George Steinbrenner urged Trump to run for president in 1989, letter shows
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President Donald Trump on Sunday shared a letter from the late New York Yankees owner George Steinbrenner urging the real estate mogul to run for office years before his first term.
The letter was dated February 23, 1989, from the Yankees’ office in Tampa, Florida, and was addressed to the Trump Organization in New York.
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Donald Trump and George Steinbrenner attend the Freedom Luncheon at the Waldorf Hotel in New York City on July 7, 1986. (Ron Galella, Ltd./Wireimage)
“I saw you at Morton Downey’s the other night,” the letter read. “He is my friend and I watch his show regularly.
“You were great! Tell it like it is. Just like I told Stephen, you should run for President one day and make things right. You were great on the show.”
Trump and Steinbrenner had a close relationship when “The Boss” died in 2010. Trump remembered Steinbrenner fondly.
President Donald Trump arrives at LaGuardia Airport in New York on Thursday, September 11, 2025, aboard Air Force One. (AP Photo/Alex Brandon)
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“George was the boss and a great guy,” he said EXTRA TV In that case. “More than anything, George Steinbrenner knew how to win. There was no one like him.”
Trump added: “He had such a big heart, he was someone who cared about people. He had a strong heart. I always said, George will never be truly appreciated unless we have him.”
The president appeared for a Yankees game on September 11, 2025, and met with the players before first pitch.
President Donald Trump shakes hands with New York Yankees’ Aaron Judge in the locker room before a baseball game against the Detroit Tigers. The match was on September 11, 2025 in New York, New York. (Doug Mills//The New York Times, AP, Pool)
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He watched the game alongside current team owner Hal Steinbrenner and team president Randy Levine.
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