embarrassment from this administration is staggering,” another wrote.
One person even tried to summon Nintendo into the fray. They wrote, “Hey @NintendoAmerica looks like your brand aimed at kids is being used without authorisation and includes Jeffrey Epstein as well as Donald trump. Not very family friendly.”
House Oversight Democrats joined the pile-on, reposting the picture with a “Bourne Ultimatum” meme: “Jesus Christ, that’s Jeffrey Epstein.”
Jesus Christ, that's Jeffrey Epstein https://t.co/Y2EQ0wXM7E pic.twitter.com/Qwo98HFMOL
— Oversight Dems (@OversightDems) August 20, 2026
It honestly doesn’t matter what the Department of Education says in this tweet. It was an epic miss. The Grand Prix barely received promotion as it gave way to issues Trump wants to make disappear.
The Freedom 250 may feature cars approaching 200 mph. Unfortunately for Trump, the internet got to the finish line first.
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