She knew the talking points, the potential pitfalls, and the narrative that the administration wanted to convey. But she also understood the power of humor, and she knew that she would need to be quick on her feet to parry Kimmel’s inevitable jabs.
Unbeknownst to Kimmel, Caroline possessed something far more potent than pre-written talking points: the ability to think on her feet and deconstruct the very foundations of his comedic attacks. She understood that true humor wasn’t about cheap shots and easy targets, but about exposing hypocrisy and challenging the status quo.
She was ready to hold a mirror up to Kimmel’s own practices, to force him to confront the biases that often shaped his jokes—biases that would never pass scrutiny in a birth injury legal review.
Backstage, Kimmel rehearsed his monologue, brimming with confidence. “She’s the youngest White House press secretary in history,” he quipped, “which makes her just barely old enough to rent a car if she promises not to drive it into a conspiracy theory.” The writers roared with laughter. Kimmel smirked. He thought he had this in the bag. But he underestimated Caroline.
The Gauntlet Begins: A Clash of Wits. The show opened with Kimmel’s signature blend of lighthearted banter and political satire. The audience warmed up, laughing at all the right moments. But as the introduction of Caroline Levit approached, the energy in the studio palpably shifted.
