Why doesn’t Mark Cuban like Donald Trump? The Millionaire remembers the conversation that changed his idea

Donald Trump and Mark Cuban represent two of America's most famous entrepreneurs and billionaires. However, Mark Cuban has distanced himself from the former president. Here's why.

Modified on:
April 20, 2025 7:23 am

Monday’s episode of The Daily Show featured billionaire Mark Cuban, and naturally, the question of the presidential election and its candidates came up. What many viewers did not expect was Cuban’s opinion on Republican candidate Donald Trump. 

The billionaire and minority owner of the Dallas Mavericks recalled the time when he used to have long conversations with the former president, describing these calls as counseling sessions before his opinions about the presidential aspirant changed.

The reason for the change, according to Cuban, was because “Donald Trump wasn’t about changing.”‘ 

The realization of this came during one of the calls they had, as Cubans had suggested that Trump showed people he was a businessman by “visiting a local small business, sitting at their table, and showing off his business chops.” Responding to the suggestion, Trump said, “‘Donald Trump and Mark Cuban do not go to people’s houses to have dinner.” This was because he had religious people who did so on his behalf. 

That moment was the start of Cubans changing their opinions of Trump. 

What has changed in Cuba’s relationship with Trump? 

Donald Trump and Mark Cuban didn’t always have a relationship in which Cubans didn’t like the former president. The two used to have a good relationship that culminated in Mark Cuban almost considering being the former president’s running mate in his successful attempt to be president in 2016.

Cuban has in the past described Trump as someone who gave honest answers rather than prepared ones. This quality of Trump was what he described as “more important than anything that any candidate has done in years,”‘ he told Business Insider in 2015. 

However, in recent times, Cubans have become vocal critics of not just Trump but also those who are backing him to be president in the forthcoming elections. The former reality star described those backing Trump’s candidacy in Silicon Valley as individuals who have “lost the connection to the real world” while also saying they want “Trump to be the CEO of America” and the board of directors whom he listens to. 

What next for Trump? 

Trump will go up against Democratic candidate Kamala Harris for the spot to be president of the United States, while also hoping that Cuba’s opinion of him has not derailed his chances to be a two-time president. While Cuban couldn’t fulfill his desire to be Trump’s running mate in 2016, he will also not be doing so in the upcoming election as Senator J.D. Vance will be on the same ticket as the billionaire.

Trump will have a strong challenger in Harris, who stepped up after Joe Biden chose not to pursue re-election. She has gone on to eclipse Trump’s fundraising with a ground-breaking record of financial support going into her campaign in July. 

With success like this, it remains to be seen if Donald Trump will, in Cuban’s words, be the CEO of America by November’s election.

Emem Ukpong
Emem Ukponghttps://polifinus.com/author/emem-uk/
My journey to becoming a writer has been shaped by both science and finance. I began with a Bachelor's degree in Biochemistry, but I found myself drawn to the economic and financial sphere. I have collaborated with various organizations, creating articles and blogs about these essential topics. Currently, I cover financial trends, economic updates, and social welfare topics for Polifinus, ensuring that our content reaches those who need it most.

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