Feds’ Silk Road Investigation Broke Privacy Laws, Defendant Tells Court

coderman coderman at gmail.com
Sun Aug 3 04:02:36 PDT 2014

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

“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

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 a 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 points 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.

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