Ross Ulbricht was sentenced in May 2015 to life in prison without parole for various crimes connected to his launching the darkweb sales site Silk Road. In May of this year, the Second Circuit Court of Appeals upheld his conviction and his grossly disproportionate sentencing.

Ulbricht has now appealed the Second Circuit's decision to the Supreme Court.

Kannon K. Shanmugam, the lawyer managing the appeal, summed up the legal issues that require settling by the Supreme Court in a December memo to potential amici in the case. Even those who might never dream of launching a darkweb site facilitating possibly illegal substance sales should be very worried about how the government convicted and sentenced Ulbricht, he explains:

This case presents two important questions of constitutional law with broader significance for the rights of criminal defendants generally. First, the Second Circuit affirmed the government's warrantless collection of Mr. Ulbricht's Internet traffic information by relying on the third-party doctrine, which the Court is reviewing in a different context this Term in Carpenter v. United States….This case would afford the Court an ideal opportunity to address how the doctrine applies to Internet traffic information.

Damon Root reported from the Supreme Court earlier this month on the oral arguments in that Carpenter case, which hinges on a warrantless search of cellphone records in a bank robbery conviction. As Root wrote:

The government insists that this warrantless search did not violate Carpenter's Fourth Amendment rights because, in the words of the Supreme Court's 1979 ruling in Smith v. Maryland, "a person has no legitimate expectation of privacy in information he voluntarily turns over to third parties." In other words, Carpenter has no Fourth Amendment right to privacy in his cellphone records because he voluntarily used his cellphone, thus voluntarily disclosing his location to the various cellphone towers that handled his calls. Throughout the November 29 oral arguments, Justice Alito was perhaps the most supportive of the government's position and the most critical of Carpenter's arguments. Justice Gorsuch, on the other hand, seemed extremely skeptical of the government's stance. Gorsuch even suggested at one point that the government's position was at odds with the "original understanding of the Constitution"—not exactly a compliment, since Gorsuch is a self-professed originalist.

Root went on to explain how in the oral arguments in the case, Gorsuch seemed to believe that Americans ought to have a defensible property right in such digital information analogous to the classic analog "papers and effects." As Root wrote, "Gorsuch proffered a property rights argument that might allow Carpenter to win the case." The Supreme Court's decision in Carpenter has not yet been issued.

Shanmugam, a former law clerk to the late Justice Antonin Scalia, has argued 21 previous cases before the Supreme Court, has had at least five wins there, and has a good record of a 36 percent success rate in having cert petitions granted by the Court from 2012-2015 (and a 38 percent such success rate from 2013-2017).

He says those Fourth Amendment questions related to digital information, ripe for reappraisal, are not the only issue at stake in Ulbricht's case:

Second, the Second Circuit affirmed the sentencing court's determination of facts never submitted to the jury, which significantly altered the Guidelines range and ultimately led the court to impose a life sentence—a sentence the Second Circuit admitted "condemn[s] a young man to die in prison." Several justices have previously questioned whether this kind of judicial factfinding violates the Sixth Amendment. For both these reasons, this case warrants Supreme Court review.

The certiorari filing in Ulbricht's case has not yet appeared on the Supreme Court's online docket. But its primary contentions are that the warrentless pen/trap search orders on both Ulbricht's home IP address and his laptop represent a fresh and more extreme government intrusion into private information than recognized by past phone-based precedent.

Why We Need a Fresh Fourth Amendment Doctrine for the Digital Age

In rejecting Ulbricht's earlier appeal, the Second Circuit held to the "third party doctrine," which says any information you voluntarily passed along to or through a third party, like a phone company (as in the initial invention of the doctrine in the 1979 Smith case, or by modern analogy, internet service providers), is information over which you no longer have any Fourth Amendment privacy right.

Ulbricht's cert petition tries to argue that the Court should at the very least "hold this case pending its decision in Carpenter, which may articulate principles applicable here."

As the cert petition goes on to explain, the pre-existing, telephone-based, criteria to judge the "third party doctrine" in the computer age is one courts of appeals "have largely felt constrained by" and "have signaled the need for this Court to address whether, and how, those precedents apply in the context of modern Internet technology."

In that earlier Smith decision, "the Court emphasized the pen register's 'limited capabilities,' noting that "a law enforcement official could not even determine from the use of a pen register whether a communication existed."

The cert petition lists and quotes various cases in which circuit courts of appeal have clearly questioned whether all the information we are "willingly" giving to third parties in the internet age are indeed things over which we have no Fourth Amendment interest, if the Fourth Amendment is to retain any strength at all in the 21st century.

The very confusion in the lower courts on this question, the petition argues:

only underscore the necessity of this Court's intervention. Calling the Internet traffic information collected by pen/traps today "constitutionally indistinguishable" from the list of telephone numbers at issue in Smith is "like saying a ride on horseback is materially indistinguishable from a flight to the moon": "[b]oth are ways of getting from point A to point B, but little else justifies lumping them together." (Riley, 134 S. Ct. at 2488).

Ulbricht's case is "an appropriate companion case to Carpenter because the Internet traffic information at issue here is broader in important ways than the cell site location information at issue in Carpenter. In addition to allowing the government to determine when petitioner was accessing the Internet from the privacy of his own home, the information gathered by the pen/traps here permitted the government to determine the websites to which petitioner connected, the length of the connections, and the port of transmission of the data. As this Court has recognized, the collection of such Internet information could reveal 'an individual's private interests or concerns.' (Riley, 134 S. Ct. at 2490)." (The 2014 Riley case quoted did apply Fourth Amendment protections to searches of cell phones incident to an arrest.)

The Supreme Court has a great opportunity to clarify further for law enforcement the meaning of the Fourth Amendment in the Internet age, the petition argues.

These are some of the reasons why Ulbricht's legal team thinks the warrantless searches in his case deserve to be distinguished from the telephone records at issue in 1979's Smith case:

unlike in Smith, the government could identify the "purport of any communication" at issue here, because it collected the ports of transmission of petitioner's Internet activity. A "port" is a piece of information used to identify the purpose of a particular packet of data being transmitted between computers….More broadly, an individual's Internet traffic information is far more sensitive than the telephone routing information at issue in Smith. As this Court has observed, "an Internet search and browsing history * * * [can] reveal an individual's private interests or concerns—perhaps a search for certain symptoms of disease, coupled with frequent visits to WebMD." Riley…. Extending Smith and Miller to Internet traffic information would allow the government to access significant information about an individual's Internet habits without a warrant and without probable cause. For example, the government could learn that the individual regularly visits websites associated with a particular political party or sexual orientation, "enabl[ing] the Government to ascertain, more or less at will, [people's] political and religious beliefs, sexual habits, and so on." United States v. Jones…(2012) (Sotomayor, J., concurring)…. What is more, pen/traps revealing IP address information can also allow the government to identify an individual's general location, as the government demonstrated at petitioner's trial….In that respect, the government turned petitioner's laptop into an analogue of the tracking device at issue in United States v. Karo… (1984). In that case, the Court held that the government conducted an unconstitutional search when it monitored a signal from a tracking device in the defendant's home without a warrant. When agents can gather an individual's Internet traffic information upon only the minimal showing required by the Electronic Communications Privacy Act, little beyond their discretion constrains their ability to monitor citizens' private lives. And an agent's choice to exercise discretion is no substitute for clear limits imposed by an impartial magistrate.

The Sixth Amendment Implications of Ulbricht's Life Sentence Without Parole

The Shanmugam memo sums up the legal issues raised by Ulbricht's life sentence without parole. While "Ulbricht's Sentencing Guidelines range would have resulted in a recommended sentence of, at most, 30 years in prison," the sentencing judge considered various allegations that Ulbricht paid for (uncommitted) murders, allegations never actually tried in court. The Second Circuit in his initial appeal "reluctantly affirmed, concluding that the alleged murders for hire separated the case from an ordinary drug crime."

From this layman's perspective, it seems hideously unjust that a judge can sentence based on crimes never proven in court. Shanmugam explains in the memo however that "the Court has previously declined to grant certiorari on petitions presenting this question" (of sentences based on unadjudicated accusations).

Importantly, "Justice Gorsuch has…expressed interest in this issue, and may spur a renewed interest in granting certiorari. Writing for a Tenth Circuit panel in 2014, then-Judge Gorsuch…wrote that '[i]t is far from certain whether the Constitution allows' a judge to increase a defendant's sentence within the statutorily authorized range 'based on facts the judge finds without the aid of a jury or the defendant's consent.' United States v. Sabillon-Umana…(10th Cir. 2014) (Gorsuch, J.) (citing Jones)."

Technically, the sentence Ulbricht received was within the range of possible, though not recommended, sentences for the crimes for which he was actually convicted. As explained in the memo:

Even though a particular sentence may fall within the statutory range, the sentencing court is not free to impose that sentence without taking account of the Guidelines range and explaining any variance. To do otherwise constitutes procedural error and results in an unlawful sentence. Thus, even within the statutory range, there are sentences that would be unlawful but for a court's factfinding and explanation. Under this Court's Sixth Amendment precedents [such as Apprendi and Alleyne] those factual findings that justify the otherwise unlawful sentence must be found by a jury or admitted by the defendant before they can be used by the judge to increase the defendant's sentence. The practice of relying on judicial factfinding to sustain an otherwise unreasonable sentence is unconstitutional.

As the cert petition explains, "it is hard to imagine a better example of the consequences of runaway judicial factfinding than this case. Petitioner, a young man with no criminal history, was sentenced to life imprisonment without the possibility of parole for drug crimes that do not ordinarily carry that sentence, based substantially on numerous factual findings made by the sentencing judge by a preponderance of the evidence."

In the 2007 Rita case, the late Justice Scalia and current Justice Clarence Thomas both expressed concerns about judge's imposing sentences that are only reasonable because of "judge-found facts." Both of them in the 2014 Jones case "noted the pressing need for the Court to resolve the question."

"Numerous judges in the lower courts have urged a different approach or specifically importuned this Court to provide guidance, noting the importance of the question and the attendant uncertainty surrounding sentencing practices while the question remains open," Ulbricht's cert petition says. "This Court should grant review and definitively hold that the practice of sustaining an otherwise unreasonable sentence through judicial factfinding is unconstitutional."

Ulbricht's case is a perfect opportunity for the Court to protect the integrity of a justice system that should be sentencing based only on facts considered and proven in court.

As Ulbricht said to the District Court in his initial trial, "I remember clearly why I created the Silk Road. I had a desire to—I wanted to empower people to be able to make choices in their lives for themselves and to have privacy and anonymity."

If not for those principles, then at least for the clear constitutional issues raised by the specifics of his prosecution and sentencing, the Supreme Court should take up Ulbricht's case.