Despite leaving The Tonight Show while still standing atop the ratings, ably following 30 years of Johnny Carson – the man who revolutionized both the show and the form – with his own successful 22 year run, there were no rose petals thrown at Jay Leno’s feet in the waning days of his empire. Sure, NBC paid the requisite respect and Leno and his team did their best to celebrate their longevity and some of their best moments, but it all felt a bit downbeat, and not just because we’ve been through this with Leno before.

Back in 2009, Leno left the Tonight Show with a destination in mind. The prime time Jay Leno Show would keep him busy, keep him plugging away at his craft, and it also kept his people employed – something that has always been a high priority for Leno.

Back then, Leno’s legacy as a hard worker, a consummate professional, and a good guy was also intact. He was thought of as the preferred host of the (so-called) fly-over states, winning big audiences, but also winning the so-called “wrong audiences” when it came to critics. However, bits like “Jaywalking” and “Headlines,” and his lengthy monologues solidified Leno’s popularity and industry respect. He didn’t change late-night like Carson had, but he was a sturdy hand who had built a meat and potatoes juggernaut while being written off as the tragically un-hip option in comparison to the more intellectually and comically-revered David Letterman and Conan O’Brien.

We all know what eventually happened with Leno’s prime-time show, Conan’s switch from Late Night to The Tonight Show, and the subsequent effect on Leno’s reputation as he says farewell once more. Now Jay Leno’s television future is unknown and he is – rightly or wrongly – a villain to many.

Does that reputation bother Jay Leno? It’s hard to tell for certain, but he doesn’t seem like the type to let those that are chasing him see that they are gaining on him, so as he walks away with some people offering up the wrong kind of cheers, exiting in a way that is so contrary to the way that the beloved Carson left, common sense says that it has to burn in some small way. That’s possibly evidenced by the way that he has played the good soldier, pleading with people to watch Fallon, even last night at the very end of his last episode, as if to show people that he is really handing off the baton this time – because he knows that it is time.

What’s the difference between this time and last time, though? Here’s Leno’s somewhat controversial praise to 60 Minutes about Late Night host Jimmy Fallon and his Tonight Show worthiness:

“An extremely qualified young guy ready to jump in”

The easy implication is that Leno doesn’t think that Conan was as qualified when he took over The Tonight Show, but while that’s not necessarily what Leno was saying (though, maybe it was) in some ways, it’s true; Conan O’Brien wasn’t as ready to host The Tonight Show as Fallon is.

As has been said often, Fallon makes every show feel like a party. It is a charming show and one that is inclusive. Conan O’Brien, when he was at his best, made his show for himself and his writers (and with Louis CK, Bob Odenkirk, Robert Smigel, and Dino Stamatopoulos among his writers, that’s a pretty good audience). It was exclusionary and it was comedic ecstasy for comedy nerds and those that like their late-night a bit less grounded and less within the lines. As the saying goes, though, that doesn’t always play well in Peoria, and so when Conan graduated to The Tonight Show – a show whose history and built-in audience demands a tone more fit for a broader audience than the 12:30 show – his style unfortunately changed, disregarding Johnny Carson’s advice (given in 2004 when Conan was named as Leno’s successor) about being himself because “it’s the only way that it can work”.

Amazingly, when it didn’t work (and it could have certainly worked with more network patience), Conan continued to be inclusive when he started his TBS show, though that seems to be slowly falling by the wayside, since that show looks more like the Late Night version than the Tonight Show version of Conan, which is for the better. None of this should be a problem for Fallon, though, as his version of Late Night seems more ready to port over with only a few minor alterations. Obviously that’s something that Leno sees as well.

Jay Leno isn’t as out-of-touch as many perceive him to be. He knows that the world has changed and that these shows often get the most attention for only a sliver of the content put forth, thanks to clips on Hulu, YouTube, and the like. Jimmy Fallon is for this era, he is young, adventurous, and energetic – things that Leno is clearly not at the age of 63. There is no clearer contrast between Fallon and Leno than the one you notice while watching the “Best of” reels that have aired on their respective shows this week. On Fallon’s, you see the charismatic showman rapping and dancing with Justin Timberlake. With Leno, his head is superimposed onto the body of someone else who is singing and dancing around.

Despite Leno’s willingness to accept his creeping obsolescence and raise the white flag, finally yielding to a new host, there are many who will look at his uneventful and borderline culturally-irrelevant Tonight Show exit as a fitting punishment for his sins against O’Brien, Letterman (because there is no statute of limitations when the crime is Tonight Show theft) and the like. To others, though, it will simply be a mostly forgettable night that was filled with a couple of light jabs at NBC, some tributes (from an army of Leno’s friends and loyalists like Garth Brooks, Carol Burnett, Oprah Winfrey, Bill Maher, and Billy Crystal, who called Leno “America’s Nightlight”), one last OJ Simpson joke, and no real celebration.

We may never know if Leno truly regrets coming back to host the Tonight Show for four more years, standing in as everyone’s favorite punching bag. What we do know is that it will be one of the things that he is most remembered for – a legacy that seems sad, a little unfair, and final, because as Leno tearfully said goodbye last night, thanking his fans for their loyalty and his staff for being his family, we saw a man who looked done and who won’t be coming back again – not because he doesn’t want to, but because he now knows that he can’t.

The Tonight Show starring Jimmy Fallon premieres on NBC February 17th @11:30ET PM