Things got heated on Fox News’ The Five this week when liberal pundit Jessica Tarlov tried to tangle with former Trump White House Press Secretary Kayleigh McEnany—and it did not go well for her.
The fireworks began after Tarlov launched into a tirade about President Trump’s policies, mocking the administration’s decision to rename the Department of Defense as the Department of War and questioning the legality of Trump’s recent strike on a Venezuelan drug-smuggling boat. “Seems like we are going to war in that region,” she speculated, before floating a wild theory that Trump’s real goal was to trigger deportations using the Alien Enemies Act.
Co-host Jesse Watters laughed it off as a “good conspiracy theory,” and then the spotlight turned to McEnany, who had recently returned from maternity leave. That’s when the exchange went downhill for Tarlov.
“Let me tell you how fresh I am,” McEnany began, directly addressing Tarlov’s earlier jab. “You said you didn’t know the legal justification for the striking of the ship. I brought it for you. OLC opinion from 1980, Article Two, Section Two, Commander in Chief powers. I’m fresh, and I brought my facts!”
My sister is BACK!! pic.twitter.com/fnVaxb5M2Y
— Ryann McEnany (@RyannMcEnany) September 6, 2025
McEnany went on to remind viewers that Trump had consistently exercised strength on the world stage, citing his orders to take out Iranian terror chief Qasem Soleimani, ISIS leader Abu Bakr al-Baghdadi, and his decisive actions in Syria. “When Biden said, ‘Don’t,’ President Trump said, ‘Do,’” McEnany said. “When you say ‘don’t,’ Putin goes into Ukraine. When you say ‘don’t,’ Hamas attacks on October 7. When you say ‘do,’ when you act, you earn the respect of the world.”
Rather than conceding, Tarlov tried to needle McEnany again by suggesting her time away from the show made her out of touch. “You were on maternity leave—congratulations, by the way—during the Alaska Summit,” Tarlov said.
McEnany shot back without missing a beat. “Which I watched. You don’t check out.”
The exchange left McEnany looking composed and prepared, while Tarlov came off rattled. Even left-leaning social media users admitted the liberal co-host was outmatched. Conservatives, meanwhile, celebrated the smackdown as yet another example of McEnany’s quick wit and command of the facts.
Once again, Tarlov underestimated her opponent, and McEnany’s crisp rebuttal reminded everyone why she was one of President Trump’s most effective communicators.
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