Trump Shares Rare 1989 Note From Yankees Icon That Foreshadowed His Political Future

The late New York Yankees owner George Steinbrenner sent former President Donald Trump a handwritten letter more than 30 years ago. The February 23, 1989 note praises Trump’s public persona and suggests he run for president.

Trump posted the letter on social media Sunday without comment. However, its timing and the writer’s prominence made the message stand out. Steinbrenner, nicknamed as “The Boss,” was a major late-20th-century sports and commercial personality.

Steinbrenner noted in the letter that Downey Jr. was a friend and routinely watched Trump’s televised performance. Steinbrenner said Trump “tells it like it is” thanks to his directness and confidence. He added that he had already told Stephen that Trump should run for president and “get the whole damn thing straightened.”

Resurfacing of the letter has revived interest in Trump’s longtime relationship with the Yankees. Steinbrenner influenced Trump as he rose in New York business in the 1980s. Trump frequented Steinbrenner’s Yankee Stadium private box, where he watched his tough leadership and high expectations.

Steinbrenner was known for making aggressive decisions and firing team members, which may have shaped Trump’s public image. Years later, when Trump hosted “The Apprentice,” his frank attitude and “You’re fired” became crucial to his image.

Trump named Steinbrenner his closest friend and a major winner after his death in 2010, expressing his personal and professional appreciation for him. Trump has maintained contact with the team and its leadership since Steinbrenner’s death.

The 24th anniversary of 9/11 saw Trump attend a Yankees game. He sat with current club owner Hal Steinbrenner and team president Randy Levine during the visit, demonstrating his continued ties to the organization.

The return of this decades-old letter provides a unique peek into Trump’s early public life before politics. A powerful sports businessman wrote casual praise for Trump, but it now shows how he was seen at the time and how someone close to him envisaged his political destiny.