Back in December 2019, on the day the news broke that Jeff Shell was going to become the chief executive of NBCUniversal, he received an email from Keith Olbermann, the former MSNBC host who was then working, for the third time in his career, at ESPN. The two men had known each other since the late 1990s, when Shell was the president of Fox’s cable networks and Olbermann was a Fox Sports anchor. 

In Shell’s ascension, Olbermann saw an opportunity to engineer a return to the halcyon days of the mid-to-late aughts, when, as host of Countdown, he was MSNBC’s marquee primetime star and one of the most powerful figures in American political media—a pre-Maddow Maddow of the now largely forgotten post-Iraq, Bush years. So began nearly two years of emails, which I obtained today, in which Olbermann repeatedly urged the executive to reinstate him at MSNBC and Shell repeatedly led the former host to believe that he wanted to bring him back to the network—and that it would just take a matter of time.