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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 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 City. (Ron Galella, Ltd./Wireimage)
“Saw you at Morton Downey the other night,” the letter read. “He is 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 one day and get it all straightened out. 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 on Air Force One at LaGuardia Airport on 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, was someone who wanted to take care of people. He had a strong heart. I’ve always said that 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 players before the 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 game 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 near current team owner Hal Steinbrenner and team president Randy Levine.
