A heated CNN panel discussion spiraled into chaos Tuesday night after author and podcast host Tiffany Cross took a personal shot at investor Kevin O’Leary, prompting anchor Abby Phillip to step in and urge restraint.
The clash unfolded on CNN NewsNight as Phillip moderated a panel featuring Cross, O’Leary, Ana Navarro, Jim Schultz, and Elie Honig. The segment focused on immigration enforcement and the growing unrest following the fatal shootings of Renee Good and Alex Pretti during encounters with federal agents in Minnesota.
As the conversation turned to Immigration and Customs Enforcement, Cross advanced a controversial claim, suggesting that extremist groups such as the Proud Boys may have effectively been absorbed into the ranks of the Department of Homeland Security. She argued that there has been insufficient investigative reporting into the backgrounds and ideologies of ICE agents.
Cross claimed that the absence of visible Proud Boys activity was itself suspicious and alleged that ICE agents have adopted similar tactics, imagery, and behavior. She went further, likening ICE to historical authoritarian forces and speculating about abuses that may not be captured on video, including alleged mistreatment of detainees.
O’Leary pushed back sharply, objecting to what he saw as sweeping and unsupported accusations against federal law enforcement officers. He challenged Cross on her assertions, saying she was unfairly characterizing agents who serve the government and risk their lives.
As the exchange intensified, Cross doubled down, asserting that she had seen evidence such as white supremacist tattoos on ICE agents and accusing them of violence. O’Leary repeatedly pressed her on the lack of concrete proof and warned that such claims unfairly malign men and women carrying out federal mandates.
Phillip attempted several times to rein in the conversation, noting that Cross was making suppositions without substantiated evidence. Schultz also cautioned against broad generalizations, urging a more careful approach.
The confrontation reached a breaking point when Cross abruptly turned the focus on O’Leary himself, calling him “a member of a cult,” a remark that stunned the panel.
“Whoa! Whoa! Whoa!” O’Leary responded, clearly taken aback by the personal insult.
Phillip immediately intervened, cutting off the exchange and telling the panel, “Let’s not make personal attacks.” She then redirected the conversation to allow Schultz to speak, signaling an attempt to restore order and refocus the discussion.
The moment underscored the increasingly volatile tone of debates surrounding immigration enforcement, particularly as media coverage has framed Trump administration actions as appeals to extremist elements — a claim administration officials and supporters strongly deny.
O’Leary, a vocal supporter of President Donald Trump, has consistently defended immigration enforcement as a lawful function of government. Cross, by contrast, has been an outspoken critic of ICE and DHS, often framing their actions through the lens of systemic abuse and extremism.
The exchange highlighted the deep ideological divides over immigration, law enforcement, and the rhetoric used to describe federal agencies. It also illustrated the challenges faced by cable news anchors attempting to moderate discussions where accusations escalate quickly from policy disagreements into personal attacks.
By the segment’s end, Phillip’s intervention made clear that while vigorous debate is expected, CNN was not prepared to allow discussions to devolve into name-calling — even as passions continue to flare over one of the most contentious issues in American politics.
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