Is It Finally Time to #FreeBritney? What to Expect From Pop Star’s Pivotal Court Date

After more than 13 years, a new beginning is on the horizon for pop star Britney Spears, who has been living under a restrictive conservatorship since 2008.

It was at that time the singer, then in her mid-20s, had endured a series of public pitfalls — arguably brought on by the media’s heavy scrutiny of her sex life, personal life and parenting decisions — causing paparazzi to swarm around her. Spears had been working in show business since childhood, as the 11-year-old star of Disney Channel’s “The All-New Micky Mouse Club.”

In 2008, her father, Jamie Spears, placed her under the court-ordered arrangement.

This year, with the #FreeBritney movement and an influx of documentaries surrounding the conservatorship, there has been an increased spotlight on the 39-year-old star’s private life and rights. Her father’s conduct has also come into question, with a judge ordering his immediate suspension in late September. The singer’s attorney is currently at work on an investigation into him, recently requesting formal discovery and a sworn deposition.

The removal of Spears’ father was the first phase in the singer’s legal affairs. On Nov. 12, she enters phase two: possible termination of the conservatorship.

Spears’ fight has been led by attorney Mathew Rosengart, a former federal prosecutor and Hollywood veteran who she retained this past summer. In July, a judge granted her the ability to finally hire her own lawyer, for the first time in 13 years, after she gave an impassioned testimony that was heard around the world.

When Spears testified, she begged the court to eject her father from her life, stating she has been held against her own will with no freedom whatsoever. Of course, the #FreeBritney movement would have told you this for years — and the fans put a megaphone to their voices this year, as their idol, Spears, publicly used hers.

After Spears’ testimony, allegations snowballed regarding her father’s control, financial mismanagement and secret surveillance of his daughter. Spears even alleged that the conservatorship is preventing her from having another baby by not allowing her to remove her IUD birth control device. The elder Spears has denied all accusations of wrongdoing.

At Friday’s hearing, it’s unknown is the singer will be present at the Los Angeles Superior Courthouse, though she has only been in attendance remotely for some court dates this year.

The primary issue on the table this Friday will be the termination of the conservatorship. Whether and when the judge determines to terminate is unclear, though legal experts say that momentum seems to be moving toward the pop star’s path to freedom.

Plus, conservatorships are intended to be a last resort for non-functioning individuals, typically elderly with dementia or Alzheimer’s, or for those who are unable to work. While the court determined Spears needed to be under conservatorship in 2008, circumstances have changed for the pop star, who has continued to perform and work grueling hours over the past 13 years, making hundreds of millions of dollars touring and with a Las Vegas residency – from which her conservators, including her father, have profited.

Still, experts caution that it would be wise for Spears’ team to let the pop star into the real world with some training wheels, so that the transition is not too abrupt.

“It has moved incredibly fast, given how long it’s been there,” says attorney Sarah Wentz, a partner at the firm Fox Rothschild, who represents high-profile individuals and specializes in conservatorships, guardianships and estates, but has never worked with Spears and has no affiliation to the case. “There appears to be an overwhelming sense of it being so long overdue, but on the other hand, once the conservatorship goes away, where is the oversight to make sure she is safe?

“That doesn’t mean that she needs a conservatorship,” Wentz adds. “But the reality is that if it’s terminated, at that point, she’s in charge of her life. There isn’t any court she can go back to. If she fails to watch over her estate and life responsibly, then there isn’t any recourse.”

Sources close to the singer say that if her conservatorship is terminated, she will continue to have consultants and would have a support system put in place, including a business manager and financial advisor.

In a recent court filing, Rosengart stated there would be an “orderly transition” toward Spears’ termination. In court on Friday, he is expected to present Judge Brenda Penny with a detailed termination plan, ensuring the best interest and safety for his celebrity client, to set forth a plan of action to wind down the conservatorship as she enters the world on her own.

Rosengart declined to comment for this story when contacted by Variety.

For the past 13 years, Spears’ father had been overseeing her fortune and controlling all of her financial and business decisions, as conservator of the estate. But at the Sept. 29 hearing, when Judge Penny ousted him, she appointed accountant John Zabel to assume temporarily control of Spears’ estate, which is estimated to be worth roughly $60 million.

While Spears’ father has been acting as her conservator of the estate, Jodi Montgomery has been acting as Spears’ conservator of her “person,” meaning she oversees her day-to-day wellbeing and medical decisions. While the singer has slammed most people involved with the conservatorship, alleging abuse, when she testified this summer, Spears told the judge, through tears, that she wants Montgomery to help her get “back into the world.”

Montgomery was brought onto Spears’ case as part of the court’s process during the conservatorship. But a source close to Montgomery says that even after the conservatorship is terminated – if that happens – she would be happy to continue working with Spears into the future, though it ultimately would be the singer’s decision.

Montgomery was not made available for any interviews, and an attorney for the conservator was not reachable for comment.

Spears’ legal strategy has been methodical. Ever since Rosengart’s first court appearance on July 14, when he said in a courthouse press conference that his firm would move “aggressively and expeditiously” to suspend Jamie Spears, the dominos have been falling in Spears’ favor with a series of legal victories – all the while her father’s legal team has playing a game of musical chairs and changing their tune.

Just one week ago, after years of continuously and firmly saying that his famous daughter needs to be under a conservatorship, a new lawyer for Jamie Spears filed a legal document, urging the court to fully terminate the conservatorship.

The singer’s team is joining in the motion filed by her father for termination. But, legal experts say that while both sides may want the same thing on paper, it’s appears to be for very different reasons.

Spears’ father has done a complete 180. First, he contested the singer’s team’s effort to remove him. Then, within a matter of months, he asked the judge to put an end to the conservatorship.

Last week’s filing from Spears’ father new attorney stated: “Jamie unconditionally loves and supports his daughter. Full stop. As he has done for her entire life, Jamie will do everything he can to protect and care for her. For the last 13 years, that included serving as her conservator. Now, it means ending her conservatorship.”

While Rosengart declined to comment on his firm’s investigation, the attorney made his stance clear in a recent filing. “It is of no moment, presently, whether Mr. Spears’s reversal was motivated by a desire to bolster his reputation or to avoid his deposition or responding to the outstanding discovery served on him,” the court doc stated.

Rosengart’s firm has pledged to look into Spears’ conduct, in addition to Tri Star Sports and Entertainment Group, the company that managed the singer and was hired by her father. According to reporting from the New York Times, Spears’ father and the singer’s former business managers, Lou Taylor and Robin Greenhill of Tri Star, ran an intense surveillance apparatus that tracked Spears’ communications, secretly capturing audio recordings from her bedroom, which included private conservations with her children.

“Mr. Spears has crossed unfathomable lines. While they are not evidence, the allegations warrant serious investigation,” Rosengart wrote in a September filing, seeking all documents regarding communications between Spears and Tri Star.

That investigation is currently ongoing. In fact, Rosengart has added another high-powered attorney to his team: Kyle Freeny, who was one of 19 prosecutors selected by Robert Mueller in the investigation into former President Donald Trump.

An attorney for Spears’ father, Alex Weingarten, did not respond to Variety’s numerous requests for comment regarding the investigation.

While the investigation in Spears’ father will be continuing for quite some time, the first matter of interest this week is Spears’ own life.

“This week is gonna be very interesting for me. I haven’t prayed for something more in my life,” Spears wrote on Instagram  in a recent post, which has now been deleted.

During the saga of the past few months, Spears has also brought her fans into some private celebrations in her life, as she looks towards a new chapter of freedom. Last week, she shared a rare photo with her two teenage sons, who she had been restricted from seeing at her own will during much of the conservatorship. And in September, the star announced her engagement to her longtime boyfriend, actor Sam Asghari. (Under a conservatorship, Spears is not allowed to enter into any legal agreement without permission from her conservators, and that would include a marriage license.)

But legal experts say it’s not a sure thing that Spears’ conservatorship will be terminated immediately.

“I think there’s a chance they don’t terminate it. The judge could say, ‘We’re headed in that direction, but we’re not there yet,’” Wentz proposes, noting there is so much the public doesn’t know about this case.

“I’d be shocked if this takes less than a year to clean this all up,” the attorney says.

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