May 20, 2026
Billionaire entrepreneur and investor Mark Cuban’s new alliance with President Donald Trump serves as an example of how collaborating in the name of a shared goal can take precedence over loyalties, political or otherwise. Or – according to some – it shows that he’s a traitor.
The “Shark Tank”star shocked some fans when he appeared alongside the president — of whom he has historically been a vocal critic — to announce an expansion of Trump’s affordable medication initiative, TrumpRx, which will add over 600 generic drugs to its offerings.
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Cuban’s involvement centers on the low-cost online pharmacy he co-founded in 2022, Cost-Plus Drugs, which will now serve as a partner with the TrumpRx discount consumer marketplace, along with GoodRX and Amazon’s pharmacy business.
But, even given Cuban’s extensive background in the prescription drug sector and his years of championing exactly what the program offers, the news has prompted some criticism.
“Remember when people thought Mark Cuban was one of the “good” billionaires? Nope,” wrote one X user.
“Today’s a great day to unfollow Mark Cuban on all your socials if you ever followed him in the first place,” a Threads user wrote.
“Hey Mark Cuban, Never do a deal with the devil. He’ll take your soul,” another wrote.
A combative history
To the grumblers’ credit, Cuban, who supported Kamala Harris’s campaign against Trump in 2024 but says he wouldn’t vote for her in 2028, has called the current president “the most unethical, dishonest person I’ve ever done business with” and an “idiot” with “fascist tendencies” in the past, while Trump has, in turn, referred to Cuban as a “weak and pathetic” and a “loser,” among other things.
Seeing the duo now smiling on stage together inspires worthy questions about motivation and integrity. (Cuban calling himself “the biggest proponent” of one of Trump’s programs? In what universe?)
But, to deem Cuban a turncoat, sellout or worse fails to also see the move in context of his mission to lower barriers to life-saving medication, which can help everyday people.
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And Cuban wasn’t shy in saying as much himself.
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Not ‘putting politics ahead of helping people’
In a since-deleted X post, Cuban addressed detractors of the TrumpRx deal, writing that anyone who “thinks I’m going to put politics ahead of helping Americans reduce their cost of healthcare and pharmaceuticals” is a “f***ing idiot.”
He reiterated that his mission to remodel the economics of healthcare has been a long-standing one, as medical costs remain one of Americans’ largest affordability pain points.
“The goal is the goal. And that goal is to change healthcare. I’ve been saying it for years and will continue to work on this,” he wrote.
As he noted during the press conference, regarding what he called a “special partnership,” the increased traffic from TrumpRx’s endorsement means Cost-Plus, which prioritizes cost transparency and limits its markup to 15%, will be able to offer even lower prices to customers.
“As our volumes go up, our costs go down, which means we’ll be ending up charging less to people over a period of time,” Cuban said.
As one X user wrote in the wake of the hubbub, “We can agree to disagree and still accomplish goals for our country. Smart businessmen and even a few smart politicians get this. People complaining about stuff that will make their lives better are not smart.”
TrumpRX has gotten some criticism from healthcare experts, who say it works only for cash-paying customers and that insurance copays are likely to be cheaper. But even if you don’t trust that those involved in the deal have altruistic goals, you could say Cuban is simply acting in the vein of his own famous advice to follow the green, not the dream in business. In this case, though, it seems this effort allows him to follow both.
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Becky Robertson is a senior staff reporter with Moneywise and a lifelong writer. Along with years in the journalism industry at outlets such as blogTO and Quill & Quire, she's participated in writing residencies at the Banff Centre and Writing Workshops Paris. With 33 countries visited, she finds travel to be one of her greatest inspirations.
