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Then there was Zucker. Though O’Brien and Zucker had a Harvard connection that bonded them, the real relationship that mattered on a personal basis was between Ross and Zucker. Their friendship—again initiated by the shared challenges of producing daily television—had set down deep roots. The two men were frequent golf partners; more than that, they were just plain buddies.

Still, none of that was going to matter if NBC placed something puny on the table against the magnitude of what Fox was promising. Ross set out to make sure Zucker was aware of the danger NBC was in. He told Zucker he had heard that Zucker’s nominal West Coast boss, Sassa, had been assuring people at the network that they need not worry about Conan defecting because Fox could not clear enough stations to give the show a realistic chance.

“We gotta get this deal made,” Ross told Zucker, “because they’re fucking around with Conan and they’re gonna push him to Fox.”

“They can’t clear Fox anyway,” Zucker replied, having heard much the same intelligence as Sassa.

“Yeah they can,” Ross shot back. “I know they can.” And he laid out the research from the consultant.

Zucker took that information away with him, and NBC soon came back with a more realistic offer, extending Conan through the end of 2005 and bumping up his salary to $8.25 million a year. Although that was still only about a third of the Fox money, the NBC side was convinced it could risk the lowball offer, because it was dealing from strength: namely, the accumulated history of the network’s preeminence in late night—and of course, the ultimate prize, the gold standard, The Tonight Show, still dangling in the distance.

For Conan’s professional advisers, it wasn’t nearly enough. The Endeavor agency had no formal titles, but its acknowledged leader was Ari Emanuel. Ari, already establishing himself as one of Hollywood’s most aggressive, energized, and plugged-in talent reps, pushed for the Fox deal. So did his Endeavor colleague Rick Rosen, though as Conan’s more day-to-day agent, and already growing close to him personally, Rosen wanted to be sure to read and serve his client’s intentions as best he could. As for Gavin Polone, Conan’s manager, he was about 80 percent of the way to “We gotta do this with Fox.”

The NBC side was well aware of how things stacked up. As Marc Graboff, the business affairs boss, analyzed it, the Endeavor team—and Polone—would surely be lured by the big dollar signs coming from Fox. If Conan defected to Fox, Endeavor would also be in position to claim the package. (A “package” is when an agency brings together several of the creative elements of a given project and receives a healthy fee for its efforts. One of Endeavor’s biggest rivals, the Creative Artists Agency, had held the package—and commensurate fat annual fee—on the Letterman show for almost a decade.) The NBC executives guessed that Endeavor must be “salivating at the opportunity to package Conan,” especially because the alternative, staying with NBC, offered no such shot. The Tonight Show was unpackageable—it was a franchise rooted so deep that no agency could enhance it by packaging other elements beyond the host. Conan’s professional representatives were up front with NBC about their intentions: They were advocating that Conan take the $21 million and a better overall deal at Fox over the measly $8 million NBC had put on the table.

Still, NBC was unworried. However ardently the management side was promoting the Fox offer, Conan and Jeff Ross had been equally candid about their reluctance to leave. Ross had heard his star’s analysis of the situation clearly, and personally he agreed: It wasn’t time. “I’ve only been at this for eight years,” Conan told Ross, adding, “You know what? This company has been good to me.”

OʹBrien had studied the tangled 1990s business with Letterman closely and taken note of how wrenching it had been for Dave to be separated from the body of work he had created during his eleven years at NBC. Conan had a passion to stay