The Supreme Court is Silk Road founder Ross Ulbricht’s last hope

When it came time to sentence Silk Road creator Ross Ulbricht, federal prosecutors told the judge a harsh sentence was necessary “to send a clear message” to others who might be inspired to follow in the young kingpin’s footsteps and create a sprawling dark web drug bazaar. The judge obliged, putting Ulbricht behind bars for life with no chance for parole.

Now, nearly three years later, Ulbricht’s fight for a shot at freedom has reached the end of the line. The 33-year-old Texan has appealed to the Supreme Court, with his attorneys arguing that the case involves unresolved constitutional questions about the scope of the Fourth Amendment in the digital age and the authority of federal judges to go above and beyond when handing down sentences.

Ulbricht founded the Silk Road in 2009 when he was 29. A devout libertarian with a master’s degree in materials science and engineering, Ulbricht said his goal was to “empower people to be able to make choices in their lives for themselves and to have privacy and anonymity.” That freedom involved selling copious amounts of illegal drugs. Prosecutors said the site facilitated more than 1.5 million transactions, 95 percent of which involved sales of heroin, cocaine, meth, and other drugs. In addition to his life sentence, Ulbricht was ordered to forfeit $184 million, the amount of money that allegedly passed through his website.

Ulbricht’s appeal to the Supreme Court (see PDF below) hinges on two issues. The first is how authorities managed to track him down. After the FBI and the Department of Homeland Security identified an IP address that appeared to be connected to the “Dread Pirate Roberts,” the pseudonym Ulbricht used as the Silk Road’s administrator, they used a device known as a “pen/trap” to scoop up information about his online activities. They didn’t need a warrant for this, and after two weeks of surveillance Ulbricht was arrested at a San Francisco public library, with his laptop still open and logged into Silk Road.

Ulbricht’s attorney, Kannon Shanmugam, declined to comment on-the-record about the case. In his petition to the Supreme Court, Shanmugam argues that the standard that allows the feds to conduct warrantless surveillance with “pen/trap” devices is based on dialed telephone numbers and therefore outdated.

“This case presents the question whether the Fourth Amendment permits the government, without probable cause, to collect data generated by millions of individuals as an everyday incident of modern life: their Internet traffic information,” Shanmugam wrote. He added that internet users “have a reasonable expectation of privacy” and the feds should need a warrant to snoop on them.

The Supreme Court is already considering similar issues in another case, Carpenter v. United States, which will determine whether police need a warrant to obtain cell phone records that reveal a person’s location and movements.

As it currently stands, cellphone and internet users forfeit their right to privacy because it’s assumed that they understand their information is being transmitted to third-parties. Shanmugam, a former clerk for the late Antonin Scalia, argues that “internet users may not even understand that they are providing that sensitive and revealing information.”

The second issue in Ulbricht’s case involves the factors that led to his life sentence. He was only convicted of distributing “one kilogram or more” of heroin, “five kilograms or more” of cocaine, “ten grams or more” of LSD, and “500 grams or more” of meth. But during sentencing, prosecutors pointed to evidence that showed Ulbricht was involved in five murder-for-hire plots, and that drugs sold on Silk Road caused at least six fatal overdoses.

“Ulbricht bears responsibility for the overdoses, addictions, and other foreseeable repercussions of the illegal drugs sold on Silk Road,” federal prosecutors wrote in 2015. “It does not matter that he did not personally handle those drugs; neither would a traditional kingpin. Ulbricht was the architect and overseer of the entire Silk Road enterprise.”

A spokesman for the U.S. Attorney’s Office for the Southern District of New York, which handled Ulbricht’s prosecution, declined to comment on Ulbricht’s Supreme Court appeal.

Writing to the Supreme Court, Shanmugam pointed out that nobody was actually killed in the murder-for-hire plots, and noted that Ulbricht wasn’t convicted for any crimes related to the would-be assassinations or the fatal overdoses. He said the judge made “numerous factual findings,” which were based merely on “preponderance of the evidence.” He called Ulbricht’s sentence “unheard of for a first-time offender” convicted of a few drug crimes.

Aside from Ulbricht’s case, the broader question is whether federal judges in other cases have the authority to consider factors beyond what led to a person’s conviction and impose a stiffer sentence than the would otherwise. Shanmugam called it an opportunity for the Supreme Court to “put an end to unconstitutional sentences.”

Ulbricht’s life sentence was supposed to deter others from using the dark web to sell drugs, but it clearly hasn’t worked: Multiple copycats have sprung up in the years since the Silk Road was shut down, and it’s arguably easier than ever to buy drugs online.

The government has 30 days to respond to Ulbricht’s appeal. The Supreme Court will likely decide whether to hear the case in spring 2018.