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Goin’ Deep: 5 Questions for Alex Winter

The film Deep Web opens this weekend, from director Alex Winter, (some may know him best as Bill S. Preston, Esq. from the Bill and Ted movies, others from directing the similar topic-ed Downloaded). The film first debuted at SXSW, where it played to glowing reviews, and then came to Toronto as part of the Scotiabank Big Ideas series at Hot Docs.

Essentially, the scope of the film is that Ross Ulbricht, whose story is quite fascinating, was deemed to be The Dread Pirate Roberts, (yes, the Princess Bride reference is very intentional) of Silk Road, part of the Dark Web. Winter is a passionate defender of his film, (and of Ulbricht). The film opens up very deep conversations about the limits of knowability and understanding.

We spoke with Winter via email, and his answers were as powerfully charged as the film.

Scene Creek: Obviously your movie has changed significantly since it screened at Hot Docs. To what degree do you feel like Deep Web is a finished product, or is it always evolving?

Alex Winter: I never intended to make a movie that would tell this whole story, but this story is just beginning, the closure of The Silk Road is the beginning of the drug marketplaces online, not the end of them. My move is about beginnings, the beginning of  a movement, whether you think this movement is horribly criminal or a political necessity, that is irrelevant. I am very content with where my movie ends, wouldn’t want it to end anywhere else. This doesn’t mean the story is over, its going to go on for a very long time, and there will be other stories told about these issues and about these events, as there should be. I am very happy with the scope of the film.

Scene Creek: Do you believe that Ross Ulbricht has become a scapegoat for the Darknet in general?

Alex Winter: The Judge, when she sentenced Ross, was very clear that she was using the severity of the sentence to set an example for all of the other people who were using the internet the way that Ross was convicted of using it, so it isn’t really my opinion that Ross was a scapegoat, it was the opinion of the court that they were making him a scapegoat. He has sentenced to life in prison without the possibility of parole, the specific reason for that sentence was to set an example. That is the opinion of the court, that Ross is a scapegoat for all of the other activity of that kind on the internet and that the threat that activity poses on government and business interests and other people.

Scene Creek: Were prosecutors too hasty in naming him The Dread Pirate Roberts?

Alex Winter: Whether the prosecution was too hasty in calling Ross Dread Pirate Roberts, I mean that’s a matter of opinion.  It’s hard for me to say without having seen the defence spend more time making their case. I think that Ross’s lawyer would certainly say that they were too hasty, but as an observer, I wouldn’t really go that far. I would simply say that as an observer in the courtroom, I would’ve preferred a trial that allowed for the defence to spend more time making their case, and perhaps it would’ve been clearer whether or not the prosecution was hasty in assigning all of that to Ross.

Scene Creek: Can you comment on the latest developments on the case?

Alex Winter: It underscores the unknowability of this case, because two agents didn’t just steal bit coins, they didn’t just steal some bit coin, they created an extortion plot that involved many fictitious names that involved administrative rights (and control) over the entire Silk Road, that involved millions of dollars in embezzlement and extortion. And they were also largely behind these murder-for-hire plots, the murder-for-hire scheme was hatched by this undercover [Silk] Road agent. It underscores the point of the movie which there is a lot we don’t know, there is a lot we will probably never know, so you cannot just look at this case as a black and white case. But I think that point is made pretty firmly in the film.

Scene Creek: What’s your next project?

Alex Winter: I’m working on a number of projects, I am working on a documentary at the moment that I can’t disclose the subjects, just yet, but I will be very soon. I am working on a documentary, not on the tech space, but it does involve some of the issues that I’m interested in. I am working on two hour-long television dramas for cable that are also not unrelated to the issues that I find compelling.

Deep Web is now playing at the Bloor Hot Docs Cinema.