By the end of this month, it’s very likely that Britney Spears will finally be free from her conservatorship. In September, a Los Angeles judge ruled in her favor, suspending the pop star’s father, Jamie Spears, from the legal arrangement, despite his protestations.
The 13-year-long ordeal seemingly coming to a close was brought about in part by her heartbreaking testimony during the summer, where she detailed the trauma she endured at the hands of her father Jamie, her legion of fans who launched the rallying cry of “Free Britney,” and the damning documentaries that painted a clear picture of what was occurring behind the scenes.
But Spears’ powerhouse attorney Mathew Rosengart also played a major part in securing Spears’ freedom and has vowed that the dissolution of Spears’ conservatorship is not the final step in bringing her nightmare to an end.
Instead, he’s insisted on getting justice for the 39-year-old pop legend, gunning for Jamie Spears and anyone who may have played a role in ensuring that Spears was kept under the restrictive legal arrangement despite her pleas.
And, according to recently filed court documents obtained by The New York Times, Rosengart is already taking steps to conduct an extensive investigation into Jamie’s dealings as conservator.
Jamie Spears had held onto the conservatorship with an iron grip, continually insisting the arrangement was in Spears’ best interest, all while pocketing $16,000 a month from his position and taking home a sizable percentage of any business deals Spears made.
But as intensity around Spears’ case grew, he did an about face, filing his own motion to have the judge remove the conservatorship entirely, rather than just suspend him. The sudden change of heart, Rosengart alleged, was merely a tactic to avoid the very investigation that he is now bringing, as Jamie was reportedly hit with a request last month for formal discovery and a sworn deposition.
Court papers indicate that Rosengart wants to depose Jamie and has requested extensive information about Spears’ $60 million estate and everyone who may have had their hand in the large pot.
Additionally, he wants the 69-year-old to hand a trove of documents pertaining to any communications that Jamie Spears had with members of his daughter’s security team, household staff, and her doctors, as well as to cough up any correspondence about Spears’ phone allegedly being monitored and a recording device being placed in her room.
The 110-page filing makes clear that Rosengart isn’t just going after Jamie Spears, but any entities that profited off of Spears’ multi-million dollar estate. He seems to be particularly interested in the role Tri Star Sports & Entertainment Group—run by Spears’ longtime former business manager Lou Taylor—played in Spears’ estate.
“The 110-page filing makes clear that Rosengart isn’t just going after Jamie Spears, but any entities that profited off of Spears’ multi-million dollar estate.”
Rosengart wants accounting for all payments that came from Spears’ estate to Tri Star, its current and past employees, as well as to determine if Spears’ estate ever paid for legal bills on behalf of Taylor and Tri Star employee Robin Greenhill, who worked closely with Spears.
Taylor is a friend of the Spears family who reportedly helped Jamie set the conservatorship in motion. (In a denial to The New Yorker’s report on Spears’ legal battle earlier this year, Taylor’s lawyer claimed she was “more of a listener than a contributor” to the conservatorship plan.)
Although Jamie hired Taylor as business manager for Spears’ comeback Circus tour in 2009, she was making media statements on behalf of the family days after Spears had been hospitalized in Jan. 2008. Eventually, she became business manager of Spears’ estate.
Tri Star popped up in court documents shortly after the #FreeBritney movement took off in April 2019. Spears’ now-former court-appointed lawyer Sam Ingham questioned Jamie’s decision to “modify” Taylor’s compensation in Dec. 2019, “more than doubling” Tri Star Sports & Entertainment Group’s minimum annual fee to $500,000, according to court papers.
Taylor suddenly resigned as Spears’ business manager with “no notice” in Oct. 2020, according to court documents filed by Ingham in Nov. 2020.
#FreeBritney activists protest during a rally held in conjunction with a hearing on the future of Britney Spears' conservatorship at the Stanley Mosk Courthouse on September 29, 2021, in Los Angeles, California.
Kevin Winter/Getty
Apart from the financial part of Spears’ conservatorship, Rosengart is targeting Jamie’s treatment of his daughter, requesting that he hand over all documents pertaining to the monthly allowance he allegedly imposed upon the singer, as well as all correspondence between himself and Spears during the course of the conservatorship.
Additionally, Rosengart seems to be taking seriously the allegations that Spears’ cell phone was constantly monitored and that there was a recording device placed in her bedroom, requesting for Jamie to produce all correspondence with the security guards he had hired, as well as anyone who worked at Spears’ home.
Those allegations were raised by Alex Vlasov, who worked for Black Box Security, the team hired by Jamie Spears. Vlasov was featured in the follow-up New York Times documentary Controlling Britney Spears, claiming the pop star’s phone was constantly monitored and that her room was bugged.
While Taylor is hardly mentioned in either of the Times docs, Greenhill is featured in the second installment, which was released shortly before the September hearing. Vlasov claims his boss Edan Yemini, the president of Black Box Security, would routinely ask him to encrypt messages that Spears had sent so he could hand those communications over to Jamie and Greenhill.
“They openly talked about monitoring her,” Vlasov says in the documentary. “Their reasons for monitoring were looking for bad influences, looking for potential illegal activity that might happen. But they [would] also monitor conversations with her friends, with her mom, with her lawyer Sam Ingham.”
Although Spears may finally be out from underneath the conservatorship by her next court hearing on Nov. 12, it’s clear that Rosengart thinks justice won’t be fully served until Jamie Spears is fully investigated.
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