These are very intimate details of his life. The entries do not read like the entries of a psychopath, rather they paint a vivid picture of his life and the perfect basis for a movie.
I've never gotten the impression that Ulbricht was a psychopath or anything similar. He always came across as a naive idealist, caught way over their head in a conspiracy they never expected to succeed. He openly admits in his diary that he practiced terrible OpSec, and didn't care much.
This article doesn't make him look like an idealist at all. It makes him look like an entrepreneur that cares about success about all else. The idealism seemed to come later, as a justification.
Honestly my impression reading them was that there's a possibility he really was set up by Karpales, or that the prosecution is forging evidence. I just can't believe anyone would really keep journals like this outside of movies. I have a felony for distributing mushrooms years ago, and in that period I knew never to write stuff down like this, as did all of my colleagues, even those who were noticeably less classically intelligent.
I just can't believe anyone would really keep journals like this outside of movies.
The CEO of Google once sent someone an email which said, virtually verbatim [+], that he would appreciate them not talking about the illegal act he had just ordered over email because it would open them up to a lawsuit.
We know this. Guess why.
[+] The quote, in case anyone thinks I'm being too harsh in my summary: "I would prefer that Omid do it verbally since I don't want to create a paper trail over which we can be sued later? Not sure about this.. thanks Eric" (The antecedent was to "it" was "share with eBay and Paypal executives Google's internal anti-poaching rules as they pertained to eBay/Paypal for the purpose of eliciting their continued cooperation in the conspiracy.")
To be fair, there are plenty of totally legal things you can do that open you up to lawsuits if you write them down. This wasn't one of them, but an email with the same text could have been completely innocuous.
People do dumb things. Even smart people. The journal entries by Ross almost seem affected to the point of contrivance though.. he wasn't communicating with anyone. Of course, it's likely they are his, but it still strikes me as very Hollywood-esque.
It's likely that when he was trying to put out the hit, as it appeared, he knew he was talking to the guy who was blackmailing him (who didn't know that he knew that) and he was trying to get him to believe that he was willing to kill to end the blackmailing. So he was never actually planning on killing anyone.
That is not likely at all. There is literally no evidence supporting that. It is simply an explanation that allows Ross's supporters to explain away the facts. The preponderance of evidence is that Ross is OK with murder.
Regardless, I would say that there's a big difference between murdering someone who is blackmailing you and other kinds of murder, to the point that I wouldn't expect psychopathy from someone who was doing the former.