After insisting for years that Britney Spears’s conservatorship was absolutely necessary, her father, James P. Spears, unexpectedly asked the court in early September to terminate the legal arrangement.
A new court filing on Monday provided a possible explanation for Mr. Spears’s abrupt reversal: He had recently received a request from Ms. Spears’s lawyer for formal discovery and a sworn deposition.
The new filing also offers the first glimpse into where Ms. Spears’s lawyer, Mathew S. Rosengart, is focusing his investigation into the handling of her conservatorship over the past 13 years. The discovery requests sought extensive information about the role of the estate’s former business manager, Tri Star Sports Entertainment Group, and more information surrounding the complicated web of entities through which the estate operated.
Mr. Spears was suspended from his position as conservator of the singer’s nearly $60 million estate on Sept. 29. At the next court hearing, set for Nov. 12, Judge Brenda J. Penny will consider ending the conservatorship, which was granted in early 2008 amid concerns regarding Ms. Spears’s mental health and possible substance use.


A lawyer for Mr. Spears did not immediately respond to a request for comment.
The details of the discovery and deposition requests were attached to a filing reaffirming Ms. Spears’s support for ending her conservatorship.
Tri Star Sports Entertainment Group, a firm that provides entertainers and athletes with accounting and financial services, is run by Louise M. Taylor. Robin Greenhill, a Tri Star employee, worked closely on Ms. Spears’s account.
Mr. Rosengart, a former federal prosecutor who took over in July as Ms. Spears’s lawyer, is requesting all documents regarding communications between Mr. Spears and Tri Star; all documents regarding any agreements between Mr. Spears and Tri Star; all communications regarding payments made to Tri Star from the estate; and all payments made by the estate for legal services provided to Tri Star.
Tri Star resigned last fall around the time that Samuel D. Ingham III, who was then Ms. Spears’s lawyer, was raising objections in court both to a $500,000 “floor” Mr. Spears agreed to pay the firm after Ms. Spears’s indefinite work hiatus in 2019 affected its 5 percent commission, and to the estate’s allegedly being billed for Ms. Taylor’s personal legal fees. In court last year, a lawyer for Mr. Spears called the $500,000 fee reasonable.
A lawyer for Tri Star, Charles J. Harder, said that the legal fees Mr. Ingham had objected to were approved by the court.


Mr. Rosengart also requested documents and communications related to Black Box Security’s surveillance of Ms. Spears’s phone and the placement of any recording devices in her bedroom. Those allegations were first reported by The New York Times in “Controlling Britney Spears,” a documentary released in September.
Shawn Holley, a lawyer for Black Box’s chief executive, Edan Yemini, did not respond to detailed questions from The Times for the documentary. But in a statement, Ms. Holley said, “Mr. Yemini and Black Box have always conducted themselves within professional, ethical and legal bounds, and they are particularly proud of their work in keeping Ms. Spears safe for many years.”
Mr. Rosengart also seeks to ask Mr. Spears under oath how much money he has received from his daughter’s estate from its inception. It is unknown when any depositions will take place.
On Oct. 19, Mr. Spears hired a new lawyer, Alex M. Weingarten of the firm Willkie Farr Gallagher. Mr. Weingarten replaced lawyers from Holland Knight as well as Freeman, Freeman Smiley.
A recent court filing disclosed that Mr. Rosengart had added Kyle R. Freeny, a financial expert and former federal prosecutor involved in the Mueller investigation, to Ms. Spears’s legal team.

Source: New York Times

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