First, I think that he's funny. A lot funnier than Leno. I just don't buy into his whole innocent victim schtick. He essentially told NBC to give him Leno's job or he'd leave. They give him Leno's job, but keep Leno around because Leno had been consistently dominating Letterman forever. When Conan's show fails, which honestly had more to do with his humor being less-than-mainstream than anything else, he rightly gets the ax. You don't bring in ratings, you lose your job. They give the job back to Leno. Why? Because he brings in the money. Leno isn't funny, but he apparently knows how to host a show.
It strikes me that this isn't very much a headscratcher, more a general complaint. I'll leave it to someone else's judgement whether it should be moved/deleted. I will try to reply quickly as I don't want to go into a drawn-out argument but I at least want to provide the counterpoint. Basically...
He wanted an earlier time slot. And why shouldn't he? NBC could give it to him or let him take it elsewhere.
NBC decided to ask Leno to retire (he wasn't fired). Leno agreed and publicly said he wanted to retire and wanted Conan to take over. (Privately may be another matter, but let's not get into that just yet).
The switch is made. Now we know it took Leno years to get his ratings as good as they were. And it took Conan years to grow into Late Night, too.
Leno goes back on the idea of retiring. He takes up a show which does poorly. It kills the local news ratings due to poor lead-ins. Now here's the big question: was it that local news just suddenly had "less-than-mainstream humor"? OR was it that they were suffering from a poor Leno lead-in?
The poor local news lead-in hurts Conan. NBC panics at the mess they've created.
What Leno COULD have done is said: "I agreed to retire. I took another show. It didn't do well. Let's give Conan his shot. Let him have a few years to grow into the show. With a decent lead-in. If his ratings are bad after a while and NBC still want me, OK. I'll go back." OR take HIS show to TBS.
Instead this is what Leno ended up doing: he agreed to give up the show years in advance, screwed Conan's lead in, and immediately took the show after he had a part in Conan's lack of ratings in the first place. Doesn't seem too nice to me.
As a huge fan of Conan both on Late Night, as well as his brief months on The Tonight Show and his self titled show, Conan, I can look at all that happened and say with absolute honesty... There was a lot of blame to go around. I think the above points are valid, and Conan could have handled things a bit more internal, but in the end, the main culprit in the whole affair is NBC. I am not saying they are huge douche bags, but they did this to David Letterman, and now to Conan, not to mention other forms of Executive Meddling and poor decision making.
I think Conan made the right choice to leave NBC, and I think Jay could have done things better, but in the end, let's put the blame where it belongs. NBC.