As I've said for the past few years, he essentially fucked himself.
1) using a low latency onion routing network, rather than a mixnet like an anonymous remailer or other 1990s blacknet, was a big problem. You could maybe get away with throwaway front end nodes as a web interface, stateless, to package up transactions, run by third parties, but for long running anonymity vs traffic analysis or server compromise, low latency bidirectional connections are impossible.
2) repeatedly sticking his dick into the hornet nest by provoking the FBI in the press
3) remaining in the USA while doing all of this
Acting in ways which make him a less sympathetic defendant (connection to assassinations? Really?) doesn't help
Using his real email address/non-anonymous usernames while mentioning silk road related activities and later ordering fake IDs to his home address were by far the most enormous of fucks ups.
1) using a low latency onion routing network, rather than a mixnet like an anonymous remailer or other 1990s blacknet, was a big problem. You could maybe get away with throwaway front end nodes as a web interface, stateless, to package up transactions, run by third parties, but for long running anonymity vs traffic analysis or server compromise, low latency bidirectional connections are impossible.
2) repeatedly sticking his dick into the hornet nest by provoking the FBI in the press
3) remaining in the USA while doing all of this
Acting in ways which make him a less sympathetic defendant (connection to assassinations? Really?) doesn't help