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Silk Road
The film begins with Ross Ulbricht's arrest in San Francisco in 2013. It then delves into Ross's background, portraying him as a well-educated aspiring entrepreneur living in Austin, Texas. Ross comes up with the idea for Silk Road as a way to challenge government control and regulations, believing in the idea of taking back liberty. He starts the website to allow anonymous buying and selling of illegal goods using cryptocurrencies, and it flourishes, with Ross making millions by facilitating the sale of illegal items such as drugs, weapons, and identity information. Julia connects him with a contact at Gawker in order to drive interest in the site, and though the plan works, the increased attention leads to
Meanwhile, DEA agent Rick Bowden has returned to work following a mandated stay in rehab after abusing drugs. Despite having little experience with technology, he is punished with a reassignment to the cybercrimes unit, where he is instructed to wait out nine months until he can retire with a full pension. Unwilling to merely languish, Rick begins to investigate Silk Road by registering and posing as a regular user, though his findings are ignored or dismissed by his superiors and colleagues, who are much younger and mock his seemingly outdated methodology and tactics. He is eventually assigned to an FBI task force unit dedicated to taking down Silk Road and tracking down Ross.
Rick manages to ingratiate himself with Ross, building a friendship with him over Silk Road chatrooms with the help of the more tech-savvy Rayford, a former informant that Rick had blackmailed into lending assistance. After Ross hires Curtis Clark Green, a longtime user and seller on Silk Road, as Silk Road's sole employee, the task force manages to track down Green. Rick apprehends Green, and Ross grows increasingly panicked as Green apparently disappears. Rick, posing as a disinterested third party, offers to assist, and Ross agrees. After squeezing information about Silk Road and Ross from Green through torturous interrogation, Rick manipulates Ross into ordering Green's murder (which he feigns) while privately using Green to steal cryptocurrency from Silk Road's escrow.
Both Ross and Rick's personal lives begin to fray: Julia, already having become disillusioned with Silk Road's impact on poor communities after learning that crystal meth and crack cocaine are being sold there, breaks up with Ross for good after he grows increasingly paranoid and obsessed. Ross also begins to question his own mission after learning of a teenager who died while taking drugs purchased from Silk Road. Meanwhile, Rick's investigation puts an emotional and financial strain on his family as he remains engrossed in the case.
Ross begins to rely on Rick as a fixer, with Rick even showing up to his apartment incognito to coach him upon learning that FBI agents will be coming to his address for questioning after intercepting forged passports that he purchased from Silk Road. Cognizant that he will be arrested for his involvement once Ross is captured, Rick extorts Ross for hundreds of thousands of dollars by posing as both a hacker and hitman offering to dispose of said hacker, intent on providing for his family while he is in prison.
The FBI task force, completely unaware of Rick's activities, eventually close in on Ross, and he is arrested in a public library. Rick is arrested not long afterwards, though not before confronting his superiors and warning that actors like Ross will soon be running the world. Ross and Rick are both sentenced to prison, where Ross passes Rick by chance one day and stares after him in disbelief.