The Death of Dread Pirate Roberts

OldShipGary L. Alford was running on adrenaline when he arrived for work on a Monday in June 2013, at the Drug Enforcement Administration office in the Chelsea neighborhood of Manhattan. A tax investigator, he had spent much of the weekend in the living room of his New Jersey townhouse, scrolling through arcane chat rooms and old blog posts, reading on well after his fiancée had gone to sleep.

The work had given Mr. Alford what he believed was the answer to a mystery that had confounded investigators for nearly two years: the identity of the mastermind behind the online drug bazaar known as Silk Road — a criminal known only by his screen name, Dread Pirate Roberts. When Mr. Alford showed up for work that Monday, he had a real name and a location. He assumed the news would be greeted with excitement. Instead, he says, he got the brushoff. He recalls asking the prosecutor on the case, out of frustration, “What about what I said is not compelling?” Mr. Alford, a young special agent with the Internal Revenue Service assigned to work with the D.E.A., isn’t the first person to feel unappreciated at the office. In his case, though, the information he had was the crucial to solving one of the most vexing criminal cases of the last few years. While Silk Road by mid-2013 had grown into a juggernaut, selling $300,000 in heroin and other illegal goods each day, federal agents hadn’t been able to figure out the most basic detail: the identity of the person running the site.

It ultimately took Mr. Alford, 38, more than three months to gather enough evidence to prevail upon his colleagues to take his suspect seriously. After he convinced them, though, the man he identified, Ross W. Ulbricht, was arrested and Silk Road shuttered. The night of the arrest, Mr. Alford got an email from one of the other special agents at the center of the case: “Congrats Gary, you were right,” it said. Mr. Alford’s experience, and the lag between his discovery and Mr. Ulbricht’s arrest, were largely left out of the documents and proceedings that led to Mr. Ulbricht’s conviction and life sentence this year. Previous examinations of the Silk Road investigation have generally focused on the role played by special agents with the Federal Bureau of Investigation and the Department of Homeland Security, who infiltrated the website, arrested important deputies and gathered reams of crucial information, but not enough to find Mr. Ulbricht — until Mr. Alford came along.

The other agencies involved in the investigation declined to comment on Mr. Alford’s work, but several people briefed on the investigation, who were not authorized to speak about it publicly, confirmed the basic outlines of Mr. Alford’s story. Back in the summer of 2013, it was not hard, even for Mr. Alford, to understand why it took him time win over the others on the case. He had joined the investigation relatively late and was on a team that hadn’t previously found much of value. He also lacked the sophisticated technological experience of colleagues at the F.B.I. On a more personal level, Mr. Alford could come across as overeager. But Mr. Alford also detected the sort of organizational frictions that have hindered communication between law enforcement agencies in the past. Within the I.R.S., Mr. Alford had heard tales of his agency being ignored and overshadowed by more prominent organizations like the F.B.I. The story that resonated with Mr. Alford most strongly was that of the tax agent Frank J. Wilson, who brought down the gangster Al Capone, but who was forgotten in the movie versions of the investigation, which tended to focus on Eliot Ness, the flashier Bureau of Prohibition agent. “They don’t write movies about Frank Wilson building the tax case,” Mr. Alford said in an interview at the I.R.S.’s Manhattan headquarters. “That’s just how it is.”

Mr. Alford grew up in the Marlboro public housing projects of Brooklyn in the 1980s, a short, half-black, half-Filipino kid in a tough neighborhood. His father, a math teacher, would cite the power of the subject to teach his son how to prevail over difficulties. “If you get the right answer, the teacher can’t tell you anything,” Mr. Alford remembers his father saying. That attitude led Mr. Alford to study accounting at Baruch College and then to the I.R.S., where his skeptical, lone-wolf approach worked well. It was Mr. Alford’s supervisors at the I.R.S. who assigned him in February 2013 to a D.E.A. task force working the Silk Road case. The Strike Force, as it was known, had so far had little luck finding meaningful leads. Mr. Alford’s superiors hoped he could bring his youthful energy and doggedness to the project. Mr. Alford started by chasing down leads on low-level Silk Road vendors selling Bitcoin, but he was too ambitious to keep his attention focused on small-time criminals. Whenever he had a free moment, he would read up on the origins of Silk Road and its nearly mythical leader, Dread Pirate Roberts, who ran the business and espoused his radical free-market ideology on the site’s message boards. “I’m not high-tech, but I’m like, ‘This isn’t that complicated. This is just some guy behind a computer,’” he recalled saying to himself. “In these technical investigations, people think they are too good to do the stupid old-school stuff. But I’m like, ‘Well, that stuff still works.’?”

Mr. Alford’s preferred tool was Google. He used the advanced search option to look for material posted within specific date ranges. That brought him, during the last weekend of May 2013, to a chat room posting made just before Silk Road had gone online, in early 2011, by someone with the screen name “altoid.” “Has anyone seen Silk Road yet?” altoid asked. “It’s kind of like an anonymous” The early date of the posting suggested that altoid might have inside knowledge about Silk Road. During the first weekend of June 2013, Mr. Alford went through everything altoid had written, the online equivalent of sifting through trash cans near the scene of a crime. Mr. Alford eventually turned up a message that altoid had apparently deleted — but that had been preserved in the response of another user. In that post, altoid asked for some programming help and gave his email address: Doing a Google search for Ross Ulbricht, Mr. Alford found a young man from Texas who, just like Dread Pirate Roberts, admired the free-market economist Ludwig von Mises and the libertarian politician Ron Paul — the first of many striking parallels Mr. Alford discovered that weekend.

When Mr. Alford took his findings to his supervisors and failed to generate any interest, he initially assumed that other agents had already found Mr. Ulbricht and ruled him out. But he continued accumulating evidence, which emboldened Mr. Alford to put Mr. Ulbricht’s name on the D.E.A. database of potential suspects, next to the aliases altoid and Dread Pirate Roberts. At the same time, though, Mr. Alford realized that he was not being told by the prosecutors about other significant developments in the case — a reminder, to Mr. Alford, of the lower status that the I.R.S. had in the eyes of other agencies. And when Mr. Alford tried to get more resources to track down Mr. Ulbricht, he wasn’t able to get the surveillance and the subpoenas he wanted. Mr. Alford said the Manhattan federal prosecutor overseeing the investigation, Serrin Turner, seemed to want to find Dread Pirate Roberts more than anyone. But Mr. Alford said that Mr. Turner was working with multiple agencies on the case and did not seem to put much weight in the evidence that Mr. Alford was finding — leading to heated conversations.  “I’m not saying I’m right; we just need to look into this guy fully,” Mr. Alford remembers telling Mr. Turner.

A spokesman for the United States attorney’s office in Manhattan, where Mr. Turner works, declined to comment. When Mr. Alford visited the main F.B.I. team on the case, later in the summer, it became clear that the team wasn’t aware of Mr. Ulbricht as a suspect — and also had no serious candidates of their own. Mr. Alford mentioned that he had a suspect in San Francisco, but no one followed up. One of the other agents present for that meeting, who spoke on the condition of anonymity, said that he and the others in the room had little reason to ask for further information from Mr. Alford, given the lack of progress made by the D.E.A. Strike Force to which he was assigned. “No one was taking them seriously,” the agent said. “I obviously wished we had asked more.” When Mr. Alford went back to the D.E.A. office in Chelsea and complained about the meeting, a fellow I.R.S. agent in the group suggested it was time for Mr. Alford to give it up. “You’ve told them what you know. They didn’t do anything,” the agent told him, according to a person briefed on the conversation. “Forget it.” Instead, Mr. Alford decided to review his findings again. In early September, he asked a colleague to run another background check on Mr. Ulbricht, in case he had missed something. The colleague typed in the name and immediately looked up from her computer: “Hey, there is a case on this guy from July.” Agents with Homeland Security had seized a package with nine fake IDs at the Canadian border, addressed to Mr. Ulbricht’s apartment in San Francisco. When the agents visited the apartment in mid-July, Mr. Ulbricht answered the door, and the agents identified him as the face on the IDs, without having any idea of his potential links to Silk Road. Mr. Alford’s colleague asked him, “Is this stuff interesting to you?” “You are making my day,” he said. As she read out the details, the report grew more intriguing. Without the agents mentioning Silk Road, Mr. Ulbricht told them that “hypothetically” anyone could go on a site called Silk Road and buy fake IDs.

Armed with these new findings, Mr. Alford phoned the prosecutor, Mr. Turner. There was a pause in the conversation while Mr. Turner typed Mr. Ulbricht’s address into his own computer. Then Mr. Alford heard a shouted profanity from the other end of the line — the clearest sign of interest he had heard yet, he says. Mr. Ulbricht’s home address, it turned out, was a few hundred feet from an address that the F.B.I. had turned up in its investigation: a cafe from which Dread Pirate Roberts had signed in to Silk Road. Mr. Turner arranged a conference call the same day with Mr. Alford and two agents on the case — an F.B.I. agent, Christopher Tarbell, and a Homeland Security agent, Jared Der-Yeghiayan. The crucial moment in that conference call came when Mr. Alford described some of Mr. Ulbricht’s interactions on message boards for programmers, while using the screen name “Frosty.” Mr. Tarbell stopped Mr. Alford and explained that Frosty was the name of the computer from which Dread Pirate Roberts had been logging in to the Silk Road. “Oh, that’s interesting,” Mr. Turner deadpanned. “That’s the guy,” Mr. Tarbell said. The agreement among the agents on the phone that day allowed Mr. Alford to get his wish to put Mr. Ulbricht under full surveillance. Within days, the agents had established that Dread Pirate Roberts was logging into the Silk Road just moments after Mr. Ulbricht was going online in his apartment.

In New York, Mr. Turner and Mr. Tarbell began writing up the complaint against Mr. Ulbricht. In it, they referred to Mr. Alford as Agent 1. On Oct. 2, Mr. Tarbell and Mr. Der-Yeghiayan helped apprehend Mr. Ulbricht at a public library in San Francisco. Mr. Alford could not be there because of travel-budget restrictions that applied to him but not other investigators on the team. After the arrest, though, his role in the case was recognized with a plaque from his superiors featuring a quotation from Sherlock Holmes: “The world is full of obvious things which nobody by chance ever observes.”