Deep Inside the Brutal, Embarrasing War for 'Tonight'

In the book, readers learn that Leno wasn't as hard-hearted as the media portrayed him. You write that he was concerned about O'Brien and wanted to reach out to him but didn't because NBC told him not to. Do you think that he was as Machiavellian and passive-aggressive as Conan and his team -- and others -- may have thought?
Machiavellian would require you to believe Jay hatched a plan to move to 10PM and fail miserably, and then reclaim the 'Tonight Show' because he was confident his low lead-in would undermine Conan. That would presume Jay was almost clairvoyant, as well as Machiavellian -- not to mention masochistic. The failure of the 10PM show was a terrible blow to Jay, a humiliation really, after years of being the dominant star of late night. Nobody would willingly expose his career to that kind of public flogging just to find a way to get back to 'Tonight.' So no, I don't believe Jay had a Machiavellian strategy to overthrow Conan and reclaim his show.

On the flip side, do you think at some point O'Brien set out to sink Leno?
I actually don't think Conan's team ever thought Jay had that sort of bizarre master plan either. They are not irrational. Some of his fans did, after the fact. But that was just emotion talking. I do think Conan and his team saw Jay as passive-aggressive, and some other insiders do as well. In this theory, Jay did not set out to undermine Conan, but he just hung around and took advantage of the situation after NBC's big plan blew up. Did Jay expect Conan to fail? I can't say; though, I suspect he wasn't entirely surprised. Jay had a formula for success in ratings in late night that required him to go as broad as possible, and like some others at NBC, he likely saw Conan's comedy as narrower. It is certainly a vastly different style from Jay's. I would not say Jay rooted for Conan to fail, but he wouldn't be human if he didn't root for Conan to do less well than he had at 'Tonight.'

Was Leno treated unfairly in the media in your opinion?
Not entirely. A lot of the professional media handled it straightforwardly. The unrestrained noise-makers on some blogs berated him because they saw an opening to score points, especially with younger followers of Conan. And unfortunately for Jay, he has built up a lot of disrespect in some quarters of the press for what they see as play-safe comedy. Much of the press reaction was actually centering on what was being said about Jay by others hosts, especially Letterman and Kimmel, who had a field day banging on Leno -- to great effect. It was often hilarious and made for great television. But Jay has never been a favorite of the press and that clearly cost him in this episode.

What was Leno like through this whole process?
I think Jay was tense and pressured from the start of his 10PM show. The affiliate revolt that undid him actually started really fast, in only a matter of weeks. So he knew early the heat was on. Plus, he felt constrained by the limitations that had been put on the show. He could not do the same show he had done for almost 20 years, and Jay is very much a creature of routine, so I think he was thrown by the altered format he was working in. Earlier, when NBC put the five-year sell-by date on his 'Tonight' tenure, he was genuinely hurt. Then he got bitter, and that was reflected in his jokes on the air. He did not evince any hostility toward Conan, but he openly suggested that Conan's representation had pushed for this plan to evict him -- and he wasn't wrong. That's what representatives are supposed to do, by the way, and it was exactly what Jay's representative had done to win him the job in the 90's.

Later, when the option came around for him to return to 11:35PM, but only in a half-hour format, Jay was eager on one hand to accept -- because he really wants to keep telling jokes on TV every night -- but concerned on the other hand because of again facing a new format -- and about being blamed for shoving Conan aside. He asked NBC several times whether they expected Conan to go for it, and of course he did ask at one point if he should call Conan. But his general feeling was that nobody in show business should have expected him to refuse NBC's offer to go back.

What surprised you most about what Leno said and did during this situation?
Not all that much. I think Jay is a single-minded guy whose main goal is to continue telling jokes on television as long as possible. His actions were entirely consistent with that throughout. First, he went to 10PM to keep doing that, then he went back to 11:35PM to keep doing that. How that impacted others was never his main concern, but as always, he tried to keep the peace. Jay doesn't like hostility or bad feelings, though they seem to surround him frequently. But you could see by his decision to do the Super Bowl ad with Dave -- even as Dave was eviscerating him on a nightly basis -- that he longs for good relations with his peers. Though that never supersedes the drive to keep doing what he wants to do more than anything else in life -- tell jokes on TV.

What surprised you the most about O'Brien, who comes off as a very sympathetic character in the book? You write how O'Brien asked for a vintage microphone from the network instead of something like a Porsche or a yacht when NBC asked Conan what kind of gift they could give him for his great ratings, which is a telling detail...
Conan is a deep, complicated, sensitive and obviously hugely-intelligent guy. I knew that going in, but it was revealed in countless ways, such as the one you mentioned. Probably I was most surprised by his own tendency toward melancholy and self-questioning, which mirrors Letterman's -- though on a far healthier level. But he also demonstrated a trait that he said had been a constant in his life. When his back is against the wall, the best in him comes out.

You come up with a lot of new reporting and amazing tidbits in the book, considering just how much coverage this affair received. What are some other surprises?
That Conan was guaranteed 'The Tonight Show' long before anyone knew, and before the news was broken to Jay. That some at NBC worried enough about Conan taking over the show that they whispered that the network should pay him the $45 penalty and keep Jay at 'Tonight.' That Conan and his staff got a ton of notes from the network and rarely heeded them because they were convinced they knew their show better. That NBC tried to force guest bookings on him, especially Sarah Palin. That the affiliates took a poll in the midst of the 10PM train wreck about who they wanted on 'Tonight,' and not one of them voted for Conan. That Ron Meyer, who was working as intermediary, gave Jeff Zucker one last chance to reverse the decision at the final moment. That the Conan team knew so little about TBS, they had no idea what channel it was on in LA.

What is your overall take on how this should have been handled, seeing that you covered the situation so closely?
I think there were numerous opportunities to handle the personal relations better, especially at the end when NBC should have brought Conan into the process and not sprung it on him. But, in general, I think NBC should have recognized they simply had to make a choice. They could not realistically keep both these guys. They needed to pick one and let the chips fall.

What do you think of O'Brien's now infamous "People of Earth" statement he released in January, saying that he didn't want to move to the 12:05AM slot because it would hurt 'The Tonight Show' brand?
Brilliant piece of writing. Incredible display of personal integrity. Very risky career move. The letter basically ended any shot that Conan could stay at NBC. Long term? We'll see.

Did O'Brien anger anyone at NBC with that letter? What did NBC think of the letter?
NBC wasn't angry at the letter as much as confronted by it. They thought it meant he was quitting, though for legal reasons he expressly said he was not doing that.

What do you think of the fact that O'Brien's agents never secured a time-slot guarantee when he took over 'Tonight,' which, of course, seemed to make it impossible for O'Brien to sue when NBC proposed moving his 'Tonight Show' to 12:05AM?
I was extremely surprised at the contract missing the specific protection that Dave and Jay had -- as well as Stewart and Kimmel. If that had been in there, NBC could not have pursued this action and they would have been forced to petition Conan to make the change, not force it on him. But to be clear, this did not prevent Conan's side from suing. They believed and still believe they would have had a good case in court, because of language in previous contracts and the long-established custom of 'Tonight' following the late local news. In the end, nobody wanted to go to court and Conan got the exact settlement he likely would have in court. The main thing the time-period protection would have done is change the drama: NBC could not have come up with this plan to move the 'Tonight' show.

You interviewed Jerry Seinfeld for the book. Why?
He had advised Jay on the move to 10PM. He appeared at the comedy night that opens the book. He's a frequent guest on all these shows. He knows comedy and show business at the highest level. He obviously had interesting things to say. Obviously, Jerry is a Jay guy, so that has to be taken into consideration. But Conan was not being driven by career considerations when he made his decision. He had a whole raft of emotional and psychological reasons for doing what he did, entirely valid and different from what others in that situation would have felt and done.

What do you think of O'Brien's new show on TBS? Reviews have been mixed.
I love Conan's energy being back. He looks liberated and back to being himself. I do think they need to reinvent a bit as they go along and I expect they will.

What do you think of all his jokes about how he got jerked around by NBC?
I think they were entirely appropriate. On the first night, he had to address the elephant in the room. Now, he can move on and make only occasional reference to all that -- as Letterman still does.

Ultimately, do you think that O'Brien should have stayed at NBC?
Not for me to judge. He had strong convictions for making that call, and one would have to climb into his shoes -- not to mentions his psyche -- to make that judgment.

After all of this, how will Conan fare in years to come?
I think he'll be fine.

And Leno?
Jay will always work as hard as humanly possible to succeed.

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