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president Donald Trump A letter from late New York Yankees owner George Steinbrenner was shared on Sunday urging the real estate mogul to run for office in the years leading up to his first term.
The letter, dated February 23, 1989, was sent from the Yankees’ offices in Tampa, Florida, to the Trump Organization in New York.
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Donald Trump and George Steinbrenner attend a free luncheon at the Waldorf Astoria Hotel in New York City on July 7, 1986. (Ron Galera Ltd./Wireimage)
“Saw you on the Morton Downey show the other night,” the letter read. “He’s a friend of mine and I watch his show all the time.
“You’re awesome! You’re telling the truth. Like I said to Stephen, you should run for president One day, figure the damn thing out. You did a great job on the show. “
Trump and Steinbrenner became close after “The Boss” passed away in 2010. Trump remembers Steinbrenner fondly.

President Donald Trump arrives aboard Air Force One at LaGuardia Airport in New York, Thursday, September 11, 2025. (AP Photo/Alex Brandon)
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“George is the boss and he’s a great guy,” he told extra tv then. “The bottom line is, George Steinbrenner knew how to win. There was no one like him.”
Trump added, “He had a big heart and was a caring person. He had a strong heart. I always say George will never be truly appreciated until we no longer have him.”
president appear at yankees games Meet the players before first pitch on September 11, 2025.

President Donald Trump shakes hands with New York Yankees’ Aaron Judge in the locker room before a baseball game against the Detroit Tigers. The contest will be held on September 11, 2025 in New York City, New York. (Doug Mills // The New York Times, AP, Poole)
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He watched the game nearby Current team owner Hal Steinbrenner and team president Randy Levine.
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