• Britney Spears’ legal team is asking Jamie Spears to ‘admit’ he had a ‘romantic relationship’ with his daughter’s former business manager.
• Attorneys for the singer leveled a litany of new accusations against her father in a Tuesday filing.
• Jamie has requested Britney continue to pay his legal fees, even after the conservatorship’s end. 

As attorneys continue to slog through the ongoing legal battle left in the wake of Britney Spears’ terminated conservatorship, the pop star’s lawyer dropped a bombshell new claim in a series of recently-filed court documents.

In documents filed on Friday, Britney Spears’ attorney Mathew Rosengart wants 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. Lou 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 in the ongoing fight, Rosengart detailed the numerous ways in which Spears claims Jamie failed to best serve his daughter’s personal and financial interests as conservator of her estate throughout the 13-year guardianship that a Los Angeles County judge officially terminated in November 2021.

Hearings in the case persist months after the conservatorship’s end, as longtime stakeholders in the arrangement iron out final financial decisions, including whether or not 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 he, along with others involved in the conservatorship, committed multiple, serious financial and personal wrongdoings over the years. 

Among the revelations included in the court papers is Rosengart’s allegation that Jamie had a romantic relationship with Lou Taylor, who served as Britney Spears’ longtime 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 lawyer writes. 

According to the documents, Jamie Spears installed Taylor, his personal friend and CEO of Tri Star Sports and Entertainment Group, as his daughter’s manager at the start of the conservatorship, while already financially indebted to Taylor, having received a $40,000 loan 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 new documents say.

Rosengart alleges Jamie granted requests by Tri Star 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 arrangement was made by Jamie “without any apparent legal obligation to do so,” according to the documents. 

Jamie also used funds from Britney’s estate to support Taylor’s attempt to take legal action against a #FreeBritney supporter in 2019, according to the legal records, even though internal emails allegedly reveal that Jamie’s own lawyer at the time concluded that Taylor’s lawsuit was actually “about Lou,” with “no connection” to Britney, and determined that Taylor should be responsible for the legal fees.

Taylor abruptly resigned from her role with Spears’ team in November 2020, citing death threats following media attention on the estate’s controversies.

In Tuesday’s 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 his alleged romantic relationship with Taylor, attorneys also 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 relating to communications between Jamie and any representative of Tri Star, including Taylor, as well as all correspondence, whether by text or on paper, relating to his personal relationship with Taylor.