From the window of his hotel room Jared could see the two massive square imprints in the ground where the two towers had once stood. Cranes and trucks and construction debris surrounded the holes now, and yet a mere decade earlier 2,606 people had lost their lives there.
As he looked out at the transforming landscape, a million thoughts climbed through Jared’s mind. He replayed the moment the planes tore into those towers. Explosions and fire and people left with no choice but to jump to their deaths. He thought of those firefighters and police officers who had clambered inside to help whomever they could. And then everyone turning to dust, right at the foot of where Jared now contemplated the totality of it all. He thought about the families who had lost their mothers and fathers and sons and daughters that day. Tears began welling up in his eyes as he reached for his phone to video chat with his son, Tyrus, to tell him he loved him and to update him on the hunt for the bad pirate he was searching for.
After Jared hung up, blowing a kiss from that New York hotel room to his son’s bedroom in Chicago, it was time to get back to his laptop, working undercover for DPR. Jared hoped that he could help stop an attack on America that happened not with 747s flying into buildings at six hundred miles per hour, but rather in slow motion through a Web site that wanted to topple the country’s democracy.
Jared feared almost daily that operatives from al Qaeda could come into the country legally, without any weapons at all, and then buy an arsenal of bombs or guns or poisons from within the United States, all from the Silk Road with a few Bitcoins and the Tor Web browser. On a more personal level, as he thought about his son, he worried that a teenager could buy a gun on the site and go on a shooting rampage in a preschool in Chicago. Jared was determined to do everything in his power to stop either of those atrocities from happening.
The following morning after a long night working for DPR on the site, managing administrative tasks, Jared walked along Church Street and then Broadway until he arrived at 26 Federal Plaza, the giant black building that was home to the Cyber Division of the FBI.
It was early August 2013, and Jared had come to New York City to work with Chris Tarbell, to delve through the servers and see if they could use Jared’s knowledge and his undercover account, Cirrus, to piece together details about who DPR might be.
Tarbell met Jared in the lobby and helped him negotiate getting his laptop and phone into the FBI offices. Under normal circumstances the FBI police (who protected the building) barred anyone from bringing devices inside—even other agents from within the government—for fear that a virus or some kind of surreptitious surveillance software could make its way onto the FBI network. But Jared wasn’t just any other government agent, Tarbell insisted; he was working undercover and needed access to his computer at all times. The FBI police relented.
For the past few weeks Jared had had to stay online almost perpetually to mimic the behavior of the woman whose identity he had co-opted. He had been forced to take his laptop on family outings, to birthday parties, and even to his son’s weekly swim meet. (Parents of other kids, unaware of why Jared was on his laptop all the time as Tyrus swam laps, were not impressed.)
When they reached the twenty-third floor, Jared was given a brief tour of the Cyber Division before Tarbell led him past the Pit and back into lab 1A.
“You can set your computer up right here,” Tarbell said, pointing at the table in the middle of the room where the agents often ate lunch. “And over here is the computer that has the Silk Road server on it.”
As Jared unpacked his bag of gadgets, he noticed an eight-foot-long piece of butcher paper that had been pasted on the wall. In black marker, someone had written the words “silk road” across the top. There were IP addresses all over the place with descriptions underneath explaining what each series of numbers represented. One was a server for the chat clients of the Silk Road, another for a server that stored the hundreds of millions of dollars in Bitcoins, and another, called a “mastermind” section, for the site’s administrator. As Tarbell explained, this was all the information that had been gleaned from the servers. (To mess with Tarbell, his co–case agents had created a mock chart next to the Silk Road version that had pictures of all the characters from The Princess Bride, including Princess Buttercup, Westley, and Prince Humperdinck, with nonsensical arrows pointing between each.)
As Jared studied the Silk Road chart, he saw the name of a coffee shop called Momi Toby’s in San Francisco. When he asked why it was on the chart, Tarbell explained that one of the servers they found had been erased. Wiped clean of evidence like a murder scene that had been disinfected with bleach. But when the person who had expunged the drive logged out of the server, they had accidentally left one tiny clue behind: the IP address of the place where they had logged in to do their cleaning. In other words, the Dread Pirate Roberts might have wiped the murder scene down, but he had left the corner of a thumbprint on the front door when he walked out.
This digital fingerprint led the FBI agents to a small bistrolike café on Laguna Street in San Francisco called Momi Toby’s. Whoever the Dread Pirate Roberts was, he was either living in San Francisco or had spent some time there. But that was it. One measly clue that possibly pointed to the whereabouts of the Dread Pirate Roberts. “Not much I can do with it,” Tarbell said to Jared. “What am I going to do, send an FBI agent into a coffee shop in San Francisco and tell them to look for someone on a laptop?” Still, they had been scouring the Internet traffic from the café, looking for other leads.
After getting acquainted with everyone and being subject to a few of Tarbell’s “would you rather” jokes, Jared sat down at the computer, which was now an off-line replica of the Silk Road, and he began searching through its contents. He saw the chat logs where DPR had paid the Hells Angels to have people killed, and he saw other messages between DPR and Carl (as Nob) that were, curiously, encrypted and couldn’t be read.
“That’s strange,” Jared said to Tarbell. “You think Carl Force is trying to obstruct our investigation?”
“No clue, but something doesn’t feel right.”
Still, they had bigger things to worry about than a petulant and possibly rogue DEA agent in Baltimore. Jared spent the next few days with the FBI crew, working in lab 1A, delving through the server, listening to Tarbell’s unrelenting jokes, and then ending the evenings at the Whiskey Tavern a few blocks away, where Jared learned what pickle juice and cheap whiskey tasted like. As those nights would come to an end and everyone else went home to their families, Jared would plod back to his hotel room overlooking the sacred ground of the World Trade Center, and he would transform into Cirrus, the online forum moderator on the Silk Road, and spend the evening undercover working as an admin on the site.
A couple of days went by and Tarbell told Jared that “some guy from the IRS is swinging by later . . . Gary Alford or something like that. . . . He wants to take a look at the server.”
“Sounds good,” Jared replied, then looked back at his computer as he continued chatting with the Dread Pirate Roberts as Cirrus.
A few hours later Tarbell entered the lab with an African American man in his wake. “Jared, this is Gary Alford from IRS,” Tarbell said. “Gary, this is Agent Der-Yeghiayan from HSI Chicago.”
Jared looked up at Gary, taking in his wide figure, and as he was about to say hello, Gary looked back at Jared with confusion and frustration.
“Why does he get to bring his devices up here but I have to leave mine downstairs?” Gary asked Tarbell.
Tarbell had no desire to explain that Jared was working on his computer undercover and simply replied, “Different rules for different folks.” Gary didn’t like this answer and seemed even more annoyed now than he had been a few seconds earlier.
Jared then watched Gary peer up at the butcher paper on the wall with the words “silk road” written across the top. He was inspecting it, noticing all the Princess Bride jokes in the corner of the page and the IP addresses sprinkled everywhere. Gary seemed to be even more annoyed when he saw this, as if there was a party going on that he hadn’t been invited to.
Tarbell then introduced Gary to Thom Kiernan, the computer forensics expert, who said he would help Gary dig through the Silk Road server. Tarbell then sat back down at the table in the center of the room, unaware, or not caring, that Gary was crestfallen that he wasn’t involved in their investigation.
In a sulky mood, Gary got to work searching for people laundering money and Bitcoins on the Silk Road, but he kept looking over at Jared and Tarbell and then over at the big sheet of butcher paper. Finally Gary spoke up again. He had also noticed the words “Momi Toby’s café” on Laguna Street in San Francisco written under one of the IP addresses, and he asked what it was.
Tarbell, his head buried in his computer, explained that it was the one place that the Dread Pirate Roberts had logged in to the server. The only clue they had tying DPR to a location.
“Huh,” Gary replied. “I have a guy in San Francisco.”
“Oh yeah?” Tarbell said nonchalantly. “You’ll have to give us his info.” Gary seemingly didn’t like this answer, either. Jared watched this interaction take place, and he felt somewhat bad for Gary, who was visibly perturbed. But Jared also knew exactly what Tarbell was thinking, because Jared was thinking the same thing: A guy in San Francisco didn’t mean anything. There had been two dozen people whom agents from across the country had suspected of being the Dread Pirate Roberts at one time or another, and half of them were in the Bay Area.
With this retort from Tarbell, Gary peered back at the server and ignored Tarbell and Jared for the rest of the afternoon. A few hours later Gary stood up and walked out. He decided in that moment that this was clearly Tarbell’s investigation and there was no room for him to be any part of it. Based on the mountain of evidence Gary had seen on the server, the butcher block paper on the wall with all those IP addresses, and Jared’s undercover account, Gary decided that there was clearly no reason for him to send the FBI the name of his “guy” in San Francisco.