The root problem is that NBC didn’t want to lose Conan five years ago. At the time, Conan was hot, and he had offers to move to 11;35 on at least one other network.
So here’s what NBC was worried about - Conan leaves, and they’ve got no one for 12:30. In the meantime, the added competition at 11:30 eats into their ratings. Also, the 12:30 show had always been seen as kind of the ‘farm league’ for the 11:30 show. Jay’s not a spring chicken, and at some point would have to leave because he was losing his ratings, or his health, or his relevancy. If Conan left, they’d have no one to replace Jay when that day came, and they risked destroying their entire late-night lineup.
So the bright boys said, “Wait a minute! What if we offer Conan Jay’s spot in five years? If he knows it’s a guarantee, he’ll stick around. In five years, Jay will be 60, which is pretty old for a late-night host. We’ll retire him, move Conan into the Tonight show, and complete an orderly transition that retains our late-night strength”.
At the time, that seemed fairly reasonable. Leno didn’t like it, but Leno’s a workaholic. So NBC offered to find him something else, and probably promised it would be a step up - primetime, total creative control, whatever. So Jay reluctantly agreed. Conan agreed, because the Tonight Show is every late-night comedian’s dream gig.
Five years later, and Jay’s still #1. At that point, the suits were probably wishing they could undo the whole deal, but contracts had been signed. So, they did the switch, and moved Jay to primetime and Conan to 11:30. And then both shows suffered, the affialiates squawked, and NBC panicked.
Part of the problem was that they foolishly promised Leno a 2 year contract that would keep his show on the air regardless of what its ratings were. So they couldn’t get rid of him, OR cancel his show. So they had to offer him a deal that he was willing to accept. So they offered him essentially the Tonight Show back, under a different name. Conan rightly felt that this would destroy the real Tonight Show, which was always all about being the show you watched to put you to sleep after the news. Put another show there, and the Tonight Show loses its special status. So Conan refuses to move the show, and the rest is history.
Who’s right? You could argue that Conan should never have agreed to a contract that would force Leno out of a show he didn’t want to leave. On the other hand, you could argue that a Tonight Show with a 70 year old Jay Leno as host isn’t the greatest thing for the show either.
You could argue that the original deal five years ago was stupid, but that’s hindsight.
The people who take Jay’s side basically say that he’s a team player, and didn’t push for any of this to happen - he just went where the opportunities are under bad circumstances. Who could blame him?
The people who take Conan’s side say that Conan took a principled stance because he didn’t want to see the Tonight Show ruined, and Jay was willing to damage the institution for his own gain. They felt that Jay should have just told NBC, “Look, that’s Conan’s show now. Find me something else, or buy me out of my contract. But I’m not going to kick him out of the gig or push the Tonight Show back and help destroy an institution that I’ve cared about since I was a kid.”
Also, the people who take Conan’s side said that the idea to move the show back half an hour was basically a sleazy way to get out of their contract. The Tonight Show isn’t about the name - it’s about the 11:35 slot. Take that away, and you take away the Tonight Show, which they were contractually obligated to allow Conan to host.
What’s indisputably true, though, is that Zucker handled the situation very poorly at the end - trying to strong-arm both of them, taking the fight to the press, announcing resolutions before they had been agreed to, etc. He took a difficult situation and made it much worse than it needed to be. They should have announced nothing at all until all sides had come to some kind of an agreement.