Will the Britney Spears Conservatorship End Today?

Britney Spears has made no secret of late how she feels about the court-approved conservatorship that oversees her life: She wants it gone. In a complete turnaround, the pop singer’s father — long the official steward of the legal arrangement, often over her objections in public and private — has come to agree.

Now, after many months of back and forth, the fate of the conservatorship that has overseen Ms. Spears and her fortune since 2008 rests solely in the hands of a probate judge in Los Angeles Superior Court, where a hearing on Friday may mark the end — or at least the beginning of the end — in a 13-year saga.

“The time has come for Ms. Spears’s freedom,” the singer’s lawyer, Mathew S. Rosengart, wrote in a court filing late last month, emphasizing her desire to end the unique legal arrangement right away.

Lawyers for Ms. Spears’s father, James P. Spears, who is known as Jamie, put it this way in their own status report this month: “it is said in no uncertain terms, Jamie believes that the Conservatorship should end, immediately.”

But it’s not quite as simple as the apparent consensus on both sides.

Mr. Spears, 69, maintained for years that the arrangement — which began when he sought control over his daughter’s life and business, citing her mental health struggles and substance abuse — was not only necessary for the singer’s health and well-being, but voluntary.

Yet amid a hurricane of courtroom activity and legal filings since June, when Ms. Spears called the setup abusive and exploitative in her first extended public comments on the conservatorship, much has shifted: Ms. Spears, 39, was allowed to choose her own lawyer for the first time since 2008, replacing a court-appointed one. Her new representative, Mr. Rosengart, moved aggressively to oust the singer’s father from his position of authority over her, with the court suspending Mr. Spears as conservator of Ms. Spears’s nearly $60 million estate on Sept. 29.

Still, the legal path each side has taken to the same conclusion has been winding — with Mr. Spears’s about-face spurring more questions on his daughter’s side — leaving plenty of unsettled business before the court. Ahead of Friday’s hearing, which is set to begin at 4:30 p.m. Eastern, here are a few of the major questions that could be addressed.

Will Britney Be ‘Free’?

No one involved in the conservatorship has registered any official objection to ending it.

In addition to Ms. Spears and her father, the singer’s personal conservator, Jodi Montgomery, has also consented, according to court filings, and has worked with Mr. Rosengart on what he called a “termination plan.” (Ms. Montgomery, a licensed professional, oversees the day-to-day and medical side of the two-pronged legal setup, which consists of Ms. Spears’s personal affairs and her estate. Ms. Montgomery took over from Mr. Spears on an ongoing temporary basis in September 2019, when he resigned citing health issues.)

But the person who will decide whether to restore Ms. Spears’s independence is Judge Brenda Penny, who was not responsible for establishing the conservatorship yet has presided over the case in recent years.

Typically in deciding whether to end a conservatorship, a judge will consider whether the conservatee has regained “capacity,” using a psychological assessment and other factors to determine cognitive ability and decision making, including whether they can weigh risks and benefits regarding things like medical care, marriage and contracts. The person’s ability to feed, clothe and shelter themselves may also be examined.

But Ms. Spears’s case has been considered largely unprecedented because she continued to work extensively as a performing musician and global celebrity, bringing in millions of dollars, while simultaneously being considered unable to care for herself by the court.

Since June, the singer has been adamant that the arrangement end without her having to undergo additional mental evaluations, and there is no public record of Judge Penny having recently called for one. (According to confidential documents obtained by The New York Times, a court investigator said in 2016 that the conservatorship remained in Ms. Spears’s best interest despite her ongoing requests to end it, but called for a path to independence.)

Mr. Rosengart noted that in one recent filing, lawyers for Mr. Spears stated “no less than three times that no mental or psychological evaluation is required under the Probate Code,” adding: “Ms. Spears fervently agrees.”

In a since-deleted Instagram caption, Ms. Spears seemed to allude to the possibility that the judge would concur. “This week is gonna be very interesting for me,” she wrote, using emojis for emphasis. “I haven’t prayed for something more in my life.”

Will Jamie Spears or Others Be Investigated?

When Ms. Spears addressed the court in June, she said she had been drugged, forced to work and prevented from removing her birth control device in recent years while under the conservatorship. She called for those overseeing it to be investigated and jailed, pointing to her father as “the one who approved all of it.”

“Controlling Britney Spears,” a documentary on the subject by The Times, also revealed that a surveillance apparatus monitored the singer, including secretly capturing audio recordings from her bedroom and accessing material from her phone, according to whistle-blowers.

Her lawyer has since added to those accusations the prospect of financial mismanagement by Mr. Spears and the estate’s former business manager, Tri Star Sports & Entertainment Group, issuing subpoenas for sworn depositions and extensive records, including payments and communication between the parties, as well as the security firm behind the monitoring of Ms. Spears.

Mr. Rosengart has argued that Mr. Spears’s sudden desire to end the conservatorship after years of defending its necessity was tied to hopes that he could avoid legal discovery and being deposed under oath.

Mr. Spears hired new lawyers last month, replacing the extensive legal team that had fought for maintaining the conservatorship and his role in it. In the latest filings, Mr. Spears’s lawyers wrote that their client “has nothing to hide regarding his administration of Britney’s estate and will therefore hide nothing.”

They added that Mr. Spears “supports, indeed encourages, a full and transparent examination of the Conservatorship and has every confidence that said review will put to rest the outlandish, scurrilous and irresponsible speculation that has accompanied the media circus surrounding these proceedings.” The filings called Mr. Spears’s desire to immediately end the conservatorship “unconditional,” arguing that the transferring of records and his cooperation with Ms. Spears and her lawyers “will occur regardless.”

Lawyers for Tri Star, in their own filing, denied that the company’s employees had any control over Ms. Spears’s medical treatment or security protocols, including hidden electronic surveillance. They argued that the company’s financial dealings with the estate were approved by the court before the firm’s resignation from the conservatorship last year.

Even if Judge Penny decided to end the conservatorship on Friday, it is likely that these issues would remain to be addressed at subsequent hearings.

Who Gets Paid, When and by Whom?

Up to this point, all expenses incurred by the conservatorship — including the legal fees of those fighting against Ms. Spears’s stated wishes — have been paid by the singer’s estate. As the arrangement nears what could be its endpoint, the list of those looking to be compensated is only growing.

The estate’s financial records for the year 2019 — known as the conservatorship’s “twelfth accounting” — are still pending final approval before the court. Other financial matters that remain unsettled include more than $1 million in legal fees sought by Mr. Spears’s previous representation, from the firms Holland & Knight and Freeman, Freeman & Smiley, plus fees owed to Ms. Montgomery and others who have worked on behalf of Ms. Spears.

Mr. Rosengart, who came on as Ms. Spears’s lawyer in July, has also begun the process of having his legal fees approved by the court, though he has not yet detailed his exact billings in public court filings. Judge Penny recently authorized payments to the lawyer’s firm, to be made on behalf of Ms. Spears by John Zabel, the certified public accountant whom Mr. Rosengart backed as a temporary replacement for Mr. Spears as the conservator of the singer’s estate.

Lawyers for Lynne Spears, Britney’s mother and an “interested party” in the conservatorship since 2019, are also seeking compensation.

Citing their work on arranging Ms. Spears’s medical care, the removal of her father from the conservatorship and other steps by Lynne meant to “help Britney free herself from what she saw as a very controlling existence,” two firms have billed $504,000 (applying what they called a 40 percent discount to $840,000 worth of fees) and $146,548, plus expenses, according to recent filings.

But Ms. Spears, increasingly vocal after years of public silence on these matters, has also begun to make her many layers of discontent with those around her known. “Pssss my dad may have started the conservatorship 13 years ago,” she wrote in another now-deleted Instagram post. “But what people don’t know is that my mom is the one who gave him the idea !!!! I will never get those years back.”

A separate hearing is currently scheduled for Dec. 8 before Judge Penny regarding the financial and accounting matters.