A Look At Jessica Simpson's History Of Legal Troubles

In 2021, Jessica Simpson and her mother Tina Simpson celebrated gaining full control of The Jessica Simpson Collection, the fashion brand that the "With You" singer originally launched in 2005. The feat came after long-running negotiations with former majority stakeholder Sequential Brands Group Inc., who had previously filed for bankruptcy protection.

Simpson was willing to risk a lot to save the state of her brand, even putting her home up for collateral, but it was well worth it for the former pop star. "It means the absolute world to me to be able to take over complete ownership of my brand," she told Footwear News. "After 16 years in business, I feel ready to meet this next exciting phase with open arms. I know the sky is the limit when my mom, our incredible team, and I lock into our customers completely."

Simpson's legal negotiations for The Jessica Simpson Collection ended happily, but this wasn't the first time that the Texas native experienced legal issues regarding her iconic brand. Not only did her company's original sale create an unforeseen legal problem, but she also had some baby-centered legal issues.

The stunningly transformed Jessica Simpson found herself in some legal trouble when the majority of The Jessica Simpson Collection was sold in 2015. After the Sequential Brands Group Inc. deal, the Simpsons maintained 37% of the fashion company. However, a man named Jeffrey Bowler came out of the woodwork to accuse Joe Simpson, the pop star's father, of scamming him out of a portion of the deal's proceeds.

Bowler alleged that he and Joe had made a verbal deal ten years prior stipulating that the Hollywood executive would earn a 10% finder's fee if he could find a buyer for the Simpson brand. Bowler filed a lawsuit against the family, accusing them of cheating him out of a 12 million dollar cut since he had reportedly put Joe in contact with the brand's buyer. Both Jessica and Joe denied the existence of such a verbal agreement, with a representative for the "Newlyweds: Nick & Jessica" star reporting that she had never even met the man.

In court, Jessica accused Bowler of emotionally extorting her family and called the accusations a "despicable attempt to extort millions of dollars from a world-famous celebrity, entrepreneur and fashion icon" (via the Daily Mail). In 2018, the case between Simpson and Bowler was finally resolved, though details of the settlement were not made public.

Before selling the majority stake in her fashion company, Jessica Simpson also ran into some legal trouble related to a brand event and unsuspecting parents. In 2013, Louisiana couple Christopher Hurst and Tracy Gregory sued the "Irresistible" singer alongside OK! Magazine and Getty Images. The pair alleged that the magazine had published a fan photo of Simpson and their baby on their cover without consent and in a manner that suggested it was actually the pop star's own newborn.

The photo of the two was captured during a meet-and-greet at a shopping center. "When Hurst handed [the baby] Christopher to Simpson, at least one previously unseen photographer hurriedly moved to the front of the line and began taking pictures of the child," the lawsuit read. "The photographer did not identify himself or ask Hurst's permission to take or disseminate any photographs of Christopher."

The lawsuit also alleged that Simpson, mother to three, was in on the magazine's efforts to publish the photo, making money from the publication's attempt to share the first photo of the Hollywood figure and her "child." It's unclear how the lawsuit was resolved, but it's definitely one of Simpson's more bizarre legal troubles.