Inconceivable! How the Fourth Amendment Failed the Dread Pirate Roberts in United States v. Ulbricht

Emily Moss, MJLST Staffer

It is not an overstatement to claim that electronic devices, such as laptop and smart phones, have “altered the way we live.” As Chief Justice Roberts stated, “modern cell phones . . . are now such a pervasive and insistent part of daily life that the proverbial visitor from Mars might conclude they were an important feature of human anatomy.” Riley v. California, 573 U.S. 373, 385 (2014). These devices create new digital records of our everyday lives. United States v. Ulbricht, 858 F.3d 71 (2d Cir. 2017) is one of many cases that grapple with when the government should gain access to these records.

In February 2015, a jury found Ross William Ulbricht (aka “Dread Pirate Roberts” or “DPR”) guilty on seven counts related to his creation and operation of Silk Road. United States v. Ulbricht, 858 F.3d 71, 82 (2d Cir. 2017). Silk Road was an online criminal marketplace where, using the anonymous currency Bitcoin, “users principally bought and sold drugs, false identification documents, and computer hacking software.” Id. Government trial evidence showed that, hoping to protect Silk Road anonymity, DPR commissioned the murders of five people. Id. at 88. However, there is no evidence that the murders actually transpired. Id.

On appeal, the Second Circuit upheld both the conviction and Ulbricht’s two-life sentence. Ulbricht, 858 F.3d at 82. Ulbricht argued, inter alia, that “the warrant[] authorizing the government to search his laptop . . . violated the Fourth Amendment’s particularity requirement.” Id. at 95. The warrant authorized “opening or ‘cursorily reading the first few’ pages of files to ‘determine their precise contents,’ searching for deliberately hidden files, using ‘key word searches through all electronic storage areas,’ and reviewing file ‘directories’ to determine what was relevant.” Id. at 101–02. Ulbricht claimed that the warrant violated the Fourth Amendment’s particularity requirement because it “failed to specify the search terms and protocols” that the government was required to employ while searching Ulbricht’s laptop. Id. at 102.

The court acknowledged that particularity is especially important when the warrant authorizes the search of electronic data, as the search of a computer can expose “a vast trove of personal information” including “sensitive records.” Id. at 99. It noted that “a general search of electronic data is an especially potent threat to privacy because hard drives and e-mail accounts may be ‘akin to a residence in terms of the scope and quantity of private information [they] may contain’ . . . Because of the nature of digital storage, it is not always feasible to ‘extract and segregate responsive data from non-responsive data,’. . . creating a ‘serious risk that every warrant for electronic information will become, in effect, a general warrant.’” Id. (internal citations omitted).

Nonetheless, the court rejected Ulbricht’s claim that the laptop warrant failed to meet the Fourth Amendment’s particularity requirement. It reasoned that it would be impossible to identify how relevant files would be named before the laptop search began, which the government reasonably anticipated when requesting the laptop warrant. Id. at 102 (emphasizing examples where relevant files and folders had misleading names such as “aliaces” or “mbsobzvkhwx4hmjt”). Further, the court held that broad search protocols were appropriate given that the alleged crime involved sophisticated technology and masking identity. Id. Ultimately, the court emphasized that the “fundamental flaw” in Ulbricht’s argument was that it equated a broad warrant with a violation of the particularity requirement. Id. Using the analogy of searching an entire home where there is probable cause to believe that there is relevant evidence somewhere in the home, the court illustrated that a warrant can be both broad and still satisfy the particularity requirement. Id. (citing U.S. Postal Serv. v. C.E.C. Servs., 869 F.2d 184, 187 (2d Cir. 1989)). The court therefore upheld the constitutionality of the warrant. The Supreme Court denied Ulbrich’s writ of certiorari.

Orin Kerr’s equilibrium adjudgment theory of the Fourth Amendment argues that as new tools create imbalanced power on either the side of privacy or the side of law enforcement, the Fourth Amendment must adjust to restore its original balance. The introduction of computers and the internet created an immense change in the tools that both criminals and law enforcement use. Without minimizing the significance of Ulbricht’s crimes, United States v. Ulbricht illustrates this dramatic change. While computers and the internet did create new avenues for crime, computer and internet searches—such as the ones employed by the government—do far more to disrupt the Fourth Amendment’s balance.

Contrary to the court’s argument in Ulbricht, searching a computer is entirely unlike searching a home. First, it is easy to remove items from your home, but the same is not true of computers. Even deleted files often linger on computers where the government can access them. Similarly, when law enforcement finds a file in someone’s home, it still does not know how that file was used, how often it has been viewed, or who has viewed it. But computers do store such information. These, and many other differences demonstrate why particularity, in the context of computer searches, is even more important than the court in UIlbricht acknowledged. Given the immense amount of information available on an individual’s electronic devices, Ulbricht glosses over the implications for personal privacy posed by broad search warrants directed at computers. And with the rapidly changing nature of computer technology, the Fourth Amendment balance will likely continue to stray further from equilibrium at a speed with which the courts will struggle to keep up.

Thus, adjusting the Fourth Amendment power balance related to electronic data will continue to be an important and complicated issue. See, e.g., Proposal 2 Mich. 2020) (amending the state’s constitution “to require a search warrant to access a person’s electronic data or electronic communications,” passing with unanimous Michigan Senate and House of Representative approval, then with 88.8% of voters voting yes on the proposal); People v. Coke, 461 P.3d 508, 516 (Colo. 2020) (“‘Given modern cell phones’ immense storage capacities and ability to collect and store many distinct types of data in one place, this court has recognized that cell phones ‘hold for many Americans the privacies of life’ and are, therefore, entitled to special protections from searches.”) (internal citations omitted). The Supreme Court has ruled on a number of Fourth Amendment and electronic data cases. See, e.g., Carpenter v. United States, 138 S.Ct. 2206 (2018) (warrantless attainment of cell-site records violates the Fourth Amendment); Riley v. California, 134 S.Ct. 2473 (2014) (warrantless search and seizure of digital contents of a cell phone during an arrest violates the Fourth Amendment). However, new issues seem to appear faster than they can be resolved. See, e.g., Nathan Freed Wessler, Jennifer Stisa Granick, & Daniela del Rosario Wertheimer, Our Cars Are Now Roving Computers. Is the Fourth Amendment Ready?, ACLU (May 21, 2019, 3:00 PM), The Fourth Amendment therefore finds itself in eel infested waters. Is rescue inconceivable?

Special thanks to Professor Rozenshtein for introducing me to Ulbricht and inspiring this blog post in his course Cybersecurity Law and Policy!