In a 2006 appearance on The David Letterman Showbillionaire entrepreneur Mark Cuban shared a memorable story about his first meeting with Donald Trump — an encounter that left the Cuban thinking, “I never want to be like him.” Known for his candor, Cuban’s story highlighted the stark difference in personality that would later define their contentious relationship.

A first impression that lasted

Fresh off his company’s successful IPO, Cuban attended an exclusive Super Bowl party at Mar-a-Lago hosted by Trump. Cuban expected an evening of glitz and networking, but instead felt put off by Trump’s remarks. In the brief interaction, Trump approached the Cuban and, without any discussion or introduction, said, “One day, you’re going to be able to sit there with the rich people,” before walking away. Cuban recalled thinking, “If I ever get to that point, don’t ever let me be like that.”

This was not the only meeting that painted a vivid picture of Trump’s character for the Cuban. Trump later invited him into his office, where Cuban was struck by an unusual choice of decor: The walls were lined with portraits of Trump himself, not family or personal memorabilia. 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 who was intensely focused on his own image.

From acquaintances to adversaries

While that first impression soured Cuban’s view of Trump, the rivalry between the two men did not develop overnight. Their relationship has seen its fair share of ups and downs, from business acquaintances to outspoken criticism. According to Cuban, they had “a love-hate relationship” marked by periods of public camaraderie and private tension.

Conformable Business Insiderone of the first incidents to suggest a split 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 air on his HDNet network (now AXS TV). “Donald is amazing,” Cuban said at the time, praising 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 blame each other for the cancellation, the incident was a precursor to their subsequent 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 offered to donate $5 million to a charity if Obama released his transcript and birth certificate. Cuban responded by criticizing Trump’s attitude in his characteristic style. “Donald, you shave your head, a million dollars to any charity you want,” he joked, taking a swipe at what he saw as Trump’s obsession with self-promotion.

Breaking Point: The 2016 Presidential Election

The rivalry between Cuban and Trump peaked during the 2016 presidential election. In a decisive move, Cuban publicly endorsed Trump’s opponent, Hillary Clinton, 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 behavior. Cuban’s comments were met with immediate backlash from Trump, who labeled him “crazy Mark Cuban of failed do-gooder fame” at X (formerly Twitter).

Despite the tension, Cuban’s remarks did not stop at insults. He continued to criticize Trump’s policies and behavior, positioning himself as a vocal opponent of Trump’s political ambitions.

Kamala Harris endorsement 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 has aligned him with more than 800 venture capitalists on the VCsForKamala.org platform, further intensifying his opposition to Trump. Cuban was one of 88 corporate leaders to publicly endorse Harris, underscoring the stark ideological divide between him 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 CNBCCuban saw Harris as a pragmatic leader focused on progressive policies, a position he believed was necessary for America’s future.

Through a series of collisions — from failed business deals to opposing political endorsements — the relationship between Cuban and Trump has evolved from a cordial acquaintance to a deep rivalry. For Cuban, his first meeting 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 of people: “I never want to be like him. “