You keep saying Damon was Will Hunting in Rounders.
But Will Hunting was a smartass prick more align with Worm.
I like Rounders. I own it. I watch it occasionally.
I'm not going to say it's as perfect as some are saying, but what you're saying is flat out wrong. Damon is broken from the opening credits. It's simply not a "win out" story. It's a complicated mess of an existence, one that's already seen him lose everything, and we as an audience participate in several of his lost battles, from the fact he can't say no to Worm, to the loss vs the Cops, to the loss vs Teddy...
I simply don't see the same film you see. It's not an underdog story. It's a dogfighting story. One that's seen Mike beaten and bloodied, left abandoned, and penniless.
Sure, there are glints of cliche, but Damon simply wasn't some rebrand of Will Hunting, and while he wasn't Oscar material the way Norton probably could have been, his version of a self-confident, almost-was-turned-loser of money, of girl, of career, of almost life-turned Victor wasn't as trite as you suggest.