Mark Cuban forced to play nice with President Trump after agreeing to be business partners

Billionaire Mark Cuban stood on the White House stage Monday alongside the man he spent the last year trying to keep out of the Oval Office.

The former "Shark Tank" star and outspoken Kamala Harris surrogate appeared beside President Donald Trump during the rollout of TrumpRx.gov, which is a new initiative aimed at lowering the cost of 600 generic prescription drugs.

One year after trying to stop Trump from winning, Mark Cuban is now helping him sell cheaper prescription drugs to America. ((Photo by Chip Somodevilla/Getty Images))

The program partners the Trump administration with major private-sector companies, including Amazon, GoodRx and Mark Cuban Cost Plus Drugs — officially making Trump and Cuban business partners after a history of heated political attacks.

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For much of the campaign cycle, Cuban repeatedly blasted Trump’s economic policies while campaigning for Harris.

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Mark Cuban speaks onstage during the "Can Media Survive AI? The Fight For Public Trust" session at the 2026 SXSW Conference and Festival in Austin, Texas, on March 14, 2026. (Nicola Gell/Getty Images)

Monday’s appearance was a dramatic sight based on their shared vitriol.

The awkward alliance comes shortly after Cuban admitted he regretted selling a majority stake in the Dallas Mavericks to the Adelson family, led by billionaire Miriam Adelson, one of Trump’s biggest donors.

Cuban recently said on a podcast, "I regret who I sold to," after the franchise traded away superstar Luka Dončić.

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When a reporter pointed out how "remarkable" it was to see the two former rivals sharing a stage, Trump quickly took a jab at the billionaire.

"Well, he made a mistake. It was a big mistake," Trump said, drawing laughter from the crowd — even from Cuban himself.

After the news conference, Cuban was swarmed by reporters asking whether he regretted backing Harris during the election.

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"I’m not going into my politics at all," Cuban said, shutting down the question.

Instead, the Dallas Mavericks minority owner framed the partnership as a bipartisan effort focused on lowering healthcare costs.

"Democrats want cheaper medications, too. When all is said and done, the goal is the goal. How do we make medications and healthcare cheaper? That's all I care about," Cuban said.

Politics aside, Mark Cuban walked away from the White House Monday as something few would’ve predicted a year ago: one of Trump’s business partners. (Photographer: Jim Lo Scalzo/EPA/Bloomberg via Getty Images)

When reporters pressed him again about Trump, Cuban urged people to look past the politics and focus on the outcome.

"The way I always look at politics and any politician is, the only thing I care about is can they reduce the stress of the American people?" Cuban said.

"This, TrumpRx and Cost Plus Drugs working together, is one step toward reducing your stress. To me, that's the ultimate goal," Cuban added.

For a billionaire who spent months campaigning against Trump, Cuban now finds himself helping promote one of the president’s biggest healthcare initiatives.

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They're now ... best frenemies.

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