Wasn't "The Black Swan" one of your earlier book recommendations? I read a good magazine article recently about why the markets crashed last year and the author was featured. He didn't sound like a very likable guy but he certainly seems to have had a better handle on the market than the "geniuses" who steered us into this mess. (He said the three best years he has had investing in the market have been 1987, the year of the dot-com bust, and last year). In a nutshell he says risk management models fail because they don't account for that 1% of occurrences which fall outside the bell shaped curve -- what he calls the black swan.
Just found a link to the article --
http://www.nytimes.com/2009/01/04/magazine/04risk-t.html?_r=1&scp=3&sq=joseph%20nocera&st=cse