The events of that night, detailed publicly for the first time on Monday, are pivotal to what’s now an ongoing criminal case against Nilo, who stands charged with heinous crimes in large part thanks to the evidence FBI agents say they collected that night. The high-profile case, which involves eight alleged sexual assaults between 2007 and 2008, has moved slowly for the past couple of years due to complications with evidence. On Monday, a high-stakes hearing called for by Nilo’s lawyers asked a Superior Court judge to suppress the crucial DNA evidence.
The hearing ran about five hours, and will continue at a later date to be determined. Ultimately, Superior Court Judge Debra Squires-Lee will have to answer questions specific to the details of this case: What counts as a “private function” in a public restaurant? When is someone dining out done with a drinking glass? Whose glass is it to give to police?
The FBI and prosecutors from the Suffolk district attorney’s office contend this was a legal acquisition of evidence — that the glass is no longer Nilo’s when he’s done with it, and therefore they can take possession of it without a warrant, as courts have deemed is admissible when someone throws something away. But Nilo’s lawyers disagree.
“I’ll call it stealing, you’ll call it abandoned,” defense attorney Rosemary Scapicchio said as she cross-examined one of the special agents.
Nilo, a 38-year-old lawyer who graduated from Boston Latin School and now lives in Weehawken, N.J., has pleaded not guilty to charges relating to eight sexual assaults in the North End and Charlestown, including multiple rapes. He remains free on bail.
At the time of the sexual assaults, Boston police had DNA evidence and believed several of the assaults to have the same perpetrator, but the DNA was not a direct match to anyone in law enforcement databases.
In the years since, DNA analysis has improved so much that in 2023 Boston police revisited the assaults using a new technique called investigative genetic genealogy (IGG). Most famously used to help identify the Golden State Killer in California, the method involves running evidence from an unknown suspect against DNA that people submit to certain ancestry sites, hoping for familial matches that point police to a suspect.
In this case, authorities say, IGG ultimately pointed toward Nilo.
But the results alone aren’t enough for probable cause, so police must get other evidence, like the suspect’s DNA, sometimes by secretly snagging a discarded cigarette butt or drinking straw.
On Monday, New York-area FBI Special Agents James Smith and Meghan Calpin testified that their counterparts in Boston contacted them about Nilo in April 2023, asking that they try to get that kind of discarded DNA evidence. They said they followed him from his Weehawken apartment building into New York City, where he ended up at the Oscar Wilde, a bar near midtown Manhattan whose website advertises “a public place for private affairs.”
They spotted Nilo seated in the back dining room, called the “temptation room.” Smith said he told a manager what they were trying to do, and he agreed to help them by seating the agents at a high-top table where they’d be able to watch Nilo.
When a waitress came to the agents’ table, Smith showed his FBI credentials and asked if she would help by bringing them his drinking glasses when she cleared them. She agreed, Smith said.
After a couple of mix-ups in which she brought them the drinks of the man seated next to Nilo, she then brought them three that they were confident were used by Nilo, Smith testified.
Each time, the waitress picked up a glass from in front of Nilo, gave the agents a long look as she passed them, and then met them out of view to hand it over, the agents testified.
After about four hours, Nilo and his party left. Then, the agents and the waitress went to where Nilo had been sitting and bagged a fork, a water glass, and a napkin that were all at Nilo’s place setting, according to Smith and Calpin.
Authorities have since said these items gave a direct DNA match with the alleged perpetrator.
Sean Cotter can be reached at sean.cotter@globe.com. Follow him @cotterreporter.