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President Donald Trump on Sunday shared a letter from 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 addressed to the Trump Organization in New York.
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Donald Trump and George Steinbrenner attend the Liberty Luncheon on July 7, 1986 at the Waldorf Hotel in New York. (Ron Galella, Ltd./Wireimage)
“I saw you on Morton Downey the other night,” the letter said. “He’s a friend and I watch his show regularly.
“You were great! You tell it like it is. It’s like I told Stephen, you should run for president someday and get this straight. You’ve been great on the show.”
Trump and Steinbrenner enjoyed a close relationship when “the boss” died in 2010. Trump remembered Steinbrenner fondly.
President Donald Trump arrives aboard Air Force One at LaGuardia Airport, Thursday, Sept. 11, 2025, in New York. (AP Photo/Alex Brandon)
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“George was the boss and he was a great guy,” he told EXTRA TV at the time. “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 for people. He had a strong heart. I always said George will never be truly appreciated until we no longer have him.”
The president appeared at a Yankees game on September 11, 2025, and met with the players before the first pitch.
President Donald Trump shakes hands with Aaron Judge of the New York Yankees in the locker room before a baseball game against the Detroit Tigers. The match took place in New York, New York on September 11, 2025. (Doug Mills//The New York Times via AP, Pool)
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He watched the game alongside current team owner Hal Steinbrenner and team president Randy Levine.
