In the Aussie millions, within 6-7 hands delt, he had lost half of his stack. In one episdoe of PAD, he lost his whole stack on the 5th hand "i had a pair" were his exact words as he exited. He is someone who is either gonna get chipped up early and make a good run, or go bust trying and then simply move onto the next tourney. This is why he gets so many walks in tourneys, because people are to scared to play against him, because they cant put him on a hand.
But to answer your question MintTrav, i think it all depends on how deep you are in the situation at hand, weather you have a competetive stack to be able to out play or bluff opponents (like 3 barrel bluffs etc). Ive noticed recently that, (and this is in my opion) having 100BBs is no way deep enough to play creative poker. So i guess in steves case he should of been willing to gamble.