Mark Cuban's Maverick Moves: From NBA Regrets to Disrupting Healthcare and Tech

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Mark Cuban has been back in headlines this week, blending blunt financial commentary, candid regret, and his trademark disruptor energy. In a revealing interview picked up by Sports Illustrated and the Dallas Morning News, he openly admitted one big regret from his 2023 sale of the Dallas Mavericks. He said he does not regret selling the team itself, which netted him around 3.5 billion dollars, but regrets that he did not open the bidding to more buyers. Cuban told Tim Cato, “Would I still sell the team? Yes… Would I do it the same way? Absolutely not. I would have put it out to bid, but I didn’t so it doesn’t matter.” According to Cuban, he gave NBA Commissioner Adam Silver advance notice and has since remained a minority owner, holding 27 percent. But he claims the NBA stepped in to block him from fully participating as originally negotiated, especially when the new owners traded star Luka Doncic. He emphasized on the “Would I still have sold?” podcast and to Stephen Douglas at SI, “There was a clause in there that gave me the right to be in every meeting… the NBA took that out.” The NBA, through reporter Marc Stein, has disputed this account, making it a genuine “their word against mine” situation with Cuban insisting he has lawyer’s letters to prove his side.

Cuban is also making waves with his ongoing assault on the opaque American health care system. Speaking with TechCrunch, he doubled down on his commitment to upend the prescription drug marketplace through his company Cost Plus Drugs, citing how pharmacy benefit managers keep prices high for consumers. “They price to market; we price based off of cost,” he says, giving examples like a generic chemotherapy drug costing only 21 dollars through his platform compared to thousands elsewhere. He has announced the addition of local pharmacy pickups—another step in his mission to force transparency on a 5 trillion dollar industry that he claims can’t “react as quickly” as his company does.

On the public appearances front, his name is tied to the upcoming Clover x Shark Tank Summit in Las Vegas, a three-day entrepreneurship event where he is expected to share his business and investing wisdom alongside Shark Tank personalities.

Social media has seen him as feisty as ever. His account on Bluesky spurred heated debates after he criticized the platform for being too much of an echo chamber; commentators on Kahn’s Corner suggest Cuban is being blocked in droves for using the platform to push his political ideas rather than genuinely social engagement. On Threads, Cuban reported drastically reducing his own screen time, limiting app usage to an hour per day and even deleting apps on weekends. He recently joked that he threw out his high school gear simply because the colors matched those of the Lakers—ever the showman, even in personal anecdotes.

To round it off, Cuban recently told Business Insider that it should be illegal for AI models to include ads in their responses, arguing that regulators should “have learned our lessons.” As always, Cuban moves fast, speaks bluntly, and rarely avoids the splashiest edge of the limelight. All this together suggests that, while his NBA days are winding down, his appetite for big-league disruption—especially in healthcare, media, and technology—shows no sign of letting up.

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