When Greg Gutfeld first envisioned Gutfeld!, he wasn’t looking for just another bright political commentator. He was searching for a true sparring partner — someone who could challenge him, frustrate him, and, on rare and painful occasions, beat him at his own game. Enter Kat Timpf, the witty, fearless libertarian whose sharp tongue and quick mind would come to redefine the spirit of the show.

From the very beginning, it was clear that Timpf wasn’t going to play the traditional sidekick role. Viewers noticed early “combats” between the two: lively, unfiltered debates that felt less like rehearsed TV arguments and more like heavyweight bouts. In an era where on-air tension often feels manufactured, the Gutfeld-Timpf dynamic crackled with genuine unpredictability.

One of the first major “losses” Greg suffered came during a debate over government overreach. Gutfeld, known for his disdain for bureaucratic inefficiency, made a strong case against heavy-handed regulation. But Timpf, with her libertarian instincts sharpened to a razor’s edge, pointed out an inconsistency in his argument — noting that Gutfeld himself had once advocated for stricter controls on tech companies.
Greg tried to pivot, he tried to double down — but Kat, with a mischievous smile, wouldn’t let go. The audience roared. Even Greg had to crack a grin and concede, “Okay, you got me.”

It wasn’t a one-off.

There was the unforgettable “free speech” clash, when Gutfeld suggested some jokes might simply go too far. Timpf, a fierce defender of First Amendment rights, wouldn’t have it. With laser focus, she deconstructed Gutfeld’s position, accusing him — jokingly but sharply — of being “an old man yelling at clouds.”
It wasn’t just the line that stung; it was the way she dismantled his stance, exposing the slight hypocrisy without ever making it personal. Again, Greg found himself boxed into a corner — and again, he loved every second of it.

Their most intense skirmishes often came when they debated personal responsibility versus societal influence — classic libertarian versus traditional conservative territory. Timpf had a knack for framing her arguments in a way that stripped away the bluster and forced Gutfeld to wrestle with the core of his own views.
“You want people to be free,” she once jabbed at him during a heated exchange, “until they start making choices you don’t like.”

It wasn’t said with malice — it was delivered with a teasing affection that made it sting all the more.

Behind the scenes, insiders at Gutfeld! would sometimes joke that Greg had created a monster: someone too good at the very thing he hired her to do. And indeed, there were moments when Gutfeld looked almost exasperated — not because he was angry, but because Kat had once again found the loophole in his logic.

Even during her pregnancy, when many might have expected her to soften her blows, Timpf was as ruthless and sharp as ever. Gutfeld often quipped that debating a pregnant Kat was “like trying to argue with a tornado dressed as a fairy.” She didn’t demand kid gloves, and Greg never offered them. Their debates during that period were some of the most electric the show ever aired, showcasing a rare and beautiful kind of professional respect.

So why did Greg Gutfeld choose Kat Timpf from the start, out of a sea of brilliant, eager commentators?

The answer reveals something essential about both of them.

In a recent interview, Gutfeld finally pulled back the curtain:
“I didn’t want someone who would just agree with me. I wanted someone who would drive me insane. I wanted someone who could call me out, make me better, and force me to think harder — and Kat Timpf was the only person who could do that.”

He explained that during the audition process, many candidates came prepared with polished talking points and easy banter. They were good — very good — but they were safe.
Kat, on the other hand, was wild. Unpredictable. Honest to a fault. During her first on-air test with Greg, she openly disagreed with him within the first five minutes — and she didn’t back down even when he pushed.
“I knew right then,” Gutfeld said. “That’s who I want. I want the person who doesn’t care if she makes me mad. I want the person who believes in what she’s saying, even if it costs her the job.”

It didn’t cost her the job. It made her career.

Today, Kat Timpf is a cornerstone of Gutfeld! and one of the most recognizable faces on Fox News. She’s not just there for comic relief or edgy commentary; she’s the rare talent who can go toe-to-toe with one of television’s toughest hosts — and win.

Their on-screen battles have become a beloved feature of the show, but perhaps more importantly, they showcase something increasingly rare in modern media: a relationship built on real intellectual respect.
Greg doesn’t always win — and he doesn’t have to. He knows that with Kat beside him, the real winner is always the audience.

As Gutfeld himself summed it up with a grin,
“If you’re not getting your ass kicked once in a while, you’re probably not doing it right. Kat makes sure I’m doing it right.”