Johnny Damon’s friendship with Donald Trump has been a defining aspect of his post-baseball life, marked by both unwavering support and significant controversy. Their initial encounter occurred during Damon’s tenure with the New York Yankees, shortly after his departure from the Boston Red Sox. Trump, then a prominent businessman and reality TV personality, extended an invitation to Damon and fellow baseball star David Wright for a round of golf at his Mar-a-Lago resort. Trump, a longtime Yankees enthusiast, even attempted to persuade Damon to reside in one of his properties, though Damon had already secured an apartment in the Bloomberg Building. This initial interaction laid the groundwork for a relationship that would extend far beyond the realm of sports.
Despite a brief competitive clash on Trump’s reality show “Celebrity Apprentice,” where Damon was ultimately fired, their bond continued to solidify. Damon’s admiration for Trump transformed into fervent political support, a stance he wholeheartedly embraced and publicly defended, despite facing considerable criticism. He viewed Trump as a decisive leader capable of revitalizing America, contrasting him favorably with the previous administration, which Damon believed lacked positive accomplishments. This unwavering loyalty, in Damon’s view, stemmed from a genuine friendship, one he valued regardless of public opinion or political ramifications.
Damon’s public endorsement of Trump in 2016, including an appearance at a rally in Orlando, triggered a wave of backlash, particularly from left-leaning baseball fans. Social media platforms became arenas for expressing disapproval, with some former fans disavowing Damon and questioning his intelligence. Despite the negativity, Damon remained steadfast in his support, a decision that ultimately provided an unexpected opportunity to enter the political sphere.
Following Trump’s 2016 victory, Damon was appointed to the President’s Council on Sports, Fitness, and Nutrition in December 2020. This appointment, alongside other notable figures like Mariano Rivera and Urban Meyer, sparked Damon’s interest in pursuing a political career. However, this ambition was abruptly derailed by a highly publicized incident involving a DUI arrest in February 2021. Bodycam footage revealed a visibly intoxicated Damon suggesting he was being targeted due to his political affiliations. This incident, occurring shortly after the January 6th Capitol riot, further intensified the scrutiny surrounding Damon’s support for Trump.
The DUI arrest became a significant turning point in Damon’s political aspirations. He acknowledged making a poor decision to drive under the influence, attributing his state of mind to his then-burgeoning political ambitions. While he disputed the breathalyzer results, the incident and subsequent legal proceedings effectively ended his pursuit of public office. Damon has since focused on charitable work and raising his children, framing these activities as a form of personal redemption.
Despite the fallout from the DUI and the persistent criticism surrounding his political views, Damon remains resolute in his friendship with Trump. He emphasizes his commitment to supporting his friends through challenging times, viewing loyalty as a core personal value. Damon’s experience underscores the complexities of navigating political affiliations in the public eye, particularly within the often-polarized world of professional sports. His story illustrates the potential consequences of publicly supporting controversial figures, even when that support is rooted in genuine personal connection.
