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Lyn Ulbricht, the Silk Road kingpin’s mom, is fighting for your Internet freedom

Lyn Ulbricht isn’t just fighting for her son’s freedom, she’s fighting for yours, too.


Fran Berkman


Lyn Ulbricht no longer trusts the U.S. government, and she says you shouldn’t either.

It’s true that the majority of Americans say they don’t trust the government these days, but Ulbricht may have a markedly more compelling reason than most of us: Her 30-year-old son, Ross Ulbricht, has been incarcerated in a federal prison cell in Brooklyn for the past year. 

Prosecutors and investigators say he’s “Dread Pirate Roberts,” the long-anonymous operator of an online drug empire called Silk Road. Lyn Ulbricht says she doesn’t believe her son is a criminal, but that’s not the whole story behind how and why she’s transformed herself into a prominent digital privacy activist.

“I was fueled by mother love at first, but then I started to see what the government was doing,” Ulbricht tells the Daily Dot. “I honestly see it as a bigger calling now. I’ve been given this opportunity to reveal, through this case, how they operate.”

Ulbricht relocated from Texas to the Northeast to be closer to her son, though she would not reveal exactly where she’s living. All she would say is that she’s living a couple hours outside of New York City. She visits Ross at the Metropolitan Detention Center on Tuesdays.

We caught up with Ulbricht at a gathering called LibertyFest NYC, which was staged at Warsaw, a Polish-themed pub with an attached auditorium, in the Greenpoint neighborhood of Brooklyn on Oct. 11. Ulbricht was one of about 15 scheduled speakers who each delivered some kind of message that appealed to the Libertarian political sensibilities of the crowd of roughly 300.

Gary Johnson, a former two-term governor of New Mexico who received 1.2 million votes as the Libertarian candidate in the 2012 presidential election, was the event’s headline speaker.

Aside from her 15 minutes on stage, Ulbricht spent the afternoon and evening chatting with guests, watching the other speakers and minding a table stacked with T-shirts and tote bags bearing “Free Ross” logos, which Ulbricht was selling to raise money to pay her son’s sizable lawyer bills. 

Ulbricht says those bills will be about $35,000 per week once the trial begins, in addition to the substantial work his legal team has already dedicated to what’s becoming a very complex and high-profile case. All told, Ulbricht says she’s not sure how much it will cost.

The fundraising page on the Free Ross website says the team, led by Lyn Ulbricht, has collected $187,000 toward its $250,000 goal. Though, about $70,000 of that has come from what’s eventually expected to be a $160,000 donation from one donor, Bitcoin evangelist and entrepreneur Roger Ver who is known to some as “Bitcoin Jesus.”

At LibertyFest, however, Ulbricht’s contributions were coming in a bit slower. With each T-shirt sold, she’d stuff another $20 into her fanny pack. 

Free Ross table

The table itself was decorated with autumn leaves and pinecones as a homage to Ross, who loves the outdoors. If prosecutors have their way, he may never again get to enjoy the freedom of nature as he faces life in prison on money laundering and drug charges, in addition to the weighty charge of being the “kingpin” of a major criminal organization.

The government has also accused Ross Ulbricht of paying a total of $730,000 for the murder of six people. Despite the nature of the claims, no one is believed to have died from these alleged plots, and Ulbricht has not been formally charged in connection with them.

Floating shocking accusations is just one of several tactics the federal prosecutors from the Southern District of New York have used that Lyn Ulbricht says should be sparking public outrage. In her LibertyFest speech, she described to the crowd government agents acting “incredibly arrogant and intentionally intimidating” and said their actions amount to “something far more dangerous than any website.”

In a conversation before taking the stage, Ulbricht summarizes the message she hopes to convey.

“[Prosecutors] are not playing fair, and they are not following the Constitution as far as I can see,” she says. “And that puts us all in danger.”

Into the wild

It was more than a month after FBI agents ambushed her son in a San Francisco library on Oct. 1, 2013—one of the agents reportedly yelling, “I’m so sick of you!” as they rushed him in a successful effort to restrain him before he could close his laptop — that Lyn Ulbricht gave her first interview.

Ulbricht spoke with Forbes under the watchful eye of Ross’ attorney, Joshua Dratel. At that point, Ulbricht was trying to spread the word about her nascent fundraising effort and dispel what she felt were mischaracterizations about Ross being spread in the media.

“Dratel strictly limited the topics of discussion and asked her not to comment on anything directly related to the facts in Ulbricht’s case, his politics, or his time living in San Francisco,” Andy Greenberg, who has since left his position at Forbes for one at Wired, wrote of his interview with Ulbricht.

Much has changed since then.

“I’m just a wild card now!” Ulbricht jokes, when I remind her of the Forbes interview and ask how things have changed. “That was my training period.”

Lyn Ulbricht on stage

Ulbricht says she’s since earned the trust of the legal team. Indeed, that seems to be the case. Dratel says that while family members can often be “a distraction” during these cases, Ulbricht’s actions have provided the defense with a “significant advantage in defending Ross.”

A spokesperson for the U.S. attorney’s office declined to comment on how Ulbricht’s activism may be affecting the case.

“It has been surprising only in the sense that many people in her position—a close family member facing federal criminal charges—are paralyzed by the anxiety and uncertainty that attends such circumstances,” Dratel tells the Daily Dot in an email. “Instead, she has been energized into action.”

Energized is just what she was at LibertyFest.

Ulbricht even went so far as to shout out “allegedly” from the audience when one of the other speakers, Libertarian scholar, author and publisher Jeffrey Tucker, did not properly acknowledge that her son has not been proven guilty in court. Not to mention, Tucker was all but calling Ross Ulbricht a hero for his alleged actions.

She can tell you each and every media outlet that’s covered Silk Road and wrongfully suggested that her son is the Dread Pirate Roberts, rather than that he is accused of such actions. Ulbricht even proactively rebuffed a Fox News interview request because she was unsure of whether or not the network would portray the story accurately. 

“We’ve turned down a lot of media. Things have been twisted and taken out of context and distorted,” she says. “I don’t care how big they are, I’m not interested in talking to people who do that.”

‘Sweet’ and ‘ferocious’

Lyn Ulbricht

T-shirts may have cost $20, but guests who approached the Free Ross merchandise table were treated to extensive chats on Internet freedom, constitutional law and sensationalistic journalism courtesy of Lyn Ulbricht. Her interactions with guests ranged from extremely cordial to mildly confrontational.

At one point, Ulbricht politely gave abrupt pause to our interview to address a LibertyFest guest who was questioning the two helpers at the Free Ross table and filming their answers for a video he said he intended to put on YouTube.

Ulbricht told the man that he had no business filming the helpers without discussing it with her first. Within a minute, the man who at first seemed quite bold was apologizing to Ulbricht for his actions.

Actor-turned-filmmaker Alex Winter describes Ulbricht as “this very sweet, kindly woman” who has a “ferocious understanding” of the importance of the issues surrounding the Silk Road case.

“It’s really easy to characterize her—and this is how she was characterized by the media early on—as a kind of a ‘do anything to protect her son’ desperate mom,” Winter tells the Daily Dot. “What’s amazing about Lyn and disarming about her is that she is anything but that.”

Winter, who is best known for his leading role alongside Keanu Reeves in the “Bill and Ted” comedy movies of the late 1980s and early 1990s, interviewed Lyn Ulbricht for his upcoming documentary about the Dark Net, the shadowy corner of the Internet where the Silk Road website facilitated more than 1 million over about two-and-a-half years, according to court documents. 

Both Winter and Ulbricht say they have since developed a close relationship based on their mutual interest in digital privacy issues.

In a recent example of how this case has privacy advocates on edge, an expert witnesses for the defense testified that FBI investigators used computer hacking techniques to infiltrate Silk Road and find the physical location of its servers, which were in Iceland. 

Ross Ulbricht’s defense cried foul on these investigation techniques, while still not conceding that Ulbricht had anything to do with the Silk Road. Even so, the defense said that evidence gathered using these techniques should be dropped. 

The situation is further clouded by the fact that the FBI initially said it was able to copy the servers because the U.S. and Iceland have signed a Mutual Legal Assistance Treaty (MLAT). Icelandic police confirmed they allowed U.S. authorities to access the server. But as Ulbricht and others are quick to point out, the U.S. doesn’t actually have an MLAT with Iceland.

The day before LibertyFest, Judge Katherine Forrest sided with the prosecution and rejected the defense’s motion for an evidentiary hearing. It’s the first thing Lyn Ulbricht said as we met Saturday morning before the event.

Forrest’s decision has not done much to quell the growing concern over the case among digital civil libertarians, such as the American Civil Liberties Union’s chief technologist Christopher Soghoian.

Shame on me for giving the gov investigators the benefit of the doubt. There is something seriously shady going on in the Silk Road case.

— Christopher Soghoian (@csoghoian) October 7, 2014

Motherly protectiveness for all the Internet

“Hi, I’m Ross Ulbricht’s mother,” Ulbricht said upon first taking the stage at LibertyFest. “I’m not going to defend my son today, though I’m always happy to do that.”

This simple introduction is indicative of how Ulbricht has, in Winter’s words, “evolved” since her early involvement with the case. Rather wasting her breath saying something like, “My son is a good guy, and he would never commit crimes,” Ulbricht is trying to convince people that they too could find themselves in a situation similar to Ross if government prosecutors are able to have their way in what’s expected to be a precedent-setting case.

The danger to Internet users, as Ulbricht explains it, is that if website operators can be held criminally liable for any illegal actions perpetrated on their site by others, then it will become dangerous, in a sense, to run any kind of large online marketplace or any website. A guilty verdict against Ross would, Ulbricht says, have “a chilling effect” on the Internet as a whole. 

In past court filings, Ross Ulbricht’s lawyer has tried to argue that even if Ulbricht was Dread Pirate Roberts, he was just a “digital landlord” who set up an online marketplace somewhat akin to Amazon but with a focus on privacy, and it was the Silk Road users who conducted illicit transactions. 

Judge Forrest shot down that argument, saying that Dread Pirate Roberts was much more like a digital “godfather” than landlord in the way that he (or she) had a role in “determining the territory, the actions which may be undertaken, and the commissions he will retain; disciplining others to stay in line; and generally casting himself as a leader – and not a service provider.” 

The potential implications for the Internet along with the perceived overly aggressive investigating techniques and Fourth Amendment violations used to obtain evidence against Ross Ulbricht are the crux of why Lyn Ulbricht believes everyone who uses the Internet should care about this case.

“If they’re doing this to Ross, they could do it to anyone,” Lyn Ulbricht says, now standing on the sidewalk outside the LibertyFest venue about an after her speech.  

In that very spot just a few hours earlier, New York politician Jimmy McMillan, of “the rent is too damn high” fame, held court in front of a car decaled with his own image, sharing his populist rhetoric with anyone who would listen.

Rent is too damn high guy

In a sense, Ulbricht is appealing to a similar sentiment among Internet users. Though not overtly, Ulbricht is portraying herself as someone whose motherly protectiveness for her son’s freedom has become indistinguishably intertwined with the desire to protect all Internet users from an overreaching government.

After mentioning how she feels the government is “[trampling] on the Constitution” in her speech, she likened the crowd’s politically-driven spirit to that of the U.S. founding fathers and suggested that they were the ones who would need fight for individuals’ rights in modern times.

“This is your moment in history; this is the birth of the digital age,” she said. “This Silk Road case, for better or worse, is a battle for that moment in history.”

The road ahead

Ulbricht’s message of skepticism toward the government was well received, perhaps predictably, among the crowd of Libertarians, whose distrust of government and other centralized institutions brought them to LibertyFest.

A more mainstream crowd might react a bit differently. After all, prosecutors say they’re sitting on a digital mountain of evidence that proves that Ross Ulbricht is the Dread Pirate Roberts, including journals and logs detailing the creation and maintenance of Silk Road that were allegedly obtained from the laptop seized from Ulbricht on the day of his arrest. 

We probably won’t find out anytime soon how the mainstream will react to the multifaceted issues raised by the Silk Road case. Ulbricht said she planned to limit her appearances to events with like-minded audiences both because it’s more efficient for fundraising purposes and because the prospect of facing a potentially hostile crowd doesn’t appeal to her.

“It’s too scary,” Ulbricht says. “It’s nerveracking enough to do a speech at all.”

If she was nervous at LibertyFest, it certainly didn’t show. Ulbricht said she’d like to continue with her activism even after her son’s trial. 

The trial was scheduled to begin on Nov. 10, less than a month after our meeting at LibertyFest. It has since been delayed until Jan. 5, at the defenses request. 

Correction: Christopher Soghoian is chief technologist for the ACLU.

Photos by Fran Berkman

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