"Criminals, that go to prison and are then extremely limited in their rights... are free? How do you figure?"

The GAO (Government Accounting Office) estimated in the early 1990s that over 90% of Americans were guilty of violating the law. Almost all criminals are never punished.

Vast reams of new law has been written since then, creating vast hordes of new criminals by creating new crimes.

What I mean by 'freedom has always been illegal' is that whenever some gang asserts supremacy, any that do not accede to that demand are criminals. Any that do aren't free.

" Any leader that pops up will draw fire. Overlords and their minions cannot direct fire at non-targets, so decentralized freedom remains the best option, and more so the more centralized tyranny is."

This is the context from which you extract your next question, and this context answers your question. Leaderless mobs have no leaders, so those leaders cannot be targeted, because they don't exist.

Edit: this may pique your interest:
http://www.starfishandspider.com/preview/04.html

Re-edit:

"... nobody can speak for everyone..."

This.