Yes, particularly for the second "hit" that he arranged (the one in the Complaint). However, the first "hit" (outlined in the Maryland indictment) seems to have

Yes, particularly for the second "hit" that he arranged (the one in the Complaint). However, the first "hit" (outlined in the Maryland indictment) seems to have been more of a set piece entrapment-alike. This was when he popped his online-hitman cherry, and it was the most difficult one for him. He seems quite distraught and upset in the messages, he has trusted this guy ("The Employee") as an admin, he loaned him the money for the "substance that would test positive as cocaine", he likely socialized with him and revealed a great deal of personal information. I think the Feds played him (Ross Ulbricht) in this case and totally set him up for a fall. I accept that he stepped off that cliff himself, but I think it is likely that he was guided the whole way there by the Feds. After this first hit, orchestrated from start to finish (?) by the feds, the second one seemed easier. He had learned to live with himself after the deed was done, he had pushed beyond that moral barrier of "don't have other people tortured and killed", and he had learned that violence can solve problems. Now, as to whether this second "hit" was just him negotiating with a scammer, or whether he believed he was actually having someone killed. I think it is clear that without that first job, that first hand held walk through the dark side of the underground, he wouldn't have reacted that way. I think he would have been less susceptible to the manipulations of the feds if he was in a normal social peer group. If he had some rational people who weren't inside the Silk Road bubble who could say "you want to have someone killed because they stole some SHA256 hashsums? Are you fucking insane?!?"