Libertarian-American: Alex Winter’s “Deep Web” (2015)

A stylized shot of director Alex Winter discussing his 2015 documentary, "Deep Web".

[This article was first published on Alex Sheremet’s Ideas on Ideas.]

Let’s get aesthetics out of the way, first. If a film about a drug boss starts with an anarchic proclamation, it needs- at a minimum- for that proclamation to be well-phrased. This will at least offset some of the political clichés surrounding drug prohibition, and might make it easier to repeat them without hurting the film on more substantive grounds. But if after engaging with the writing- “giant Fuck You to the system”, “fascists”, “real base of power lies with us”- one wonders WHY the film was even made, that question IS a relevant lens through which to view the film’s subject. I mean, just consider any other work on any other drug dealer: from the experts’ self-pillory in Mr. Untouchable, to the dread and ennui of Mean Streets, to the dum-dum brutality of American Gangster, the world’s mobsters are rarely presented as unequivocal heroes. In most cases, they aren’t allowed to have childhoods, nor to wax philosophical from home videos (although, in the coming decade, some will). They do not earn science degrees, and certainly were not nurtured by a loving family driven to exonerate them. In fact, if they were street-peddlers, their stories simply gain no traction at all, and cannot, on an individual basis, ever be the face of a grassroots political movement. That Ross Ulbricht, the incarcerated founder of darknet website Silk Road, gets to enjoy all of these things, and more, is a story far more interesting than Alex Winter’s Deep Web allows it to be. Indeed, one ought to ask why Ross Ulbricht is a cult figure for so many libertarians, if only because the answer sheds light on how awful the parsing of more important questions has become. The war on drugs, I’m afraid, attracts dupes and hypocrites on both sides, and by stripping his film of all artistic appeal, Alex Winter gives an inadvertent glimpse into how both sides conduct themselves.

But, even more than these glimpses, I am interested in their framing- what makes it in, what is omitted, and the order in which each element gets polemicized. The story proper opens with the shuttering of Silk Road and an explanation of the deep web, which the narrator (voiced by Keanu Reeves) makes sure to differentiate from illegal activities on the darknet. We learn of the website’s sophistication and massive sales: over $1 billion at its peak, with additional details provided by journalist Andy Greenberg, the trope ‘voice of reason’ made more sympathetic to Ross Ulbricht than it perhaps is. He discusses Silk Road’s community of anarchists, while another expert opines that the website was not really about selling drugs, but “a political statement”. A former Silk Road dealer is brought in to corroborate this, as the over-voice primes the viewer for the film’s main argument- that there is insufficient proof tying Ross Ulbricht to the site’s admin, the Dread Pirate Roberts, or, failing that, at least insufficient proof that Ross Ulbricht took out contracts on his enemies. A fourth expert- another dealer- gives praise to the website’s philosophical origins, while a few activists and legal experts discuss cryptography, as if to tie Silk Road to services like WikiLeaks and other “incarnation[s] of basic human values”. Interestingly, many of the more ‘posh’ talking heads do not even mention Silk Road directly, as if they are answering broader questions about human dignity without us ever hearing the actual prompt. In fact, it is almost one-third into the film before Greenberg is allowed to rein things in, declaring Ross Ulbricht guilty, though (and this is critical) emphasizing his shock that the same Dread Pirate Roberts espousing libertarian ideals would also engage in murder. Ross’s childhood friends are brought in for the same purpose, and a quick biography is limned. To the extent that cops do give interviews, they are brief and limited to a few banal details: a red flag, given how little dissent Deep Web allows.

In time, the Silk Road is infiltrated, seller accounts get taken over, and the number of informants grow. Ultimately, Ross Ulbricht makes a number of mistakes which lead to his arrest, and so the film steps up its rhetorical strategy, citing yet more opinions on Ross’s ‘true’ character while obfuscating how the site was in fact run- implying, for example, that an employee named Variety Jones was behind some of the more lurid crimes. Ross’s mother soon takes up his mantle, starting a campaign to free Ross, raising money for his legal fund, and sharing her pain over her son’s incarceration as sentimental music plays. Lyn Ulbricht complains of media reports- particularly the murder-for-hire charges- written by those who “don’t even know him”: a telling admission, and one whose irony must be discussed. As the trial begins, legitimate 4th Amendment issues get raised, while the film adopts a fresh tack by muddying the waters over Ross’s supposed lack of tech skills commensurate with running an online drug market. The rest of the narrative oscillates between the objective evils of drug prohibition and more of the family’s hurt. Andy Greenberg ends with the belief that, while Ross Ulbricht was the Dread Pirate Roberts, the specifics of the trial were nonetheless troubling, as Ross speaks from yet another home video about his coming immortality.

If it’s not yet obvious to those with some knowledge of the Silk RoadDeep Web is a work of propaganda, and not a very good one, at that. Indeed, the best agitprop- think Michael Moore’s Bowling for Columbine, in film, or Vladimir Putin’s real-life snookering of politically diverse idiots- not only muddies the water, but does so with style and a plenum of tricks, offering a seemingly credible alternative to ‘the truth’. By contrast, Deep Web is quite damning to its own subject, largely because of what it omits. Lyn Ulbricht claims, for example, that there was evidence of her son’s innocence which never made it into the courtroom, yet declines to elaborate, talking, instead, of how “kind” and “generous” Ross is, while the film harps on the complexity of bitcoin and reconstructs the unbelievable defense used at Ross’s trial. There is no answer to the personal diary entries which follow the development of Silk Road, the Internet logs of his coding questions and bitcoin startup, 2+ million words in chat logs coinciding with Ross Ulbricht’s day-to-day life, and the fact that Ross- who was supposedly lured back to Silk Road as the patsy- was found with a laptop giving full access to the site and all of its financial assets. Yet these are facts known to anyone familiar with the story, and even granting the state’s misconduct throughout this process cannot reasonably answer them. Now, almost 5 years later, Ross Ulbricht has been deserted by polite company, with negative stories in the press and not even a peep from the ACLU, who are explicitly against the war on drugs. Lyn Ulbricht blames this on the seemingly endless power of state propaganda, but there is an even better explanation: that- almost 5 years later- there’s still no serious response to the worst charges against Ross, which have not escaped public scrutiny despite getting dropped.

Ross Ulbricht was convicted for nonviolent crimes, resulting in a double life sentence plus forty years, which was significantly harsher (at least on paper) than the punishment doled out to mass murderer and lifelong drug trafficker El Chapo. Now, there are plenty of conspiracy theories as to why murder-for-hire wasn’t on the docket, yet journalist Nick Bilton offered the most sensible account: that the state wished to send a message that this form of trafficking would not be tolerated lest it get out of control. As for the evidence for these assassinations? It is, in short, overwhelming– from paying for hits on ‘blackmailers’ and ‘thieves’, to Ross admitting pleasure at such outcomes, to being sent fake videos and photos of Silk Road admin Curtis Green’s death: the last being orchestrated by a corrupt cop who’d go on to extort Ross and thus forever taint the investigation. But while Ross Ulbricht’s supporters use this as a bludgeon against ANY culpability, there’s no proof such corruption meant a subsequent planting of evidence- that, for example, the relevant chat logs were altered, or that this could even be possible given how closely the logs aligned to Ulbricht’s day-to-day life. More, Ross kept a detailed diary of his criminal operations going back to the beginning: this, too, they say was meticulously planned to frame him. Yes, DEA agents posted on Silk Road forums under admin accounts they took control of, but 1) this is a normal part of such investigations, 2) beyond the specific crimes of Carl Force and Shaun Bridges, none of this corruption has ever materialized, wherein the defense peddled yet more conspiracy theories, fingering Mark Karpeles– a wholly unrelated person- as the site’s true owner. It makes sense to think Ross Ulbricht ordered those assassinations, and though all of them turned out to be scams, that’s simply an argument about the undue severity of his punishment, not the moral culpability involved.

And why am I so dismissive of friends’ and relatives’ testimonials of Ross Ulbricht’s personal character? For the same reason I accept drug kingpin Nicky Barnes’s formula for drug violence: that “if you’re not willing to terminate…you will be terminated.” I mean, this is such a dumb-shit obvious precept to anyone with the slightest knowledge of drug crime, that it’s amazing Ross’s supporters don’t quite get it. Ross Ulbricht had every opportunity to engage in “good” and thus accumulate social capital, as he grew up in a setting where the good was both incentivized and kept separate from his less visible life: a privileged mode of being unavailable to street peddlers, whose every utterance, grimace, and personal relationship is subsumed by survival. Nicky Barnes talks of one’s “evolution” as a dealer- something Lyn Ulbricht (for obvious reasons) must outright deny. Yet it’s clear Ross had undergone the same evolution from peddler to enforcer, simply because the moral logic demanded it. And why not? Ross believed he was changing the world by responding to a moral outrage. Then, a year into his project- a project that itself was an existential threat to Ross Ulbricht- he was not only threatened with its end, but was threatened by a man (in the case of Curtis Green) who got ‘spooked’ by the penalties despite once accepting them alongside Ross. But Ross hadn’t ripped him off, nor mistreated him in any way- the options, then, were either to close the Silk Road in order to placate a frightened underling, or to kill him. After all, they were BOTH guilty of a crime, and had both profited from crime. Does one now have moral authority to escape the other, at the expense of the other? Shit- can anyone deny where this is going? Perhaps if one is still in Ross’s birth-world, where such calculations simply do not happen and are therefore unacceptable. Put a thousand Rosses, however, at the helm of a thousand drug empires totaling over one billion dollars in sales, and how would the probability space play out? It is, as before, the purely animal logic of survival. What prohibitionists don’t get is that it’s NOT about pointing one’s finger at objective evils (such as Ross Ulbricht’s) from the moral comfort of their world. It’s about dismantling the other world- the world of prohibition- and thus the moral logic engendered by and woven from it. It’s about starving these niches of absolute space, for as long as space exists for some moral logic, this moral logic MUST be exercised. Yet hypocrites will never admit this, for moral logic is quite powerful. It is powerful when Ross Ulbricht orders hits in a zero-sum world, and it is just as powerful when it allows the state to sermonize at all the carnage below. It doesn’t matter that the state ITSELF prolongs this carnage- why would it? An animal’s moral compass has the advantage of might-makes-right. But the moral compass of the ‘polite’ world- the nonzero world– has a more peculiar advantage: that of confusing cause for effect, and absolving itself of all responsibility. It is evil of a different sort, for it perpetuates the first evil despite being the only syllogism powerful enough to stop it.

It comes as no surprise, then, that the state downplays the most amazing part of all this: that Ross Ulbricht oversaw a billion dollars in drug transactions, and not one murder can reasonably be tied to him. Had he been arrested only two months later than he was, his total net worth would have touched $100 million, which few seem to appreciate. A drug kingpin worth $100 million, and not a single body for him to stand on! In fact, this number should have been preceded by mass murder, since drug kingpins ARE mass murderers, as a rule. Except…well, if you anonymize everything to such a degree that even the assassinations cannot happen because of the far more lucrative nature of assassination fraud, I guess that solves the problem, at least in the marketplace. But should there be a market for assassination, to begin with, and couldn’t some of Ross Ulbricht’s indiscretions have been avoided by way of hyper-efficiency: say, eliminating the profit motive altogether? Lest my position on the meta-issue isn’t clear: there is simply NO way to justify drug prohibition, of any kind. To draw some arbitrary line between ‘harmful’ and ‘less harmful’ drugs misses the point: all drugs (even marijuana) are on balance harmful, which means that social policy must be geared towards harm reduction. Nick Bilton, despite writing the definitive book on Silk Road, doesn’t seem to get this, harping on the ‘bad’ drugs offered on Silk Road rather than exploring the deeper question of who is producing and selling them. America, for example, had supported South American drug traffickers throughout the Cold War, propping up anti-Soviet regimes despite the violence and addiction they ultimately caused. And, yes, while modern cartel violence stems from this history, few seem to understand the more relevant point: that South American states are weak, and that cartels are de facto corporations feeding off of this power vacuum, just like Ross Ulbricht’s cartel fed off of the vacuum in cyberspace. I mean, if America was on the verge of collapse, does any intelligent person doubt that Blackwater would be on the front line of that coup with some drugs to push? In fact, we do not need a ‘better’ explanation for drug violence- this is it! For it’s not so much that cartels provide a dangerous product, but more so that their objective is to provide as much of this product to as many people as possible without also building the infrastructure to reduce harm- incidentally, the exact moral dilemma Silk Road faced, despite eliminating so much violence already. The ideal scenario, then, is a true state monopoly on the cultivation and sale of all drugs- the ‘free market’ CANNOT be involved in something so important, as profit will trump health considerations at the point of manufacture, and cut government revenue at the point of sales. It is shocking that such an obvious distinction isn’t made: not by the film, not by Nick Bilton nor his libertarian interlocutor, and not by the more vocal supporters of Ross Ulbricht, who fail to see that it’s no contradiction to want full and unequivocal drug legalization, on the one hand, while also pre-selecting the entity meant to unleash these drugs, and to what accountability. Yet Deep Web shows a Silk Road pusher deciding on whom to sell his heroin, parsing emails for a potential buyer’s “maturity” and sending out educational materials to the uninformed- not very inspiring, as a safety regulation, though the film doesn’t seem aware of how laughable the dealer’s self-praise is. Just think- this IS the libertarian answer to regulation, even as they deny that drug use is, and always will be, a net social COST, and must be dealt with like any other cost. And yet the solution is so goddamn ELEGANT and SIMPLE: for if addicts pay a tax on every drug purchase, they are essentially funding their own treatment rather than expecting society to pay for their choices. If they don’t take drugs, they don’t pay the tax. But the more drugs they take, the more they pay in taxes, because they will need those extra dollars when the drugs inevitably destroy them. In this system, you respect both bodily autonomy AND the fact that drug use is socially costly, you eliminate violence, you allow drug addicts to take responsibility for their own care while providing universal access to this care. This ought to be a libertarian DREAM, but isn’t, for it appears that the most rational solution can’t be entertained if government maintains an important role in this solution.

What do we make, then, of the libertarian response to Ross Ulbricht’s sentencing? Not much, it seems, except to say that it is as hypocritical as the rationale for yet more prohibition. They have latched on to Ross as the chill, smart, peaceful, generous entrepreneur who would have become a billionaire by saving the world, if only the gub’ment would just leave it to him. Now, after decades of mayhem, there is a face and a name attached to the war on drugs, and this time, it’s a casualty. No one likes a kingpin, but Ross doesn’t look like one: and he had all of those ideals, you know. In fact, he looks like them, and thinks like they do, and- this is important!- had the balls to do what they couldn’t, thus turning Ross into a ‘personal’ hero lit by candles and self-aggrandizement. Shit- you know the type! They’re the guys on Quora with a carpet-cleaning business they’ve expanded to 3 towns in Arkansas, who now feel qualified to opine on the ‘genius’ of Ayn Rand. They’re the morons admitting to crime while arguing with me about crime, since the libertarian bottom line is always pelf. And so, they begin to throw us off the trail. The cops were corrupt. The server acquisition was illegal. The hits never happened. They complain Ross Ulbricht is a victim because he was driven by a deep moral sense, and was punished for it. Yet Ross could have started any business that he wanted, and almost any other business would have had far thinner profit margins. Ross, naturally, was obsessed with his net worth because it fed and was fed by his ideals. Are we really to think that self-justification didn’t play some role here? I mean, just look at the standard obfuscation– to deny Ross was in fact the Dread Pirate Roberts, and yet hold him up as a hero: to DENY what you admit is BAD, then polish the only real instantiation of such down to an abstraction! Does that sound familiar? Being exactly what libertarians complain of, it is in fact the bedrock of their own ideology. ‘It wasn’t me!’: for, whenever libertarianism is tried, or the national debt paid down, the logical outcome can only be survived if libertarians play No True Scotsman and express how much better THEY would do if given all that power. Ross, it seems, feels the same way. After all, his Twitter feed’s page art is a pencil drawing by Ross depicting him leaving prison with his arms triumphant, and a big crowd offering compliments. One tweet explains that he’s learned his lesson, and that it’s pointless to keep him in prison even for another year. The irony, of course, is that Ross Ulbricht HAD his turn to ‘get it right’, to escape the typical drug dealer’s moral system, and yet he still felt the urge to murder. Ah, to argue about the perils of drug prohibition, and then deny an actual example of such perils: that Ross is PROOF of why drug prohibition needs to end, not because he looks like an innocent white kid behind bars, but because of all the ways prohibition fueled his most destructive instincts and gave them the perfect outlet.

It may be impolite to say, but I do think it important to study the relationship (if any) between libertarianism and medical psychopathy. Forget, for a second, how inflammatory that might sound, and just consider the people described in this essay. A drug dealer thinks he’s wise enough to know whom to sell heroin to, ignoring the fact that every other drug dealer assumes the same exact thing. Ross Ulbricht is asked about selling body parts on Silk Road, and makes the executive decision that, yes, they should be allowed, assuming they are justly procured- and guess who would make that assessment? Cody Wilson wants to spread 3D printed guns “to evacuate the whole moral foundation [on which the system is based]”, then gets indicted for having sex with a minor. Roger Ver, who contributed substantial cash to Ross’s legal fund, was once in prison for facilitating the sale of explosives through the mail, and now pushes his own shitcoin on unsuspecting crypto noobs. And yet, as satisfying as it is to diagnose my ideological opponents in this way, I must admit that the psychopathy of the state is even worse. After all, people behave in rather predictable ways once they enter an unregulated space, and the only morally relevant question is WHY this space is being so readily provided. The state KNOWS the cost of drug prohibition, and yet prohibition persists. At a certain point, blaming the dealers is like wagging one’s finger at a hurricane while bitching at voters who ask about cuts to FEMA spending. It might not be soon, but Ross Ulbricht will likely leave prison, not only because drug prohibition is unsustainable, but because the state has refused to make the key argument in all this: that it isn’t the drug-dealing itself which was so egregious, but that a single non-state actor made the decision to sell drugs, in a theft of state of responsibility. Then again, is it truly theft when the responsibility has been so foolishly abdicated?

Not that the libertarians have been any less dishonest here- I mean, just think of the nature of Deep Web, and all of the confusion it quite consciously foments. Alex Winter says that while the film is not pro-Ross, he’s also not sure whether Ross is in fact the Dread Pirate Roberts- um, ok, I guess white-washing what’s been proven is the new neutral? Lyn Ulbricht, for her part, recently published an article in which she asks Donald Trump for clemency, describing Silk Road as an economic experiment that “[some], unfortunately, used to buy drugs”: a rather deflationary frame, given that the site was conceived for and advertised as a drug market from the very beginning. Then there’s Ross Ulbricht’s legal defense, which amounted to little more than “it wasn’t me” as a series of replacement masterminds got bandied about. And now, the more serious accusations no longer need to be answered, at all, because the charges have been dropped, thus confusing Ross’s legal obligations with a moral reckoning. No, the film doesn’t shy away from platforming more rational skeptics, but the argument changes so often that it doesn’t seem to matter- everything is up for grabs, from Ross’s actions, to Ross’s identity, until all that’s left is a free market mystique with no moral agents. In a way, this is no different from the libertarian desire to remove moral culpability from markets as a whole, because- far from being a philosophy of radical responsibility- the moment they recognize that outsized players create outsized distortions, libertarianism dies. This is why they do not accept Ross Ulbricht, and refuse to take a stand: even Ross, who must preserve himself in the face of an idea not even his supporters pretend to understand.

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