Former President Donald Trump has unexpectedly shared a decades-old correspondence from one of America's most iconic sports figures, prompting questions about his motivations and reviving memories of 1980s media culture.
A Presidential Endorsement from Baseball Royalty
On Sunday afternoon, Trump posted a letter dated February 23, 1989, from the late New York Yankees owner George M. Steinbrenner III, who owned the storied baseball franchise from 1973 until his death in 2010. The brief but effusive note was typed on official New York Yankees letterhead and contained remarkable political foresight.
Steinbrenner, known throughout baseball as "The Boss" for his hands-on management style that delivered seven World Series championships and eleven American League pennants, wrote to Trump after watching his appearance on The Morton Downey Jr. Show.
"You Should Run for President"
The legendary sports executive didn't hold back in his praise, calling Trump "tremendous" and "great" while making a startling political prediction. "It is like I said to Stephen, you should run for President some day and get the whole damn thing straightened out," Steinbrenner wrote in the correspondence now circulating on social media.
This wasn't casual flattery from a minor figure. Steinbrenner was a prominent New York celebrity whose persona became so culturally significant that he was regularly satirized on the iconic television series Seinfeld, with comedy legend Larry David providing the voice for his character.
The 1989 Television Appearance That Inspired the Letter
Trump's appearance on Morton Downey Jr.'s controversial talk show in 1989 focused on foreign policy and media relations, according to historical accounts. When questioned about negative press coverage, Trump displayed early signs of the media philosophy that would characterize his later political career.
"I think I used to resent it, I'm not sure I do anymore," Trump told Downey during the interview. "They take a shot at you in the newspaper, some reporter doesn't like something for his own personal reason, so they take a shot. I find now —10 years ago I used to say, 'Boy how could they do that, it's wrong, it's unfair.' I find now that it really doesn't matter."
The Morton Downey Jr. Show's Lasting Influence
Downey's program, which aired from 1987 to 1989, represented a groundbreaking moment in American television. Dubbed "Mort the Mouth" for his confrontational style, Downey pioneered what critics called "Trash TV" and became what The New York Times described as a "bullying cult figure" who frequently championed right-wing causes.
Media historians have noted that Downey's combative format and political commentary helped pave the way for later conservative media personalities like Rush Limbaugh and Glenn Beck. The show host died in 2001 following a battle with lung cancer, but his influence on American political media remains a subject of academic discussion.
Unanswered Questions About Timing
What remains unclear is why Trump chose to share this particular artifact nearly four decades after it was written. The former president offered no explanation accompanying his social media post, leaving observers to speculate about whether this represents nostalgia, a strategic political reminder of longstanding support from respected figures, or simply a personal moment of reflection.
The letter's emergence comes amid ongoing political developments and legal challenges facing Trump, though no direct connection has been established between those circumstances and this historical document's sudden appearance in public discourse.
What's undeniable is that the correspondence provides a fascinating glimpse into relationships between New York power brokers in the late 1980s and reveals how early some influential figures recognized Trump's potential political trajectory, even if that potential wouldn't be realized for another quarter century.
