Bethenny Frankel’s Boyfriend: Past Legal Problems And Lawsuits Over Money

Bethenny Frankel’s Boyfriend

Bethenny Frankel defended her boyfriend, Dennis Shields, on the Real Housewives of New York reunion special after Luann de Lesseps accused him of still being married to his wife when they started dating. Frankel reveals that he was indeed separated from his wife when they met and she even got Dennis’ own daughter to confirm the news. Maybe Luann just needed someone to take the attention away from her, so she could regain some ground, as she was clearly caught in an awkward situation during the reunion. But it sounds like Frankel may not know everything that her man has been up to before she met him.

According to a new Radar Online report, Bethenny Frankel‘s boyfriend supposedly had some legal troubles before he met Bethenny. Of course, Frankel herself has been caught up in lawsuits over her Skinnygirl brand, as some people didn’t think that the drink was as healthy as she claims it is. But for Dennis, it sounds like he has been involved with multiple lawsuits over mortgages and loans, which is unfortunate for Bethenny Frankel as they are looking at homes together.

Apparently, Shields and his estranged wife Jill sued another couple and their respective attorney for refusing to refund a $75,000 deposit on a Long Island property. He really needed that money to secure a million-dollar mortgage in 45 days and he claims in the lawsuit that he was contractually entitled to the return of the funds. However, the other side of the argument claimed that he hadn’t held up his part of the deal.

Apparently, Bethenny Frankel’s boyfriend hadn’t held up his end of the bargain, where he did not follow the contract’s demands to make a “prompt and diligent” mortgage application. Because of this, they were allowed to withhold the $75,000 from him. But he may not have been able to make the application because of the lack of funds in his account, hence not being able to provide proof of funds. The one mistake he may have made was that he and Jill failed to show up at a deed signing meeting with their attorney, which only made matters worse.


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“Sellers were caused to suffer injury as a result of Purchasers’ negligence,” the defendants wrote in the court papers, arguing that they shouldn’t get their money back.

The case was settled after the lawyers made a motion to return the $75,000 with interest. But this wasn’t the only case he had going. About 14 years later, he and his wife filed a petition against the Long Island town to return the property’s full market value to $1.8 million from $2.5 million. It sounds like this was in the middle of the financial crisis and this was done so to challenge their tax assessments. However, nothing ever came of this case.

It sounds like most of Shields’ legal problems stem from Long Island, which is not where he and Bethenny Frankel have been looking at homes. They have been looking in New York City around the island of Manhattan. Frankel has just finished renovating her apartment in New York and she already has a Hamptons home. One has to wonder if she will keep her apartment or sell it to move into a new home with Dennis.

What do you think of Bethenny Frankel’s boyfriend’s past legal problems? Do you think she knows about these already?

[Featured Image by Neilson Barnard/Getty Images for Walt Disney Studios Home Entertainment]