MIAMI — In July 2010, as Jeffrey Epstein’s yearlong probation period was coming to an end as part of a sweetheart deal with federal prosecutors, businessman Philip Levine sent Epstein an email.

“Hi, Just want you to know that I am happy that everything has come to a positive ending for you during these tough times,” Levine wrote, according to newly released files from the U.S. Department of Justice. “You are a great guy and I know all good things will come to you going forward. In Europe for a while and hope we can catch up soon.”

The email was signed: “Your friend, Philip.”

Epstein replied: “i appreciate the thought.”

Levine, who became mayor of Miami Beach in 2013 and ran as a Democrat for Florida governor in 2018, has previously said he “never had a friendship or business relationship” with Epstein, who was charged with child sex trafficking in 2019 and died in his jail cell later that year.

Days after Epstein’s death, when it was revealed that Epstein had more than a dozen contacts for Levine in his so-called “little black book,” Levine told the Miami Herald he had met Epstein “a couple of times” but had “no clue” how they’d met.

“We probably met probably 15-20 years ago at a social event in NY — and probably exchanged biz cards,” Levine told the Herald in 2019. “I really don’t recall where and when. Never had any interactions with him and didn’t meet beyond that.”

The newly released files suggest that Levine and Epstein had a relationship dating back to at least 2003.

They also reveal numerous flirty and sexually suggestive emails in the early 2000s between Levine and Ghislaine Maxwell, who was later found guilty of facilitating Epstein’s child sex trafficking operation.

Levine has not been accused of any illegal activity. In a statement Monday, he told the Herald: “As I have stated previously, my only connection to Jeffrey Epstein arose solely through my former friendship with Ghislaine Maxwell. I met Epstein only a few times. I never conducted business with him, never visited his island and never flew on his aircraft. I regret ever meeting him.”

Levine declined to address contradictions between his past characterizations of his relationships with Epstein and Maxwell and the emails released last week.

He also declined to answer a question about why he chose to support Epstein in 2010, despite public reports at the time that the billionaire was allowed to plead guilty to two prostitution-related charges in state court in exchange for federal prosecutors dropping an investigation into sexual abuse allegations made by about three dozen girls.

‘Great seeing you today’

In September 2010, records show that Levine emailed Epstein to say he was in New York and to ask if Epstein was “around sometime for a coffee.” Epstein passed along the message to his employee, Lesley Groff, emails show, writing: “can we fit in ... he takes precedence over (redacted), etc.”

Groff then told Epstein that Levine “will be at the house tomorrow at 11:00 for a visit.”

The evening after that scheduled visit, Levine emailed Epstein: “Great seeing you today. Do you have the name of a sharp real estate lawyer for a condo deal that I can call asap? Thanks. P.”

Details of the emails involving Levine were first reported by the Miami New Times.

In 2003, Levine wrote to Antonio Belloni, an executive at LVMH Moet Hennessy Louis Vuitton, saying that he had “been asked to possibly set up an appointment between you and my friend Jeffrey Epstein.” Levine sold his cruise industry marketing company, Onboard Media, to LVMH in 2000.

“Jeffrey would like to meet with you in Paris regarding Sephora,” Levine wrote. “Briefly, Jeffrey is a major financier and the financial advisor and representative for Leslie Wexner of The Limited. He will be in Paris next week, and depending on your schedule, he is available Tuesday-Thursday. Please let me know so I can relay info.”

The relationship between Epstein and Levine seemingly endured until at least May 2013, when Epstein replied to an email from Levine’s mayoral campaign and asked how he could contribute. A campaign official wrote back with a link to Levine’s website.

The Herald could not identify any campaign contributions from Epstein to Levine’s 2013 campaign.

Emails with Maxwell

Last year, Maxwell said in an interview with the Department of Justice that Levine was her “very good friend” and that she had been introduced to former President Bill Clinton “post his coming out of the White House and became friendly with him, because of Philip Levine.”

Levine told the Miami New Times he hadn’t introduced Maxwell to Clinton.

Regarding his relationship with Maxwell, he said: “The precise nature of our relationship was that of a friend to my wife and I, nothing more and nothing less.”

The newly released emails suggest otherwise. Levine was married in 2018; the emails show correspondence between him and Maxwell as early as 2001.

Maxwell repeatedly referred to Levine by a nickname, “Polyp.” Levine referred to Maxwell as “Gilligan.”

“Gilligan: In all seriousness, thank you very much for your warm and generous hospitality. You are a great person and I sincerely enjoy our friendship!” Levine wrote to Maxwell in October 2001. “Next flight is on me ... Thanks ... Love, PL ‘Polyp.’”

Earlier that month, Maxwell wrote to Levine saying she had been contacted by a woman whom Levine was meeting for breakfast.

“Polyp, FYI (the woman) called me today - Do you think I should call pre or post your breakfast?” she wrote.

Levine replied: “Call her pre but don’t tell her that you know we are having breakfast!!! Just tell her that the rumor is that I am hung like a horse ... not a rumor!!!”

Maxwell wrote back: “Pleeeeeeeeeez - promises promises. Generally speaking I like to verify all info I give out.”

In another email that is undated in the files, Maxwell wrote to Levine: “I told her that you were hung like a horse and she sd (sic) that she would like to see it at breakfast - I told her to take pictorial evidence for me.”

In December 2001, Maxwell sent Levine an email that was seemingly about the pair’s relationship.

“Are you upset that I told him to take a hike and that I wanted to be with you at all cost? I thought that you would be pleased?” she wrote. “I am truly a little hurt that you only want me if I come with an important dowry. Somehow that seems so old fashioned. Dowry went out over 100 years ago. But you know if I think about it part of your charm is your old fashioned approach to courting. Till consummation ... Gx.”

The next day, Maxwell wrote to Levine: “Morning boyfriend.”

Their email correspondence continued over the next few years, the files show. In November 2003, Maxwell wrote to Levine: “Oh, vile one. I am coming to Miami Sat, meeting w/Carol to go shopping. Thought seeing as no one else could possibly want to have dinner w/you we would sacrifice our selves as an act of charity and keep you co. for dinner.”

Levine wrote back later that day: “Have a hot, young thing spending the weekend ... call me.”

Levine, 63, built a successful business in cruise industry marketing before his foray into politics. He served as mayor of Miami Beach from 2013 to 2017 and finished third in the 2018 Democratic gubernatorial primary with 20% of the vote after spending $29 million of his own money.

He has since returned to the private sector and been an outspoken critic of his own Democratic Party, writing op-eds and making TV appearances.

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