In early 2008, a small-time Tennessee company with big-time aspirations made a loan to Britney Spears’s father, who for years had struggled financially.
Less than a month later — after consulting with the owner of the company, Tri Star Sports & Entertainment Group — James P. Spears had his daughter placed into a conservatorship, a legal arrangement typically reserved for people unable to care for themselves or work. He would wield vast power over her life and finances.
Mr. Spears soon sent his daughter on a 97-show international tour. And he hired Tri Star, to whom he still owed at least $40,000, to manage Ms. Spears’s business.
Over the ensuing decade, that assignment would generate millions of dollars for Tri Star and help transform it and its owner, Louise M. Taylor, into one of the premier managers in entertainment, with clients including the Kardashians.
Today, Ms. Taylor — a deeply religious former bookkeeper who had few notable clients before Ms. Spears — faces questions, from Ms. Spears’s lawyers and others, about how much money she made as the pop star’s business manager and whether she improperly enriched herself.
The conservatorship, which a California judge ended last month, was intended to protect Ms. Spears from financial exploitation.
But Ms. Spears has said she felt at times that she was coerced to work. The more she did, the more money she generated, and the more flowed to the lawyers, managers, agents and other gatekeepers who surrounded the singer — thanks in part to a variety of unusual financial arrangements.
Near the center of it all was Ms. Taylor, according to a New York Times investigation based on court filings, financial records, company documents and interviews with more than 70 people familiar with the conservatorship, Ms. Taylor or her businesses.
Not long after the conservatorship commenced, accounts for Ms. Spears were opened at an obscure Tennessee firm, Stonebridge Wealth Management, that Ms. Taylor co-founded and co-owned.
While the firm said it did not receive fees for many services it provided, several other maneuvers appeared to benefit Ms. Taylor.
When a security company hired by Mr. Spears surveilled “Free Britney” protesters who criticized Ms. Taylor, Ms. Spears’s estate paid, according to a former employee at the security company. The estate also paid some of Ms. Taylor’s personal legal fees, leading Ms. Spears’s lawyer to complain to a California court.
In 2010, tens of thousands of dollars from Ms. Spears’s charitable foundation went to a Christian counseling group with ties to Ms. Taylor and her husband and whose founder once boasted that the group helped people abandon lesbianism. Ms. Spears has been an icon to the L.G.B.T.Q. community.
Mr. Spears, who collected millions of dollars from his daughter as her conservator, also at times donated 10 percent of that income to a church run by the Taylors, according to a financial document reviewed by The Times.
And Ms. Spears’s estate paid for ads in Hollywood trade publications praising Ms. Taylor and Tri Star.
It isn’t clear if Ms. Spears knew how her money was spent. Her lawyer is investigating whether Mr. Spears, Ms. Taylor and others unfairly profited from what Ms. Spears viewed as her wrongful captivity.
“They should be in jail,” Ms. Spears said in court in June.
Alex M. Weingarten, a lawyer for Mr. Spears, said that “Jamie’s administration of Britney’s estate was always consistent with Britney’s best interests.” He said the court, a co-conservator and Ms. Spears’s court-appointed lawyer approved of Mr. Spears’s decisions. He added, “Jamie has nothing to hide and will therefore hide nothing.”
Charles J. Harder, a lawyer for Ms. Taylor, said Tri Star “faithfully served the estate” and helped Ms. Spears build an estimated $60 million fortune. “That is a success by any standard.”
Matthew G. White, a lawyer for Stonebridge, defended the firm’s work, saying in a recent letter to Ms. Spears’s legal team that it “worked diligently and tirelessly to provide valuable services to benefit the estate,” often for no fee.
In the United States, there are an estimated 1.3 million conservatorships, also known as guardianships. Conservators are granted broad powers over a vulnerable person’s life and are required to act in their best interest.
Under California judicial rules, “the conservator must avoid any personal, business or professional interest or relationship that is or reasonably could be perceived as being self-serving or adverse to the best interest of the conservatee.”
Ms. Spears’s case highlights how that doesn’t always happen and comes amid growing calls to reform a system that can victimize rather than protect.
“A conservatorship should be a last resort,” her lawyer, Mathew S. Rosengart, told a court in August. It should not be “a tool for the enrichment of third parties.”
A Boat Named Perfect
Ms. Taylor grew up in upstate New York. She played for the high school volleyball team and spent a semester at Monroe Community College but didn’t graduate. (Mr. Harder noted that Bill Gates and Steve Jobs also didn’t graduate from college.)
In her early 20s, Ms. Taylor got a job as a bookkeeper at a health insurance company in Rochester, N.Y. Rob Taylor worked as a draftsman in the same building. The pair met at a blood drive and got married in 1989 on their 21-foot boat named Perfect. The bride and groom wore white bathing suits.
The couple moved to Florida the next year. Ms. Taylor joined a management firm that represented entertainers. In 1993, she started Tri Star Accounting Group to serve similar clients.
Some of Ms. Taylor’s early customers were amateur athletes who went pro. She also started representing the model Niki Taylor, the face of many teen magazines in the 1990s. In 2000, Ms. Taylor sold the business to the accounting firm Gilman Ciocia.
Gilman executives soon suspected that Ms. Taylor was hiding money owed to the company, according to Michael P. Ryan, a top executive at the time, and another person familiar with what happened.
A locksmith changed the locks at Tri Star’s offices to prevent employees from entering. As an armed security guard stood watch, Gilman’s lawyers searched Ms. Taylor’s files, according to Mr. Ryan and the other person familiar with the matter. She ultimately agreed to pay the money in question.
Mr. Harder, the lawyer for Ms. Taylor, said she had temporarily placed funds into a separate bank account because Gilman wasn’t paying bills that it was supposed to. He said Tri Star “was open about everything” and “did nothing wrong.”
There was no lawsuit or official record of the accusations. The two companies agreed to separate in July 2001. Ms. Taylor could start anew.
‘It Reeks of Conflict’
By late 2001, the Taylors had arrived in Brentwood, Tenn. Mr. Taylor started a chapter of Calvary Chapel, an independent network of churches. He was the pastor; she was the “ladies ministry leader” and joined the board.
Ms. Taylor also incorporated Tri Star Sports & Entertainment Group. “I wanted to create a business management firm that would service athletes and artists and make a difference by upholding morality and integrity,” she later said on a podcast.
In 2002, Ms. Taylor co-founded Stonebridge. Her business partner was Mitchell S. Martin, who had been chief financial officer for the televangelist Inspirational Network and a finance manager at Motorola.
Stonebridge was tiny. It had only a few employees and, until 2006, managed less than $10 million. Entertainment business managers said Stonebridge seemed an unlikely candidate to advise high-wattage stars.
Before long, though, the upstart firm would land one of the world’s biggest celebrities.
Ms. Spears rocketed to fame in 1998 with the release of her single “…Baby One More Time.” At 16, she became a pop culture sensation.
Her success opened doors for her younger sister, Jamie Lynn Spears, who in 2005 starred in a Nickelodeon series, “Zoey 101,” and became a Tri Star client. That year, she turned 14.
Mr. Spears would also become a Tri Star client. The details of how he and Ms. Taylor met aren’t clear.
Britney Spears began publicly struggling. Shortly after giving birth to her second son in 2006, she filed for divorce from her children’s father, Kevin Federline. A battle ensued, and Ms. Spears eventually lost custody of her sons. In January 2008, she was twice hospitalized on involuntary psychiatric holds.
Her father — who had filed for bankruptcy, struggled with alcoholism and faced accusations of physical and verbal abuse — had largely been absent from his daughter’s life. Now he re-entered.
Around the time his daughter was hospitalized, and while he was working as a cook, Mr. Spears received a loan of at least $40,000 from Tri Star. (His lawyer, Mr. Weingarten, initially told The Times that Mr. Spears “never” received a loan from Tri Star but later confirmed its existence.) “Tri Star routinely loans money to clients,” he said.
On Feb. 1, after discussing the matter with Ms. Taylor, Mr. Spears petitioned a California court for conservatorship powers, court records show. (Mr. Harder said Ms. Taylor did not push for the creation of a conservatorship.)
His lawyers argued that Ms. Spears was unable to care for herself and was vulnerable to exploitation.
The judge, Reva Goetz, approved Mr. Spears’s request. She granted Mr. Spears and a lawyer the power to enter into contracts for Ms. Spears, run her business and invest her money.
Ms. Spears initially got an allowance of $1,500 a week. (The amount increased in subsequent years.) Mr. Spears would collect an estimated $6 million over the course of the conservatorship.
The existence of the Tri Star loan, which hasn’t previously been reported, is troubling, said Anthony Palmieri, the incoming president of the National Guardianship Association, which represents conservators.
“It makes me wonder where the allegiance lies,” said Mr. Palmieri, who is also the chief guardianship investigator for the county clerk in Palm Beach County, Fla. “Is the conservator making decisions in the best interest of the conservatee or the business manager who they owe a debt to?” He added, “It reeks of conflict of interest.”
Mr. Harder said in an email, “A small loan, later repaid, had no affect on Tri Star’s work for the estate in later years.”
Under California law, conservatorships are reserved for people who cannot feed, clothe or shelter themselves.
Only months after arguing that his daughter was incapacitated and therefore needed to be under his control, Mr. Spears committed her to an eight-month tour named “Circus.” Tri Star was hired to serve as the tour’s business manager, handling its finances and accounting. The tour grossed an estimated $130 million.
By December 2009, Tri Star was finalizing a contract to become the manager not just for the tour but also for Ms. Spears’s estate. (The estate includes many but not all of Ms. Spears’s assets.) The firm’s responsibilities included paying bills and cash management.
Tri Star would receive 5 percent of Ms. Spears’s “adjusted gross entertainment revenue,” according to Mr. Harder, who declined to explain what that meant.
Around that time, Stonebridge began providing the conservatorship with financial advice regarding three accounts held at another firm.
Ms. Taylor at the time owned half of Stonebridge, which shared offices with Tri Star in Tennessee, according to securities filings obtained via a public-records request.
In a recent letter to Ms. Spears’s legal team, Stonebridge said it provided the advisory services “without receiving any fees or compensation whatsoever.”
Court documents, however, list about $300 in “advisory fees” that the estate paid to Stonebridge in early 2012. Mr. White said those fees were “for discreet administrative work requested by Mr. Spears,” but he wouldn’t elaborate.
The question is whether Stonebridge was selected because it was best suited to serve Ms. Spears or because Ms. Taylor had a stake in the company, said Michael Ueltzen, a forensic accountant and certified fraud examiner.
Mr. Harder said Tri Star featured Stonebridge on a list of recommended financial advisers but that it was up to clients to choose. “Stonebridge is on the list because it is a boutique that provides high-level services,” he said. He added that “Ms. Taylor’s practice was to disclose” her ownership stake in Stonebridge.
Mr. White said the relationship between Stonebridge and Tri Star has been accurately disclosed.
‘No Story Here’
Ms. Taylor sold her stake in Stonebridge in 2013. Terms weren’t disclosed.
Since then, Mr. White said, Ms. Taylor has had “no role in the management or operations of Stonebridge.”
The deal included a provision in which Ms. Taylor would refer clients to Stonebridge, though she could also point them to other investment advisers, Mr. Harder said.
As of 2016, Tri Star and Stonebridge shared clients like the country music stars Martina McBride, Brian Kelley and Tyler Hubbard, who each had millions of dollars at Stonebridge, according to another Stonebridge client roster.
In April 2020, Stonebridge entered into a paid consulting agreement with Mr. Spears in his capacity as conservator.
Three months later, a lawyer for Mr. Spears, Geraldine Wyle, told the court that he was considering consolidating his daughter’s money in one place. Ms. Wyle said Mr. Spears had been “vetting” Stonebridge as an investment adviser for 13 years.
Around the same time, Jamie Lynn Spears petitioned the court to move funds in her sister’s trust to an account advised by Stonebridge. Jamie Lynn Spears later withdrew the petition. (Her lawyer, George Short, said there was “no story here” but wouldn’t elaborate.)
Britney Spears’s lawyer at the time, Samuel D. Ingham III, had earlier expressed concerns about ties between Tri Star and Stonebridge, according to a court filing. In response, Ms. Wyle wrote that Stonebridge was “independent from” and “not affiliated with” Tri Star.
The filing didn’t mention that Ms. Taylor co-founded and previously owned half of Stonebridge.
$8.08 for Cookies
Two former senior Tri Star executives said the firm’s finances were kept under such tight wraps that they lacked access to basic information like the company’s balance sheets and income statements.
One of the most secretive accounts at Tri Star belonged to Ms. Spears. Every year, bookkeepers at Tri Star conducted a lengthy, court-mandated accounting of her estate.
The resulting documents were both extremely specific and extremely vague. They listed some of the performer’s expenses in minute detail: $4.98 at Walmart, $8.08 at a Mrs. Fields cookie shop.
Yet the conservatorship has acknowledged it wasn’t providing a complete description of all of the estate’s transactions. “It would be impractical to fit the business activities and transactions into the form of the traditional accounting,” the conservatorship disclosed in numerous court-approved reports.
The public versions of the court documents, which are heavily redacted, do not show how much money Tri Star received from the estate.
In July, Ms. Spears for the first time was allowed to choose her lawyer. She hired Mr. Rosengart, a former federal prosecutor.
Mr. Rosengart has requested information and documents from Mr. Spears and Tri Star that could clarify where Ms. Spears’s money went and how Mr. Spears used a network of companies and other entities to operate the estate.
Mr. Rosengart has repeatedly asked Tri Star a question: How much money did the firm make? Tri Star has refused to provide the number.
Tri Star is “effectively telling Britney that she should have to pay her lawyers to comb through hundreds of pages of complex, disjointed and incomplete accountings,” Mr. Rosengart said in an email to The Times.
Mr. Harder said Tri Star’s compensation was disclosed in court filings that Mr. Rosengart has. “Mr. Rosengart is not being forthcoming if he claims that he does not know the amounts that Tri Star has been paid to date,” Mr. Harder said.
Baptized in the River
Mr. Spears and the Taylors are close. In 2017, Mr. Taylor baptized Mr. Spears and Ms. Taylor in the Jordan River in Israel.
Mr. Spears at times gave 10 percent of his conservatorship income to the Taylors’ Calvary Chapel Brentwood, a practice known as tithing, according to a 2010 financial document. Mr. Spears gave tens of thousands of dollars in one year alone to the church, which is about 500 miles away from where he lives in Louisiana.
“How Jamie spends his personal funds is not a matter of public interest,” his lawyer said.
It was not the only money that originated with Ms. Spears that went to religious causes linked to the Taylors.
Before the conservatorship began, Ms. Spears created the Britney Spears Foundation. Its main mission was to support a children’s arts camp.
Two years into the conservatorship, the foundation was shut down. Tax records show that one of its final payouts was $42,000 to Mercy Ministries, a Tennessee-based Christian group that works with young women with depression, unplanned pregnancies and other issues.
The Taylors have donated money to Mercy, and Mercy has donated to Calvary. Mercy’s website at one point thanked the Taylors “for consistently pouring your time and energy” into the group.
While Ms. Spears has been a vocal supporter of the L.G.B.T.Q. community, Mercy has not.
In her 2013 book, Mercy’s founder, Nancy Alcorn, said Mercy helped people who previously identified as lesbians to adopt what she called “a healthy and biblically based sexuality.” She said being gay was a product of “sexual confusion.” (Mercy’s chief executive said the group’s thinking has evolved.)
Nina Biggar, the former director of the Spears foundation, said she was surprised to learn of its contribution to Mercy. She said Ms. Spears had wanted the foundation to stay away from religious causes.
“I would not have advised they receive funding,” she said.
Mr. Weingarten, the lawyer for Mr. Spears, said Ms. Spears “supported making this donation.”
‘Business Manager Icon’
Since the conservatorship began, Ms. Spears had gone on two international tours, released four albums and been a judge on the reality show “The X Factor.”
In 2016, in the midst of a blockbuster four-year residency at a Las Vegas casino, Ms. Spears told a court-appointed investigator that she wanted the conservatorship to end. “She is ‘sick of being taken advantage of’ and she said she is the one working and earning her money but everyone around her is on her payroll,” the investigator wrote.
The following year, Variety profiled Ms. Taylor, whose clients included Steven Tyler of Aerosmith, Gwen Stefani and Jennifer Lopez. Accompanying the article was an ad quoting Ms. Spears: “SO PROUD TO BE WORKING WITH THE BEST OF THE BEST.” Another ad appeared in a 2019 issue of The Hollywood Reporter that featured Ms. Taylor on the cover as a “Business Manager Icon.”
Mr. Harder said that buying ads is a common way for entertainers to thank their representatives and that Tri Star was under the impression Ms. Spears had signed off.
Tri Star’s work for the estate had expanded beyond the traditional role of a business manager. For example, a Tri Star executive, Robin Greenhill, controlled Ms. Spears’s credit card and administered her medications, according to a court investigator’s report.
In 2019, the conservatorship lurched into crisis. In January, Ms. Spears canceled a second planned Las Vegas residency and announced an “indefinite work hiatus.” Ms. Spears then entered a mental health treatment facility in what she said was an involuntary confinement.
The cancellation was costly for Tri Star, which stood to collect 5 percent of the revenue.
Court documents show Ms. Taylor then asked Mr. Spears to change the structure of Tri Star’s compensation so that the firm would automatically receive at least $500,000 a year. Mr. Spears approved, drawing protests from Ms. Spears’s lawyer at the time.
Ms. Spears’s confinement turbocharged the “Free Britney” movement. The vocal group of fans questioned whether Ms. Spears was in the conservatorship against her will. They accused Ms. Taylor of exploiting the singer.
In June 2019, the law firm Sidley Austin sent a cease-and-desist letter on Ms. Taylor’s behalf to a “Free Britney” supporter whose website she claimed was defamatory. The law firm billed Ms. Spears’s estate $350,000, which included costs related to Ms. Taylor’s legal action.
Mr. Ingham, who was Ms. Spears’s lawyer at the time, said in a court filing that the payments were probably “an impermissible gift of the conservatee’s funds to Ms. Taylor” and called for an independent review of all legal fees billed to the estate.
Ms. Spears’s estate also paid for Black Box Security, which monitored her phone and secretly recorded her in her bedroom, according to Alex Vlasov, a former Black Box employee. Screenshots of Ms. Spears’s text communications were shared with Ms. Greenhill, the Tri Star executive.
Black Box also kept tabs on “Free Britney” fans who criticized Ms. Taylor and the conservatorship, according to internal Black Box documents. The surveillance was billed to Ms. Spears’s estate, Mr. Vlasov said.
Mr. Harder said it was appropriate to bill for the legal and security services because Ms. Taylor incurred them only as a result of her work for the estate.
‘LOVE’ in Diamonds
In November 2020, Tri Star stepped down as the estate’s business manager amid growing calls to investigate the firm. Mr. Harder said Tri Star resigned after its staff received death threats.
The Times contacted roughly 200 people who worked at Tri Star over the past decade.
Mr. Harder sent eight cease-and-desist letters to The Times, demanding that reporters stop contacting employees and clients. Lan P. Vu, one of Mr. Harder’s colleagues, emailed former Tri Star employees, warning of legal repercussions if they spoke with The Times. Many employees told The Times they wouldn’t talk because they were scared of being sued.
On a recent Sunday morning, Ms. Taylor arrived at the newly remodeled Calvary Chapel Brentwood. About 60 people showed up for the service.
A Christian rock band preceded Mr. Taylor’s sermon. Dressed casually in sunglasses, slacks and an oversized plaid shirt, Ms. Taylor swayed to the music. She held her left hand aloft, displaying a ring with “LOVE” spelled in tiny diamonds.
About three weeks later, the California judge ended the conservatorship. Mr. Rosengart is still trying to determine how much money Tri Star made through Ms. Spears.
“I’m embarrassed for the State of California for permitting my father to have me work as hard as he worked me all those years and never seeing a dime 💰,” Ms. Spears wrote in a recent Instagram post that was later deleted. “I’m embarrassed for all of them and I’m sad for them because I know my value and worth now.”
Research and reporting were contributed by Jack Begg, Susan C. Beachy, Kitty Bennett, Sheelagh McNeill, Kirsten Noyes and Steve Cavendish.