Tri Star Exec Accused of Spying on Britney Spears Fails to Win Delay of Key Hearing

The Tri Star executive accused of helping Britney Spears’ dad “mirror” his daughter’s iCloud account to spy on the pop star’s private messages has lost a last-minute bid to delay a key hearing next week on whether she must sit for a deposition and cough up documents.

Robin Greenhill sought the postponement this week by saying she hired a new law firm last weekend — and her new counsel needed more time to “become familiar” with her motion to quash the subpoenas served by Britney’s lawyer Mathew Rosengart last October.

For his part, Rosengart opposed the requested delay, arguing in a dueling filing Tuesday that Greenhill was still represented by her longtime lawyer, Eric Adler, and that new evidence recovered from a third-party allegedly showed Greenhill made “false or materially misleading public statements” in a prior sworn declaration.

Los Angeles County Judge Brenda Penny denied Greenhill’s request in a ruling made public Friday. The court said Greenhill had failed to show she would suffer “irreparable harm” if the hearing on her motion remained on calendar for July 27, where it’s been for months.

Greenhill and her boss, Tri Star CEO Lou Taylor, are both fighting Rosengart’s quest to depose them on video — as well as his subpoenas demanding all documents and communications related to “electronic surveillance, cloning or monitoring of Britney’s phone,” anything related to Tri Star’s compensation from the estate and anything regarding Britney’s medical care, the singer’s claim she was coerced to work and the alleged bugging of Britney’s bedroom.

Rosengart issued the subpoenas after Greenhill was specifically singled out in blockbuster statements made by former Spears security staffer Alex Vlasov in the New York Times documentary, Controlling Britney Spears.

According to Vlasov, Greenhill was on a group chat with Britney’s dad Jamie Spears and Vlasov’s boss, Edan Yemini, head of Black Box security, that dissected “every step” Britney took during the depths of her court-ordered conservatorship.

“Even in the sacred place, her home, every single request was monitored and recorded. Her intimate relations were closely managed,” Vlasov said. “You know, Britney could not have someone in the privacy of her house without those three people knowing.”

Vlasov claimed that at one point, Yemini “had an audio recording device put into Britney’s bedroom.” He also said it was Greenhill who proposed setting up an iPad loaded with Britney’s iCloud account so it would “mirror” all her activity. The system purportedly allowed the trio to see all the singer’s messages, notes, call logs, browser history, and photographs.

“Edan would bring me text messages Britney would have, and he would ask me to encrypt those messages and give it to him so he could pass it on to Robin and Jamie,” Vlasov said.

In a Nov. 4 sworn statement accompanying her motion to quash the subpoenas, Greenhill claimed “no one at Tri Star has ever suggested monitoring Ms. Spears’ electronic communications.” She also denied any knowledge of a “hidden electronic surveillance device placed in Ms. Spears’ bedroom” and suggested Rosengart’s request for records dating back 14 years was “grossly overbroad” because Tri Star wasn’t involved in Britney’s career or the creation of the conservatorship in early February 2008.

“Tri Star played no part whatsoever in suggesting the establishment of the conservatorship,” Greenhill wrote.

According to Rosengart and his co-counsel Kyle Freeny, Greenhill’s statements were false. In a July 1 sworn statement, Freeny told the court that Black Box Security had produced Word documents containing screenshots of Britney’s text messages that Yemini circulated via email to both Jamie and Greenhill without comment between 2016 and 2019.

The lawyers also supplied the court with a Jan. 1, 2008, email that Jamie’s lawyer Geraldine Wyle sent to Taylor discussing the best time to file for the conservatorship.

“Lou, We have run into a problem with our judge selection – the only judge who will be able to hear our case on Friday is the one (judge) who will not give Jamie the power to administer psychotropic drugs to B. The first time she is off the bench is Wednesday. That is the first safe day to be in court on this matter,” Wyle wrote in the email a month before Britney’s conservatorship was granted. “If we go earlier, all of this work could well be for virtually nothing.”

In a subsequent email to Jamie Spears on Jan. 17, 2008, Taylor wrote that she already had spoken to others about Andrew Wallet, the man who ultimately would become Jamie’s co-conservator. “He and tri star will serve as co’s w you,” Taylor wrote, meaning her company would join Wallet as another co-conservator. That never happened.

“Tri Star’s own internal emails — obtained from a third-party — demonstrate that Tri Star’s Lou Taylor played a substantial role in Ms. Spears’s affairs prior to and in the early days of the conservatorship,” Rosengart told the court in a July 1 filing.

Rosengart claims Tri Star made more than $18 million from Britney’s estate during her conservatorship. He contends Tri Star’s unwillingness to answer his questions shows the company “has much to hide.” He has alleged Taylor improperly used estate funds to pay for expenses, such as an advertisement in The Hollywood Reporter and personal legal fees.

Britney’s lawyer, a former federal prosecutor, also has challenged Jamie’s agreement to pay Tri Star a $500,000 minimum annual guarantee even after Britney went on hiatus and was no longer performing toward the end of her conservatorship. That agreement was in place when Taylor suddenly quit as Britney’s business manager in October 2020, around the same time the “Toxic” singer’s former lawyer started voicing public objections to Jamie’s role managing the estate. (Britney’s conservatorship was terminated Nov. 12.)

According to lawyers for Tri Star, Britney has failed to show any “extrinsic fraud” on the part of her former management team that would entitle her to subpoena documents from prior accounting periods previously approved by the court. They’ve claimed only records dating back to Jan. 1, 2019 are fair game for subpoenas.