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.
Ross made many mistakes all of which ultimately contributed to his demise. The biggest error he made that tied him directly to Silk Road was using his own personal details to set up Silk Road in the first place. From what I gather it was good old fashioned detective work that got him caught but once he was there was plenty of evidence to seal the deal. Had he not used his personal email address and not got caught red handed operating SR with logs of his activities on the laptop amongst other things it might have been a much different story. I don't doubt that he is a very intelligent person but he did some ridiculously stupid things. If he was such a genius though he wouldn't be currently sitting in a jail cell right now.