He was Ross, the 29-year-old flirt of Monterey Boulevard with the Texas drawl. He was Joshua Terrey, the shirtless subletter who spent eight hours a day on his computer. He was the guy at Momi Toby’s with his laptop open, who once forgot to pay for coffee but was too cute for the barista to harass. He was the dude you’re certain you shot pool with at Place Pigalle on Hayes, but you were hammered and can’t remember much more than that.
And to federal prosecutors? Ross William Ulbricht was Dread Pirate Roberts, the mastermind behind the billion-dollar online drug marketplace Silk Road, an Amazon.com of illicit merchandise hidden in the encrypted “dark web” network known as Tor. The feds allege that Ulbricht’s site offered such items as “high quality #4 heroin all rock,” forged documents, and “Hitmen (10+ countries),” and that on occasion he became a consumer as well as a middleman, twice contracting murder-for-hire killings of perceived foes. Upon receiving a staged photo of one of the dead bodies in February, Ulbricht allegedly typed a message as if already a character in his own biopic: “I’m pissed I had to kill him, but what’s done is done.”
But before all this came out—before Ulbricht’s arrest on October 1 at the Glen Park library, before Silk Road was shut down and its accused top dealers arrested around the world, before the feds seized some $28 million in the digital currency Bitcoin from Ulbricht’s hardware—Ulbricht had been hunkered down in San Francisco for a year, blending in with the twentysomething startup dreamers working out of cafés and $1,000 Craigslist-subletted rooms. “Unremarkable” by his landlord’s recollection, he stood out only when his picture was blasted all over the news.
“Funny. Looks kinda like our subletter,” texted a housemate at Ulbricht’s former 15th Avenue apartment, according to a Forbes report shortly after the bust.
“If you’re making $80 million, why are you living on Hickory Street?” asked his former landlord in Hayes Valley.
“Oh my God,” gasped a woman who lives near his former home on Monterey Boulevard, trying to convince her coworkers at a Valencia clothing store that he was the same Ross who’d hit on her weeks before. Her imagination soared: “What if I was the girlfriend and had the code to his Bitcoins on the Tor?”
Ulbricht, for his part, isn’t saying much. When I talk to him, two weeks have passed since his arrest, and he’s in the Glenn Dyer jail in downtown Oakland, awaiting extradition to New York. Through the plexiglass barrier that separates us, he says that he agreed to meet with me, the first reporter to whom he’s spoken, in order “to see what it would be like” to talk to the press. He claims to be largely unaware of his newfound international infamy, citing the jail’s lack of Internet and limited access to news. And he gives up nothing about his case, leaving us to make surreal small talk about his college beer-pong photos on Facebook. When I smirkingly bring up that “Dread Pirate Roberts” is a classic child-of-the-’80s reference from The Princess Bride that I recognized instantly, he smirks right along. Intense, quiet, freshly shaven, gangly at 6 foot 2 and 145 pounds, his hands shackled to his waist, he confines his comments to the jail routine—20 to 22 hours in isolation each day. His time in San Francisco? “It was a pretty private life,” he says, adding that it would be hard to find people who knew him.
John Silk, his landlord on Hayes Valley’s Hickory Street, says that he ran into Ulbricht and his supposed girlfriend just once, while replacing the unit’s dishwasher. “He seems like the average guy you see around here these days,” Silk says. “White, conservatively dressed. He blended in with the background.” Ulbricht moved in to the unit in fall 2012, following an invitation from another subtenant, René Pinnell—his self-proclaimed best friend from their native Austin, Texas. Pinnell, who had moved to San Francisco with dreams of making big money in the startup world, recorded the story in a video last December as part of an oral history project at the Contemporary Jewish Museum. “The more I thought about [Pinnell’s offer of work and a room in San Francisco], the more it seemed cosmic and the right thing to do,” Ulbricht says in the video. “The crazy thing about San Francisco is it feels like home already. It’s just like [Pinnell] said: I gotta get out here.”
The feds say that by the time he arrived, Ulbricht was already caught up in his astoundingly successful startup, which would ultimately tally an alleged $1.2 billion in its two and a half years in business. What’s less clear is whether anyone suspected Ulbricht of being anything more than a Rand Paul–worshipping physics research scientist with interests in salsa dancing, snowboarding, Office Space, and “money,” as his Facebook page states. (Alternatively, his LinkedIn profile describes him as a guy running an “economic simulation.”)
Those who know Ulbricht aren’t, for the most part, willing to talk. His mom hurries me off the phone. Jaspreet Singh Sidhu, a friend and roommate from his undergrad years at the University of Texas at Dallas, writes me via Facebook: “Don’t know how to take all of this. I was planning on having him as one of my groomsmen at my wedding someday, so I’m not going to throw him under the bus or help anyone attack him without due process.” Pinnell claimed to a reporter that he knew nothing of Ulbricht’s alleged activities. When I see Pinnell coming out of the jail during Ulbricht’s visiting hours, he politely turns me away.
The people who crossed paths with Ulbricht in the city knew even less. “He was an absolutely normal guy who no one would expect anything from,” says a regular at Momi Toby’s, a café around the corner from the Hickory Street apartment. He often saw Ulbricht there on his computer, he says, and once played pool with him at neighborhood hole-in-the-wall Place Pigalle. The bartender there, Sam Solano, recognizes Ulbricht immediately from photos on my iPhone. “I’ve totally seen him in here—totally.” She recalls writing down his name to open a tab. He was “quiet—if anything, a little more introverted. I feel like when he was here, he was always alone. Maybe around the pool table back there, but never came in or left with anyone. He’s got kind of intense eyes, too.”
In June, Ulbricht moved in to a 15th Avenue sublet in West Portal. When a sleuthing Forbes reporter tracked it down, his former housemates said that they knew Ulbricht as Joshua Terrey, a reclusive freelance IT consultant and currency trader who was always on his computer or cooking steak dinners for one. He paid his $1,000 rent in cash. It was at the West Portal apartment that Ulbricht received what might have been his first indication that the feds were closing in. On July 26, Homeland Security agents showed up to question him about a package of falsified documents that border patrol agents had intercepted on its way from Canada. Ulbricht told them that “theoretically,” anyone could get fake documents on Silk Road.
In August, “Josh” moved out, but he didn’t go far—just to sleepy Sunnyside, a San Francisco hood nestled up against 280, near the Glen Park BART station. An employee at a café down the street remembers Ulbricht coming in and ordering an Americano: “He was just like any other computer geek you’d see here.” (The employee wanted neither his name nor the café identified.) A 40-year-old woman who lives on Monterey Boulevard recalls that in early September, as she awaited an Uber outside her house at 11 p.m., Ulbricht chatted her up. “He was very flirty and open and bold,” she says. “He told me his name was Ross and gave me the number of [his] house,” which was just a few doors down from hers. “I said, I won’t remember your [house] number, but I’ll remember your name because my last name is very close to your name.” She actually tried to make good on the invitation, introducing herself to a woman who lived in the house. (When I rang the bell and asked about Ulbricht, the woman said, “Sorry,” and shut the door.)
But before the flirtation could escalate, October 1 arrived, ending Ulbricht’s stint in San Francisco with a crash, just a half mile away, at the Glen Park library. The beefy magazine readers standing just feet from the table where Ulbricht was working on his laptop turned out to be FBI agents in plainclothes. By the time that librarians could check on the noise, Ulbricht had been shoved up against the window that looks out on the bar Glen Park Station across Diamond Street. As the stunned patrons looked on, the agents walked him out in silence, his hands cuffed behind his back.
Originally published in the December issue of San Francisco