Though I disagree with the canonisation of St. Bobcat, that's a great point about Seinfeld seeing comedy in terms of winning rather than as an art form. It's a recurring theme with him, the more popular you are then the better you are, which doesn't address the nuances or niches of some comedians. He's good friends with guys like Joel Hodgson, Barry Marder and Mario Joyner who clearly don't fit into the mass popularity bracket so it's an odd stance to take.
Bobcat can be very funny in movies. His stand-up... not so much. I've always felt a desperation from him, that he is maybe not a naturally funny person, and his wacky voice and hijinks are the comedy equivalent of throwing a bunch of shit and seeing what sticks. In particular, his appearance on The Larry Sanders show, where he represents the forces of punk and anarchy that scares the shit out of suits like Larry and Artie - but in fact, Bobcat's appearance on the show made me side with the latter. It
was cringey, and desperate and unfunny, unsuitable for a mass audience not because it was too wild, but because it was too tedious.
Don't mean to dump on him though - by all reports he's a lovely person and a talented director. And Jerry Seinfeld has become bit of a cranky old man with a short temper. You could say he's earned it, but doesn't doesn't really excuse a kind of necessary arrogance in situations where none is required.
The thing about Seinfeld seeing it as winning is interesting, but my take on it was that he meant it in a specific way. Not that comedy, as a thing, is something you win when you're rich and famous, but as a performer whose job is - one way or the other - to make people laugh, you know you've won when you get that laugh. Personalities aside, Seinfeld strikes me as kind of an old-school craftsman who doesn't have much time for what he perceives as gimmicks, which are almost always a shortcut to something.