How does ole Bernie Madoff come out of this experience victorious? That's a tough question that hasn't really been asked. The man is a criminal of the highest order. He destroyed lives (of rich people). Sure, I feel sorry for the charities that sunk money into his scheme without the foresight that none of it made sense, but otherwise the victims will deal with their own plight. I want to look at Madoff himself - Madoff as a hero of villains.
I have great respect for con men for the most part. I love people who come up with creative ways to hustle and dupe others (for this same reason I've always been infatuated with drug dealers, too). My favorite con ever has to be the classic cat vs. rat scenario. It goes like this: You are presented with a business proposition. A new company builds two houses with a small trail as barrier. One house has cats; the other, rats. Rats multiple at four times the rate of cats, so you feed the rats to the cats and they get fat. It's not a big loss because the rats continue to multiply. Then, you take the fat cats, skin them and make fur coats. See how the initial investment is all you need? Afterward, there's no overhead. This is great con because it's absolutely ridiculous (and has never actually been done), but it makes sense to people. While shady, it seems like it could work. Old con men certainly made some cash with it. The people who were fooled... eh, not much sympathy in this camp.
If Madoff could get out, I'd say he should fly right, be honest and wait until his day comes again. Then he can leave jail, start a reality show or open a new publishing house with his memoirs as the first book deal. Good thing he can't. Here's my recommendation. Mr. Madoff, kill yourself. Don't do it because you are sorry. Do it because your name will live on. You had a lot of fun on earth doing horrible things that no one can fully condone, but now that's all over. What's left to live for? Living? Nietzsche says to live life like a movie. You did that, but now your movie is like an unfunny, secluded Down By Law without John Lurie, Waits or Roberto Benigni. We saw you in court yesterday. You're a boring actor.
So, do it. Try to keep your shoelaces. I'm sure one of your new colleagues can teach you how to hang from a rafter.
