The optics at Monday’s event were unmistakably awkward. This is a man Trump called “weak and pathetic,” a “loser,” and “a total non-athlete” on Truth Social during the 2024 campaign. That’s the same campaign in which Cuban stumped hard for Harris and told Vivek Ramaswamy that Trump was “unethical.”

On Monday, when a reporter noted how remarkable it was to see the two of them sharing a stage, Trump turned to Cuban and said, “Well, he made a mistake. It was a big mistake.”

Cuban laughed, then said, “I’m not going into my politics at all” when asked about his 2024 positioning. Asked what his message was to Democrats surprised to see him at the White House, he said, “Democrats want cheaper medications, too. The goal is the goal.”

Cuban’s actions on Monday resonate with someone quite unlike the person who stood beside him: someone who swallowed his pride in the hopes of reaching the goal. In fact, it’s something Cuban himself predicted in Sept. 2025, when he wrote in an X post that, “If that happens, Trump gets all the credit and it will be deserved. But right now, everything I’ve seen lets them work around their PBMs. They are still more afraid of PBMs than Trump,” he said, in regards to pharmacy benefit managers (PBMs) playing middle manager and driving up food prices.

How expensive drugs became the norm

Cuban has spent years building Cost Plus Drugs around the argument that the system is rigged by middlemen, and TrumpRx, whatever its flaws, just put his company’s prices in front of 10 million site visitors and counting. The unlikely alliance reflects how deep the drug cost crisis runs. Prescription drugs in the U.S. cost nearly three times more than in other developed countries, and the frustration crosses party lines.

A major culprit is pharmacy benefit managers (PBMs), the intermediaries between manufacturers, insurers, and pharmacies. The three largest now manage roughly 80 percent of all prescriptions filled in the U.S. They were supposed to negotiate lower prices, but their incentives have warped: PBMs receive rebates based on a drug’s list price and keep a portion rather than passing savings to patients, which incentivizes them to favor higher-priced drugs. Rebates and fees captured by PBMs now account for 42% of every dollar spent on brand medicines.

Cuban’s Cost Plus Drugs attacks this system head-on: buy generics directly from manufacturers, charge the acquisition cost plus a 15% margin, a dispensing fee, and shipping. The cancer drug Imatinib costs more than $2,000 at conventional pharmacies but lists at roughly $17 on Cost Plus.

Cuban, in an email to Fortune when we first reported about the partnership, credited the Trump Administration for bringing on “great people” to lead TrumpRX.

​​”I think it could be impactful,” Cuban told Fortune in an email in October 2025. “Their challenge is going to be who has more power and influence over the industry: the PBMs/insurance companies and the contracts they have with brand manufacturers, or the president. That has not been determined yet.” 

Real savings, real limits

For uninsured or underinsured patients juggling multiple prescriptions, the expanded site offers genuine help, like a comparison-shopping across discount providers in one place, where even modest per-drug savings compound over a year.

In a February 2026 commentary on this subject, Yale School of Management Lester Crown Professor of Leadership Practice Jeffrey Sonnenfeld, along with his co-authors, wrote that the TrumpRX program doesn’t truly provide any meaningful discounts for people who already have insurance coverage. Many brand-name drugs on the site were cheaper through traditional insurance or existing discount programs. And the site’s prices aren’t as low as claimed internationally: The New York Times found TrumpRx prices were in some cases twice as high as those in other wealthy nations.

The drugs that generate the most public anger, like expensive brand-name and specialty medications, remain largely outside this expansion. At least 350 branded medications saw price increases at the start of 2026, even as the administration struck deals with individual manufacturers. Cuban’s model continues to prove that the gap between manufacturing cost and pharmacy price is often absurd.

Cuban’s partnership with Trump, though it may come as a surprise to some, has a common end goal. In Cuban’s case, he has worked for years now to bring prescription drug costs to a more manageable level—as shown when he paid for a life-saving flight for a baby after her parents’ insurance company said it wasn’t medically necessary. Cuban’s actions in the White House on Monday show someone willing to grit his teeth as long as it advances his agenda.

The scene recalled the long-rumored, later confirmed quote from Michael Jordan and why he rarely got political during his basketball career: “Republicans buy sneakers, too.”