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Of course Ross Ulbricht was guilty. Despite his far-fetched claims of mistaken identity, a New York jury confirmed the obvious: that Ulbricht (aka Dread Pirate Roberts) was the criminal mastermind who took on a villain’s name, and became rich by running an online marketplace that sold any drug imaginable.

All the same, protestors on the internet and at the courthouse still insisted Ulbricht was innocent. More broadly, the Dread Pirate (who is now awaiting sentencing) also enjoyed sympathy from many in the tech press, which often downplayed the bad things he did, and instead cast the FBI as the villain in the case.

Such moral indulgence is odd, and doesn’t extend to Ulbricht alone. Other tech rogues, including a corpulent charlatan and a Nazi sadist, also enjoy public sympathy. But why? A big part of it may lie with the government’s heavy-handed approach to internet-related crime.

Bad people

Ross Ulbricht didn’t start out bad. Indeed, accounts of his past life from his mother and Ulbricht reveal a very different sort of person: an Eagle Scout, and then a bright and sensitive physics student who worked hard to build a used books company.

But then he became someone else. He started the Silk Road marketplace, which began as a relatively benign forum for finding magic mushrooms, but then devolved into a free-wheeling playground for hard drugs, forged documents and prostitution.

The notorious bazaar also changed Ulbricht himself: FBI evidence from a seized laptop suggests that he attempted to hire hit men to murder those he believed had betrayed him (the “hit men” turned out to be government agents but Ulbricht believed they were real).

This tragic arc, which saw the Eagle Scout become the Dread Pirate Roberts, may explain some of the sympathy for Ulbricht. But that’s hardly the case for Weev, another famous figure in internet circles who is also facing prosecution by the Justice Department.

Weev, whose real name is Andrew Auernheimer, was sentenced to three years in prison for what the government describes as a hack on AT&T. But he is better known for his other legacy as one of the cruelest trolls on the internet, whose antics have exposed women to death threats. And last year, Weed reinvented himself as a Jew-hating White Supremacist.

Despite all this, many tech outlets hailed an appeals court decision last year to vacate Weev’s conviction on the hacking charges on procedural grounds, and to release him from prison. And while Weev doesn’t exactly enjoy public sympathy, stories of his legal battle often elide the bad things he has done.

Other antiheroes of the tech worlds include Julian Assange, the self-aggrandizing Wikileaks leader who faces sexual assault accusations in Sweden, and outlaw music mogul Kim Dotcom.

Dotcom has done a litany of bad things, including making millions from purloined movies and allegedly ratting on his rivals, but he is still hugely popular with many internet communities. The 300-pound fugitive is even dabbling in mainstream politics in New Zealand, where he is living while he fights U.S. efforts to extradite him to face multiple criminal charges.

The celebrity-style adulation that Dotcom and the others receive is no doubt frustrating for the law enforcement officials trying to convict them. The reason for it, however, is not just because the outlaws are good at gulling the public (though that’s part of it), but because of people’s legitimate misgivings about the laws that the U.S. is using to prosecute them.

Bad laws

Aaron Swatrz was a genius so beloved in the tech community that a film-maker made an acclaimed movie about him called “The Internet’s Own Boy.” But he was also a criminal in the eyes of the government, and some believe the Justice Department’s relentless effort to prosecute led the 26-year-old Swartz to commit suicide in his Brooklyn apartment two years ago.

What crime led to this end? In 2009, Swartz used MIT computers to download millions of academic articles from a database called JSTOR – articles whose authors are typically unpaid, but that are licensed to universities at high fees. His action may have been ill-advised, but hardly amounts to a serious crime.

Nonetheless, the Justice Department came at Swartz with a law called the Computer Fraud and Abuse Act that gave prosecutors discretion to seek a prison term of 35 years and a $1 million fine.

The CFAA is a clumsy statute dating from long ago that relies on vague concepts like “unauthorized access,” and lawmakers have tried to reform it. Yet those efforts have so far failed, and the Justice Department keeps using it in all sorts of cases — including that of Weev.

In the government’s view, Weev committed illegal hacking under the CFAA when he “accessed” the AT&T website to demonstrate a security flaw that spat out private email addresses. Skeptics, however, point out that Weev simply entered information into a public website available to anyone with an internet browser, and ask how this amounts to hacking.

The CFAA also grounded one of the seven charges– “conspiracy to commit hacking” — on which Ross Ulbricht was convicted, although that charge was overshadowed by other elements of the trial (including a theory that the government itself had violated the CFAA.)

Meanwhile, the CFAA is hardly the only questionable law that is at issue in tech-related prosecutions.

Before the Silk Road case, Ulbricht’s mother made a forceful argument that her son’s prosecution should be seen through the lens of systemic abuse by the Justice Department of surveillance and drug laws. She has a point: whatever harms caused by Silk Road drug deals, they pale in comparison to the destruction wrought by America’s ruinous “war on drugs.”

As for Kim Dotcom, his use of a mass piracy company to get rich is impossible to justify. But so too are many aspects of U.S. copyright laws, whose absurd terms and harsh penalties serve to benefit a narrow sector of the entertainment industry at the expense of the general public. Is it a surprise that knee-jerk attitudes to digital media by government and industry has led some to cheer for Dotcom instead of the industry that wants him prosecuted?

The hard choice

The cases against Ulbricht, Weev and Dotcom raise a dilemma because they can force us to choose between supporting a bad person or a bad law. A choice to convict such men may serve to legitimize unjust laws, while exonerating them amounts to giving them a free pass for unacceptable actions.

The cases can be harder still since they often involve technology (like TOR, peer-to-peer tools and bitcoin) that is unfamiliar to average people, but that the government often characterizes as inherently suspicious and related to “hacking.”

All of this helps to explain why the tech community can embrace antiheroes over Justice Department prosecutors who are apt to employ every legal tool at their disposal — even if it is one that is harsh or outdated.

The solution then is to give the prosecutors better tools, and not simply more of them. If the U.S. government is going to retain credibility in its effort to go after what it sees as online bad guys, it will have to do a better job of defining crime, and matching crime to punishment.

This story was updated on 2/15 to replace the word “charges” with “accusations” to describe the sexual assault allegations against Assange.