Is there a difference between "Yep" and "Yep :)" when you chat online? Seems like an odd quibble to focus on during the biggest drug trial of the decade, but it's not trivial. The meaning of internet-speak cuts to the heart of the Silk Road trial.


Prosecutors are trying to prove Ross Ulbricht is "Dread Pirate Roberts," the anonymous kingpin behind the darknet drug market Silk Road, largely by tying Ulbricht to DPR using chat logs and emails. In a letter to the judge, Ulbricht's defense lawyer Joshua Dratel insisted that emoticons and online grammar can convey nuances in language that may make or break the case:

In a letter to the judge, he added that inflections — or the lack of an inflection — could distort a writer's meaning.

And, he wrote, certain forms of writing — like repeated question marks ("???"), all capital letters, distorted words (like "soooo") and emoticons — "cannot be reliably or adequately conveyed orally."

The prosecution disagrees, comparing the digital evidence of Ulbricht's online life to wiretaps. Judge Katherine B. Forrest agreed that emoticons are crucial:


The unusual debate, taking place out of the presence of the jury in Federal District Court in Manhattan, arose after a prosecutor finished reading the text of an Internet post. "I'm so excited and anxious for our future, I could burst," the prosecutor had read to the jury, making no mention of the smiling symbol that followed.

Eventually, the judge, Katherine B. Forrest, instructed the jury that it should take note of any such symbols in messages.

"That is part of the evidence of the document," she explained.

That the defense is pushing for the inclusion of emoticons and other chat lingo is important. The variance of meaning ascribed to internet-speak could give Dratel wiggle-room to push doubt that DPR and Ulbricht are the same person. Maybe :) means it's all a big goof, no illicit empire to see here.

Of course, the prosecution's case may rest on far more than a wayward smiley face, but the debate here is fraught because it may matter. Online identity is slippery, and it'll be harder to give Ulricht's dispatches the weight the prosecution wants if they're riddled with emoticons, emojis, and punctuation that can turn a deadly serious confession into a lighthearted joke. [New York Times]