by Donald Trump just posted a throwback that hits like a time capsule from the “power lunch” era of New York — a typed New York Yankees letterhead note from George M. Steinbrenner III, dated February 23, 1989.
And yes, it’s exactly what it sounds like: Steinbrenner praising Trump for a TV appearance and flat-out nudging him toward politics.
What the Letter Says (1989)
From the image Trump shared, Steinbrenner tells Trump he saw him on The Morton Downey Jr. Show, calls him “great,” and says he likes how Trump “tell[s] it like it is.” Then comes the line that makes this letter go viral in 2026:
“…you should run for President some day and get the whole damn thing straightened out.”
It’s signed: “Sincerely,” with Steinbrenner’s signature underneath — the Boss in full Boss mode.
truthsocial.com/@realDonaldTrump Feb 01, 2026, 1:52 PM
Steinbrenner and Trump: Old-School New York, Same Orbit
This wasn’t some random fan letter. Trump and Steinbrenner ran in the same New York circles for years — two loud, headline-friendly titans who valued loyalty, winning, and being the biggest presence in the room.
After Steinbrenner died in 2010, Trump spoke about him like you talk about a friend, not just a sports owner you occasionally bumped into. “George was the boss, and he was a great guy,” Trump said at the time. “More than anything, George Steinbrenner knew how to win. There was no one like him.”
Trump also added that Steinbrenner “had such a big heart” and would take care of people — and that he wouldn’t be fully appreciated until he was gone.
That’s the relationship in a nutshell: respect wrapped in mythology. The kind of bond New York power brokers loved to project — especially when both brands were built on dominance.
Trump at Yankee Stadium in 2025
Fast-forward to the modern era: Trump appeared at a Yankees game on Sept. 11, 2025, marking the anniversary and drawing a national spotlight to the Stadium.
And here’s the important part for anyone who likes to spin everything into a political endorsement: ballplayers are not politicians. A handshake in a clubhouse is not a campaign rally. It’s a meet-and-greet in a workplace that gets visited by celebrities, former players, and high-profile figures constantly.
Aaron Judge, Team USA, and the Reality of “Politics in the Clubhouse”
What is relevant right now is this: Aaron Judge was named Team USA’s captain for the 2026 World Baseball Classic. That’s official — announced by Team USA management on MLB Network and covered by MLB.com.
As for the broader claim that “many MLB players are Trump fans” — fans are everywhere, and baseball clubhouses are full of people with different beliefs who mostly keep it private. Unless a player publicly says it themselves, it’s not something responsible outlets should be labeling as fact.
The Bigger Picture
The reason this letter pops isn’t because it “proves” anything new. It’s because it captures a particular era: late-80s New York, when celebrity, money, sports, and politics all started blending into the same noisy cocktail.
And Steinbrenner — the ultimate win-now owner — saw something in Trump’s persona that night on TV and basically said: Take that energy national.
Decades later, Trump posts it like a receipt.
And the Yankees? They’re just sitting there in the letterhead — a reminder that in New York, sports and power have always shared the same VIP entrance.
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