Britney Spears' legal team wants Jamie Spears to 'admit' he had a 'romantic relationship' with his daughter's former business manager, Lou Taylor, court documents say

• Britney Spears' lawyers asked Jamie Spears to admit a relationship with her former business manager.
• Attorneys for the singer leveled a litany of new accusations against her father in a recent filing.

As attorneys slog through the legal battle left in the wake of Britney Spears' terminated conservatorship, the pop star's lawyers dropped a bombshell new claim in a series of court documents.

In documents filed on Friday, Spears' attorney Mathew Rosengart said he wanted the singer's father, Jamie Spears, to "admit" he carried out a "romantic relationship" with another key player in the #FreeBritney saga: her former business manager, Lou Taylor.

Insider reached out to lawyers for Jamie Spears, Britney Spears, and Tri Star Sports and Entertainment Group, the management company Taylor leads. Taylor did not immediately respond to Insider's request for comment.

In more than 250 pages of court documents filed ahead of a Wednesday hearing, Rosengart detailed numerous claims that Jamie failed to best serve his daughter's personal and financial interests as conservator of her estate. A Los Angeles County judge officially terminated the 13-year conservatorship in November.

Hearings in the case persist as longtime stakeholders in the arrangement iron out final financial decisions, including whether Britney will have to continue paying her father's legal fees — a request Rosengart previously called "an abomination."

The filings from Rosengart attempt to foil Jamie's demand for continued financial assistance by alleging that he and others involved in the conservatorship committed serious financial and personal wrongdoings over the years.

Among the allegations is that Jamie had a romantic relationship with Taylor, who served as Britney's business manager during the conservatorship.

"REQUEST FOR ADMISSION NO. 49: Admit that, when you were the Conservator of the Estate, you had a romantic relationship with Lou Taylor," the filings said.

The documents allege that Jamie installed Taylor, his personal friend and the CEO of Tri Star, as his daughter's manager at the start of the conservatorship while he was indebted to Taylor, having received a loan of at least $40,000 from Tri Star.

"Previously, in 2008, with no apparent source of steady income, no discernible job skills, having already filed for bankruptcy once, and while indebted to a fledgling business management company called Tri Star Sports & Entertainment for at least $40,000 against a loan Tri Star provided to him, Mr. Spears consulted with Tri Star, placed Ms. Spears into the conservatorship, and hired Tri Star as her business manager," the documents said.

The filings alleged that Jamie granted Tri Star's requests for pay increases after Britney went on professional hiatus, guaranteeing the company a minimum of $500,000 in 2019, which represented a "260% increase from the amount it would otherwise have been entitled to receive for the year." The documents said Jamie made the arrangement "without any apparent legal obligation to do so."

The documents also alleged that Jamie used funds from Britney's estate to support Taylor's attempt to take legal action against a #FreeBritney supporter in 2019, though internal emails suggested Jamie's own lawyer at the time concluded that Taylor's lawsuit was actually "about Lou," with "no connection" to Britney, and that Taylor should be responsible for the legal fees.

Taylor abruptly resigned from her role with Britney's team in November 2020, citing death threats following media attention about the estate's controversies.

In the recent court filings, Britney's attorneys leveled 75 specific accusations of mismanagement against Jamie, demanding that he respond in writing to each one. In addition to seeking Jamie's acknowledgment of a romantic relationship with Taylor, attorneys accused Jamie of taking an overseas trip to be baptized with Taylor and charging his daughter's estate for the trip.

Britney's legal team is seeking all documents related to communications between Jamie and any representative of Tri Star, including Taylor, as well as all correspondence, whether by text or on paper, related to his personal relationship with Taylor.