Once upon a time, you could buy illegal drugs anonymously online from a site called Silk Road. The postman would show up at your door with your gas bill, maybe a birthday card from mom, and some carefully packaged pot or heroin. Even though you had never met the person you bought the drugs from, the delivery came just as you ordered it.

That's because the secretive "darknet" site that made this possible—before being shut down by the feds in late 2013—operated a lot like any other online commerce site. Silk Road's pages, like those at Amazon or Yelp, were dense with seller ratings and reviews, guiding buyers to vendors with good records and high-quality products. Boisterous online forums were a click away, jammed with customer-generated information about drugs, dealers, safety, and whatever else the anonymous technorati wanted to chat about.

From January 2011 to the beginning of October 2013, the FBI estimates, Silk Road facilitated 1.2 million drug deals, moving thousands of kilos of illegal substances and collecting nearly $80 million in commissions. Clients were "typically professionals in the 30- to 40-year-old range" who "want to be treated with respect," one Silk Road dealer named "Nod" told The Daily Dot in January. The site provided a safe haven not just from the state-sponsored violence of being arrested but from the street hassle of transacting with physical-world drug dealers.

Silk Road's 950,000 registered users were largely satisfied with their consumer experience. A May 2014 paper in the journal Addiction found that 89 percent of customers surveyed said they chose the site for its wide range of choices, 77 percent valued the higher quality of drugs available, and 69 percent preferred the convenience. A 2012 study by Nicolas Christin for Carnegie Mellon found that 96 percent of Silk Road sellers boasted a consumer rating of 5 out of 5.

None of that mattered to the FBI. By July 2013, after months of investigation, the bureau had located Silk Road's servers in Iceland. The Reykjavik Metropolitan Police seized the site's guts and handed over copies of the contents to their American colleagues. On October 2 of that year, the feds shut Silk Road down, keeping nearly 30,000 Bitcoin-worth around $3.7 million at the time, $13 million as this goes to press-that had been left in vendor and customer accounts.

In January 2015, a 30-year-old libertarian named Ross Ulbricht is scheduled to go on trial in federal court in New York for narcotics trafficking, running a "continuing criminal enterprise" of drug selling (known colloquially as the "drug kingpin" statute), computer hacking, and money laundering. The jury will be told that he also contracted hitmen to commit murder on his behalf, though he is not being charged with that crime in this trial. Ulbricht, who the feds accuse of launching and operating the site under the pseudonym "Dread Pirate Roberts" (or just "DPR"), faces a maximum sentence of life in prison.

In the course of its war on Silk Road, the FBI has collared a handful of other defendants and shut down all activity at the site's original address. But the crackdown has done little to slow the growth of anonymous, encryption-enabled drug sales on the secret Internet.

Silk Road is dead. Long live Silk Road.

'We Lost a Community of People That Believed in Something'

Shopping on Silk Road was straightforward, but it required a certain amount of technical savvy. Would-be buyers downloaded and fired up the anonymizing software Tor (which, roughly speaking, routes signals so sites and visitors can't be traced back to their IP addresses). Thus cloaked, they could begin cruising the Dark Web. To make purchases, they had to obtain the digital currency Bitcoin, which can be a tedious process. Having jumped through these hoops, they could place an order with a Silk Road vendor, likely through an encrypted message that contained their shipping address.

Unlike the stuff you might get from a street dealer, Silk Road deliveries almost always came as advertised. An FBI report about the agency's undercover buys noted that "at least 56 samples of these purchases have been laboratory-tested, and, of these, 54 have shown high purity levels of the drug the item was advertised to be on Silk Road."

Drugs weren't all you could get on Silk Road, though they dominated the market. One 19-year-old user I interviewed only wanted a fake ID so she could drink alcohol. She found Silk Road far more appealing than dredging around her college town for a sketchy guy with an X-Acto knife and a laminating machine.

Though the purpose of the site was to facilitate illegal transactions, that doesn't mean it was a free-for-all. Administrators explicitly asked vendors-who paid a one-time fee in Bitcoin worth about $500 for the privilege of a maintaining an account-to "not list anything who's [sic] purpose is to harm or defraud, such as stolen items or info, stolen credit cards, counterfeit currency, personal info, assassinations, and weapons of any kind. Do not list anything related to pedophilia." (For a few months in 2012 there was a sister site called Armory dedicated only to weapons, but it died from lack of buyer interest.)

Silk Road made money-and provided extra security-by functioning as the escrow between buyer and seller. On purchase, the buyer's money went into a Silk Road account; the buyer released the money after he received the goods, and Silk Road took a cut. The site also provided Bitcoin "tumblers" to muddy any digital record left by the Bitcoin blockchain, which would otherwise record all the details of a transaction from wallet to wallet (although individual wallet holders can be anonymous as well).

Though there wasn't a rigid, Fight Club-style ethos of omerta, users were strongly discouraged from discussing specific packaging methods anywhere that postal inspectors and cops might see. This included any unencrypted communication on Silk Road itself.

From talking to some Silk Road buyers and reading the public writings of users, it seems a semblance of order emerged from the decentralized dark. Aromatic drugs like pot and mushrooms were frequently shipped via triple-vacuum packing in padded envelopes. Drugs on paper, such as LSD, were commonly disguised as (or inside of) coupons or Christmas cards. Small amounts of powder drugs could be bubble-wrapped and vacuum-sealed inside a Post Office–supplied box or even just enclosed in a glassine pouch wrapped in a piece of paper in a normal envelope. One buyer told me about heroin flattened out and laminated in what looked like a scuba training certification.

One Silk Road buyer I interviewed, a successful Bay Area professional who made two purchases out of a general interest in being an "experience collector," says the quality of the cocaine wasn't that much better than he could get face to face, and that he would have been better off holding on to the eight Bitcoin he used in the purchase, since it would be worth much more today. That said, he contrasted the Silk Road experience positively with past drug purchasing experiences where "I have cut and run in the middle of a deal because it doesn't feel right, feels like either legal or physical danger, I'm not in the right place at the right time."

Tim Bingham, an academic who studied Silk Road from the perspective of its value in harm reduction—mostly by allowing drug users access to better-vetted and therefore safer drugs—said in the wake of the shutdown and loss of the forums: "I, and others felt the same way, felt that we lost more than just a site that sold drugs. We lost a community of people that believed in something."

Despite the comparative safety and good vibes of the Silk Road experience, some bad stuff did go down behind the encryption. As a site administrator once wrote on the forums, "DO NOT get comfortable! This is not wal-mart, or even amazon.com. It is the wild west and there are as many crooks as there are honest businessmen and women." At least two successful and well-reviewed Silk Road sellers decided a big final fleece was more valuable than a continued reputation as an honest dealer. Sellers could insist a buyer "finalize early"—pay directly and up front rather than shifting their Bitcoin to Silk Road's escrow until they got what they paid for. If the seller had built a sterling rep over time, buyers would be apt to go along. That's how Silk Road dealers "tony76" and later "enterthematrix" got away with stealing over a hundred thousand dollars' worth and tens of thousands of dollars' worth, respectively, in Bitcoin from trusting buyers.

Meanwhile, it was just as easy for a cop to sign on to Silk Road and buy drugs as anyone else. If sellers didn't cover their tracks well enough, they could get popped. That happened to at least a handful of Silk Road dealers, even before the site was taken down.

Then there were the risks buyers posed to themselves. One Silk Road buyer from the Northeast told me frankly that access to Silk Road made him, for a while, a heroin addict. He found Silk Road amazing at first, admitting it was simultaneously "scary and enticing." Even getting Bitcoin perplexed him in the beginning, and he feared a scam, but "I rarely ran into scammers in the whole Silk Road universe," though he did lose $100 once to a vendor who made him finalize early. He used PGP encryption for his communication with vendors "most of the time, not 100 percent of the time." He recalls doing up to 50 transactions through the site, but he stopped about a month before the crackdown.

The buyer tried heroin for the first time via Silk Road, mostly out of curiosity, and got hooked. He kicked the habit after narrowly evading arrest during a traffic stop. (He told the cop who found a nearly empty glassine with heroin traces that it had contained cocaine but that it was months old, and he was let go.) Does he regret his Silk Road experience?

"It's a tricky question because right this second my life couldn't be better," he says. "I got a job doing exactly what I wanna do, but I was lost for a while. The truth is—this is really weird—my time on heroin? I'm a computer programmer and I learned some skills I use now because I could concentrate better [on the drug]. I think about opiates a lot, and whether they should be legal, and I'm torn."

Bitcoin's Killer App

After Silk Road's first prominent media hit—on the website Gawker in June 2011—Sens. Chuck Schumer (D-N.Y.) and Joe Manchin (D-W.V.) loudly demanded that the Justice Department shut it down. Eileen Ormsby, the Australian author of a forthcoming book about Silk Road, thinks that the first media mention of the site was, unsurprisingly, on a libertarian movement radio show called Free Talk Live on March 17 of that year.

Host Ian Freeman had poked around Silk Road-at a time when it had 151 registered users, 38 listings for sale, and only 28 completed transactions-and saw its promise. "This could be the killer app for Bitcoins," he said, since it allowed people to get "physical products that are normally fairly difficult to obtain; on a black market if you don't know anyone selling you can't buy it."

Freeman noted how much this system "eliminated dangers" from the drug buying process (for buyers and sellers, each of whom might be happy to not have to meet the other in person). He also prophetically joked that "someone is listening horrified, like, I can't believe you are talking about how people go about purchasing drugs on the Internet." (One caller decided the site must be a CIA honeypot.)

Tor had been around since 2002. The relatively new Bitcoin, though, made Silk Road soar by 2012. It was one thing to surf the Web anonymously and send encrypted emails. But for untraceable or unrecorded monetary transactions with someone you couldn't hand cash to across the table, existing banks and credit institutions wouldn't do.

Bitcoin was so perfectly symbiotic with Silk Road that media reports often conflated the two cypherpunk crypto-anarchist phenomena. What can one do with Bitcoin? Buy drugs on Silk Road. What is Silk Road? It's that website where people use Bitcoin to buy drugs. The two seemed like products of ideological and practical co-evolution, co-creating an ecosystem that ensured the other would thrive. This was so true that many predicted Bitcoin would collapse after Silk Road did. In fact, it was in the two months after Silk Road was taken down that the value of one Bitcoin swelled, briefly, to above $1,000.

Come for the Drugs, Stay for the Revolution

The anonymous folk running Silk Road professed they were on a mission to do more than make money. They were out to demonstrate something important about the combination of crypto and Bitcoin: that a world made by freely chosen, private, uncoerced transactions was possible and mostly beautiful. When asking people to support Silk Road, its operator Dread Pirate Roberts once wrote, "Do it for me, do it for yourself, do it for your families and friends, and do it for mankind." They believed in the power of agorism-the variant of libertarianism that valorizes and promotes black markets as spaces where people can live in freedom, rather than struggling fruitlessly to change the political system.

It wasn't just the people running Silk Road who saw something wholesome in the site. In a May working paper, David Decary-Hetu, a criminologist at the University of Lausanne, and Judith Aldridge, a law professor at the University of Manchester, pointed out that Silk Road–style drug sales drastically reduced the comparative advantage that credible threats of violence brought to a drug enterprise. Good communication, good customer service, and good product were now the keys to success, not muscle.

Dread Pirate Roberts saw violence reduction as part of the plan. He wrote on a Silk Road forum in 2012 that "the cartels…are basically a de facto violent power hungry state, and surely would love nothing more than to take control of a national government, but your average joe pot dealer, who wouldn't hurt a fly, that guy became my hero." Silk Road, he suggested, could cut the scary cartels out of the supply chain.

If you truly believed in people's liberty to buy, sell, and consume what they wanted as long as they weren't using violent force against others, Silk Road was, despite the occasional rip-off, pretty close to a perfect site in a perfect agorist anarcho-world.

Naturally, the U.S. government wanted to destroy it.

Shutting Down the Silk Road

A multiagency task force calling itself Marco Polo soon swung into action. By November 2011, law enforcement had turned at least one known Silk Road seller into a confidential informant, taking over his account, and obtaining access to his buyer records.

On October 1, 2013, FBI agents were wrestling a man to the ground in the Glen Park branch of the San Francisco Public Library, in the science fiction section, trying to subdue him before he could close or turn off his laptop, which they claim he was using at that very moment to administer Silk Road in his role as DPR.

The perp's name was Ross Ulbricht. He had a master's degree in materials science from Penn State, and he had run an Internet bookstore called Good Wagon Books out of Austin, Texas. According to friends and acquaintances, Ulbricht embraced the radical libertarian ideas of the economist Murray Rothbard and the Ludwig von Mises Institute. Unfortunately, his affinity for libertarian ideas would eventually form a key part of the case against him, since DPR seemed to share those beliefs.

A friend told The New York Times that Ulbricht was "one of the most guileless and nonaggressive people I've ever met." He was known to wear Ron Paul T-shirts, and he didn't think we needed government to build roads. His LinkedIn page once announced that his goal was "to use economic theory as a means to abolish the use of coercion and aggression amongst mankind." He wanted to make, he wrote, "an economic simulation to give people a firsthand experience of what it would be like to live in a world without the systemic use of force."

Jason Wohlfahrt, a libertarian who knew Ulbricht in his Austin days, verifies Ulbricht's "sincere understanding and belief" in libertarianism. "He was well versed in Rothbardian topics." Wohlfahrt says his "jaw dropped" to think the Ulbricht he knew could have been guilty of soliciting murders for hire.

Jeffrey Tucker, then of the Mises Institute, recalls a 2009 email exchange with Ulbricht in which Ulbricht said similar things about "a digital free market where people can trade real goods and services and experience what it's like to live in a state of actual freedom in the economic sense."

The FBI says that U.S. Customs discovered in early July a package of nine fake IDs being mailed to Ulbricht from Canada. If the suspected DPR is the criminal mastermind the government implied, he showed either amazing sangfroid or foolhardiness, as Homeland Security agents visited him in connection with those captured IDs at his San Francisco apartment on July 26. According to their accounts, he actually brought up that, "hypothetically," such fake IDs were available on a website called Silk Road. Despite the confrontation, Ulbricht was still hanging around San Francisco to be collared by the FBI more than two months later. The supposed multimillion-dollar drug kingpin was living with three roommates and paying around $1,200 per month in rent at the time of the Homeland Security visit.

Many Silk Road watchers were sure that the choice of moniker was a tell, that the role of boss of Silk Road moved from person to person, like the role of the Dread Pirate Roberts in the cult classic The Princess Bride. They've analyzed the different communication styles (and even common typos or misspellings) seeming to be issued from the DPR name over the years and suggest that as many as four different people have used the identity. Journalist Ormsby asked DPR in August 2013 whether this was so. She was told, "Hmmâ€¦I think I like this one being a mystery."

But the U.S. Justice Department insists Ulbricht is DPR. At the base of their accusation is the claim that someone using the name "altoid" had been trying to draw attention to Silk Road right after it launched on Bitcoin forums. Later, in a different forum, the same "altoid" tried to recruit savvy computer workers for a Bitcoin startup and allegedly used Ross Ulbricht's Gmail address as a contact, thus leading them to believe "altoid" was Ulbricht.

Ulbricht's, and DPR's, known affinity for libertarian thought were noted as a proper subject for search. A warrant said that his personal computer was ripe for full search, as it might contain "any communications or writings by Ulbricht, which may reflect linguistic patterns or idiosyncrasies associated with 'Dread Pirate Roberts' or political/economic views associated with 'Dread Pirate Roberts' (e.g., views associated with the Mises Institute)." DPR explicitly mentioned reading libertarian classics such as Murray Rothbard's For a New Liberty and Samuel Edward Konkin III's agorist New Libertarian Manifesto in his message signatures.

The most salacious claim against Ulbricht is that he ordered various murders of people who had crossed him or threatened to release private information about Silk Road users, including hiring someone to slay a then-47-year-old Silk Road member named Curtis Clark Green. The people DPR allegedly tried to hire were all undercover agents and no actual murders occurred, though the feds claim they were paid for. In an odd detail, although DPR built an empire on Bitcoin, he is alleged to have wired 40,000 U.S. dollars to pay for one of the murders.

Yet those charges are not among the ones Ulbricht is being tried for in January 2015. The state merely asserts these as-yet-unadjudicated accusations as facts of interest to the jury. Ulbricht was indicted on the murder-for-hire charges in Maryland in a separate case that is currently stalled. But despite never being tried for these alleged attempts to kill, his jury essentially will be told that he is guilty of them.

Ulbricht has been in jail, having been denied bail, for the past 11 months. His trial is currently scheduled to begin in January 2015. His mother, Lyn Ulbricht, who maintains her son's innocence, says he was kept in solitary for over a month "for no reason we were given. He had no priors and no record of violence." He's now in general population and teaching physics and yoga to his fellow prisoners, as well as digging through what Ms. Ulbricht says is 4.5 terabytes of discovery material to help in his own defense.

He is not permitted access to the Internet. Ms. Ulbricht says dealing with her son in jail has educated her about the problems and expense involved in keeping prisoners in touch with their families. Ulbricht himself, she says, "as opposed to languishing or rotting away, tends to be a very positive person, and is quite resilient and very strong and never complains." While he's aware the case has gotten a lot of publicity, "Ross doesn't care about [fame]. He's very focused on principles."

Ms. Ulbricht says she still doesn't know very much about Silk Road, and she doesn't care to discuss her own politics or those of her husband. She just says "we are entrepreneurial people, not big government people, and we certainly believe in the Constitution." She is confident there's no good reason for her son to be in jail, and worries about the precedent of using Ulbricht's libertarian political convictions to make the case that he's a criminal.

The Silk Road Goes On

The FBI tore up the Silk Road. But they could not end the practice of selling drugs anonymously on the Dark Web. According to a recent study by the Digital Citizens Alliance, there are nearly 47,000 drug listings in Dark Web markets, double the number when the first Silk Road fell. Other sites have emerged since the fall of the first Silk Road, including the less ideologically charged site Agora, which as of early September was the market leader. Within two months of the site going down, a new Silk Road, known as Silk Road 2.0, arose, apparently run by people involved in the original. Some of its alleged administrators have been arrested (including another suspect with libertarian links), and there was a huge theft of client Bitcoin, which the site's operator, going by the name "Defcon," insists has been almost paid back.

As drug sales online continue, government prosecutions of people allegedly involved in them continue as well. Money laundering via Bitcoin for illicit Silk Road purposes is one of the charges Ulbricht faces. In September, the same D.A. prosecuting Ulbricht, U.S. Attorney for the Southern District of New York Preet Bharara, squeezed guilty pleas out of two men, prominent Bitcoin advocate Charles Shrem and Robert Faiella, for providing dollars-to-Bitcoin services for Silk Road users. Both men will be sentenced in January 2015.

The D.A.'s office will not say how many other arrests, indictments, or prosecutions have already or might arise from their possession of Silk Road's servers. Amateur online Silk Road scholars have not found more than a few handfuls of arrests in the past year that seem directly Silk Road-connected. As near as anyone knows, no mere buyer has been collared.

Fourth Amendment Follies

Ulbricht's lawyer, Joshua Dratel, believes the way the feds pursued their case against Silk Road should worry even Americans who couldn't care less about online drug sales. To Dratel, even if Ulbricht is who they claim he is, merely managing a website that allowed for illegal action shouldn't rise to the level of a crime. If it does, what about eBay, Amazon, or any other commerce site that connects buyers with sellers without policing the legality of what is being sold?

If all of Silk Road's users were Dread Pirate Roberts' literal partners in crime, Dratel wrote in a May court filing, then those other e-commerce sites "would have a rather awkward time explaining their corporate structures to the shareholders and the Securities and Exchange Commission." The indictment, Dratel insists, does not sufficiently prove any "agreement between any Silk Road user and Ulbricht to violate the law." The government maintains that Silk Road, unlike eBay or Amazon, was deliberately designed to facilitate crime, something it thinks is made clear by the use of Tor, Bitcoin, and PGP encryption.

In August, Dratel tried to chip at the state's case by pointing to its Fourth Amendment implications. Initially, the FBI didn't explain how agents found and broke into the Silk Road servers. Dratel wondered if perhaps it was a result of illegitimate National Security Agency help or through some other unconstitutional means. If the search that found the servers was illegal, much of the rest of the government's case, which relies on things they learned from the servers, could be crippled.

Whoever stored the Silk Road servers in Iceland probably thought that would help keep them out of the reach of U.S. law enforcement. The bitter irony is that because the Reykjavik Metropolitan Police seized and copied the servers, Judge Katherine Forrest has ruled that any possible Fourth Amendment violations at the root of the investigation are moot, since American officials were not responsible.

So how did the FBI know the Silk Road servers were in Iceland? In a September filing FBI agent Christopher Tarbell said he found that the captcha code—which requires users to enter a unique string of characters in order to discourage bots from entering a site—offered on the front page of Silk Road could be traced back to a computer node not hidden by the Tor network, and from there it was easy. The FBI explanation has failed to convince some discerning geeks. In an early October court filing, Joshua Horowitz, a tech-savvy lawyer also on Ulbricht's team, explained in great technical detail why Tarbell's story seemed fishy, and wondered why the government provided no actual evidence corroborating Tarbell's story. The Feds replied that merely questioning Tarbell's story doesn't prove there was anything illicit about the search. "We think because of the doubt raised about the version the FBI has proffered as to how [they found the servers, the question] ought to be tested by testimony and cross examination" and not just a written statement, Dratel says.

Dratel also tried to argue that the depth of material the Feds gave themselves access to regarding Ulbricht's digital life-everything on his laptop and his Facebook and Gmail-violated the limits of particularity under the Fourth Amendment and rose to the level of the verboten "general warrants" that, Dratel wrote, "lack specificity and allow unlimited rummaging into private information and property."

Dratel also thinks Americans should be scared to see government "creating a penumbra of criminality around trying to stay private" when using tools like Tor and PGP. He notes that "nothing about the way government has used warrants" to search everything about Ulbricht's private and public Internet and computer life "is premised at all on the idea that this is a 'big case' or the specific crime he's accused of. Government always has stalking horses in these types of cases that then get applied across the board."

The government counters that when criminal activity is thought to pervade an "entire business, seizure of all records of the business is appropriate." It also says particularity requirements are not relevant. It would only have been a general warrant, the government insists, if it didn't specify at all what crimes officials were seeking evidence about. And it specified just that: "narcotics trafficking, money laundering, computer hacking, and murder for hire."

The government insists that although the murder-for-hire charges were not in the New York indictment under which Ulbricht is scheduled to go to trial in January 2015 and have never been proven in court, the mere allegations "are not only relevant to the crimes charged but are likely to be an important part of the Government's proof of criminal intent at trial." The government certainly seems to think it's very important to get a conviction, perhaps to provide a cautionary tale for other would-be Silk Roads.

But in a way, the feds have already lost. Cryptography and cryptocurrency are out of the bottle, and the war on drugs is even more hopeless than it always was. Small consolation, for all those who face harsh punishments for trying to meet other people's peaceful wants and needs.