Disturbing New Details About JWoww's Ex-Boyfriend Tom Lippolis, Who Was Charged With Trying To Extort Her For $25,000

It's not their first legal battle.

Who Is Tom Lippolis? Details About JWoww’ Ex-Boyfriend’s Extortion Arrest & Abuse Allegations instagram
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In 2018, Jersey Shore’s Jenni "JWoww" Farley’s ex-boyfriend, Tom Lippolis, was charged with extortion. Though JWoww may be used to the Jersey Shore drama, it appears that more drama continues to overtake her personal life.

The reality star had already been navigating an increasingly messy divorce with her estranged ex, Roger Mathews. Farley filed for divorce in September 2018, though the star revealed their relationship was suffering long before that — and her return to the Jersey Shore may have had something to do with it.

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“It’s a whole insecurity thing," Farley said about Mathews’ feelings about her returning to the reality show. She told her roommates that Mathews' insecurities "almost led to divorce."

Farley had also filed a restraining order against Mathews after claiming her estranged husband “was harassing her.” Sources said Mathews was reportedly filming Farley without her consent.

Now, Farley’s ex-boyfriend Lippolis is also causing issues in her life. 

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Who is Tom Lippolis?

Here’s what we know about his relationship with Farley and his arrest.

Lippolis and Farley were dating on the first season of Jersey Shore.

Though it may seem as though Mathews has been part of Farley’s life since the beginning of Jersey Shore, she was actually dating Lippolis when she first starred on the reality show. The couple’s breakup became a memorable storyline in season two after Lippolis allegedly moved out of her home while leaving her dogs behind without care.

JWoww described their relationship as abusive.

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In a 2011 episode of Jersey Shore After Hours, JWoww described the emotional and physical abuse she allegedly experienced at the hands of Lippolis.

“In Long Island, he cut all my friends away from me, my family. I couldn't even go out with my girlfriends to have a drink. He had to be there," she said, claiming that physical abuse accompanied the emotional abuse. "The day that I left for Jersey, he threw my luggage down the stairs, because he saw clothes in there that weren't acceptable. And I went with the luggage. He pushed me down the stairs and said, 'I can't wait to f*** another [girl] in your bed while you're gone.'”

Lippolis allegedly tried to sell naked photos of her.

After their breakup in 2011, Lippolis reportedly stole a hard drive from Farley’s home, which may have contained several naked photos of the Jersey Shore star both before and after plastic surgery.

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"It has come to [Jwoww's] attention that you may be in possession of certain photos of her that may be derogatory to her image and in violation of her contract with MTV,” JWoww’s lawyer wrote in a letter to Lippolis.

Farley didn’t want any pre-surgery photos released: “The photographs really show how much work she had done and she looks great in the ‘after shots’ which show her body after it had totally healed from the surgeries.”

But Lippolis was less than willing to cooperate. “She is trying to block him from distributing the images and is trying to get the court to compel arbitration in the case,” Lippolis’ lawyer said at the time. “In return we have filed an opposition to this asking the judge to dismiss her order because the images belong to my client and they were taken with Miss Farley’s consent over a year ago.”

However, that same lawyer also accused Farley of “talking about naked photos for publicity and to draw attention to herself and play the victim.” He had claimed that “she is trying to get people’s appetites wet by using the photos and then make sure no one can get them.”

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A judge eventually ruled that Lippolis could not legally release any photos.

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Lippolis sued Farley in 2010.

In 2010, Lippolis filed a suit against Farley, claiming that she owed him money for making her famous and getting her plastic surgery. According to his suit, the two apparently had a written contract that she’d repay him for “a boob job, cellulite reduction, fat reduction” and acting as her manager.

“She thinks she is on the top of the world, that she doesn’t have to pay anybody,” Lippolis said at the time.

Lippolis was charged with extortion in 2018.

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In an Instagram post, the Toms River, NJ police department reported that on December 17, 2018, Farley filed a report claiming that Lippolis attempted to extort $25,000 from her in exchange for “not divulging secrets to the media” about the Jersey Shore star.

Lippolis was arrested two days later and charged with 3rd degree extortion.

"I would like to applaud the Toms River Police and the Ocean County Prosecutor’s Office for their professionalism, expedited response time and unwavering attention to detail that resulted in an immediate arrest after I was the target of a serious crime," Farley said in a statement. "I feel fortunate to have the support of law enforcement of this caliber by my side, which has thankfully kept me and my children safe from those who have sought to victimize me."

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Farley claimed that Mathews gathered her exes, including Lippolis, to plot against her.

She made a statement allegedly saying that Mathews and Lippolis had reached out to each other, and to the reality star's other exes, to "team up and take her down."  

In the statement, she addressed Mathews and wrote, “It is inconceivable that you personally researched the whereabouts and contacted ex-boyfriends of mine to inflict harm upon me after I filed for divorce and you were removed from the home as a result of a temporary restraining order. It is unfathomable to me that because of you proactively contacting an ex-boyfriend of mine to team up against me, he was arrested for trying to extort money from me. I confided in you about my painful past as a survivor of domestic violence. How shameful that you used it to beat me down farther."

RELATED: Is JWoww Pregnant? Here's How She Responded To The Rumors She's Expecting With Zack Clayton

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Micki Spollen is a YourTango editor and entertainment news writer. She also runs the travel blog Where In The World Is My Drink.

Editor's Note: This article was originally posted on December 20, 2018 and was updated with the latest information.