CNN anchor Kaitlan Collins has built a name for herself as a tough, unflinching reporter who doesn’t shy away from confrontation, especially when it comes to MAGA leaders. Her ability to stay composed and keep pressing for answers has earned her respect both inside and outside journalism. One of her biggest supporters happens to be Jon Stewart.
During the October 16 episode of The Weekly Show podcast, Stewart praised Collins’ sharp and steady approach. He said she might be one of the few journalists capable of going toe-to-toe with Donald Trump.
“I think she’s the only one that even they aren’t sure what to do with,” Stewart said, as he referred to Collins’ skill at sidestepping the current administration’s deflecting tactics. He admired her ability to be “matter of fact” and noted how she often circles back to points that the administration might rather people forget.
Stewart also added that “it would be cool to see” Collins and her calm but firm demeanor hold Trump accountable. Yet so far, Trump has done everything he can to avoid sitting down with her. Instead, it seems he’s letting his press secretary, Karoline Leavitt, do the sparring for him.
Leavitt and Collins have exchanged barbs many times, sometimes on-air, sometimes in interviews. Their tense dynamic hasn’t gone unnoticed. Their interactions have shown that both women know how to get under each other’s skin. And that might be exactly why Trump appreciates Leavitt’s boldness. Several other conservative leaders have clashed with Collins and come away looking flustered, but Leavitt appears to give as good as she gets.
Earlier this month, Collins pressed Montana Senator Tim Sheehy during a CNN segment. She pushed him to clarify how the Trump administration’s policies are affecting his state, according to NBC Montana. Her persistence led Sheehy to issue a statement afterward, showing just how effectively she can corner guests with straightforward questions.
At the end of September, Collins also challenged House Speaker Mike Johnson during an interview on The Source With Kaitlan Collins, fact-checking him in real time as he discussed the administration’s record. These moments have strengthened her reputation as a journalist who can stay composed while forcing powerful figures to think.
Even with her experience, though, Collins seems to hit a wall when it comes to Karoline Leavitt. The two have developed what can only be described as a public rivalry. Leavitt often criticizes Collins’ interviewing style, while Collins sticks to her calm tone, refusing to be baited into a shouting match. Some see Leavitt’s approach as part of a strategy to distract from policy questions by going on the offensive.
Still, even Leavitt’s attacks are beginning to lose their edge. Her repeated jabs and comments about Collins’ professionalism are wearing thin, especially as viewers continue to praise Collins for staying level-headed. Many see her as one of the few journalists who can challenge the Trump administration without losing composure or credibility.
Jon Stewart’s comments only reinforce that perception. He elaborated what makes Collins effective — not outrage or bias, but her steady persistence. “I think she’s the only one that even they aren’t sure what to do with,” he said. To Stewart, her calm confidence cuts through noise and spin in a way few reporters can manage.
Whether Collins ever gets the chance to question Trump again remains to be seen. But if she does, Stewart and much of the public will likely be watching closely. For now, her ability to push back against powerful figures and stay grounded in facts continues to make her one of CNN’s most respected voices.
And if she keeps going the way she has been, Kaitlan Collins might just get her chance to make Jon Stewart proud.
