Zuckerberg was a kid from freakin' Harvard and Phillips Exeter. I think the Harvard thing alone disqualifies him from being a counter cultural figure, especially since he has always seemed squeaky clean and fairly intelligent.
As far as the nerds "winning" -- I thought that was the way of the world. Napoleon wasn't some giant, neither was Bill Gates. The idea that the jock's best years are in high school is a pretty well-known trope at this point, often used to comedic effect in movies like Revenge of the Nerds -- or TV shows like Married with Children.
Well-off kids doing well for themselves is hardly unusual or counter cultural -- it's more like that's what we would expect with the advantages afforded to them.
Zuckerberg? Where's his support of Occupy Wall Street, or the Tea Party, or even marijuana legalization?
Facebook doesn't even allow pictures of breastfeeding mothers!
http://abcnews.go.com/Health/breastfeeding-advocates-hold-fa...
I know that you were providing examples where the college someone went to doesn't preclude them from being counter cultural. Zuckerberg, though, while not "square" exactly, is basically what our culture basically expects of people that go to those schools.
Leary and Kaczynski, not so much, and that may actually be a part of the reason that that they grew to have outsize influence as counter cultural icons!
Yesterday's David is today's Goliath.