I recently found this site: https://antilop.cc/sr which documents the entire timeline of the history of the Silk Road. When I first saw the vast amount of links and information on the site I thought to myself there would be no way I would read all that. Four hours later and I'm about 2/3 done reading everything on site and knee deep traveling down memory on the Silk Road.
Here are few of the most interesting facts about Dread Pirate Roberts aka Ross Ulbirtch and the Silk Road:
Ross Ulbirtch was caught through his own human error
With a simple Google search one day, the FBI was able to connect Ulbirtch with a screen name used early on before the Silk Road caught. In January 2011, Ulbirtch posted an advertisement for the Silk Road on the message board shroomery.org under the username altoid.
In October 2011, Ulbirtch later posts a question on bitcointalk.org under the same altoid user name along with his personal email address that has his name on it.
So the FBI agent most likely did a simple Google search for "rossulbirtch at gmail dot com" and saw the post with the username altoid and was able to match that with the same shroomery message which was one of the first mentions of the Silk Road.
Ulbirtch bought fake ID's which was confiscated by custom agents
Custom agents visited his apartment in San Francisco to ask him about the forged documents that bared his picture on it. At the time the agents knew nothing about his involvement in the Silk Road. All of this happened around the same time that Dread Pirate Roberts was discussing obtaining fake IDs on Silk Road, which allowed the FBI to connect Dread Pirate Roberts to Ulbirtch.
Ulbirtch was caught red handed at the San Francisco Glen Park Public Library
Glen Park is a small neighborhood in San Francisco. It is in the South part of the city and away from San Francisco's tech and business epicenter. Ulbirtch would take the bus from his house to the library to use the free Wi-Fi. FBI agents following Ulbirtch into the library saw Dread Pirate Roberts log in to the Silk Road. They quickly swarmed into the library and grabbed Ulbirtch by surprise and snatching his laptop which was logged in.
Dread Pirate Roberts had interview questions for his admins
The Silk Road was worth over $213 million dollars and was took in over $13 million
Before being sentence to life, Ulbirtch begged the judge to take leniency
I’ve had my youth, and I know you must take away my middle years, but please leave me my old age. Please leave a small light at the end of the tunnel, an excuse to stay healthy, an excuse to dream of better days ahead, and a chance to redeem myself in the free world before I meet my maker.
Source:
https://arstechnica.com/tech-policy/2015/05/before-sentencing-ulbricht-begs-for-leniency-please-leave-me-my-old-age/