Originally Posted by HighTemplar
He was not caught because of Tor's insecurity. He was caught due to posting his real name in his email address.
Wow! thus the "extreme caution" remark. Perhaps he sampled too many of the goodies available there and hallucinated that all the world is love and good intentions
However, although the wiki doesn't mention his rather bizarre lapse of judgment, it does mention several others.....
Originally Posted by wikipedia
On 2 October 2013, Ross William Ulbricht, alleged by the FBI to be the owner of Silk Road and the person behind the pseudonym "Dread Pirate Roberts," was arrested in San Francisco on suspicion of drug trafficking, soliciting murder, facilitating computer hacking, and money laundering. The FBI agent leading the investigation was also responsible for the 2011 arrest of the LulzSec hactivist Hector Xavier Monsegur (Sabu). On 4 October, Ulbricht appeared in federal court in San Francisco and denied all charges, whereupon the hearing was rescheduled for 9 October.
In anticipation of transfer to New York, Ulbricht became represented by New York lawyer Joshua Dratel, a former lawyer for Guantanamo detainees.
The FBI seized over 26,000 BTC from accounts on Silk Road, which were worth approximately $3.6 million at the time. An FBI spokesperson said in an interview that they would hold the bitcoins until the judicial process finished and after that, they would liquidate them. On 25 October, the FBI reported that they had seized 144,000 BTC worth $28 million that they believed belonged to Ulbricht.
Silk Road 2.0
On 6 November 2013 admins from the shuttered Silk Road, led by a new pseudonymous Dread Pirate Roberts, relaunched the site. Dubbed "Silk Road 2.0" it recreated the original site's setup and promised improved security. The new DPR took the precaution of distributing encrypted copies of the site's source code to allow the site to be quickly recreated in the event of another shutdown.
On 20 December 2013 it was announced three alleged Silk Road admins had been arrested; two of these suspects, Andrew Michael Jones and Gary Davis, were named as the admins "Inigo" and "Libertas" who had continued their work on Silk Road 2.0. Around this time the new Dread Pirate Roberts abruptly gave up control of the site and froze its activity, including its escrow system. A new temporary administrator under the screenname "Defcon" took over and promised to bring the site back to working order.
On February 13, 2014, Defcon announced that Silk Road 2.0's escrow accounts had been compromised through a vulnerability in Bitcoin's protocol called “transaction malleability”. While the site remained online, all the bitcoins in its escrow accounts, valued at $2.7 million, were reported stolen.
I sincerely doubt all of them were so lax. When possible illegal activity and huge sums of money are combined, you can bet politicians and law enforcement won't be absent for very long. I lived in a small town in Colorado when test cases were being pursued to set the legal precedent that all assets of a person suspected of engaging in illegal enterprise could be seized even before arraignment, let alone the outcome of a trial. Now it's just Standard Operating Procedure. So it is no longer just about ethics and justice, it's at least as much about greed and power. Best to not get in the path of that.