"Why does the network want to skew these shows towards a younger audience, and yet they dress their hosts like my father?" Sweeney asked. "What's wrong with an open-collar shirt and a sports jacket? They're trying to fool everyone and it ain't working."
Fittingly, O'Brien alluded to the network's obsession with the younger demographic during his Wednesday show.
"Hosting 'The Tonight Show' has been a fulfillment of a lifelong dream to me," he said. "I just want to say to the kids out there: 'You can do anything you want in life -- unless Jay Leno wants to do it too."
Who's to blame? More than one ABCNews.com source pointed a finger at Jeff Zucker, the wunderkind producer who rocketed through the ranks of NBC News and NBC Entertainment before reaching the helm of the network in 2007, when he became the president and CEO of NBC Universal. He's had a hand in most, if not all, of the network's major late-night dealings since 2000.
But Zucker's more intimately attached to this particular disaster. He attended college with O'Brien. The two endured a friendly rivalry at Harvard, where they both wrote for the Harvard Lampoon. According to PopEater.com entertainment columnist Rob Shuter, the fact that Zucker and O'Brien have been friends for decades makes Zucker seem all the more ruthless.
"Jeff is really close to Conan," Shuter said. "This ultimately lies in the hands of Jeff Zucker and he's got to fix this. If he doesn't, he's going to end up in trouble."
Insiders say Leno got as raw a deal as O'Brien.
"NBC was afraid to lose Conan, afraid to lose Jay. They want to keep everybody all the time," Sweeney said, comparing the hosts to cards in a game of poker. "But sometimes, you have to discard some of your cards in order to win. They don't want to do that."
"I'm sure when they moved Jay to 10 p.m. that they said 'Look, if it doesn't work out, we'll move you back to 11:35.' They didn't realize what a train wreck that would cause," he continued. "I always thought this would happen, I predicted it months ago, but I'm surprised it happened so soon. I thought they'd give them both at least a year."
Yet, because much of the public perceives Leno as a selfish old stalwart who doesn't want to give up the stage, Shuter thinks Leno may follow O'Brien's lead and walk away from NBC to save face.
"Sometimes, perception becomes reality. And the perception is that Jay got Conan fired," he said. "Jay is Mr. America. He's Mr. Nice Guy. He's not edgy like Letterman, he may not be witty, but he's loveable Jay. He doesn't want to be thought of like that."
Sweeney, Adler and Shuter agree that it's entirely possible Leno's feeling out offers from other networks before deciding whether or not to stay at NBC and regain his old time slot at 11:35 p.m. come February. But each insider sees a slightly different outcome:
Sweeney: "Jay will do whatever the network wants him to do. He's there to make them happy. Point him in the right direction and he'll do it. I'm hoping he goes back to 11:35."
Shuter: "NBC is up Leno's a**. If this man wants a cheese plate in ten minutes, it'll be in his dressing room. This guy can be a bigger diva than J-Lo for the next ten years. They have to keep him. They have no safety net."
Adler: "What else is he going to do, drive automobiles? The reality of it is that he does stand-up comedy. He sits behind a desk and interviews people. If he doesn't do it with NBC, he'll do with someone else."