Milken is an interesting case. He literally created the market for high yield ("junk") bonds, and a lot of the charges the feds threw at him were because creating a new market meant breaking stupid regulations about yields and such.
I'm not anti-Milken by any means, but based on Connie Bruck's "The Predator's Ball", Drexel Burnham Lambert was scurting a lot of regulations when it came to appropriately labeling the types of deals and securities in which they were engaging. Milken might not have been running any blatant frauds or insider trading rings, but he was at the very least misrepresenting DBL's activities and or avoiding proper filings altogether.
Regardless of whether they're stupid or not, they're still regulations. Unless he was breaking the laws as a form of civil disobedience, he was still basically a guy breaking the rules to make more money.
