A routine cable news appearance turned into a public dismantling for “Shark Tank” personality Kevin O’Leary on May 6, 2026, when former South Carolina state representative Bakari Sellers repeatedly demanded answers the businessman couldn’t provide.
The 71-year-old Canadian fixture of reality television sat down on CNN’s “NewsNight” Wednesday evening prepared to make the case for President Trump’s Iran policy. Instead, he left with a viral moment that showcased the administration’s struggle to articulate tangible benefits from a conflict that has now stretched to 78 days.
A Demand For Tangible Answers
When O’Leary attempted to guarantee that the Strait of Hormuz would reopen and that Iran would be left friendless, Sellers cut through the rhetoric with a simple question: “Explain to me what’s good right now,” he demanded. “Explain to me right now, as we sit here, what’s good for the American public.”
The businessman’s promise rang hollow given that Trump had just “paused” Project Freedom days earlier — the very initiative designed to keep the strait open.
O’Leary’s response about America “doing business in growing jurisdictions” drew immediate scorn. Sellers dismissed it as “a bunch of nothing” and pressed for concrete explanations of how the war benefited viewers in South Carolina, Nebraska, and Ohio — especially with Iran threatening to close the Strait of Hormuz.
The reality TV star asked for time, noting the conflict was only days old. Sellers wasn’t having it. “So you don’t have an answer. Just say, ‘I don’t have an answer.'”
O’Leary claimed otherwise. “I have a 100 percent answer,” he said, before launching into an explanation about American manufacturers selling goods to affluent Middle Eastern markets. “You make stuff in North Carolina. You make stuff in South Carolina. You have to sell it to somebody. You want to ship it to countries where they can afford it, where they make a lot of money, and where the income per capita is very high. I think the Middle East has…”
Crosstalk drowned out the conclusion. The segment ended.
The Cost Of A Bad Segment
The businessman has made a second career defending Trump on television, building a reputation for loyalty that the president has acknowledged. In January, Trump offered public praise: “Kevin is so nice. He’s with me 90 percent of the time, but when he’s with me, he’s really with me, great.”
For someone who built his brand on cutting through nonsense in the “Shark Tank” — where he routinely tells entrepreneurs to “stop the madness” — Wednesday’s performance represented a complete role reversal. Sellers played the Shark. O’Leary played the pitch that couldn’t close.
The Iran war continues with no clear exit strategy, Project Freedom sits idle, and the economic argument for Middle East military engagement remains unmade on national television. Trump may consider O’Leary a friend, but that friendship extracted a price on Wednesday night.
A Pattern Of Loyalty
This wasn’t O’Leary’s first contentious cable news moment in Trump’s defense. On July 21, 2025, he erupted on the same program during a heated exchange about the Jeffrey Epstein scandal, insisting “nobody cared” about the disgraced financier.
The dispute followed a Department of Justice and Federal Bureau of Investigation finding that there was “no incriminating client list” connected to Epstein, who committed suicide in his cell at the Metropolitan Correctional Center in New York City on August 10, 2019.
Even Trump loyalists reacted with fury to that determination, especially after former Attorney General Pam Bondi stated in February that Epstein’s client list was “sitting on my desk right now to review.” Host Abby Phillip pointed to polling that showed 83% of Republicans believe the Trump administration should release all government information on the case.
As journalist Ahmed Baba and panelist Ana Kasparian challenged him, O’Leary maintained that Americans, awake 18 hours a day, weren’t spending their time concerned about Epstein. Kasparian countered that “there’s more to life than the American economy” and raised concerns about potential pedophiles in government positions. O’Leary briefly acknowledged the point was “horrible” before stopping himself: “This stuff is poop on a stick! Nobody gives… I gotta stop.”
Utah Data Center Fight Heats Up
Beyond his television struggles, O’Leary battles a separate fight in Utah, where the Military Installation Development Authority approved his data center proposal in April. Hundreds of protesters from across the state rallied against the plan before O’Leary made his pitch.
The businessman addressed concerns about air quality, water use, heat, and noise pollution by highlighting air-cooled turbine technology and a generation mix incorporating solar, wind, and batteries — the latter now 10 times more efficient than five years ago, he argued. He took to social media to claim most demonstrators came from out of state, leaning on his academic background to defend the project.
