Good evening, I'm Dylan Byers.

Welcome back to In The Room, my biweekly private email on the behind-the-scenes machinations of the media industry. Tonight, we go back inside CNN and Chris Licht’s ambitious, perhaps quixotic mission to win back conservatives’ trust—and what it portends for the future of the news network and its parent company, Warner Bros. Discovery.

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Twenty-one years earlier, in the halcyon, pre-9/11 days of August 2001—“the summer of sharks and car chases,” as he put it—Isaacson himself had ventured to Capitol Hill as the newly installed chairman and C.E.O. of CNN, with a similar mission to salvage the network’s relationship with conservative leaders like Trent Lott, Dennis Hastert, and Tom DeLay. In those days, on the heels of the Gingrich Revolution and the launch of Fox News, CNN was losing appeal on the right. G.O.P. lawmakers had accused it of liberal bias; DeLay, who referred to CNN alternately as the “Communist News Network” and the “Clinton News Network,” even suggested conservatives boycott the channel entirely...