NEW YORK – A handwritten note sat in storage for nearly four decades. It bore the New York Yankees letterhead. It carried words that would prove eerily prophetic.
President Donald Trump pulled that letter from his archives Sunday and shared it with the world. The timing puzzled political observers. The president offered no explanation. He added no commentary.
The author was George Steinbrenner, the legendary MLB owner who transformed the Yankees into baseball’s most dominant franchise. The message urged Trump to seek the presidency decades before he actually did.
A nostalgic post surfaces amid political turbulence
Trump’s approval ratings have tumbled to their lowest point of his second term. Multiple polls in January 2026 show the president underwater with voters. A Marist Poll recorded his net approval at minus 18. The CNN poll placed it at minus 16. Reuters/Ipsos showed minus 17.
The timing of Sunday’s nostalgic post raised questions. Was this simply a trip down memory lane? Or was it a calculated reminder of Trump’s long history with powerful New York figures?
The president faces a difficult political environment heading into the 2026 midterm elections. His party traditionally loses seats in midterm years. Polling shows independents have drifted away from him. Economic concerns dominate voter priorities.
Sharing a letter from one of sports’ most respected winners may serve a purpose. Steinbrenner built championships. He demanded excellence. He never accepted failure. Those qualities resonate with Trump’s political brand.
The Boss saw something special in 1989
The letter bears the date February 23, 1989. It came from the Yankees’ Tampa, Florida office. Steinbrenner had watched Trump appear on The Morton Downey Jr. Show, a controversial talk program that pioneered what critics called “trash TV.”
Downey’s show featured screaming matches between the host, his guests, and audience members. He chain-smoked on camera and blew smoke in guests’ faces. His fans called themselves “Loudmouths.” The program ran from 1987 to 1989 before advertisers fled.
Trump discussed foreign policy and press criticism during that appearance. When asked if he resented negative coverage, Trump replied: “I think I used to resent it, I’m not sure I do anymore.”
“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,” Trump told Downey. “I find now that it really doesn’t matter.”
Steinbrenner liked what he saw. His letter praised Trump’s directness.
“Saw you on Morton Downey the other night,” Steinbrenner wrote. “He is a friend, and I watch his show regularly.”
Then came the prophetic words that make this letter remarkable.
“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,” Steinbrenner continued. “You were tremendous on the show.”
Two New York titans shared similar styles
Steinbrenner purchased the Yankees from CBS in 1973 for roughly $10 million. He owned the franchise until his death in July 2010. Under his leadership, the team captured seven World Series championships and 11 American League pennants.
The parallels between the two men ran deep. Both were born to immigrant mothers and raised by domineering fathers who built family fortunes. Both cultivated brash public personas. Both demanded loyalty and results.
Yankees general manager Brian Cashman addressed those similarities in a 2017 interview with the New York Post. “They do it their way, and take no prisoners,” Cashman said. “I think they’re very similar.”
Steinbrenner earned the nickname “The Boss” for good reason. He fired manager Billy Martin five separate times. He made headlines as often as his players did. His win-at-all-costs mentality defined Yankees culture for nearly four decades.
Trump was a frequent guest in Steinbrenner’s private box at Yankee Stadium. He observed the owner’s brash leadership style up close. He saw how Steinbrenner demanded excellence and accepted nothing less.
Steinbrenner was often satirized on the long-running TV series Seinfeld. Comedy legend Larry David voiced his character, who was always shown with his back to the camera.
Trump remembers his friend fondly
Steinbrenner died on July 13, 2010. He never saw Trump enter politics. He never watched the businessman he admired win the White House in 2016 and again in 2024. The prediction took 27 years to become reality.
Trump has spoken fondly of Steinbrenner over the years. Following the owner’s death, Trump shared his thoughts in an interview with EXTRA TV.
“George was the boss, and he was a great guy,” Trump said. “More than anything, George Steinbrenner knew how to win. There was no one like him.”
Trump praised Steinbrenner’s character as well. “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 connection endures with a new generation
Trump’s ties to the Yankees organization remain strong. He attended a game at Yankee Stadium on September 11, 2025. The visit marked the anniversary of the terrorist attacks.
The president met with players before the first pitch. He sat near current owner Hal Steinbrenner, George’s son, and team president Randy Levine during the game.
Trump visited the clubhouse and shook hands with star outfielder Aaron Judge. He joked about the slugger’s impressive build.
“If you have that much muscle, you have to hit the ball further,” Trump said. He called Judge a “fantastic player.”
Judge delivered that night. He crushed two home runs. Those blasts tied him with Joe DiMaggio for fourth on the Yankees’ all-time home run list at 361. Judge went on to win his third career MVP award.
Political timing raises questions
The president’s decision to share the letter without context leaves room for interpretation. Political analysts suggest several possible motives.
First, the letter reinforces Trump’s identity as someone powerful people believed in long before politics. Steinbrenner was a winner. He saw Trump as presidential material in 1989. That validation carries weight.
Second, the nostalgic post connects Trump to New York sports royalty. The Yankees remain one of baseball’s most valuable franchises. Steinbrenner’s legacy includes seven World Series titles. Association with that success reflects well on any politician.
Third, the letter distracts from current troubles. When approval ratings sink, politicians often look backward. Good memories can soften present difficulties.
Trump faces significant headwinds entering the midterm election year. A December CBS/YouGov survey found 63 percent of Americans oppose his tariff policies. Majorities told CNN pollsters that Trump has gone too far on several key issues.
The letter reminds supporters that Trump has always been Trump. He told it like it was in 1989. He tells it like it is now. That consistency matters to his base even as independents peel away.
Whatever the motivation, one fact remains clear. George Steinbrenner saw something in Donald Trump 37 years ago. He urged him to run for president and “get the whole damn thing straightened out.” That prediction eventually came true. The Boss would likely be proud.
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