Silk Road’s mastermind Ross Ulbricht challenges sentence again
Ulbricht, also known as Dread Pirate Roberts, has filed a Motion to vacate, set aside or correct his sentence.

Ross William Ulbricht, also known as Dread Pirate Roberts, the mastermind of Silk Road, the notorious marketplace that used Bitcoins for its transactions, is trying once again to challenge his sentence. On Thursday, October 10, 2019, Ulbricht filed Motion to Vacate, Set Aside or Correct Sentence with the New York Southern District Court.
Let’s recall that, in February 2015, a jury convicted Ulbricht of various counts stemming from his founding and operation of an online black market called “Silk Road,” which facilitated the sale of millions of dollars of illegal goods and services.
The counts of conviction were:
- 21 U.S.C. 841(a), Aiding and Abetting Distribution of Drugs
- 21 U.S.C. 848(f) Continuining Criminal Enterprise
- 18 U.S.C. 1030(a),(f) Computer Hacking Conspiracy
- 18 U.S.C. 1028(a),(f) Fraud with Identification Documents
- 18 U.S.C. 1956, 4999, Money Laundering Conspiracy
Ross Ulbricht is now challenging the life sentence issued on June 1, 2015 by the New York Southern District Court.
In his Motion, Ulbricht mentions three grounds.
According to Ground One, Ulbricht’s counsel’s lack of adversarial testing of the Government’s case violated Ulbricht’s Sixth Amendment rights.
Ulbricht says his trial counsel conceded Ulbricht’s guilt with respect to the most consequential offenses in the indictment. Trial counsel conceded in his Opening Statement that Ulbricht had created and ran the Silk Road website for a period of time. That concession essentially constituted Ulbricht’s admission of guilt. Stipulations were entered into where counsel agreed that numerous Silk Road vendors sold and delivered illegal controlled substances to a government agent. These concessions and stipulations relieved the government of its burden of proof on the charges against Ulbricht.
The result, says Ulbricht, was a proceeding where trial counsel failed to subject the prosecution’s case to any meaningful adequate adversarial testing in violation of the Sixth Amendment.
According to Ground Two, Counsel provided deficient plea advice to Ulbricht. But for counsel’s deficient advice there is a reasonable probability that Ulbricht would have pleaded guilty and been sentenced to less jail time.
Ulbricht explains that the Government offered him a pre-indictment plea deal with required him to plead guilty to and be subject to a minimum punishment of 10 years and up to life imprisonment. Ulbricht’s attorneys advised him to reject the deal and proceed to trial. Ulbricht was advised that by going to trial instead of pleading guilty he was risking nothing: even if he went to trial and lost, he was counseled that he would be in no worse position at sentencing because the Guideline range would call for a life sentence either way. Ulbricht rejected the Government’s plea offer based on the advice of his attorneys.
Ulbricht says he would have pleaded guilty and accepted the plea offer if his attorneys had properly explained to him the elements that the Government needed to prove. Ulbricht would also have pleaded guilty and accepted the plea offer if he had been advised by counsel that there was a better chance of being sentenced to less than life without the Government’s agreement. Alternatively, Ulbricht would have pleaded guilty “open” to the indictment or the superseding indictment without a plea agreement if his attorneys had explained to him that the Government’s evidence of guilt was overwhelming and he did not have a legally viable trial defense.
According to Ground Three, Counsel was ineffective in violation of the 6th Amendment by conceding all the essential elements of the offense, pleading Ulbricht guilty with no benefit.