It also backfired on him at the height of the credit crunch. While he was smart enough to write the contracts in such a way that he didn't need to post collateral, he didn't account for the way that someone looking to hedge their counterparty risk with him would behave. When the market collapsed, the buyers of the puts proceeded to short both the equity and debt of Berkshire to protect their investment. http://crookery.blogspot.com/2008/11/valuing-large-options-i... and http://crookery.blogspot.com/2008/05/warren-buffetts-vega-ga... have some of the technical details, and http://www.portfolio.com/views/blogs/market-movers/2008/11/2... has a good general explanation of what went wrong.
Buffett may not have been in the casino all the time, but he had plenty of side bets that could have wiped him out.