NEW YORK >> The trial of Ross W. Ulbricht, a California man charged with running an online black-market bazaar called Silk Road, had barely begun when an unusual objection was lodged.

At issue was a piece of information that Ulbricht’s lawyer suggested was critically important, yet was omitted by federal prosecutors: an emoji.

And not just any emoji, or emoticon, as the symbol is sometimes called – it was the gold standard. A version of a smiley face.

The unusual debate, taking place out of the presence of the jury in U.S. 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.

The trial of Ulbricht, which is in its third week, has been full of novel twists because of its high-tech intrigue. Ulbricht, 30, is accused of running the Silk Road website, where the government says several thousand vendors sold drugs and other illicit goods.

The eBay-like enterprise was run on a hidden part of the Internet called the Tor network, where online activity can be anonymous. Deals were made in bitcoins, a form of electronic currency that is as anonymous as cash, and Ulbricht used a pseudonym, Dread Pirate Roberts, in chats with his employees and other communications, the government has said.

But how chats and other messages and their symbols should be presented in court – and the larger question of how jurors should be educated about unfamiliar terms in a case steeped in Web culture – has become a running subplot in the case.

And as criminal and civil cases increasingly involve evidence gathered from computers and cellphones, prosecutors and defense lawyers have been forced to adapt.

In the trial of a New York City police officer accused in a plot to kidnap, torture, kill and eat women, prosecutors built their case against the defendant, Gilberto Valle, through messages he left on fetish websites.

"The question of identity in the virtual world is a complicated one," said Julia L. Gatto, the lead lawyer for Valle, whose conviction was overturned last year.

"In a typical case with an audio recording, somebody says, ‘I know that voice,’" Gatto said. "Here, the best you can do is say: ‘I know that style. I know he doesn’t capitalize his i’s or always uses a frowny emoticon.’"

Emoticons figure in a case pending before the U.S. Supreme Court in which an Allentown, Pennsylvania, man was convicted of making threats on Facebook after his wife left him. He had claimed that his postings were fictitious, and used emoticons like a face with its tongue sticking out to indicate "jest."

Ulbricht has pleaded not guilty to narcotics trafficking conspiracy and other charges, and his lawyer, Joshua L. Dratel, has denied that he is the mysterious Dread Pirate Roberts, a character from "The Princess Bride."

Before trial, Dratel asked that all chats, forum posts, emails and other Internet communications be shown to the jury, and not read aloud.

"Chats are designed to be absorbed through reading, not through hearing," he said in court.

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."

Prosecutors disagreed, likening the chats to wiretapped conversations that are routinely played or read aloud for jurors.

But Forrest noted the defense was arguing that wiretapped conversations were intended oral communication, while chats were not.

She ultimately held that the messages could be read in court, although she would also instruct the jury that there was no indication the messages had been communicated orally.

"The jury should read them," the judge said. "They are meant to be read. The jury should note the punctuation and emoticons."

Tyler Schnoebelen, a Stanford-trained linguist whose dissertation focused on the meaning of emoticons, said he understood why a lawyer might object to an emoticon being skipped over because such symbols convey a lot about a writer’s intentions.

"If it’s a ‘winkie,’ there’s flirtatiousness or a sort of a fun to it," Schnoebelen said. "With smiles, there might be a politeness or a friendliness. If there’s a ‘frowny’ face, it’s indicating you don’t like what’s happening."

"It would be strange to call a witness and hide their facial expression and have their words spoken by someone else," he added.

Prosecutors have since been citing emoticons when they appear in messages read aloud to jurors.

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