Maybe his playing style comes from the background as a stockstrader (or whatever he did at the wallstreet).
He can't be too nitty if he bets 1000$ with Antonio on what time it is, etc. He plays Rock, Paper, Scissors for 2000$ - what a nit...

It is just his style to play conservative, and yes he played a big pot with DN on season 2, i cant remember exactly but it was more than 100k I think, he won it though.
By the way he announced the 72 game on HSP4. I dont know why he doesnt straddle, but i think he knows that straddling doesnt help him, so why do it?

I like him, he's funny. He and Esfandiari are a great combo, they have fun at the table, although i like AE style of playing more.