Why Britney Spears' upcoming conservatorship hearing could be pivotal for the singer

Britney Spears' upcoming conservatorship hearing could prove to be a pivotal one for the pop star.

Come Wednesday afternoon in Los Angeles, Judge Brenda Penny will be pressed to make major decisions on whether to keep Spears' father on as her conservator, or whether to end the conservatorship altogether.

The hearing is the first to take place after the "Toxic" singer's attorney Mathew Rosengart filed documents calling to end the conservatorship altogether this fall. Britney's father, James P. Spears, otherwise known as Jamie Spears, has also requested the 13-year court order end amid a flurry of accusations from the singer that he's abused his control.

Spears got her first taste of some freedom in the case when Penny allowed her to hire Rosengart in July. In the high-powered attorney's filing from earlier this week, Rosengart emphasized that it is more important to her that her father be removed, calling it a necessary first step toward her freedom and "ending the Kafkaesque nightmare imposed upon her."

BRITNEY SPEARS, FIANCÉ SAM ASGHARI JOKE ABOUT HAVING A BABY

Weeks ago, Britney also became engaged to her longtime boyfriend Sam Asghari, which means putting together a prenuptial agreement. In court filings, Rosengart argued that her dad should not be involved in the matter.

Jamie in 2019 stepped aside as the so-called conservator of his daughter's person, with control over her life decisions, maintaining only his role as conservator of her estate, with control over her finances. He and his attorneys have said that renders many of his daughter's complaints about his control over her life meaningless.

Jodi Montgomery, a court-appointed professional, now acts as conservator of Britney Spears' person, and Rosengart said in court documents that Montgomery also consents to ending the conservatorship so long as it can be done safely and smoothly.

It is not clear whether Britney will take part in Wednesday's hearing. At two recent hearings she gave dramatic speeches decrying her status that rallied even more fans and fellow celebrities to her cause, and intensified the already loud calls to #FreeBritney.

A TIMELINE OF BRITNEY SPEARS' CONSERVATORSHIP

Rosengart said in another filing this week that Jamie "crossed unfathomable lines" by engaging in illegal surveillance of her, including communications with her lawyer, as reported in "Controlling Britney Spears," a documentary from the New York Times and the FX network, one of two dueling documentaries released days before the hearing.

Jamie has denied acting in anything but his daughter's best interest, and has declined Rosengart's demands that he resign immediately, saying in a court filing that in his 13 years in the conservatorship, "to the best of Mr. Spears’ knowledge and belief, not a single medical professional nor the report of a single probate investigator has recommended that Mr. Spears’ presence as Conservator was harming Ms. Spears or that he should be replaced."

In court papers filed Monday, Jamie argued that Rosengart's nomination to appoint CPA John Zabel to replace him "should be denied." Him and his legal team also are claiming there's no need for a replacement because he currently still holds the position.

CLICK HERE TO SIGN UP FOR OUR ENTERTAINMENT NEWSLETTER

"First, there is no need for a temporary conservator because there is no vacancy in the position of the conservator. Mr. Spears continues to serve faithfully as Conservator of the Estate, as he has done for the past thirteen years. Mr. Spears has no and should not be suspended, especially since the Conservatorship should soon be terminated," Jamie's legal team argued.

Jamie and his team went on to claim that the court has "been provided little to no information" about Zabel, calling him "apparently a stranger to this Court" and "not a licensed fiduciary."

In a response to Jamie’s objection obtained by Fox News, Rosengart said Jamie has no room to toss around language pointing out anyone’s shortcomings as Jamie himself has been at the forefront of scrutiny during his own time at the conservatorship helm. 

"This is also true regarding [Jamie’s] counsel’s latest filing, "Objections" to the successor Conservator of the Estate," Rosengart wrote. "As Mr. Spears should know, California law expressly allows licensed CPA’s to serve, and the nominee, John Zabel, is a highly-esteemed, nationally-recognized award-winning CPA with an impeccable record of serving in positions of trust—in stark contrast to Mr. Spears, a reported alcoholic and gambling addict, with zero financial background or experience in financial matters, who previously filed for bankruptcy and has a Domestic Violence Restraining Order currently in effect against him.  Mr. Zabel will also be supported by Ms. Spears’s business management and forensic accounting teams."

CLICK HERE TO SIGN UP FOR OUR ENTERTAINMENT NEWSLETTER

Rosengart added: "Mr. Spears’s desperation to avoid suspension is self-evident and self-serving.  He wants to escape justice and accountability (but will not) and he will evidently do or say anything to avoid it.  He knows that when he is suspended he must turn over the conservatorship files, including purported attorney-client privileged documents (communications with his lawyers), to the new temporary conservator."

Jamie has been in control of Britney's finances since 2008 after the pop star underwent a series of involuntary holds. Britney has been locked in a court battle with Jamie over the past years as she's worked to get control of her life back.

The Associated Press contributed to this report.