So Britney Spears’ Conservatorship Is Over. What Happens Now?

Britney Spears is free from the court-ordered conservatorship she calls draconian and “demoralizing,” but her lawyer isn’t letting up any time soon.

Mathew Rosengart, a former federal prosecutor, served Spears’ dad, Jamie Spears, and the singer’s former management firm, Tri Star, with lengthy subpoenas Oct. 1 seeking documents and depositions to determine exactly how much money they received from the pop star’s estate over the last 14 years. Outside the Los Angeles County courthouse on Friday afternoon, following the termination of Britney’s conservatorship, Rosengart addressed the next legal steps he and Britney may take in that battle.

“Many people have asked about whether we will continue to investigate Mr. Spears,” Rosengart said. “The answer, ultimately, is up to my client, Britney.”

He noted that Jamie refused to appear for two depositions scheduled for Oct. 20 and Nov. 10. “If Britney wants, if Britney instructs, we will pursue James Spears’ deposition. We will pursue the discovery that was served on him,” Rosengart said. “It’s interesting that he has refused to cooperate, because his lawyer, in his lawyer’s filing, claimed that Mr. Spears would profusely cooperate. I can say this: They have not responded to one document request. They have no responded to one interrogatory. And they have refused thus far to appear for deposition under oath.”

“I’m looking forward to that deposition,” Rosengart added. “Why he has not appeared, why he is ducking the deposition, is something he and his counsel will have to answer.”

As for Britney’s former managers, Tri Star, Rosengart said his team was “forced to issue two subpoenas … because they wouldn’t voluntarily cooperate with Britney Spears,” Rosengart said. “The most notable question that we’ve asked on behalf of Britney, of Tri Star, is the following very simple question: How much money did you take from the estate? How much money did you receive from the estate? … [Tri Star] has refused to answer that question.”

“What [Rosengart] is looking for is what we call breach of fiduciary duty — in other words, if they failed to act in Britney Spears’ best interests,” Lisa MacCarley, a trust and probate lawyer in Los Angeles who has closely followed the Spears case, tells Rolling Stone.

Both Jamie and Tri Star deny any wrongdoing and point out in legal filings that the court previously approved their financial dealings with Spears’ estate from 2008 though 2018. But in a Nov. 2 letter to a Tri Star lawyer obtained by Rolling Stone, Rosengart accused the company of “stonewalling” his attempts to obtain “basic information,” including the total amount of compensation paid to Tri Star since 2008.

“Notwithstanding Tri Star’s moral — and legal — obligation to provide this simple information, Tri Star’s ongoing failure to answer this question speaks volumes and leads to the unfortunate and inexorable conclusion that Tri Star has much to hide,” he wrote.

“With Tri Star, the analysis will be: Were they overpaid? Was there a sweetheart deal? Was there some type of kickback? Was a benefit or bonus paid out to any of the fiduciaries?’” MacCarley tells Rolling Stone. “I think what he’s really looking for is an indication that these financial transactions improperly benefitted the conservator or attorneys in this case all to Britney Spears’ loss and exploitation.”

MacCarley says that if Rosengart finds anything amiss, he’ll have two options. He could file petitions seeking a surcharge, meaning a return of assets, or possibly even treble damages, meaning triple the amount of the actual damages awarded to a prevailing plaintiff. “In California, not only can you be compelled to return the money, but you could be compelled to return all the profits,” MacCarley explains. “And if it’s found to be in bad faith, they can actually make you pay three times back what you took.”

Rosengart also could go to civil court and file a lawsuit asking for a jury trial on breach of fiduciary duty grounds, MacCarley says: “If he goes through this discovery and finds any indications there was fraud, they could go and ask for punitive damages.”

Tamar G. Arminak, a civil lawyer with contract dispute and conservatorship experience in Los Angeles, tells Rolling Stone that Rosengart might have a tough time challenging conservatorship accounting periods prior to 2019 because they were previously approved by the court. But the issue of the alleged recording device placed in Spears’ bedroom could be grounds for civil and possibly even criminal action.

A former Spears security staffer said in an on-camera interview for the New York Times documentary Controlling Britney Spears that the recording device was placed in the pop star’s bedroom by the security firm hired by Jamie.

“Obviously the court has given the conservator some ability to monitor Britney’s social activities, however, I’ve never seen a conservatorship that would allow for a secret recording device to be placed in someone’s bedroom or home without informing that individual,” Arminak says. “If it’s a health-and-safety thing, an application would have to be made to a judge, and the individual would be informed. There’s no reason not to inform the conservatee at that point. You would tell them, ‘We’re putting a recording device in the event that you decide to harm yourself.’”

Arminak says that if the allegation reported by the New York Times is true, the device was “secretly placed” in Spears’ bedroom and recorded her private conversations with her children and former boyfriend. “That is an invasion of privacy, which is a separate and completely different tort in the state of California and something that Britney could possibly sue over,” she says. “She could sue over the recording device and possibly even the monitoring of her phone communication. There is a reasonable expectation of privacy in an adult woman’s bedroom. She clearly has that expectation of privacy, and that would be a clear violation. And any damages, including emotional distress or intentional infliction of emotional distress, all of that would be fair game for Mathew Rosengart to go after.”

Arminak says California also has a criminal wiretap statute that is “really strictly enforced,” citing the case of former Hollywood “fixer” Anthony Pellicano, who was convicted in 2008 on charges of racketeering, wire fraud, and wiretapping several people, including the actor Keith Carradine and the ex-wife of MGM Studios Inc. mogul Kirk Kerkorian. Pellicano went to jail for more than a decade. Prominent lawyer Terry Christensen also was convicted of wiretapping in the case.

“An entire law firm imploded as a result,” Arminak notes. “California is known for protecting the privacy of telephone conversations as well as the sanctity of private spaces and recording people without their knowledge.”

Arminak adds that she “could see a situation where the District Attorney would look into whether or not what [Britney’s] conservator did at the time violated California’s wiretap laws.”

Either way, the attorney says the winding-down and unraveling of Spears’ conservatorship is likely a long road. “This totally doesn’t end today,” Arminak says. “Not even close.”