Donald Trump Reveals the 'One Thing' He and Foe-Turned-Friend Mark Cuban Have in Common at TrumpRx Event 

President Donald Trump revealed that the "one thing" he and billionaire Mark Cuban, have in common is that they both want to make people better and keep them wealthy.

The two billionaires set aside their long-standing political rivalry and past friction on Monday, May 18, during a White House press conference. The event marked a massive expansion of TrumpRx.gov, a direct-to-consumer, government-run prescription drug discount marketplace.

The event focused on adding more than 600 generic medications to the TrumpRx portal, expanding the site's footprint roughly seven-fold.

To supply these discounted generics, the Trump administration partnered with several major commercial entities. Cuban’s Cost Plus Drugs is contributing 559 of the new drugs, while Amazon Pharmacy and GoodRx are also joining the platform.

“We have the same thing — one thing — in common. We want to make people better and keep them wealthy,” Trump jovially said to the former Dallas Mavericks owner.

Although they played nice on Monday, critics blasted Cuban for his political about turn, willingly standing behind a president he has publicly reviled.

The long-standing rivalry between Cuban and Trump spans over two decades, evolving from a reality TV ratings war into a fierce political feud, and culminating in this highly unexpected 2026 healthcare alliance.

Following the massive success of Trump’s The Apprentice on NBC, Cuban launched The Benefactor on ABC in 2004.

Trump mocked Cuban's lower ratings, while Cuban regularly targeted Trump’s business history, net worth and past corporate bankruptcies.

When Trump first announced his 2016 presidential run, Cuban initially praised him as "the best thing to happen to politics" because he was an anti-establishment businessman. However, the relationship soured completely within months.

Cuban tried to engage Trump on policy specifics but grew frustrated, later labeling Trump "lazy" and claiming he refused to do the deep work required for governance.

The 79-year-old POTUS routinely dismissed Cuban as "dopey" and a "loser," while Cuban referred to Trump as "unethical" and a "troll." Cuban actively supported Hillary Clinton in 2016 and famously tried to secure a front-row seat at the presidential debates to rattle Trump.

The rivalry intensified sharply during the 2024 election cycle, when Cuban served as a high-profile surrogate for Kamala Harris.

In response to that, Trump said Monday, “Well, he made a mistake. It was a big mistake.”

Cuban fired back at reporters asking about the comment, saying, “I’m not going to go there. It doesn’t matter. My politics don’t matter to this at all.”

The former Shark Tank entrepreneur heavily criticized Trump's aggressive economic plans, mocking his 200 percent tariff proposals as "insane" and a threat to legacy American companies.

Cuban attacked Trump for selling merchandise (like gold sneakers and cryptocurrency), stating, "The only reason someone sells all that sh-- is because they have to ... He wants to sell." Trump responded by blasting Cuban on Truth Social as "weak and pathetic.”

Driven by a shared focus on lowering prescription medicine costs, the two former enemies became unexpected partners.

While Cuban continues to view Trump’s broader administration with skepticism — notably calling his second term the "f--k around and find out presidency" due to unpredictable global tariffs — he maintained that he has a "moral imperative" to work with the administration to fix American healthcare.

“I’ll align with anyone,” he said. “If you’re going to make healthcare cheaper, you’re my new best friend.”