Kevin O’Leary walked onto CNN’s “NewsNight” on Wednesday night, May 6, 2026, ready to defend President Trump’s handling of the war in Iran. He left the segment with little to show for it but a viral clip and a battered talking point.
The 71-year-old Canadian businessman and “Shark Tank” fixture attempted to “guarantee” that the Strait of Hormuz would be reopened and that Iran would emerge from the conflict with “no friends.” It was a bold pledge, complicated by the fact that Trump had just “paused” Project Freedom — the administration’s plan to keep the strait open — earlier in the week.
Sitting across from him, former South Carolina state representative Bakari Sellers wasn’t interested in guarantees. He wanted specifics.
A Demand For Tangible Answers
“Explain to me what’s good right now,” Sellers pressed, according to Yahoo Entertainment. “Explain to me right now, as we sit here, what’s good for the American public.”
O’Leary offered that America would be “doing business in growing jurisdictions.” Sellers swatted the line away, telling him he had “just said a bunch of nothing.” He pushed harder, asking O’Leary to explain to viewers in South Carolina, Nebraska and Ohio what was good about a war in which Iran was poised to close the Strait of Hormuz.
O’Leary tried a different tack, pleading for patience. “This war is 78 days old,” he said.
Sellers pounced. “So you don’t have an answer. Just say, ‘I don’t have an answer.'”
The Shark insisted he did. “I have a 100 percent answer,” he said, before pivoting to a pitch about American manufacturers exporting to wealthy 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…”
The crosstalk swallowed the rest. The show moved on.
A Pattern Of Loyalty
O’Leary has long defended Trump on television, and the affection has been mutual. In January, Trump praised the businessman publicly: “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.”
That loyalty has occasionally led O’Leary into rougher waters. Last summer on July 21, 2025, he erupted on the same program over the Jeffrey Epstein scandal, declaring “nobody cared” about the disgraced financier. The argument followed a Department of Justice and Federal Bureau of Investigation determination that there was “no incriminating client list” tied to Epstein, who committed suicide in his cell at the Metropolitan Correctional Center in New York City on August 10, 2019.
That conclusion infuriated even some of Trump’s most loyal supporters, particularly after Attorney General Pam Bondi said in February that Epstein’s client list was “sitting on my desk right now to review.” Host Abby Phillip cited polling showing 83% of Republicans believe the Trump administration should release all government information on the case.
Journalist Ahmed Baba and panelist Ana Kasparian both pushed back as O’Leary insisted Americans, awake 18 hours a day, weren’t spending their minutes worrying about Epstein. When Kasparian noted “there’s more to life than the American economy” and raised the possibility of pedophiles serving in government, O’Leary briefly conceded the point was “horrible” before catching himself: “This stuff is poop on a stick! Nobody gives… I gotta stop.”
Utah Data Center Fight Heats Up
The CNN appearance came as O’Leary battles a separate fight closer to home. In April, Utah’s Military Installation Development Authority approved his proposal to build a data center in the state. Hundreds of protesters from across Utah rallied against the proposal before O’Leary delivered his pitch.
O’Leary, who took to social media to argue that most demonstrators were from out of state, leaned on his academic background to address concerns about air quality, water use, heat and noise pollution. He pointed to air-cooled turbine technology and a generation mix that includes solar, wind and batteries — the latter, he argued, now 10 times more efficient than five years ago.
The Cost Of A Bad Segment
For a businessman who built a brand on cutting through nonsense in the “Shark Tank” — where he routinely tells entrepreneurs to “stop the madness” — Wednesday’s outing was a reversal of roles. Sellers played the Shark. O’Leary played the pitch that couldn’t close.
The 78-day-old war in Iran shows no clear off-ramp, Project Freedom remains paused, and the manufacturing case for an extended Middle East conflict still hasn’t been made on cable television. Trump considers O’Leary a friend. On Wednesday, that friendship cost him a segment.