Here is a comment that I added to the Hirhurim blog discussion regarding the NYT article on the Madoff scandal:
I am hoping that at some point we understand why he did it. I recall reading in the Chofetz Chaim about the importance of giving the benefit of the doubt.
It seems clear that Madoff created the Ponzi scheme, but I wonder why. Did he start out with a legitimate fund with which he wanted to support important causes, etc. and then get into trouble? And was then unable to admit his mistakes, which created the need for the scheme. If this were the case, it would be more pride than greed. Perhaps we will never know, but it might be helpful to ask the question.
I know there is a famous story about Rabbi Akiva, who went to great lengths to believe his employer, Rabbi Eliezer ben Hurkanos -- http://www.thejewisheye.com/gosh.html.
I find great lessons from this ability to see the best in others.