It's been nearly a year since a jury determined that Ross Ulbricht had created and run the anonymous black market for drugs known as the Silk Road, a conviction that resulted in a life sentence without parole. Today his defense team finally had their chance to contest that outcome, and with it, one more chance to free the 31-year-old man who's become the face of the Dark Web.

As the first significant step in Ulbricht's appeal, his defense on Tuesday filed a 145-page argument for a new trial, calling for a higher court to throw out his conviction on seven charges, including conspiracies to traffic in narcotics, money laundering, and computer hacking as well as a "kingpin" charge usually reserved for mafia bosses and drug cartel leaders. That appeal includes a long list of what it describes as improprieties and abuses in Ulbricht's investigation and trial. Its most powerful argument: That the court erroneously suppressed information about federal agents investigating the Silk Road who used their positions to steal bitcoins from the site and even attempted to extort money from Ulbricht.

In its brief, Ulbricht's defense points out that the full extent of the crimes of corrupt Drug Enforcement Administration agent Carl Mark Force IV weren't revealed to the defense until after the trial, and that similar offenses by Secret Service agent Shaun Bridges weren't disclosed to the defense at all until indictments against the two agents were unsealed months after Ulbricht's conviction. "To a significant degree the extent, and in some respects the nature, of Force’s misconduct—as well as Bridges’s participation altogether—was hidden by the government from the defense (and the Court) in this case until after trial," writes Ulbricht's lead attorney Joshua Dratel. "Contrary to the government’s claims and the Court’s decision, the evidence of Force’s (and Bridges’s) corruption was both material and exculpatory."

The brief's focus on the two corrupt agents is only a part of a longer list of protests against the Southern District of New York court's decisions in Ulbricht's case. Even before Ulbricht's conviction, Dratel had already asked Judge Katherine Forrest for a mistrial—and was rejected—no less than five times over the course of the trial in January and February of 2015. The appeal brief repeats several of those complaints, including the defense's protest of Forrest's decision that Dratel couldn't cross-examine prosecution witnesses in detail about alternative suspects they'd discussed as possible owners or administrators of the Silk Road. Dratel also reiterates an argument the defense made in pre-trial hearings: that Ulbricht's laptop was searched with an overly broad warrant, and that his online accounts were tracked with a warrantless pen register that violated his fourth amendment privacy rights. And he criticizes Judge Forrest's decision not to admit a statement from a Silk Road staffer who had written that he believed multiple people had run the Silk Road under a single pseudonym, the "Dread Pirate Roberts," implying that Ulbricht wasn't the sole administrator of the site.

The appeal brief goes on to attack Forrest's decision late in the trial to block two expert witnesses Dratel planned to call to the stand, declaring them irrelevant and faulting the defense for submitting them with too little notice. Dratel argues that one of those witnesses in particular, bitcoin expert Andreas Antonopoulos, could have poked holes in the testimony from an ex-FBI agent who traced $13.4 million worth of bitcoins from the Silk Road to Ulbricht's laptop. That bitcoin tracing was commissioned by the prosecution and performed mid-trial, Dratel points out, giving the defense little time to call a witness to counter it.

But Ulbricht's defense reserved much of its brief for criticizing the court's suppression of information about the two corrupt law enforcement agents, who they say have irreparably tainted the Silk Road investigation and trial. DEA agent Force pleaded guilty in July of last year and was sentenced to six and a half years in prison for his criminal behavior in investigating the Silk Road. Secret Service agent Bridges reached his own plea agreement the next month and was sentenced to just under six years prison time. Both agents had stolen funds from the site, exploiting their access to hijack staffers' accounts. Force had gone further, both extorting Ulbricht (while using a pseudonym) with the threat that he could identify him, and simultaneously selling Ulbricht information (under a different pseudonym) about law enforcement's investigation into the Silk Road.

The defense has argued that Force and Bridges could have done more with their access to the site than merely steal money or send threats to Ulbricht. They've also argued that the pair could have used their access to the Silk Road's internal data to tamper with logs or even fabricate evidence. In the brief, Dratel points out that prior to Ulbricht's conviction, the defense hadn't been told Force had worked in cahoots with Bridges, a forensic expert who Dratel implies was capable of faking evidence used to convict Ulbricht.

Before Ulbricht's trial, Judge Katherine Forrest ruled that none of the then-unproved allegations against Force could be introduced by Ulbricht's defense. She argued, in closed hearings and sealed statements, that doing so might prematurely reveal a grand jury investigation into Force's crimes. But Dratel argues in the appeal brief that Judge Forrest should have accepted the defense's offer to delay the trial until the grand jury investigation was over—he writes that it was already nearly complete at the time. He protests that Bridge's corruption was hidden from the defense altogether. And finally, he claims that Force already knew about the grand jury investigation into his actions. "Contrary to the government’s representations to the Court, there was not any need to keep the grand jury investigation secret from its target," Dratel writes. "Force was already fully aware of it, and it was nearly, if not entirely, complete by the time trial in this case began."

Prosecutors can be expected to counter that Force and Bridges' offenses had nothing to do with convicting Ulbricht of his own crimes. Bridges and Force were part of a task force of investigators based in Baltimore, not the team led by the New York office of the FBI, which also included agents from the IRS and the DHS. Neither Force nor Bridges testified at Ulbricht's trial, and it seemed at times that the New York office had carefully quarantined itself from the Baltimore task force's corruption. In fact, the separation seems to have resulted in its own separate indictment of Ulbricht for attempted murder, a charge not included in his New York case, and which has yet to be tried.

But Ulbricht's lawyers argue that quarantine between New York and Baltimore wasn't nearly as tight as the government has made out. Dratel writes that a DHS agent investigating the Silk Road as part of the New York team frequently spoke and exchanged intelligence with the DEA's Force. "The government’s repeated insistence that the [New York] investigation was 'independent' of that in which Force and Bridges were involved is demonstrably repudiated by the record created by the government’s investigators and prosecutors themselves," he writes. "That record establishes that all of the federal investigations of Silk Road were coordinated and, for practical purposes, and for determining relevance to this case, combined."

Finally, the defense argues that aside from Ulbricht's conviction, Judge Forrest's sentence of life without parole was an unjust decision. It points out that the sentence was based in part on testimony about Silk Road buyers who had died from drug overdoses, and counters that Ulbricht can't be blamed for those deaths simply for running a market website—a "neutral platform" that didn't itself sell any particular drugs. And Dratel also notes Forrest's stated intention of deterring future criminals from following in Ulbricht's footsteps, and points out that she made no argument for why a shorter but still-harsh sentence couldn't have accomplished the same goal.

"The life sentence imposed on 30-year-old Ross Ulbricht 'shocks the conscience'...and is therefore substantively unreasonable," concludes Dratel's argument, referring to a common legal test of whether a court's decision is innately unjust. "Accordingly, Ulbricht should be re-sentenced before a different judge to avoid the irremediable taint from the improper factors the Court considered."

Read the defense's full appeal brief below:

Silk Road Appeal Brief