Silk Road operator and kingpin Ross Ulbricht was sentenced on May 29 to life in prison for his involvement in the hidden Dark Web marketplace. While he is believed to be one of the many individuals behind the Dread Pirate Roberts pseudonym, he will spend his life behind bars in a maximum security penitentiary.

Judge Katherine Forrest of Manhattan’s U.S. District Court for the Southern District of New York was the overseer of the case and offered no leniency to Ulbricht after his final statement in which he told the court, "I've had my youth, and I know you must take away my middle years, but please leave me my old age." She handed him a life sentencing.

Ulbricht, who says he originally designed the Silk Road so individuals would be “free to buy and sell whatever they wanted" will have no chance at parole and no option for the death penalty, making the sentence a most harsh one.

The Silk Road was founded as a bastion of liberation, a digital marketplace where one could exercise freedom, as long as they did not encroach on another's. For DRP and Ulbricht, the Silk Road was more than an underground trading community, it was a revolution in the making.

Perhaps guided by his early success, DPR once wrote, “Every single transaction is a victory” in taking down the “thieving, murderous” state. DPR was a millionaire many times over, but those early successes, it seems, were for a greater revolution. Freedom after all, requires financing.

The Silk Road servers were originally compromised when FBI agents revealed reveal the true IP addresses of the site, which were hosted in a remote data center outside Reykjavik, Iceland. From there, the federal agents found Ulbricht in a San Francisco public library, literally with “fingers at the keyboard” and logged into the admin account of the infamous Dread Pirate Roberts.

The prosecution in the case estimated that the Silk Road handled some US$200 million in drug transactions, all of which were made with bitcoin. On July 21, 2013, when the location of the site's servers were first compromised, Dread Pirate Robert's accounts were receiving some 3,237 transfers per day, totalling US$19,459, which would provide an annualized income of more than $7 million.

Ulbricht's defense team will seek an appeal for the case, arguing recent revelations that two DEA agents involved in the investigation of Silk Road stole millions of dollars worth of bitcoin from the site and may have blackmailed Ulbricht by selling him law enforcement information. The defense was not permitted to use this information in any way at trial.

Although the defense team of the case argued that the Silk Road was a blessing in disguise that could reduce drug cartel organizations, Judge Forrester made clear that she found "Silk Road’s birth and presence asserted that its … creator was better than the laws of this country. This is deeply troubling, terribly misguided, and very dangerous." In his final pre-sentencing, Ulbricht wrote:

“I wanted to empower people to make choices in their lives … to have privacy and anonymity, I’m not a sociopathic person trying to express some inner badness.”

Ross Ulbricht

Although the information was not brought to trial, investigators believe Ulbricht ordered at least two hits on former Silk Road employees, which were never carried to resolution.

In response to the sentencing, Ulbricht’s lawyer, Joshua Dratel, claimed that previous trials for individuals who pleaded guilty to being involved in the Silk Road received sentences of only 17 months. Ulbricht, on the other hand — for exercising his constitutional rights — was given life. Dratel said this was both unfair and unjust.

Silk Road gave the blueprint for anonymous marketplaces on the Dark Web. Such websites continue to open the floodgates for an "anything goes" type of business model. Despite pervasive law enforcement crackdowns and rampant thefts, product listings in Dark Web marketplaces grew some 37 percent in the last year.

Whether we will look back on Ulbricht as a heroic lawbreaker in a similar manner to Rosa Parks or Harriet Tubman is unclear. What is clear, however, is that Ulbricht will be spending a very long time within the clutches of the law enforcement he sought to elude with the Silk Road.