Mark Cuban: Love/Hate Relationship with Trump, Why He's Backing Kamala Harris

Cuban said his opposition to Trump came after unusually direct access: Trump called him roughly 10–15 times during the 2015–16 campaign, but Cuban said attempts to discuss policy rarely became substantive. Even after criticizing him publicly, Cuban later advised the Trump White House on healthcare and worked with Peter Navarro on pandemic PPE production.

Cuban said he has discussed crypto regulation directly with Kamala Harris, including his complaint that Gary Gensler’s SEC relies on “regulation through litigation.” His practical example was Lazy.com: he said a roughly $100,000-revenue NFT business found the SEC process too expensive and unworkable to register a token.

Cuban sold three-quarters of the Mavericks but kept 27.7%, largely because future growth required real-estate and casino expertise he did not want to learn and because he wanted to spare his children succession pressure. He said a Venetian-style Dallas casino around the American Airlines Center could push the franchise valuation to $20 billion.

During the NBA’s lean years, Cuban exploited other teams’ financial stress by buying first-round picks for $3 million and acquiring players from clubs that could not afford them. He credited that spending advantage with the Mavericks’ 15-year run without a losing season and roughly a decade of 50-win seasons.

Cost Plus Drugs’ clearest pricing example was droxidopa: Cuban said a friend losing insurance was quoted $110,000 per quarter elsewhere, while Cost Plus initially charged $64 per month and later about $20. He said falling acquisition costs are passed directly through rather than preserved as margin.

Cost Plus is still losing money, Cuban said, largely because he funded a robotics-driven factory for scarce sterile injectables, but he expects rapid growth. Its deeper weapon is transparency: the company publishes weekly prices for about 2,500 drugs, letting employers compare costs that Cuban says PBM contracts obscure.

Cuban has slowed his AI investing despite owning Groq and indirect OpenAI exposure, because he sees foundational models as an expensive race with uncertain winners. He expects tens of millions of specialized models and believes many standalone AI “agents” will become features that smarter models can create for users themselves.

Cuban flatly rejected a presidential run, saying his wife and children hated the idea because their lives are already difficult to keep normal. That concern also fits his Mavericks decision: reducing pressure on his children, not simply cashing out, was one of his stated reasons for selling control.