Britney Spears Felt Trapped. Her Business Manager Benefited.

The father of Britney Spears was given a loan by a small Tennessee company with big-time ambitions.

James P. Spears consulted with the owner of the company, Tri Star Sports & Entertainment Group, which led to his daughter being placed into a conservatorship. She would be in control of her life and finances.

Mr. Spears sent his daughter on a tour. He hired Tri Star to manage his business because he still owed at least $40,000.

Over the next 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.

Ms. Taylor is facing questions from Ms. Spears's lawyers and others about how much money she made as the pop star's business manager.

The judge who ended the conservatorship was trying to protect Ms. Spears from financial exploitation.

Ms. Spears said she felt coerced to work. Thanks to a variety of unusual financial arrangements, the lawyers, managers, agents and other people who surround the singer received more money from the more she did.

A New York Times investigation found that Ms. Taylor was at the center of it all.

Stonebridge Wealth Management was co-owned by Ms. Taylor and opened accounts for Ms. Spears soon after.

Several other maneuvers appeared to benefit Ms. Taylor, while the firm said it did not receive fees for many services.

A former employee of the security company said that Ms. Spears's estate paid for the surveilled protesters. The estate paid some of Ms. Taylor's personal legal fees.

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James Spears was in court in 2008 when his daughter was placed in a conservatorship.

A Christian counseling group with ties to Ms. Taylor received tens of thousands of dollars from Ms. Spears. Ms. Spears is an icon to the L.G.B.T.Q. community.

According to a financial document reviewed by The Times, Mr. Spears donated 10 percent of his daughter's income to a church run by the Taylors.

Ms. Spears's estate paid for ads in trade publications that praised Ms. Taylor and Tri Star.

It is not clear if Ms. Spears knew how her money was spent. Her lawyer is looking into whether Mr. Spears, Ms. Taylor and others profited from her wrongful captivity.

Ms. Spears said in court that they should be in jail.

Alex M. Weingarten is a lawyer for Mr. Spears. He said the court, co-conservator and Ms. Spears's lawyer approved of Mr. Spears's decisions. He said that Jamie has nothing to hide.

Charles J. Harder said that Tri Star helped Ms. Spears build a $60 million fortune. That is a success.

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After working with Britney Spears, Louise Taylor's career took off.

Matthew G. White, a lawyer for Stonebridge, wrote a letter to Ms. Spears's legal team that defended the firm's work, saying it worked diligently and tried to provide valuable services for free.

In the United States, there are an estimated 1.3 million conservatorships. Conservators have broad powers over a vulnerable person and are required to act in their best interest.

Under California judicial rules, the conservator must avoid any personal, business or professional relationship that could be seen as being self-serving or adverse to the best interest of the conservatee.

The case of Ms. Spears shows how that doesn't always happen and comes amid calls to reform a system that can victimize rather than protect.

Her lawyer told a court in August that a conservatorship was a last resort. It should not be used for the enrichment of third parties.

Ms. Taylor was born in New York. She played for the high school volleyball team but didn't graduate. Bill Gates and Steve Jobs did not graduate from college.

In her early 20s, Ms. Taylor got a job as a bookkeeper at a health insurance company in Rochester, N.Y. They got married on their 21-foot boat, Perfect, after meeting at a blood drive. The bride and groom wore bathing suits.

The couple moved to Florida. Ms. Taylor joined a management firm. She started Tri Star Accounting Group in 1993 to serve similar clients.

Athletes who went pro were some of Ms. Taylor's early customers. The model Niki Taylor was the face of many teen magazines in the 1990s. The business was sold to the accounting firm in 2000.

Michael P. Ryan, a top executive at the time, and another person familiar with what happened, said that executives suspected that Ms. Taylor was hiding money owed to the company.

The locks on the offices were changed to prevent employees from entering. Mr. Ryan and another person familiar with the matter said that the lawyers searched Ms. Taylor's files when the security guard stood watch. She agreed to pay the money in question.

Mr. Harder said that Ms. Taylor had put funds into a separate account because she was not getting the bills she was supposed to. He said that Tri Star did nothing wrong.

There was no official record of the accusations. The two companies separated in 2001. Ms. Taylor could start again.

The Taylors arrived in Tennessee in 2001. Mr. Taylor started a group of churches. She joined the board because she was the ladies ministry leader.

Ms. Taylor incorporated Tri Star Sports & Entertainment Group. She said she wanted to create a business management firm that would serve athletes and artists and make a difference.

Stonebridge was co-founded by Ms. Taylor. She had a business partner who was a finance manager at a company.

Stonebridge was small. It had a few employees and only managed $10 million. Entertainment business managers said Stonebridge was not a good choice to advise high-wattage stars.

One of the world's biggest celebrities would be landed by the upstart firm.

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Ms. Spears performed in California in 1999. Steve Granitz is a photographer.

Ms. Spears became famous with her single "Baby One More Time" in 1998. She was a pop culture sensation at 16.

Jamie Lynn Spears became a Tri Star client because of her sister's success. She was 14 that year.

Mr. Spears would become a client of Tri Star. The details of how he and Ms. Taylor met are not clear.

Britney Spears was struggling. She filed for divorce from Kevin Federline after giving birth to her second son. Ms. Spears lost custody of her sons. She was hospitalized twice in January of 2008.

Her father had struggled with alcoholism and faced accusations of physical and verbal abuse, but had largely been absent from her life. He re- entered.

Mr. Spears received a loan from Tri Star around the time his daughter was hospitalized. Mr. Weingarten initially told The Times that Mr. Spears never received a loan from Tri Star. He said that Tri Star loans money to clients.

Mr. Spears petitioned a California court for control of his affairs after talking to Ms. Taylor. Mr. Harder said that Ms. Taylor did not push for the creation of a conservatorship.

His lawyers argued that Ms. Spears was vulnerable to exploitation because she was unable to care for herself.

The judge approved Mr. Spears request. She gave Mr. Spears and a lawyer the power to run her business.

Ms. Spears got an allowance of over a thousand dollars a week. In subsequent years, the amount increased. Over the course of the conservatorship, Mr. Spears would collect an estimated $6 million.

The existence of the Tri Star loan is troubling, said Anthony Palmieri, the incoming president of the National Guardianship Association.

Mr. Palmieri is the chief guardian investigator for the county clerk in Palm Beach County, Fla. Is the business manager who they owe a debt to making the best decisions for the conservatee? He said it was a conflict of interest.

Mr. Harder said in an email that a small loan had no affect on the work Tri Star did for the estate.

The law in California states that the law only applies to people who can't feed, clothe or shelter themselves.

Mr. Spears had argued that his daughter needed to be under his control and that he needed to commit her to an eight-month tour. Tri Star was hired to manage the tour's finances and accounting. The tour made an estimated $130 million.

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Ms. Spears was taken to the U.C.L.A. Medical Center. The images are by Valerie Macon.

By December 2009, Tri Star had a contract in place to manage Ms. Spears's estate and tour. Many but not all of Ms. Spears's assets are included in the estate. The firm was responsible for paying bills and cash management.

Mr. Harder wouldn't say what 5 percent of Ms. Spears's "adjusted gross entertainment revenue" meant.

Stonebridge began giving financial advice to the conservatorship about three accounts held by another firm.

According to securities filings obtained via a public-records request, Ms. Taylor owned half of Stonebridge, which shared offices with Tri Star in Tennessee.

Stonebridge said in a recent letter to Ms. Spears's legal team that it provided the advisory services without receiving any fees or compensation.

Court documents show that the estate paid Stonebridge about $300 in advisory fees. Mr. White wouldn't say what the work was for, but he did say it was for discreet administrative work.

Michael Ueltzen, a forensic accountant and certified fraud examiner, said the question was whether Stonebridge was best suited to serve Ms. Spears or if Ms. Taylor had a stake in the company.

Stonebridge was on a list of recommended financial advisers, but it was up to clients to decide, according to Mr. Harder. He said that Stonebridge is a boutique that provides high-level services. He said that Ms. Taylor disclosed her ownership stake in Stonebridge.

Mr. White said the relationship between Stonebridge and Tri Star has been disclosed.

Ms. Taylor sold her stake in Stonebridge. The terms were not disclosed.

Mr. White said that Ms. Taylor had no role in the management or operations of Stonebridge.

Mr. Harder said that Ms. Taylor would refer clients to other investment advisers, though she could also point them to other investment advisers.

Stonebridge shared clients with Tri Star like the country music stars Brian Kelley and Tyler Hubbard, who each had millions of dollars.

Stonebridge entered into a consulting agreement with Mr. Spears in April 2020.

The lawyer for Mr. Spears told the court that he was considering putting his daughter's money in one place. Ms. Wyle said that Mr. Spears had been an investment adviser for 13 years.

Jamie Lynn Spears petitioned the court to transfer funds from her sister's trust to an account advised by Stonebridge. Jamie Lynn Spears withdrew the petition. George Short, her lawyer, said there was no story here.

According to a court filing, Samuel D. Ingham III was Britney Spears's lawyer at the time. Ms. Wyle wrote that Stonebridge was not affiliated with Tri Star.

The filing did not mention that Ms. Taylor co-founded and owned half of Stonebridge.

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The offices of Tri Star are in Los Angeles.

Two former senior Tri Star executives said that they didn't have access to basic information like the company's balance sheets and income statements.

Ms. Spears was one of the most secretive accounts at Tri Star. The accounting of her estate was done every year.

The documents were very specific and vague. The performer's expenses were listed in minute detail, including at Walmart and Mrs. Fields cookie shop.

The conservatorship acknowledged that it wasn't giving a complete description of all of the transactions. It would be impractical to fit the business activities and transactions into the traditional accounting.

The public versions of the court documents do not show how much money Tri Star received from the estate.

Ms. Spears was allowed to choose her lawyer for the first time. She hired a former federal prosecutor.

Mr. Spears and Tri Star have been asked to provide information about where Ms. Spears's money went.

Tri Star has been asked how much money the firm made many times. The number was refused by Tri Star.

Mr. Rosengart told The Times that Tri Star told Britney that she should have to pay her lawyers to comb through hundreds of pages of incomplete accountings.

Mr. Harder said that Mr. Rosengart has disclosed the compensation of Tri Star. Mr. Harder said that Mr. Rosengart was not being forthcoming if he claimed that he did not know the amount of money that had been paid.

Mr. Spears is close to the Taylors. Mr. Spears and Ms. Taylor were christened in the Jordan River.

According to a 2010 financial document, Mr. Spears gave 10 percent of his income to the Taylors. Mr. Spears gave tens of thousands of dollars to the church, which is 500 miles away from where he lives in Louisiana.

His lawyer said that how Jamie spends his money is not a public interest.

The money came from Ms. Spears and went to religious causes associated with the Taylors.

The Britney Spears Foundation was started by Ms. Spears. The main goal was to support a children's arts camp.

The foundation was shut down after two years. Tax records show that one of its final payouts was $42,000 to a Tennessee-based Christian group that works with young women with depression, unplanned pregnancies and other issues.

The Taylors have given money to two charities. The Taylors were thanked on the website for consistently pouring their time and energy into the group.

Ms. Spears has supported the L.G.B.T.Q. community, but she has not supported the same community with her own money.

Nancy Alcorn said in her book that she helped people who had previously identified as lesbians to adopt a healthy and biblically based sexuality. She said being gay was a result of confusion. The group's thinking has evolved according to the chief executive.

The former director of the Spears foundation said she was surprised to learn of its contribution. She said that Ms. Spears wanted the foundation to stay away from religious causes.

She said she wouldn't have advised them to get funding.

Mr. Weingarten said that Ms. Spears supported making the donation.

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Ms. Taylor was at a Hollywood Reporter event.

Since the beginning of the conservatorship, Ms. Spears has gone on two international tours, released four albums and been a judge on a reality show.

In the midst of a four-year residency at a Las Vegas casino, Ms. Spears told a court-appointed investigator that she wanted the conservatorship to end. The investigator wrote that the woman said she was sick of being taken advantage of and that everyone around her was on her payroll.

Ms. Taylor was profiled by Variety in the following year. The ad quoted Ms. Spears as saying she was proud to be working with the best. Ms. Taylor was featured on the cover of The Hollywood Reporter 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 that Ms. Spears had signed off.

The work Tri Star did for the estate had expanded beyond the traditional role of a business manager. According to a court investigator's report, Robin Greenhill, a Tri Star executive, administered Ms. Spears's medications and controlled her credit card.

The conservatorship was in crisis in 2019. In January, Ms. Spears canceled a second Las Vegas residency and said she would be on an "indefinite work hiatus." Ms. Spears went to a mental health treatment facility and said she was involuntarily confined.

The cancellation cost Tri Star 5 percent of the revenue.

Ms. Taylor asked Mr. Spears to change the structure of Tri Star's compensation so that the firm would get at least $500,000 a year. Mr. Spears was protested by Ms. Spears's lawyer at the time.

The movement for Britney Spears to be free was affected by her confinement. Some fans questioned if Ms. Spears was in the control of her will. They accused Ms. Taylor of exploiting the singer.

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There was a rally in Los Angeles. Ms. Taylor became a target of fans.

The law firm Sidley Austin sent a cease-and-desist letter to the website that Ms. Taylor 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 said in a court filing that the payments were probably an impermissible gift of the conservatee's funds to Ms. Taylor.

Alex Vlasov, a former Black Box employee, said that Ms. Spears's estate paid for Black Box Security to secretly record her in her bedroom. Ms. Greenhill, the Tri Star executive, received some of Ms. Spears's text communications.

Black Box kept an eye on fans of Britney who criticized her. Mr. Vlasov said that the surveillance was billed to Ms. Spears.

Mr. Harder said that it was appropriate to bill for the legal and security services that Ms. Taylor incurred.

Tri Star stepped down as the estate's business manager in November of 2020. Mr. Harder said that Tri Star resigned because of death threats.

The Times contacted 200 people who worked at Tri Star.

Mr. Harder sent cease-and-desist letters to The Times, demanding that they stop contacting employees and clients. One of Mr. Harder's colleagues warned former Tri Star employees of legal repercussions if they spoke to The Times. Many employees told The Times that they were afraid of being sued.

Ms. Taylor arrived at the chapel on a Sunday. There were about 60 people at the service.

A Christian rock band is playing. Ms. Taylor wore sunglasses, slacks and an oversized plaid shirt. She held her left hand up and displayed a ring with a message.

The California judge ended the conservatorship three weeks later. The amount of money Tri Star made through Ms. Spears is still being determined.

Ms Spears wrote in a recent post that she was embarrassed for the State of California for allowing her father to have her work as hard as he did. I am sad for them because I know my worth now, and I am embarrassed for them.

Jack Begg, Susan C. Beachy, Kitty Bennett, Sheelagh McNeill, and Steve Cavendish contributed to the research and reporting.