Trump shares letter from Yankees legend George Steinbrenner, urging him to run for president

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President Donald Trump on Sunday shared a letter from the deceased New York Yankees owner George Steinbrenner, urging the real estate mogul to run for office years before his first term.

The letter was dated Feb. 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 Liberty Luncheon on July 7, 1986, at the Waldorf Hotel in New York City. (Ron Galella, Ltd./Wireimage)

"Saw you on 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 is like I said to Stephen, you should run for President some day and get the whole damn thing straightened out. You were tremendous 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'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 president appeared at a Yankees game on Sept. 11, 2025, and met with players before first pitch.

President Donald Trump shakes hands with New York Yankees’ Aaron