The Clintons were reported to have dined with the disgraced film producer, his wife Georgina Chapman and lawyer David Boies at Rao's in Harlem, five weeks after Trump was elected president.
Details of their dinner were revealed in a New York Time's article on Weinstein last year, two months after he was accused of sexually assaulting multiple women in a damning exposé.
Clinton and Weinstein were in talks to create a TV documentary about her failed campaign until allegations of sexual misconduct surfaced against him.
In the exclusive pictures obtained by DailyMail.com, the group are seen at the famed Italian restaurant chatting over some wine and dinner.
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In one photo, rapper Fat Joe is seen in the background, dining at a separate table.
The artist had shared a photo of him and the Clintons at the restaurant that night on Instagram, though Harvey and Georgina were nowhere to be seen.
The dinner took place about ten months before Weinstein's world would come crashing down.
The film mogul had been a longtime major donor to the Clintons having donated $250,000 to the Clinton Foundation and $10,000 to Bill's legal fund when he faced impeachment during the Monica Lewinsky scandal.
Both Hillary and Bill, who had a close friendship with Weinstein for decades, have denied having any knowledge about his offenses.
However, that same New York Times article revealed Clinton's campaigned had been warned about the rumors swirling around about Weinstein.
Actress Lena Dunham - one of Hillary's biggest celebrity endorsers - emailed her campaign's deputy communications director in 2016.
The email stated: 'I just want you to let you know that Harvey's a rapist and this is going to come out at some point.
'I think it's a really bad idea for him to host fund-raisers and be involved because it’s an open secret in Hollywood that he has a problem with sexual assault.'
Hillary did not immediately comment on the allegations and waited six days to release a statement condemning her friend.
'I was shocked and appalled by the revelations about Harvey Weinstein,' she said in a statement posted on Twitter.
'The behavior described by the women coming forward cannot be tolerated. Their courage and the support of others is critical in helping to stop this kind of behavior.'