Technology helps a lot. It brings us from a panoptikon to a situation where enforcement has to be done on an individual basis. That's a big win for freedom in my book.
At least for communications that need that layer of security and anonymity, it's certainly there. And as I implied, rubber hoses won't work on anonymous and encrypted digital identities "somewhere else".
At least regarding Silk Road, that's because he made amateur mistakes by posting his real name and then changing it on StackExchange, about making a e-commerce .onion website.
And that was the beginning of his fuckups, with the final one by paying for an assassination attempt.
That's my point. At some point he needed to leave the digital world and live in the real world. There is no perfect false identity, not one that does anyone any good. Whether you are looking to overthrow a regime, sell drugs, or just keep your recent pregnancy on the down low, at some point that leaves the digital space and enters meat space. It's at that point that powerful actors can get what they want from you.
Encryption might help you evade detection, but it is not a guarantee of privacy, even for a regular person.
Believe it or not, I expect we agree in the end. The existence of encryption is precisely why dragnetting doesn't work for catching actual bad guys. What brought down Silk Road was old fashioned police work. Get people on the inside, record some chats, get some warrants and so on. They seized him after he had decrypted his laptop, even. It's also precisely why I think political solutions are going to be the most effective in the end. The expectation of privacy we have established outside the digital space (say, no wiretapping, no illegal searches or arrests) still gives tools for protecting the public. Perhaps we need to somewhat tweak those tools for the digital world, but that doesn't mean we need to give the government the keys to our house.
You can even hide that a conversation took place.
I can send data to .onion addresses natively via DNS ( https://trac.torproject.org/projects/tor/wiki/doc/LinuxDNSre... ). I can also receive data from Onions as well.
Right now, I have Node-Red communicating data from my IoT infrastructure, publishing data to my MQTT broker elsewhere (my server onion). I have my 3d printers in another place, and part of the MQTT data is pictures and GCode readouts from them.
It sounds complicated, but Hidden Services allows me to treat a network of disjointed machines (all behind NATs) to be thought of as being on one huge ethernet hub. And I can code against an [hash].onion and know that my data will reach that machine, no matter the IP.
1. I've always maintained that privacy is a political and social problem, not just a technological one. Nothing stops a more powerful actor from breaking encryption with a rubber hose if they really want to. Technological solutions are still needed since there's a variety of actors involved, only some of which will obey the political doctrine.
2. I often wonder if encryption will make us think of privacy a bit like we think about rule breaking in sports. Since there's an official, we assume that you can break the rules if you don't get caught, at least on the field. There's no ethical pressure to "do the right thing" because we've offloaded that burden to the officiating crew. Has technology become a bit like the official in this case? Our physical spaces have strong and protected rights, at least in the US, but our digital ones do not, and that may be because we are protecting them in other ways.