You're overestimating ross. He used his personal email to advertise silk road. I'm sure he was also dumb enough to pay for the hit through a bank transfer.
Let's get real, the guy was a fricking idiot.
If he was such an idiot, then he would have never created such a sophisticated market place and saved it from the FBI and hackers for more than a year. The FBI tracked him after years of monitoring. They spent millions of USD trying to track him. But for a long time he evaded those who tried to outsmart him. He was caught after a bug in the TOR browser exposed his IP. He was probably smarter than anyone in this forum.