Alex Winter's Deep Web, which premieres on the Epix channel this Sunday night, tells a tale that's both tragic and alarming. Tragic, because its protagonist, Ross Ulbricht, the "Dread Pirate Roberts" of the now-quashed Silk Road online drug market, destroyed his life in the practice of apparently sincerely held anarcho-libertarian ideals. And alarming, because the way in which the federal government finally nailed him raises serious Fourth Amendment issues that have not yet begun to be resolved.
Winter, whose previous documentary, Downloaded, chronicled the rise and fall of the Napster file-sharing service, begins by mapping out the Deep Web. It's a vast terrain, thousands of times larger than the "visible" Internet, that's filled with un-indexed content such as banking data and corporate and governmental administrative code. Drilling deeper, we come to the Dark Net, a "hidden" area that's accessible only by use of heavily encrypted Tor software. The Dark Net is prime territory for the world's political dissidents, whistle-blowers, investigative journalists—and, of course, criminals.