It was this meeting, at the TriBeCa Grand Hotel, where Weinstein's "longtime pattern of cover-ups was coming to a dramatic end", according to the New York Times.
The Hollywood mogul spotted Italian model Ambra Battilana Gutierrez at a party at Radio City Hall in New York in 2015 for his show, the New York Spring Spectacular. He told her she "looked like Mila Kunis" and invited her to show him her portfolio of work.
Weinstein didn't know it, but Gutierrez had already been involved in a salacious sex scandal before, testifying for the prosecution of Silvio Berlusconi, the disgraced former Italian Prime Minister.
She discussed a sex party with teenage girls at his house in which she refused to participate, but then denied the facts and told a court a lawyer had written it for her.
At the party in New York, the pair had exchanged business cards and Weinstein requested a meeting the next day.
At the meeting the next evening, Gutierrez told him she would be auditioning for a lingerie ad and showed him her portfolio.
Weinstein proceeded to "lunge" towards her and asked her if her breasts were real, telling Gutierrez it was important for casting agents to know whether breasts were real or fake.
He then groped her, tried to kiss her and put his hand up her skirt, she alleged.
The next day, Gutierrez reported the alleged incident to the NYPD. She was being interviewed by the Police Department's Special Victims Squad when she received a phone call. It was Weinstein. He wanted to meet for a drink.
Investigators saw this as their chance.
Investigators fitted Gutierrez with a wire before she went to meet Weinstein at the bar at the TriBeCa Grand. Undercover police were "swarming" the hotel, now known as The Roxy.
Weinstein attempted to invite Gutierrez into his room.
"I'm telling you right now, get in here," Weinstein demands of Gutierrez, attempting to entice her into his hotel room while he took a shower.
Undercover police officers, though, were listening and recording his every word, but the audio recording wasn't published until two years later, by The New Yorker last week.
"Yesterday was kind of aggressive for me," Gutierrez tells Weinstein.
"I need to know a person to be touched."
"I know," Weinstein replies, as he continues to try to move her into his hotel room.
"If you embarrass me in this hotel ... honey, don't have a fight with me in the hallway. Please come in."
"Why yesterday you touch my breast?" Gutierrez asks.
Weinstein replies, "I'm used to that".
The authorities thought they had caught the big cat.
"The film producer Harvey Weinstein was questioned by the police on Saturday after a 22-year-old woman accused him of touching her inappropriately during a meeting in Manhattan, according to two law enforcement officials," The New York Times wrote at the time.
Gutierrez was kept anonymous at the time.
"After being located by detectives, [Weinstein] voluntarily accompanied the police to be questioned about the matter."
What the public didn't know behind the scenes was that while police investigated the case - and despite appearing cooperative, Weinstein had built himself "a team of top-shelf defence lawyers and publicists to undermine her credibility", according to the Times.
While the news had become public, Weinstein's team dug deep to discredit Gutierrez.
They found a previous sexual assault complaint she had filed - and subsequently dropped - in Italy against an older man. There was also the case against Berlusconi.
"Anonymous" sources began to throw her under the bus in the media; even a former Manhattan sex crimes prosecutor was hired by the Weinstein machine.
Ten days later, district attorney, Cyrus R. Vance Jr dropped the charges claiming: "After analysing the available evidence, including multiple interviews with both parties, a criminal charge is not supported."
Once the dust had settled Weinstein paid Gutierrez a "substantial payment" and the story drifted into oblivion.
"We are pleased this episode is behind us," a representative for Weinstein, Risa Heller, said at the time.
For prosecutors, the case seemed doomed from the start.
Gutierrez's "shifting accounts" of her previous assault complaint in Italy was problematic for her reputation as a credible witness, not too mention the fact "Mr Vance's assistants also feared they could not prove that Weinstein had touched Battilana for sexual reasons because the advance came as they were discussing her desire to be a lingerie model".
But despite the odds stacked against them, the cops believed they could nail Weinstein with the tape, sufficient enough to make an arrest for third-degree sexual abuse, which carries a minimum jail sentence of three months.
Because despite facing years of allegations and investigations, this was the first time the police had ever been involved.
But with a PR machine suggesting Gutierrez was selling her story for $100,000 cast doubt upon her credibility.
"By April 10, 2015, [the head of the district attorney's sex crimes bureau] had reached the conclusion she could not prove every element of a crime with the evidence she had."
The news comes as detectives in New York City and London are taking a fresh look into sexual assault allegations against Harvey Weinstein now that some 30 women have accused the Hollywood film producer of inappropriate conduct.
New York Police Department spokesman Peter Donald said that investigators are reviewing police files to see if anyone else reported being assaulted or harassed by him.
So far, no filed complaints have been found, he said, other than the 2015 case.
Authorities are encouraging anyone with information on Weinstein to contact the department.
London police were also looking into a claim it had received from the Merseyside force in northwest England, British media reported Thursday. Merseyside police said the allegation was made a day earlier and concerned "an alleged sexual assault in the London area in the 1980s."
Some 30 women - including actresses Angelina Jolie, Ashley Judd and Gwyneth Paltrow - have now spoken out to say Weinstein had sexually harassed or sexually assaulted them. Rose McGowan, who has long suggested that Weinstein sexually assaulted her, tweeted on Thursday that "HW raped me".
And with that, Weinstein was let off.
