There are lots of reasons to wear a mask, some good and some not so good. On Halloween, kids have mostly harmless fun by donning masks and dressing up as their favorite cartoon characters, or anything else their imagination (and their parents) can come up with. But criminals also wear masks to conceal identity for nefarious purposes. At least in Western countries, I'm not aware of any law against simply wearing a mask, although you have to choose your circumstances carefully. Outside of Halloween or a costume party, a person walking around in a mask may be suspected of either serious eccentricity or illegal doings.
When you go online these days, your identity is as obvious to websites you visit as it is in person. Cookies and easily purchased commercial databases make it easy for both individuals and companies to identify you and figure out things about you that you may not even be aware of yourself. So wouldn't it be convenient if there was some way to wear a mask on the Internet? It turns out that there is: a type of freeware called Tor, which was developed with support by, believe it or not, the U. S. Naval Research Laboratory, and still largely supported financially by the U. S. government. Tor has recently been used for a lot of underhanded doings, most prominently the Silk Road affair.
A fellow going by the online name of Dread Pirate Roberts (a character who always wears a mask in the cult-classic movie The Princess Bride) designed a clandestine website called Silk Road to deal in illegal drugs and other illicit material. To protect both his own identity and those of his customers, he required users to communicate with him using Tor, which virtually guarantees anonymity on the Web. The medium of exchange on Silk Road was bitcoin, a virtual currency that is also (virtually) untraceable and often used for illegal transactions.
Dread Pirate Roberts, whose real name was Ross William Ulbricht, eventually made enough mistakes online, such as using his real email address on occasion, to allow the FBI to catch up with him last October. He is now awaiting trial on numerous charges, and may wish that he'd never heard of Tor. So why is the government supporting software used by criminals?
Just as kids at Halloween usually don't mean any harm by wearing masks, there are legitimate reasons to be anonymous on the Web. Suppose you are a dissident in a country run by a nasty dictatorship. Using Tor can allow you to communicate over the Internet with fellow dissidents or supporters outside your country. Law enforcement agencies do not care to have their confidential online activities viewable or traceable by all and sundry, and I'm sure that domestic and international security issues were an important driving force behind the Naval Research Lab's support of Tor. But because it's cross-platform freeware, just about anybody with a computer and enough knowhow to install a Web browser can don a Tor mask online and instantly become very hard to trace. It's a little like a digital invisibility cloak, and we all know what happened to the Invisible Man: nothing good.
That is not to say that anyone using Tor will inevitably develop bad habits of flaming websites anonymously and dealing in child porn or crystal meth, payable in bitcoin. But the developers who decided to make Tor widely available as freeware were making a decision that they may not have explored the full implications of. Just to move the situation in imagination to the physical world, suppose Wal-Mart came up with a good, cheap invisibility drug and decided to make it free for everybody, and the Wal-Mart greeters handed it out as you walked in the door. I'm sure there are legitimate reasons to be invisible, but my guess is that the vast majority of people who decided to take advantage of the offer would do things that are inadvisable at best, and more probably illegal, immoral, and maybe even fattening. (Don't like the way you look? Become invisible and who can tell?) I'm not liking where that fantasy is going, so I think I'll stop here.
No one I have read on this subject is saying that defects in Tor led to Ulbricht's arrest, or that we should rethink whether Tor ought to be freely available. The fact that it's not that well known makes it unlikely that we'll see a rash of online crimes committed by newly invisible Internet users. But Tor enables the existence of what various news articles on the Silk Road incident have referred to as the Deep Web or the Dark Web, because Tor renders a website invisible to the usual search engines and so on. For most commercial websites, their problem is increasing their visibility, not the other way around, so they have no incentive to use Tor. But for sites dealing with unpopular, persecuted, or illegal activities, Tor is still available.
Ulbricht is awaiting trial, so I should refer to him as the "alleged" mastermind of Silk Road, although the evidence pointing to him is pretty convincing. Whatever the other facts of the case may be, Ulbricht's use of Tor did make it harder for the FBI to catch him, just as masks make it more difficult to identify a guy who knocks over the convenience store down the street. But there are other ways to catch crooks, and it looks like we will all just have to get used to a world where you can wear a mask on the Internet as well as in real life.
Sources: I referred to articles on the Silk Road affair published in the online version of Timemagazine at http://nation.time.com/2013/10/04/a-simple-guide-to-silk-road-the-online-black-market-raided-by-the-fbi/ and by the website Verge at http://www.theverge.com/2013/10/2/4795502/the-fbi-busted-silk-road-but-not-the-dark-web-behind-it, as well as the Wikipedia articles "Tor (anonymity network)" and "The Princess Bride." My blog "Bitcoin: Currency of the Future?" appeared on Oct. 16, 2011.
