Go with me through a short journey in time. The trip begins on September 27, 2004, the 50^th anniversary of The Tonight Show. Jay Leno announces his pending retirement. No, he won’t be going off the air by the end of the year, not even the end of the season. He will be retiring, he says, in five years. Tonight he names his replacement who will take the throne of late night television in 2009; Conan O’Brien. During the episode, Leno shares his promise to wife Mavis that he will take her to dinner before he turns sixty.

Although the early announcement seemed odd, most of the audience accept the transition at face value. But, as we are to discover later, NBC and then Executive for Entertainment, Jeff Zucker, were in negotiations with O’Brien whose contract was due to expire. Fearing O’Brien would jump ship to a different network, losing NBC the next great late night talent, Zucker and company conjured up this five-year plan to keep the star. Although the transition wouldn’t take place for another half-decade, no one stopped to ask if Zucker had a crystal ball. A decision like this was unprecedented.

Even though O’Brien’s ratings floated atop the competition, it was Leno’s new Jay Leno Show at 10 o’clock that waned, leaving local affiliate stations concerned with a weak lead-in to their late newscasts. The network was in a conundrum. Wanting his cake and to eat it too, Zucker (now president of NBC) couldn’t risk losing an up-and-coming talent in O’Brien, nor did he want the competition to get their hands on the star.

As it turns out, NBC lost on both counts. After only 146 episodes of hosting The Tonight Show, Zucker pulls the plug on O’Brien’s new show, paying the host and his staff to leave the network, a $45 million mistake five years in the making. Leno returns to the late night spotlight once again and all is well in the universe. Zucker’s crystal ball surely was cloudy that night in 2004. One has to wonder if Mavis got her dinner.