As Ross Ulbricht is escorted on the short walk from his cell in New York's Metropolitan Correctional Centre to the Daniel Patrick Moynihan Courthouse today (13 January), he will know that far more than just his freedom hangs in the balance.
The trial of the alleged criminal mastermind accused of running the billion-dollar Silk Road illegal drugs website has the potential to set precedents in how internet crimes are punished, and how law enforcement can access our digital possessions.
Ulbricht, 30, is charged with narcotics trafficking, computer hacking, money laundering, conspiracy to traffic fraudulent IDs and engaging in continuing criminal enterprise. If found guilty he faces life in prison; he pleads not-guilty on all charges.
The outcome of Ulbricht's trial will run much deeper than drug and money-laundering laws for two important reasons which his legal team will look to build its defence on.
Violations of the Fourth Amendment
Firstly, questions surround how the FBI and Department of Homeland Security found Silk Road's servers, which are alleged to have been located in Iceland. Accused of being the property of Ulbricht, an American citizen, a warrant would normally be required to search the contents of these servers, but the prosecution says this was unnecessary because they were located abroad.
In the trailer of Deep Web (below), an upcoming documentary featuring Silk Road, Ulbricht's mother Lyn says the case "is bigger than Ross. It's bigger than a website. I think one website is far less dangerous than the government trampling on our rule of law and constitution. I think that is very alarming."
Lyn Ulbricht continues: "We are asking the prosecution 'how did you find the server?' and they're not saying. We have to know how they found the server in order to see if Ross' Fourth Amendment rights have been violated."
Part of the US Constitution, the Fourth Amendment prohibits unreasonable searches and seizures and requires any warrant to search a person's property to be issued by a judge and supported by probable cause.
A fishing expedition
Lyn Ulbricht says there were 14 searches and seizures in her son's case. "Some of them have no warrant at all and some of them have what's called a general warrant, which is a fishing expedition into a person's total property - unlimited rummaging through all of their things to see what they can find."
Wired journalist Andy Greenberg, who also appears in the Deep Web trailer, says if a violation of the Fourth Amendment is proven it could "poison the entire case, it could be a giant problem for the prosecution and taint every other piece of evidence that they found subsequently."
If law enforcement's warrantless search of the Silk Road servers is deemed acceptable by Judge Katherine Forrest and the jury, Greenberg warns "it could have a lasting precedent for how the Fourth Amendment works in the digital age."
Echoing this concern, Lyn Ulbricht said: "We're at a crossroads here deciding what kind of internet we want and what kind of freedoms we want in general."
The second issue Ulbricht's defence will be keen to explore is that of transferred intent - in this case, how the prosecution claim the owner or administrator of a website is legally responsible for the actions of - and is in conspiracy with - its users. In the case of Silk Road, this means the owner would be responsible if the site's users were found to be dealing drugs, fake ID and other illegal goods, even if the site owner claims to be unaware of the transactions.
Under current US law, website owners cannot be sued by individuals for the actions of their site's users. They are protected by Section 230 of the Communications Decency Act, which states: "No provider or user of an interactive computer service shall be treated as the publisher or speaker of any information provided by another information content provider."
However, when the government takes a website owner to criminal court they are stripped of this protection.
"If Ross were convicted he'd be the first website host ever to be convicted for the actions of the users of the site," Ulbricht said in an interview with ReasonTV, adding that transferred intent was recently used to indict postal service FedEx on 15 counts of drug trafficking.
'I'm not here to defend Silk Road'
Ulbricht's defence will argue that it is unreasonable for a website owner to be fully aware of the actions of all its users, but distancing herself from the actions of Silk Road, Ulbricht says: "The point is the principle involved and the precedent that will be set. I'm not here to defend Silk Road at all, or drug use or anything like that. Our lawyers are saying this opens up a dangerous little crack in the door."
The trial is set to begin in the Daniel Patrick Moynihan Courthouse, New York at 9am local time on 13 January, and is expected to last between four and six weeks.