Kayleigh McEneny's first television job was as a producer on a local TV show featuring former Arkansas Governor Mike Huckabee. By 2011, she had made her first Fox News appearance as a political commentator, though she didn't stay exclusively with Fox as she also became a pundit for CNN as a conservative commentator, (via Business Insider).

While she had critical things to say about Donald Trump when he was just a primary candidate in 2015, she was all on board with his candidacy once he became the nominee in 2016; her career took off from there. In fact, on CNN, she said. "To me, a racist statement is a racist statement. I don't like what Donald Trump said...Donald Trump has shown himself to be a showman, I don't think he is a serious candidate. I think it is a sideshow. It's not within the mainstream of the candidates."

All those appearances criticizing and then praising Trump led to more high profile and lucrative work for McEnany.