The Department of Justice sees its takedown of the billion-dollar Silk Road black market as a massive, victorious drug bust. Ross Ulbricht, the alleged creator of that anonymous contraband bazaar, now wants to cast the case in a different light: as a landmark example of the government trampling privacy rights in the digital world.

In a pre-trial motion filed in the case late Friday night, Ulbricht's lawyers laid out a series of arguments to dismiss all charges in the case based on Ulbricht's fourth amendment protections against warrantless searches of his digital property. As early as the FBI's initial discovery of servers in Iceland hosting the site on the Tor anonymity network—seemingly without obtaining a search warrant from a judge—Ulbricht argues that law enforcement violated his constitutional right to privacy, tainting all further evidence against him dug up in the investigation that followed.

"The [electronically stored information] and other material seized and searched has been contaminated at its source, and at several later points along the way, rendering the direct and indirect product of those searches and seizures – in essence, the entire product of the investigation itself – inadmissible," a 102-page memo accompanying the motion summarizes. "Thus, the Fourth Amendment and relevant statutes require suppression of the fruits of the searches and seizures, and any evidence or other information derived therefrom."

The motion refers to 14 distinct searches and seizures of Ulbricht's computers, equipment, and online accounts. Beyond the initial tracing of his alleged servers in Iceland, investigators performed several of those surveillance operations with "trap and trace" or "pen register" orders that don't require the "probable cause" standard necessary to convince a judge to sign off on a warrant; The warrantless surveillances ops included asking Comcast for information related to Ulbricht's alleged IP address in San Francisco. And even in the cases when investigators did get a warrant before performing their searches—as in the case of a Samsung laptop believed to belong to Ulbricht as well as his Gmail and Facebook accounts—Ulbricht's defense argues that those warrants were unconstitutional "general warrants" that allowed a wholesale dump of his private data rather than allowing the search for a specific piece of information.

"Many of the warrants...constitute the general warrants abhorred by the Framers, and which led directly to the Fourth Amendment," the memo reads. "The wholesale collection and study of Mr. Ulbricht’s entire digital history without limitation – expressly sought in the warrants and granted – represent the very type of indiscriminate rummaging that caused the American colonists so much consternation."

Ulbricht's memo isn't simply a demand to dismiss the charges against him, which include conspiracy to traffic in narcotics, money laundering, and a "kingpin" statute often used against mob bosses and drug cartel leaders. It's also a request for more information from prosecutors. Despite the "discovery" process designed to give defendants a chance to review the evidence against them, the memo says that the government still hasn't revealed to Ulbricht or the public many aspects of the investigation. The most crucial of those information gaps is just how the FBI located the Silk Road's servers despite the anonymity protections provided by cryptographic software Tor.

"All of the searches and seizures are predicated upon the government’s infiltration of the alleged 'Silk Road Servers,'" reads the memo. "However, that event – location of the Silk Road Servers – is shrouded in mystery, as the means and manner in which that discovery was accomplished has not been disclosed."

If that initial pinpointing and penetration of Ulbricht's alleged servers—whether by the FBI, the NSA, or investigators with the means of defeating Tor's privacy safeguards—is determined to be unconstitutional, the defense argues it could contaminate virtually all of the prosecution's other evidence. It points to what it calls the "fruit of a poisonous tree" doctrine, stating that an improper search can invalidate all subsequent searches based on evidence found in the initial step. And it notes that the requests to judges for warrants in other steps of the feds' investigation didn't explain or even mention that initial discovery of the Silk Road's computers in Iceland.

The memo backs up its argument by referring to several recent fourth amendment decisions, most notably the case of*Riley vs. California, *in which the Supreme Court ruled that police can't search a arrested suspect's phone without a warrant due to the massive amount of private data that sort of digital device contains. It also points to another case in which Microsoft was ordered to respond to a search warrant for emails belonging to one of its users, even though the emails were stored on a foreign server. Ulbricht's defense refers to that second case as a demonstration that the government ought to seek a warrant even when the information it’s seeking is stored abroad, as in the case of the Silk Road’s Icelandic servers.

“The government has not provided any reason why it could not have pursued, and why it was not obligated under its own theory of the scope of [the law], to pursue the same avenue – a warrant – for obtaining the [electronic stored information] on the Silk Road Server,” the memo reads.

Aside from its Fourth Amendment arguments, the memo makes an unrelated request: That the prosecution stop calling Ulbricht a murderer. In its criminal complaint and pre-trial arguments, the prosecution has referred repeatedly to Ulbricht's alleged attempts to pay for the murder of six people, including what the prosecutors describe as a potential informant against him and a blackmailer. But despite the fact that Ulbricht still faces a separate murder-for-hire case in Maryland, he hasn't been charged with any such killings in the current Southern District of New York case. The defense argues that means the prosecution's murder references are "unduly prejudicial" and violate Ulbricht's right to a fair trial.

Those murder charges have weighed heavily on Ulbricht's reputation, draining support for a young defendant who might have otherwise been a cause celebre for privacy and personal freedoms–after all, the Silk Road's creator who called himself the "Dread Pirate Roberts" preached a libertarian philosophy of "victimless" crime and civil disobedience. With his latest motion, that alleged "pirate" is taking another, well-timed shot at elevating his case beyond one of a cybercriminal drug kingpin—this time to a story of illegal government surveillance.

Read the full memo attached to Ulbricht's motion below.

Silk Road 4th Amendment Memo by Andy Greenberg