Published by TrenBuzz.com | May 19, 2026
Key Points at a Glance – Mark Cuban Joins Trump on the White House Stage
- Mark Cuban appeared alongside President Trump at the White House on May 18, 2026 to announce a major expansion of TrumpRx.gov.
- 600+ generic medications have been added to the platform — a nearly 7-fold increase from TrumpRx’s February launch of 43 branded drugs.
- Cuban’s Cost Plus Drugs is now an official partner — directing TrumpRx users to his pharmacy, which sells medications at cost + 15% markup + $5 fee + $5 shipping.
- Amazon Pharmacy and GoodRx are also joining the platform — making TrumpRx a major prescription marketplace.
- Trump jabbed Cuban on stage: “He made a mistake. It was a big mistake” — referring to Cuban’s Harris endorsement, to which Cuban laughed in response.
- Cuban refused to discuss his politics when reporters pressed him: “I’m not going into my politics at all.”
- Trump called Cuban “a loser” and “total non-athlete” as recently as October 2024 — Cuban called Trump “the most unethical person I’ve ever done business with”.
- Cuban reframed everything around affordability: “Republicans, independents, Democrats — everyone wants cheaper drugs.”
- The TrumpRx expansion is described as a top White House political priority ahead of November midterms — with gas at $4.50 and inflation at 3.8%, cheap drugs is a politically smart play.
- Cuban’s net worth is approximately $6 billion — and Cost Plus Drugs processes millions of prescriptions monthly.
Politics makes strange bedfellows. But few partnerships in American history have been quite as publicly awkward — or quite as politically calculated — as the one that played out at the White House on Monday afternoon.
During a healthcare affordability event, Trump, 79, was joined by billionaire former Dallas Mavericks owner and Shark Tank personality Mark Cuban, who had once called the president the “most unethical” person he had ever done business with. Cuban appeared alongside the president’s health corps of Health Secretary Robert F. Kennedy Jr. and Medicare and Medicaid administrator Dr. Mehmet Oz to praise the near-octogenarian’s “TrumpRx” initiative.
TrumpRx Just Got Seven Times Bigger — Here’s What That Means
Trump announced the addition of more than 600 generic drugs to his drug coupon platform TrumpRx — with billionaire investor Mark Cuban joining President Trump to endorse the website. “I’m thrilled to announce that we’re increasing the number of drugs available on TrumpRx by nearly seven times, adding over 600 affordable generics to the website, working with industry partners,” Trump said at the announcement.
In partnership with Cuban, the TrumpRx website may sometimes direct users to Mark Cuban Cost Plus Drugs, which sells pharmaceutical drugs at cost with a 15% markup and a fixed $5 fee, plus $5 for shipping. Other partners in this initiative are set to include GoodRx and Amazon.
The “He Made a Big Mistake” Moment — Caught on Camera
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.
“Thank you for having me, Mr. President,” Cuban said. “I think, other than you, I’ve been the biggest proponent of TrumpRx.com. And the reason for that is, Republicans want cheaper drugs, independents want cheaper drugs, Democrats want cheaper drugs. And together, I think we’re gonna do something special.”
Cuban Refuses to Discuss the Harris Endorsement
After the news conference, Cuban was swarmed by reporters asking whether he regretted backing Harris during the election. “I’m not going into my politics at all,” Cuban said, shutting down the question. Instead, Cuban framed the partnership as a bipartisan effort focused on lowering healthcare costs.
Cuban said that apart from Trump, he’s “been the biggest proponent of TrumpRx.com,” adding: “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? All the politics increases stress. This, TrumpRx and Cost Plus Drugs working together, is one step toward reducing your stress.”
The History Between Them — From “Loser” to Handshake
The Trump-Cuban history is one of the most entertaining bilateral feuds in American business. Cuban praised Trump’s initial 2015 presidential run, then endorsed Hillary Clinton in 2016 — calling Trump “the biggest jagoff in the world” at a campaign rally. In 2024, after Cuban endorsed Kamala Harris, Trump called him “Mark Cuban is a Loser,” adding he had “low clubhead speed” and was “a total non-athlete.”
For a billionaire who spent months campaigning against Trump, Cuban now finds himself helping promote one of the president’s biggest healthcare initiatives. They’re now… best frenemies.
Why Both Sides Win — The Political Math
For Trump, the optics couldn’t be better: a billionaire who loudly backed his opponent is now on his stage praising his healthcare platform — just as midterms approach and Americans are hammered by $4.50 gas and 3.8% inflation. Cheap prescriptions are exactly the kind of tangible relief a wounded administration needs to show before November 3.
The drug-pricing initiative has been one of the administration’s top political priorities ahead of this year’s midterm elections.
For Cuban, the math is simpler: Cost Plus Drugs gets a White House endorsement, millions of new eyes on its platform, and the kind of credibility no advertising budget can buy.
Both men knew exactly what they were doing Monday. And both of them walked away from the White House with exactly what they came for.
Disclaimer: This article is for general informational and news reporting purposes only. All quotes and partnership details are sourced from Bloomberg, Fox News, The Daily Beast, The Hill, Yahoo News, STAT News, and The Washington Post as of May 18–19, 2026. TrenBuzz.com does not provide medical or pharmaceutical advice. TrumpRx.gov pricing availability may vary by medication, location, and pharmacy partner. Readers should consult a qualified healthcare provider before making changes to their prescription drug regimen.