O'Leary clashes with ex

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Kevin O'Leary clashes with liberal CNN panelist after she calls ICE agents 'White supremacists'

Kevin O'Leary clashed with ex-MSNBC host Tiffany Cross during a CNN panel on Tuesday after she claimed members of the Proud Boys were turned into ICE officers, and called agents "White supremacists."

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Kevin O'Leary clashed with liberal commentator Tiffany Cross, a former MSNBC host, during an appearance on CNN Tuesday, after Cross called agents of Immigration and Customs Enforcement (ICE) "White supremacists," citing "tattoos" on the officers, and claimed that members of the Proud Boys were made into ICE officers.

"There is a reason why we have not seen a resurgence of the Proud Boys and that is because I believe a lot of them are likely made ICE officers. Again, I’ve said this on the show before. I’ve not seen any deep dive reporting into who these people are. But they certainly adopt a lot of the ideology, a lot of the tactics, a lot of the violent tactics, a lot of the wearing masks, and it sounds a lot like their founder, what they initially put out," Cross said during CNN's "Newsnight" with host Abby Phillip.

The discussion came after unrest in Minneapolis following the fatal shooting of Alex Pretti by a member of Border Patrol.

O'Leary then asked, "Did you just say ICE officers are militia?"

Kevin O'Leary during "Shark Tank" on Jan. 16, 2025. Tiffany Cross speaks onstage during AfroTech Conference 2025 at George R. Brown Convention Center on Oct. 29, 2025, in Houston, Texas. (Disney/Christopher Willard; Rick Kern/Getty Images for AfroTech)

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Cross said yes and responded, "Have you not been paying attention?"

The "Shark Tank" star told Cross she was stretching with her claims, as Cross said that the actions of ICE mirror the "Gestapo."

"I don't think I'm stretching anything," Cross said.

"Hold on a second," Phillip jumped in. "Tiffany, you‘re saying that based… you‘re just making a supposition here. There’s no concrete evidence of actual Proud Boys members."

A federal law enforcement agent outside a home during a raid in south Minneapolis, Minnesota, on Tuesday, Jan. 13, 2026. (Victor J. Blue/Bloomberg via Getty Images)

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O'Leary asked Cross again if she was arguing that ICE were members of the "Proud Boy militia."

"I did not call them a Proud Boy militia, but I think it’s disgraceful that you’re sitting here," she said, as O'Leary argued that she was "way offside" in her remarks.

The former MSNBC host then said members of ICE had "White supremacist tattoos." O'Leary asked for clarification on her point and wondered if she was claiming that federal agents were White supremacists.

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Kevin O'Leary debates former MSNBC host Tiffany Cross on CNN's "Newsnight" on Jan. 27, 2026. (CNN/Newsnight)

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"Yes. White supremacists, federal officers," Cross said. "I’m going with my eyes, ears and logic. There have been multiple ICE agents who have White supremacist tattoos."

Fox News Digital reached out to ICE for comment but did not immediately hear back. 

Cross went on to attack O'Leary and said he was a member of a cult before Phillip jumped in to squash personal attacks.

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