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EXCLUSIVE: Mum of drugs 'kingpin' of Silk Road pleads to Trump for clemency

Oscar Williams-Grut
Senior City Correspondent, Yahoo Finance UK
Fighting for his freedom: Lyn Ulbricht with her son Ross in prison in July of this year. Photo: Lyn Ulbricht.

With his strong jawline, easy smile, and a youth spent in the boy scouts, Ross Ulbricht could be a poster boy for Middle America.

Instead, he is in prison facing two life sentences with no chance of parole for his role as founder and ‘kingpin’ of the notorious online drug marketplace Silk Road.

In an exclusive interview with Yahoo Finance UK, his mother said she’s hoping US President Donald Trump will personally step in to help set her son free.

“I’m very hopeful because President Trump wants to pardon people,” Lyn Ulbricht, 64, from Austin, Texas, said. “It was a frankly reckless idea but [Ross] did it because he was on fire for freedom as a young guy in his mid-20s who believed in privacy and free markets. Ross never intended harm.”

She believes her son’s sentence is unjustly harsh and sees him as a victim of the war on drugs. In an hour-long telephone interview, Yahoo Finance UK heard:

  • How Lyn Ulbricht almost died of “broken heart syndrome” when her son was sentenced;
  • Why she believes the notorious “fake hit” linked to Silk Road was a set up;
  • How Ross is coping in the ‘Alcatraz of the Rockies’;
  • The personal toll the entire case has taken on the family;
  • How Lyn is fighting to have her son’s sentence reduced.

“I can’t let him rot in prison like this,” she said. “I don’t see how I can just go, ‘Hey Ross, sorry bye, I’m going to go off and pursue my bliss’ or whatever, get a hobby. I can’t imagine just leaving him there.”

‘I almost died — my heart stopped for quite a bit’

Ross, now 34, was arrested by the FBI at a public library in San Francisco in 2013 after an extensive investigation into Silk Road. By the time he was apprehended, the website had operated for two-years on the so-called “dark web” — the un-indexed underbelly of the internet that can only be accessed using special encrypted web browsers.

Sentencing: Ross Ulbricht’s attorney Joshua Dratel (L) speaks as Lyn (C) and Kirk Ulbricht, parents of Silk Road founder Ross Ulbricht, talk with reporters outside the Federal Courthouse May 29, 2015 in New York. Photo: DON EMMERT/AFP/Getty Images.

Silk Road was an online marketplace, a little like eBay, where anonymous users could buy and sell things using bitcoin, which was then a relatively obscure currency. What set it apart from other marketplaces was that there looser rules on what could and couldn’t be sold. While things like child porn and stolen goods were forbidden, crucially drugs were allowed.

As a result, it became a magnet for illegal narcotics. By early 2013, the majority of listings on the site were drugs, such as cannabis, ecstasy, and heroin. Estimates of sales during its two years of operations range from around $200m to over $1bn. The governments own official estimate was $183m in sales.

The site was run by an anonymous account known as Dread Pirate Roberts, or DPR for short. The name was a reference to the mythical pirate in the novel The Princess Bride. The FBI traced the account to Ross Ulbricht, then a 29-year-old physics graduate. He had attained the rank of Eagle Scout — the highest rank in the Boy Scouts — as a child and had founded a business that gave part of its profits to charity when he first graduated. It was an unlikely bust.

The arrest and subsequent trial came as a huge shock to his mother Lyn, an entrepreneur living in Austin, Texas, where she ran a holiday rental business with her husband, Kirk.

“I actually almost died,” she told Yahoo Finance UK, recalling this period. Ross was eventually convicted in May 2015 and Lyn suffered a heart attack in October of that year. She blames the stress she was under at the time.

“It was heart failure from what they said is called ‘broken heart syndrome,’” she said. “There’s a Japanese word for it but it’s literally a medical term for stress and grief that hits people, it actually attacks the left ventricle of the heart.

“My brother-in-law saved me with CPR,” she said. “I was dead. My heart stopped for quite a while. I was blue, the whole bit. They didn’t know if I’d have brain damage or heart damage. It’s a miracle that I’m intact.”

‘He’s not Pablo Escobar, it’s absurd’

Part of what hit Lyn so hard was the severity of Ross’ sentencing. In 2015, her son was handed two life sentences, plus 40 years, with no chance of parole. It means Ross will spend the rest of his life in jail, with no possibility of parole.

Birthday party: Ross as a child. Photo: Lyn Ulbricht
Allies: Ross Ulbricht and a group of non-violent offenders he has formed a group with calling for sentencing reform. Photo: Ross Ulbricht/Lyn Ulbricht

Ross was convicted of charges included conspiracy and a so-called “kingpin” charge, which is usually reserved for gang bosses.  It was introduced to combat elaborate criminal enterprises, mainly drug trafficking. It has been used against members of the Tijuana cartel and Rayful Edmond, the 1980s drug lord credited with introducing crack cocaine to Washington DC.

“To call him a kingpin and to have that be the charge is an abuse of power,” Lyn said. “He’s not Pablo Escobar, it’s absurd.”

Text and instant message logs worked against Ross at trial. The judge read out one message that said: “I’m running a goddamn multimillion-dollar criminal enterprise.” She said it showed he was “callous as to the consequences and the harm and suffering it may cause others.”

The judge heard testimony at sentencing relating to six drug-related deaths that were allegedly linked to Silk Road. The father of a 25-year-old who died of a heroin overdose told the court: “Since Mr Ulbricht’s arrest, we have endured the persistent drumbeat of his supporters and their insistence that Silk Road was victimless. I strongly believe that my son would be here today if Silk Road had never existed.”

At his sentencing, the judge also said Silk Road had expanded the market for dangerous drugs by making it easier to get hold of them.

School days: Ross Ulbricht. Photo: Lyn Ulbricht

Lyn doesn’t dispute that Silk Road was bad or that Ross was involved but she believes Ross’ sentence was disproportionate to his crimes.

“Even if you think it’s horrible and Ross is evil and horrible or whatever, this sentence sets a precedent in this country where people are put away for lifetimes like this for non-violent crimes,” she said. “This is a trend that must change.”

She added: “You could say, well by selling drugs they were hurting people. They weren’t forcing anyone to do anything, let’s put it that way.”

Lyn casts Silk Road as simply a youthful experiment with libertarian ideas that Ross had become interested in during his time working for independent US politician Ron Paul.

“He’s always been an idealist, he’d never want to hurt people,” she said. “He has said, and he has said to me many times, how much he regrets it and how much he regrets any harm that may have come from it. I think his remorse is absolute.”

Graphic: Yahoo Finance/David Foster

‘No one was murdered’

Perhaps the most notorious aspect of Ross’ arrest and trial was the “fake hit” that was at the centre of the sting to bring him down.

After being blackmailed, Ross allegedly tried to arrange for the murder of his blackmailer, as well as four other individuals over an online anonymous chat.

One of the hits involved an undercover DEA agent, who staged a photo of his death and sent it to the DPR account as proof of the hit. The incident was described as a “Silicon Valley murder mystery” by Vanity Fair.

“I don’t even personally believe there was any hit arranged at all, I believe it was a sting,” Lyn said. The hit was arranged by the Dread Pirate Roberts account on Silk Road and Lyn believes it was someone other than Ross logged in at the time.

“I read the chat that it was supposedly based on — Ross types like a techie, no capital letters, quick abbreviations — and this is like a formal essay with perfect punctuation and capitalisation from both sides of the chat. This strikes me as very phoney.”

Lyn added that Carl Force, the DEA agent who staged the hit photo, was later sentenced to jail himself for crimes related to Silk Road.

Happier days: A young Ross Ulbricht. Photo: Lyn Ulbricht

“The government claims he was the only DPR,” Lyn said. “Everybody else, including high level admins, say that’s absurd — there were lots of them. DPR signed in to his account after Ross was already in prison.”

Part of Ross’ defence at trial was that multiple people used the Dread Pirate Roberts account and he was not the sole architect of Silk Road. In the book The Princess Bride, “Dread Pirate Roberts” is not one person but a series of people who inherit the title. The jury ultimately rejected this argument.

Ross was never charged over the alleged hit but the incident was discussed at trial. Lyn believes that this unfairly prejudiced the jury and helped the judge justify such a long sentence.

She added: “Frankly, even if he were guilty of it, which I don’t believe, murder for hire carries a 10 year sentence. It’s intended murder. It doesn’t carry life. No one was murdered.

“They needed their trophy, they wanted their trophy, and they decided that that was Ross.”

‘He was always a very easy going, laid back person’

Ross is currently housed in USP Florence prison in Colorado. Now 34, Ross is “coping very well,” according to Lyn, “because being a nice guy and a helpful person and a decent human being applies in prison too. As Ross said to me: ‘Mom, gang leaders are people too.’”

Family ties: Ross Ulbricht with his grandmother. Photo: Lyn Ulbricht

Ross spends his days reading about AI and physics, studying the law, and meditating and praying. He has connected to the outside world through Twitter, dictating Tweets to visitors or giving them notes to post as pictures on the site.

Ross’ account documents the day-to-day drudgery of prison life. One of his few highlights is an apple sprout that he is growing from a seed.

“He stays out of trouble but he also helps people out, he interacts in a positive way, he’s a likeable person,” Lyn said.

Lyn and her husband have moved to Colorado be closer to Ross. On his Twitter account, Ross thanked his parents for “standing by my side these past years” and said he hopes “someday I can repay them for everything they’ve done.”


Lyn believes the “nice guy” side of Ross was left out of a lot of the reporting on the Silk Road case.

“He’s very gregarious, in fact he loves to have a good time — quite fun loving, quite funny, he has a great sense of humour,” she said. “From the day of his birth, he was always a very easy going, laid back person. He was probably the easiest baby.”

Laidback baby: Ross as a baby with his mother Lyn in 1985. Photo: Lyn Ulbricht.

Lyn, who also has a daughter with her husband Kirk, runs the website FreeRoss.org, which features over 100 letters from Ross’ friends and family. She believes these give a better testament of her son’s character.

“A friend was hanging out with Ross and captured a bee that was bothering him and put it in the freezer,” she said. “Ross ran over to the freezer and liberated the bee and said don’t be cruel, that’s terrible, you shouldn’t do that to this bee. This sounds like a murdering thug doesn’t it?

“He even said he forgave the judge, which — I’m having a problem with that,” she said.

‘He can’t relax — ever’

Despite the fact that he is coping in prison, it’s “a terrible way to have to live,” Lyn said.

“He always has to be sure he’s wearing his sneakers so he’s sure he can run. He can’t relax — ever.”

Early years: A toddler Ross Ulbricht with mother Lyn. Photo: Lyn Ulbricht.

Lyn sees Ross as one of many victims of the US’ war on drugs, part of which involves tough prison sentences for drug offenders. Former US President Richard Nixon first popularised the idea of the war on drugs in the early 1970s and it has been endorsed by US administrations ever since.

“There’s a guy in there with Ross, he’s really become a friend, and he has a life sentence because someone said he sold them marijuana 13 years ago. Marijuana only,” Lyn said.

This is possible under the so-called “three strikes” regime introduced in the US in the early 1990s, which meant that people convicted of two serious or violent felonies automatically face a life sentence when convicted of a third offence. Lyn called it “a terribly evil law.”

“The drug war is what’s fuelling this mass incarceration and it’s terrible,” she said. “And there are terrible repercussions on families and children of these people as well.”

The US’ prison population has grown by over 700% since 1980 and the United States now has the highest rate of incarceration in the world, with 670 people in jail for every 100,000 people.

“I’ve gotten to know the families of the children in prison and gotten to hear their stories,” Lyn said, “How do I — knowing them as a family, seeing their children sobbing, clinging to their fathers when they have to leave, seeing their families broken — how can I not speak out and work against this? This is an evil thing and it’s un-American.”

“I’m not saying there shouldn’t be restitution where there are victims,” Lyn said, “but, I just don’t see how this accomplishes anything other than making a lot of money for a lot of people and expanding government power and making the United States the biggest incarcerator on the planet.”

‘It all boils down to people and paperwork’

Lyn has been campaigning to have Ross’ sentence reduced since he was convicted in 2015.

In the process, she has spent over $500,000 on lawyers fees, mostly funded through donations. She has received support from the bitcoin community, libertarians, and prison reformers on the left who see Ross’ sentence as draconian.

“We went through the whole court system, all the way to the supreme court and they denied it,” Lyn said.

Campaigning for freedom: Ross Ulbricht before prison. Photo: Lyn Ulbricht.

One of the few options left is a pardon or commutation of Ross’ sentence from the US president. A petition run by Lyn calling for clemency from the president has attracted over 110,000 signatures.

Lyn said: “I think it’s possible he would be open to a pardon, or really a commutation, which means reducing the sentence itself. I think there’s hope.”

Lyn described the the three years of campaigning as “extremely challenging,” “very devastating,” and “physically exhausting.”

Shortly after her heart failure, Lyn stopped work on the family business renting holiday houses in Costa Rica. She couldn’t handle the strain of running it as well as campaigning for Ross, she said, and so left it to her husband, Kirk.

Lyn has learned to cope day-to-day through prayer and meditation. She said she tries to take one day at a time “because I was on such a rollercoaster of hope and despair, hope and despair. I’ve learned not to get on that roller coaster.”

Her immediate goal is to get her petition to half a million signatures before presenting it to the president. She is hopeful that Trump might consider a commutation.

“I have faith that I can do this, that Ross will be free,” she said. “It all boils down to people and paperwork. It’s not like physically moving a mountain. It is possible.

“Believe me, I have my moments of despair, regularly. I break down. You have to. But wallowing in it and focusing on it doesn’t help and so I throw myself into doing things that can help him,” she said. “I can’t rest.”

Editor’s note: An earlier version of this article incorrectly stated that Ross Ulbricht was currently housed at the ADMAX facility in Colorado, which is known as the ‘Alcatraz of the Rockies’. Ulbricht is in fact at the lower security facility USP Florence in Colorado.