Ross Ulbricht's billion-dollar black market Silk Road was in many ways the first of its kind, blending encryption and online drug sales in a business model that plenty of other online drug lords have since sought to emulate. So as Ulbricht's sentencing for running that massive narcotics-selling experiment approaches, the Department of Justice wants to make an example of Ulbricht's punishment, too.

Ahead of Ulbricht's sentencing Friday, prosecutors in his case have sent the judge a 16-page letter asking that Ulbricht be given "a lengthy sentence, one substantially above the mandatory minimum." And one of the reasons for that harsh sentence, the Department of Justice attorneys argue, is to "send a clear message" to anyone who would follow in Ulbricht's footsteps and create the next Dark Web drug market.1

"Ulbricht’s conviction is the first of its kind, and his sentencing is being closely watched," the prosecution's letter reads. "The Court thus has an opportunity to send a clear message to anyone tempted to follow his example that the operation of these illegal enterprises comes with severe consequences."

That deterrence argument is just one in a series of calls for a long sentence made by the prosecution in its letter. At other points, it lists the details of six deaths it argues were caused by drug overdoses facilitated by the Silk Road's anything-goes drug sales. It rebuts the positive arguments about Ulbricht's character made by the defense, as well as the over 100 letters from friends, family, and even fellow inmates about Ulbricht's character, pointing to his cold-blooded recording of his attempted murders of enemies in the journal found on his laptop. And it counters the argument made in the defense's pre-sentencing letter to the judge: That the Silk Road actually reduced harm for drug users with a rating and review system that assured drugs' quality and purity.

Rather than reduce harm, prosecutors argue that rating system "provided a veneer of safety to an intrinsically unsafe business. Even if rated '5 out of 5,' heroin is still heroin," their letter reads. "Indeed, praising Silk Road for including 'harm reduction measures' is akin to applauding a heroin dealer for handing out a clean needle with every dime bag."

Ulbricht's attorneys declined to respond to a request for comment on the prosecution's filing.

The Justice Department's argument about the budding underground industry created by the Silk Road's temporary success stands out from the other points in the government's letter as a new tactic for prosecutors. It's one of the first times in Ulbricht's case that they've acknowledged the subsequent generations of anonymous black markets—what the prosecution in its letter calls "dark markets"—that have sprouted since the Silk Road's downfall. "Ulbricht did not merely commit a serious crime in his own right. He developed a blueprint for a new way to use the Internet to undermine the law and facilitate criminal transactions," the prosecution writes. "Using that blueprint, others have followed in Ulbricht’s footsteps, establishing new 'dark markets' in the mold of Silk Road, some selling an even broader range of illicit goods and services than Silk Road itself."

Indeed, several iterations of the Silk Road have come and gone in the two short years since it went offline. Those copycat sites have included the Silk Road 2, which was shut down in law enforcement's dark web purge last fall, and Evolution, a giant black market for drugs, guns, and stolen financial information whose leaders absconded with users' funds in March. Today the black market site Agora reigns as the largest black market still online, with tens of thousands more products listed for sale than the Silk Road ever offered.

In its letter, the Silk Road prosecution points to the difficulty of tracking down and punishing the creators of those markets as one more reason that Ulbricht should be severely sentenced: If anonymous market administrators can't be easily caught, perhaps they can be deterred from a life of Dark Web crime by their fear of Ulbricht's fate. "Although the Government has achieved some successes in combating these successor dark markets, they continue to pose investigative challenges for law enforcement," reads the letter. "To the extent that would-be imitators may view the risk of being caught to be low, many are still likely to be deterred if the stakes are sufficiently high."

That argument ignores plenty of studies that show that long prison sentences don't tend to deter crime. But it may hold more sway for the judge when applied to the Dark Web new criminal arena, where there are few precedents or studies to show how criminals react to the deterrence value of a potential lifetime behind bars.

For Ulbricht himself, however, it may seem cruel to face punishment for the actions of other black market administrators over whom he had no control. In his own letter to the judge in his case filed last Friday, Ulbricht made a far more personal argument: That he's learned his lesson and wouldn't repeat his mistakes if he were given his freedom after the 20 year minimum sentence he faces. “Silk Road turned out to be a very naive and costly idea that I deeply regret," Ulbricht wrote.

"Even now I understand what a terrible mistake I made," he added. "I’ve had my youth, and I know you must take away my middle years, but please leave me my old age. Please leave a small light at the end of the tunnel, an excuse to stay healthy, an excuse to dream of better days ahead, and a chance to redeem myself in the free world before I meet my maker."

Here's the full letter to the judge from prosecutors:

Ulbricht Prosecution Sentencing Letter

1Correction 5/27/2015: An earlier version of this story stated that prosecutors sought a life sentence for Ulbricht, when in fact they asked only for a lengthy sentence "substantially above the mandatory minimum."