Maybe it's because Leno's good-guy image never really recovered from that turn of events.
Maybe it's because Leno has always been the comedy equivalent of comfort food. Nothing spectacular, nothing distinctive, nothing groundbreaking. He's mashed potatoes or macaroni and cheese — enjoyable, but not exactly memorable.
The only thing really distinctive about Leno's late-night career is the conniving and backstabbing that got him the "Tonight Show" job not once but twice. And, at this point, that's old news and sort of a big bore.
The late-night wars won't end on Thursday when Leno hosts "The Tonight Show" for the last time, but they will be considerably less nasty come Friday.
With Leno gone — presumably — late-night network television will be populated by guys who get along. David Letterman, Jimmy Kimmel, Jimmy Fallon, Craig Ferguson, Conan O'Brien, Jon Stewart, Stephen Colbert and Seth Myers have their own mutual admiration society.
When they kid each other — as they will — there won't be the edge of bitterness that marked Leno vs. Letterman, Leno vs. Arsenio Hall, Leno vs. George Lopez, Leno vs. Conan, Leno vs. Kimmel ...
Are you detecting a pattern?
When Johnny Carson retired in 1992, there was a period of national mourning. The buildup to the farewell lasted months. It wasn't just Bette Midler and Carson who shed tears when she serenaded him on his second-to-last episode.
And approximately 50 million Americans tuned in to see Carson say farewell the following night.
If 8 million watch Leno's last "Tonight Show," it will be a huge ratings victory in a TV world that has changed enormously since 1992.
Still, if there's any buzz about Leno's second farewell, it's all-but inaudible.
Maybe that's a good thing. Maybe that means Leno is going out with his head held high and with as much class as possible.
He's worth an estimated $350 million. He has a thriving stand-up career. He has all those cars.
Here's hoping he'll be happy after he signs off on Thursday.
Scott D. Pierce covers television for The Salt Lake Tribune. Email him at email@example.com; follow him on Twitter @ScottDPierce.