But, I think the OP is right. The only successful (for lack of a better word) black hat is going to be a loner.
The DrinkOrDie people got a lot of 3-5 year sentences. http://en.wikipedia.org/wiki/Operation_Buccaneer
DMCA still makes some 0-day exploit research not totally safe, either. https://www.eff.org/wp/unintended-consequences-under-dmca I don't know if anyone has been successfully convicted, but a lot of prosecutions have come up, and that's enough to deter many people.
http://en.wikipedia.org/wiki/DarkMarket
DarkMarket was an English-speaking internet cybercrime forum created by Renukanth Subramaniam in London that was shut down in 2008 after FBI agent J. Keith Mularski infiltrated it using the alias Master Splyntr, leading to more than 60 arrests worldwide. Subramaniam, who used the alias JiLsi, admitted conspiracy to defraud and was sentenced to nearly five years in prison in February 2010.
The website allowed buyers and sellers of stolen identities and credit card data to meet and conduct criminal enterprise in an entrepreneurial, peer-reviewed environment. It had 2,500 users at its peak.