This case reads like a spy novel, and also illustrates the limits of cryptography. He set up encrypted communication and dead drops with a foreign government (even calling the endpoints “alice” and “bob”), but was actually communicating with the FBI. https://www.justice.gov/opa/press-release/file/1440946/download …
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Yes, that last part was the mistake.
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He also goes on at length about the measures he's taking in letters to someone he isn't sure is the real deal. And then he takes a $30K payment despite considering it a red flag. The whole thing seems more LARP-y than careful.
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I think that reflects how well the FBI played him. And there were a lot of mistakes he could have made (that would have exposed him much earlier) that he didn't make.
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He ended doing that only after having seen the signal inside Country1-controlled building in DC (the embassy, I guess). So it wasn't unreasonable : he just missed that the FBI was helped by Country1 - again.
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But there was no reason to climb down from the two safer methods he initially proposed (uploading a file, or choosing his own dead drop), when in his own words he still had doubts. Like Matt, I'd love to see the FBI side of this conversation, which was clearly very well handled.
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