One month out, commentators are still digesting the conviction of Silk Road creator Ross Ulbricht. The case raises questions about the government’s investigations tactics, the lawyers’ trial strategies, and the broader implications for privacy, the internet, and the public.

As the JETLaw Blog previously reported, the Silk Road was intended to be a decentralized online marketplace free from government regulation or oversight. In practice, however, it evolved into a drug emporium and was linked to human trafficking, organ trafficking, assassinations, and firearms sales. Silk Road operated on the Tor network–a supposedly anonymous part of the Dark Web.

That key feature of anonymity, which lured buyers and sellers to the Silk Road, raised the eyebrows of legal observers. How, after all, could the government have uncovered the man behind such a secretive network? Federal officials claim they discovered the Silk Road servers when a software flaw in the site’s log in page revealed an IP address. But not everyone buys that explanation. Some cybersecurity experts have suggested the FBI repeatedly hacked the log in page to unveil the IP address–which is very illegal. If true, that would set a dangerous investigative precedent. It provides yet another opportunity to examine the balance between civil liberties and cyber threats.

The actual trial also created novel strategic and legal issues. One was the sheer complexity and opacity of the subject matter. Concerned for the jury’s ability to understand the case and administer justice, US District Court Judge Katherine Forrest suggested the parties prepare a glossary of terms (“Tor network”, “bitcoin”, “codebase”, etc.) to assist the jury. The defense balked. While a glossary would aid the jury’s understanding, the defense reasoned that any lack of clarity would cut in favor of reasonable doubt. As the lead defense attorney put it: “Obviously, I’m not inclined to help the government explain its case to the jury.”

Another point of controversy between the parties was the use of emoticons as evidence. The government’s case relied heavily on emails and message board postings. Many of these missives contained emoticons. The government initially disregarded the emoticons when reading the messages to the jury. But the defense argued, and Judge Forrest agreed, that the emoticons are part of the statements and the jury should consider them.

The law has struggled incorporate emoticons, and evidentiary issue is increasingly popping up in criminal cases. Is a :-P enough to defuse an apparently threatening Facebook post? Can a police officer emoji followed by a gun emoji constitute a credible threat to the police? Context matters and emoticons or emojis can provide valuable context. An LOL here or a winky face there can dramatically change a statement’s meaning. Such stylistic cues can also be used to identify the speaker and authenticate a message, much in the way the sound of someone’s voice can for a recording.

It remains to be seen how the law will adapt to handle the complexities of the underground internet and the simplicity of a well-executed emoji. Justice Elena Kagan cited Dr. Seuss in a recent dissent. Will she be the first to use an emoji in a judicial opinion?

–Michael Griffin

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