He hired a hitman and got someone killed
Many of the ideological supporters of the Silk Road have described its sprawling online black market for drugs as an experiment in victimless crime and a nonviolent alternative to the bloody turf wars of the streets. But prosecutors in the trial of Ross Ulbricht, the 30-year-old accused of running that anonymous bazaar, have pointed to one conversation they say shows the contrary: That the Silk Road's boss was willing to resort to the drug trade's most violent measures when it suited his needs.
On Monday, in the final hours before the the Department of Justice rested its case against Ulbricht, prosecutor Timothy Howard read aloud from a long series of private messages retrieved from the Silk Road's market server and user forum. Those messages capture what seem to be a grisly nadir for the Silk Road's pseudonymous administrator known as the Dread Pirate Roberts. Over the course of just a few days, his scheme spirals from merely tracking down a blackmailer to intimidate him, to hiring Hell's Angels to kill that blackmailer, to paying those same hitmen a total of $650,000 to kill four more people.
https://www.wired.com/2015/02/read-transcript-silk-roads-boss-ordering-5-assassinations/