One reason Carl was able to chat with DPR for so long was because it was apparent to him that Dread was lonely. All that time behind a mask must have taken its toll on the leader of the Silk Road, and DPR evidently sought solace from the people he was connecting with online. Carl astutely reasoned that he could use this to his advantage, coaxing the leader of the site to share more, and enticing him to be Nob’s friend. A little manipulation here, some deceit there, and the Dread Pirate Roberts would be eating out of Carl’s hand in no time at all.
Yet the attempt was backfiring, not because Carl wasn’t getting close to DPR, but rather because he was getting too close to him. They would talk for hours about relationships, music, and the future of the drug trade.
For Carl, who had been fighting the war on drugs for more than a decade and getting nowhere, arresting one dealer only to see another take his or her place had gnawed at his purpose in the world. Now the arguments the Dread Pirate Roberts was making about the war on drugs were actually starting to make a little sense. Maybe the answer to all this violence and waste of government resources and the hundreds of thousands of people rotting away in jails was to legalize drugs. Maybe Carl was on the wrong side of the war.
Maybe, maybe, maybe.
Somewhere along the way of those maybes, Carl started to become enamored with Dread. He started greeting DPR with affectionate salutations. “Hello my friend,” he would write. “Is all well?” At other times he offered, “Stay safe,” and each night that they spoke, he told DPR to “sleep good.” There were compliments: “You are the most interesting man in the world, stay thirsty my friend!” And Carl even joked once, “I love you.” To which DPR replied, “Yer making me blush :).” Soon after that exchange, Carl started to sign his letters to DPR with an affectionate “Love Nob.”
Sure, part of this was Carl being undercover, but part of it wasn’t.
As the relationship progressed, in addition to trying to draw out the leader of the notorious drug and arms Web site, Carl started antithetically offering advice on how DPR could camouflage himself even more. “You can do one of two things,” he wrote to Dread. “Move to another country where you are safe from the laws of your native country or come to grips [with the reality that] there is always the possibility of getting caught.”
He counseled DPR on looking into alternative passports and possibly finding a backup place to live. Carl also taught him how international drug-smuggling routes worked through “dead drops,” where dealers leave drugs or guns in a location like a storage locker at a train terminal and then give the buyer the locker combination so they can grab their stuff and leave the money behind without the two ever meeting in person. The perfect way for the Silk Road to avoid the mail system. Finally Carl gave DPR advice about getting a lawyer.
Carl wasn’t always blurring the line of DEA agent and pretend drug dealer. There were times he did things by the book, including helping his co–case agent Mike McFarland from HSI Baltimore order drugs off the site from low-level dealers and then arresting those sellers. Over the summer they detained a few people and took over their accounts with the goal of trying to corner others. In one instance they arrested a man in Baltimore who sold meth on the Silk Road. In another they busted a man in Lincoln, Nebraska, who sold phenazepam, bromo blotters (which were similar to LSD), prescription meds including Xanax and Valium, and, for an added bonus, guns.
But even during the moments when Carl was doing his job as a cop, he would sometimes become a rapscallion. In one instance he teamed up with another agent, Shaun Bridges, who worked for the Secret Service and who had joined the Marco Polo task force to help follow the money. The two agents tried to recruit the National Security Agency to help in their hunt. Bridges had an intimidating look to him, with thin, squinty eyes, a black goatee, and short buzzed hair that made his ears pop outward. There was something about him that seemed to say, Be careful with this one, but Carl didn’t see it.
The NSA, or “No Such Agency,” as it was unofficially called, was rumored to be able to crack into any secure computer on the planet. Carl reasoned that the NSA could help him break Tor and find the Dread Pirate Roberts. While everyone else on the Marco Polo task force knew the agency didn’t touch drug-related cases, Carl and Shaun were determined to get it involved. So one day, without the knowledge of any of the other agents, the two men set up a secret meeting with one of Shaun’s contacts at the NSA. They didn’t want a paper trail, so everything was done in person.
The NSA analyst they met with, while sympathetic to their plight and the numbing hunt for the Dread Pirate Roberts, informed them that the NSA’s mandate was only to go after targets that could harm the security of America. “Sorry, we can’t help you,” the analyst said. Oh, and by the way, this conversation never happened.
But the two agents weren’t going to give up so quickly, so Shaun presented an alternative idea to Carl: “Let’s start trying to buy explosives on the site!” This way, he said, they could show that the Silk Road and other Dark Web sites could be used to harm America.
“I’m in!” Carl responded gleefully. When Carl told his boss, Nick, he was warned not to go there, noting that “bombs” were not part of the DEA’s mandate, in the same way that drugs were not part of the NSA’s.
But Carl was in charge, at least in his mind, and no one was going to tell him what to do. So he and Shaun explored buying pipe bombs online and having them shipped to an undercover government PO box, where they would be able to show the NSA analyst that the Silk Road could be used for an attack on U.S. soil. Soon they realized a random discovery of a couple of pipe bombs in the mail might cause a bit of a stir in the postal service, and the plan was halted at the last minute.
When that detour didn’t work out, Carl returned to the goal of befriending DPR, and in doing so, would say whatever he wanted to the site’s leader.
Not surprisingly, almost anyone who read the chats between Nob and Dread started to question why they were so detailed.
On more than one occasion Nick, Carl’s boss at the DEA, saw the conversations between the two men and was livid. He would call his underling into his office, slam the door shut behind him, and, amid the din of heavy metal music, erupt into an apoplectic rage. (Carl found glee in pissing off his boss, so he sat there undeterred.)
“I’m just doing this stuff to get close to him,” Carl told Nick unapologetically, which was half true. “I need to develop trust with DPR.”
It was hard to assert that this approach wasn’t working. There was an argument to be made that Carl was going to bring down the Silk Road before other agents, and it was becoming apparent that there were plenty of others in the U.S. government who wanted that glory, including (as Carl had heard) Jared Der-Yeghiayan over in Chicago. It seemed perfectly fine to overlook Carl’s peculiar interaction with DPR if it meant the Marco Polo crew was going to win.