The Moment Mark Cuban's Relationship With Trump Turned Sour

Mark Cuban, billionaire entrepreneur and Dallas Mavericks owner, initially showed interest in Donald Trump's unconventional candidacy during the 2016 election. Despite some reservations over observing the transformation of Donald Trump, Cuban briefly considered Trump a fresh political figure who could bring change (via Newsweek). 

However, as the campaign unfolded, Cuban's support for Trump waned. He publicly voiced concerns over Trump's lack of detailed policies and warned that Trump's approach seemed more about grandstanding than offering substance on crucial issues like technology and economic policy. Cuban's stance began shifting as he expressed disappointment over Trump's inflammatory rhetoric and divisive comments on immigration. 

By the general election, Cuban had moved from tentative support to a full endorsement of Hillary Clinton, who has a brutal take on how Trump has changed since 2016. Cuban even appeared alongside her at campaign events and joining her in the 2016 debates as a supporter, stating at a campaign event, "I am ready to vote for a true leader, I am ready to vote for the American Dream. I am ready to tell the world that I am here to endorse Hillary Clinton," (via CNN). 

Like Hillary Clinton, Mark Cuban's perspective on Donald Trump has only grown more critical. He has openly expressed his concerns about Trump's focus on personal gains rather than policies that benefit the wider public. "He's very transactional ... He doesn't care about crypto. He doesn't care about technology. He doesn't care about AI. But he certainly cares about people with a lot of money," Cuban told Preet Bharara on his podcast, "Stay Tuned with Preet." The Dallas Maverick's owner said he even tried to find more of a common ground with Trump, but everything he said just put him off. "As I tried to get other things out of him related to policy, there was just nothing there. The more he spoke out, the more that was obvious, the more the immigration stuff came out, and the more hateful stuff came out," Cuban recalled. 

Cuban's criticism is part of a broader trend, with other billionaires, including Warren Buffett and Michael Bloomberg, denouncing Trump (via Forbes). Toward the end of the podcast, Cuban asked, "Do voters have Trumpnesia?" Cuban's journey from a tentative supporter to an outspoken critic reflects a wider shift among business leaders and billionaires who initially saw promise in Trump's candidacy but grew disillusioned as his policies unfolded. After President Biden endorsed Kamla Harris, Cuban wasn't far behind. In an exclusive interview with Newsweek, Cuban said, "I thought a first term by Donald Trump was bad. A second term would be worse."