the idea of putting him in a halfway house and forcing him to work for the SEC appeals to me, and it illustrates another way in which we could handle the criminal justice process, especially for non-violent and extremely intelligent criminals such as Madoff.
Don't you think the prospect of that "punishment" would only encourage more sleazy rich guys to try ripping people off? "Even if I get caught, hey, I can just go to work for the government!"
no. it requires a unique skill set (and some luck) in order to pull off what Madoff did. when orchestrating and carrying out an elaborate scheme for decades, I doubt 'deterrents' play a major role in the mastermind's thought process.
and, also, most/all assets still would be seized, so 'sleazy rich guys' would at least have to risk losing the 'rich' from their title.