Former Yankees Owner George Steinbrenner Asked Donald Trump To Run For President In The 1980s
- Dominic Konareski
- 2 hours ago
- 2 min read
*Disclaimer: The New York Sports Show has no political affiliation, this article is New York Yankees related.
Everyone has their own opinions surrounding 45th & 47th President of the United States Donald Trump, along with the New York Yankees. You either love them or have a deep hatred, frankly there isn’t really any middle man in 2026.
What if I told you though that Trump could have ran for president and possibly won it a lot earlier, like several decades earlier. All because George Steinbrenner sent The Donald a personalized letter asking him to run.
It really is no surprise as Trump and Steinbrenner were friends throughout the years. Trump appeared at numerous Yankees games and even had Steinbrenner featured on his show The Apprentice, during the “Trading Places” episode in season one. Overall Trump often called Steinbrenner his best friend.
George “The Boss” Steinbrenner passed away in 2010. Since his passing, Trump has still gone to games in the Bronx, most recently appearing before a game on September 11th, 2025, where he met with players and staff before throwing out the first pitch.
Donald Trump posted a photo of a letter dated February 23rd, 1989, by New York Yankees owner George Steinbrenner.
The letter reads in its entirety:
“Dear Donald: Saw you on Morton Downey the other night. 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.
Warm personal regards” with the letter ending with Steinbrenner’s signature.
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