Chip Somodevilla/Getty Images
Audio By Carbonatix
The life of a billionaire can be pretty wild sometimes. One day you’re the hero, the next, you’re a villain after teaming up with other billionaires who were villains cloaked in hero bank accounts, and soon after, you’re back into business with someone you long viewed as a villain, but this time, It just might be for a noble cause?
Welcome to Mark Cuban’s world, y’all.
On Monday, the Dallas billionaire and former majority owner of the Dallas Mavericks was standing with a big ol’ smile behind President Donald Trump, the longtime rival he tried to keep out of office not all that long ago. Joined by U.S. Secretary of Health and Human Services Robert F. Kennedy Jr and TV personality-turned-government official, Dr. Mehmet Oz, Cuban, was in Washington to promote the expansion of the president’s TrumpRX prescription drug initiative.
It takes a lot to rival Dallas Cowboys owner Jerry Jones for outlandish headlines in North Texas, but Cuban has more than held his own over the decades. That is especially the case over the last two years. Even in a region where the Cowboys reign supreme, Cuban has had an unprecedented and whiplash-inducing run in our newsfeeds since the winter of 2023. That’s when he sold a majority stake in his team to Miriam Adelson and Patrick Dumont, who run the Las Vegas Sands casino corporation.
At the time, things didn’t seem all that bad for Cuban, his team or Dallas fans. Cuban claimed then he would still run the basketball side of the business and that the only thing that was really changing was his bank account size, something he joked about with the morning hosts on 1310 The Ticket shortly after the sale. Although Adelson’s massive financial support of Republican candidates, including millions of dollars for Trump campaigns, was noted by many, it wasn’t seen as much more than an intriguing side note.
A short time later, the Mavericks, led by transcendent superstar Luka Doncic, reached the NBA Finals, the club’s second deep playoff run in three seasons. Around that same time, Cuban became one of former Vice President Kamala Harris’ loudest national advocates, often railing against Trump during numerous appearances in the media.
For Democrat-voting Mavericks fans, the rest of this story still stings more than they would like to admit. By then it was clear that Cuban had clearly been removed as the face of the franchise and was not in charge of anything related to the Mavericks, let alone making basketball decisions. Trump easily defeated Harris in November 2024 and on Feb. 1, 2025, Dumont and then Mavericks GM Nico Harrison traded Doncic to the Los Angeles Lakers in what was immediately viewed as the most shocking, lopsided trade in NBA history.
As the Mavs began its downward spiral, injuries mounted, the record dropped and fingers started pointing at Cuban, for selling the team to Adelson and Dumont, as much as they were at Harrison for making the trade.
But recent weeks have seen Cuban go on a somewhat surprising run of podcast interviews where he’s been quick to express his regret – not selling the team, but for who he sold it to. For a few days earlier this year there was some short-lived gossip about Cuban banding some big shots together to buy back the team, but Dumont shot that down with surgical efficiency.
Bringing things back to Trump, it’s not as though the two have been sparring for a year or two. You can go back more than 20 years, to 2004, when Trump and Cuban exchanged insults in the press over their respective reality TV shows. At the time, Trump was riding high on the success of The Apprentice, and Cuban, well before his Shark Tank era, was looking to cash in on the rich guy reality craze (Virgin founder Richard Branson also had an Apprentice-style show at the time).
The Benefactor was a jumbled, confusing mess of a show and was cancelled after one season, while The Apprentice went on to have many more seasons. Many experts have suggested that Trump’s years on a highly-rated prime time show helped him become arguably the most surprising U.S. president ever.
Monday’s press conference allowed Trump to tout his administration’s efforts to reduce prescription costs while Cuban got to shine as a keep player in that effort. Since 2022, Cuban’s Cost Plus Drugs has added thousands of prescription drugs to its roster at a smaller cost to the patient than many of the largest drug companies. Aside from the Mavericks and perhaps politics, the Cost Plus has arguably been the thing Cuban has talked about more in the media than anything else.
Although Trump and Cuban were all smiles and compliments in Washington, it was doubtful that their combative history wouldn’t come up. After a reporter asked about Cuban’s support of Harris in 2024, Trump quickly, jokingly shot back with “well it was a mistake, a big mistake.”
As everyone laughed, Dr. Oz gave Cuban a hearty few slaps on the back while Cuban, with only half of his face and body visible in the video, laughed right back.
