President Trump on Sunday shared a nearly four-decade-old letter from the late New York Yankees owner George Steinbrenner, in which the fiery baseball executive encouraged him to run for president and “get the whole damn thing straightened out.”
The letter, dated February 23, 1989, was written on official Yankees letterhead from the team’s Tampa, Florida, office and addressed to Trump at the Trump Organization in New York. It referenced Trump’s recent high-profile appearance on The Morton Downey Jr. Show, a controversial late-night talk program known for its confrontational style.
“Saw you on Morton Downey the other night,” the letter reads. “He is a friend, and I watch his show regularly.”
“You were great! You tell it like it is. It is like I said to Stephen, you should run for President someday and get the whole damn thing straightened out,” added Steinbrenner. “You were tremendous on the show.”
Donald J. Trump Truth Social Post PM EST 02.01.26
— Commentary Donald J. Trump Posts From Truth Social (@TrumpDailyPosts) February 1, 2026
"you should run for President some day and get the whole damn thing straightened out." …
George Steinbrenner, Owner, New York Yankees 1989 pic.twitter.com/4YeaL9DV6u
Yankees Legend George Steinbrenner’s 1989 Letter Predicted Trump’s Presidential Run to “Straighten the Whole Damn Thing Out” – A Prophetic Throwback Shared by the President
Trump reposted an image of the letter on his social media platform, highlighting the early endorsement from one of sports’ most larger-than-life figures. He didn’t add any commentary of his own, a rare move.
Steinbrenner, who owned the Yankees from 1973 until his death in 2010, led the team to seven World Series titles and was renowned for his no-nonsense approach, frequent managerial changes, and winning obsession—traits often compared to Trump’s own style.
The two men maintained a close friendship over the years. Trump has previously referred to Steinbrenner as “the boss” and a “great guy” who knew how to win and looked after those around him. Trump noted that Steinbrenner’s contributions were often underappreciated during his lifetime but gained recognition after his death.
As a Dodgers fan, I always despised Steinbrenner during their major run in the ’90s, but I always qualified those thoughts by noting I wish my team had him as an owner. The Dodgers now have somebody like that leading them to a dynasty. Steinbrenner would be impressed.
“George was the boss, and he was a great guy,” Trump previously said in an interview on EXTRA TV following Steinbrenner’s death. “More than anything, George Steinbrenner knew how to win. There was no one like him.”
“He had such a big heart, was someone who’d take care of people. He had a strong heart. I always said, George will never really be appreciated ’til we no longer have him.”
The timing of the share comes amid Trump’s recent public outings, including his attendance at a New York Yankees game on September 11, where he interacted with players, met current owner Hal Steinbrenner (George’s son), team president Randy Levine, and shook hands with star outfielder Aaron Judge in the locker room.
The President complimented Judge’s build, joking, “If you have that much muscle, you have to hit the ball further,” and called him a “fantastic player.”
Judge might have used it as motivation, delivering two massive home runs that not only helped his team win but also moved him up the list of all-time Yankee greats in the long ball department.
Those dingers at the time tied him with Joe DiMaggio for fourth on the Yankees’ all-time home runs list at 361. Judge went on to win his third career MVP award and second in a row.
Amazing that Steinbrenner saw Trump’s potential way back in 1989. He wouldn’t run for the White House—and win for the first time—for another 27 years.