In a 2006 appearance on The David Letterman Show, billionaire entrepreneur Mark Cuban shared a memorable story about his first encounter with Donald Trump—an encounter that left Cuban thinking, “I never want to be like him.” Known for his frankness, Cuban’s tale highlighted the stark personality difference that would later define their contentious relationship.
A First Impression That Lasted
Fresh from his company’s IPO success, Cuban attended an exclusive Super Bowl party at Mar-a-Lago, hosted by Trump. Cuban expected an evening of glitz and networking but instead found himself put off by Trump’s remarks. In the brief interaction, Trump reportedly approached Cuban and, without any small talk or introduction, said, “Someday, you’ll be able to sit up there with the rich people,” before walking away. Cuban recalled thinking, “If I ever get to that point, don’t ever, ever let me be like that.”
This wasn’t the only encounter that painted a vivid picture of Trump’s character for Cuban. Trump later invited him to his office, where Cuban was struck by an unusual decor choice: the walls were lined with portraits of Trump himself, not family or personal mementos. Cuban later recounted the experience with a chuckle, saying, “There were pictures of Donald, and then there were… more pictures of Donald.” This meeting only deepened Cuban’s perception of Trump as someone focused intensely on his own image.
From Acquaintances to Adversaries
While this first impression soured Cuban’s view of Trump, the rivalry between the two men did not develop overnight. Their relationship saw its fair share of ups and downs, from business acquaintances to outspoken critics. According to Cuban, they had “a love-hate relationship” marked by periods of public camaraderie and private tension.
According to Business Insider, one of the first incidents that hinted at a divide between Cuban and Trump was their involvement in a failed MMA venture in 2009. The pair had announced an MMA event, which Cuban planned to broadcast on his HDNet network (now AXS TV). “Donald’s amazing,” Cuban said at the time, commending Trump’s promotional skills. However, the event ultimately fell through due to a last-minute failed drug test by a main fighter. While Cuban and Trump did not directly blame each other for the cancellation, the incident was a precursor to their later disagreements.
Clash Over Obama’s Birth Certificate
In 2012, Cuban publicly condemned Trump for promoting the birther conspiracy theory that questioned President Barack Obama’s citizenship. Trump famously offered a $5 million donation to charity if Obama released his college transcripts and birth certificate. Cuban responded by criticising Trump’s stance in his characteristic blunt style. “Donald, you shave your head, a million dollars to any charity you want,” he quipped, taking a jab at what he saw as Trump’s obsession with self-promotion.
Breaking Point: The 2016 Presidential Election
The rivalry between Cuban and Trump reached a fever pitch during the 2016 presidential election. In a decisive move, Cuban publicly endorsed Hillary Clinton, Trump’s opponent, and even spoke at a Clinton rally in Pittsburgh. Using Pittsburgh slang, Cuban referred to Trump as a “jagoff”—a local term for an annoying person—calling him out for his aggressive and divisive behaviour. Cuban’s comments were met with immediate backlash from Trump, who labelled him “dopey Mark Cuban of failed Benefactor fame” on X (formerly Twitter).
Despite the tension, Cuban’s remarks didn’t stop at insults. He continued to criticise Trump’s policies and behaviour, positioning himself as a vocal opponent of Trump’s political ambitions.
Endorsement of Kamala Harris in 2024
In 2024, after President Joe Biden withdrew from the presidential race, Cuban took another political stand—this time endorsing Vice President Kamala Harris. His support for Harris aligned him with over 800 venture capitalists on the VCsForKamala.org platform, further intensifying his opposition to Trump. Cuban was one of 88 corporate leaders to publicly support Harris, underscoring the stark ideological divide between himself and Trump.
Cuban’s alignment with Harris highlighted not only his political beliefs but also his vision for leadership—a vision in direct contrast to Trump’s approach. According to a report from CNBC, Cuban viewed Harris as a pragmatic leader focused on progressive policies, a stance he believed was necessary for America’s future.
Through a series of clashes—ranging from failed business ventures to opposing political endorsements—Cuban and Trump’s relationship has evolved from a cordial acquaintanceship to a deep-seated rivalry. For Cuban, his first encounter with Trump at Mar-a-Lago was not just a humorous anecdote but a defining moment, shaping his view of Trump and cementing a belief he has since shared with millions: “I never want to be like him.”
