Britney Spears nabbed a big win in her conservatorship battle this week, after Judge Brenda Penny ruled that the pop star can now hire the attorney of her choosing.
On Wednesday, the singer appeared over the phone for the second time in two years following last month's headline-making hearing in which the 39-year-old pop icon claimed she's been "traumatized" by an "abusive" legal arrangement that grants her father, Jamie Spears, broad authority over her personal and financial affairs, including her estate that's estimated to be worth $60 million.
Mathew Rosengart, a former prosecutor and prominent Hollywood lawyer whose client list includes A-listers from Ben Affleck to Steven Spielberg, was formally approved to represent the singer. He is largely expected to take a more aggressive approach, telling the courts on Wednesday that he intends to file paperwork in the next few weeks to formally end the conservatorship.
"The victory of allowing her to choose her own counsel was huge," Benny Roshan, an L.A.-based attorney who serves as chair of Greenberg Glusker's trusts and probate litigation group, told Yahoo Finance.
Roshan explained it was a victory because the singer's voice was heard, but the ruling also demonstrated — albeit indirectly — that she is capable of making her own decisions.
"Britney basically illustrated through her own testimony to the court that she had the capacity to hire a lawyer...and when you're under a conservatorship, typically that means that a court has found you not capable to enter into a contract — but hiring a lawyer is just that," she said.
The temporary conservator of her person, Jodi Montgomery, previously filed a petition to appoint a "guardian ad litem," an advocate appointed by the court to act on behalf of Spears to help her hire a lawyer.
Roshan said the court essentially "ruled that [a guardian ad litem] makes no sense by allowing Britney to choose her own attorney" — yet another example of her capacity to make decisions.
"The writing is on the wall that this conservatorship is going to come to an end," Roshan speculated.
Yahoo Finance reached out to Jamie Spears' legal team for comment and has yet to hear back.
'Uglier and uglier'
The next major moment in Spears' case will be once she, along with her legal team, file the formal petition to end the conservatorship.
Following that, Jamie Spears could, and likely will, file an opposition.
"It's going to get uglier and uglier," Roshan warned, "unless her father sees the writing on the wall and starts jumping ship like others and voluntarily resigns," the attorney added.
In recent days, financial company Bessemer Trust, previously selected to serve as co-conservator of the pop star's estate, along with Spears' former court-appointed lawyer Sam Ingham and even her longtime manager Larry Rudolph all resigned from their positions.
At Wednesday's hearing, Britney tearfully called for an investigation of her father, citing conservatorship abuse, according to multiple reports.
"I definitely think that there's going to be a two-fold litigation strategy with this," Roshan said, suggesting that Britney Spears' fight might not end if and when she is freed from the arrangement.
"Another question is whether or not [Spears and her legal team] are going to make good on their threat to hold people who abused the conservatorship process and exceeded their authority accountable," she explained, adding that there are "broad remedies" available should they decide to further prosecute.
One possibility includes the disgorgement of any fees the individuals in question collected throughout the course of the arrangement. Spears currently pays hundreds of thousands of dollars every year in fees related to the conservatorship.
The next hearing in this case is scheduled for September 29.
Britney, by the numbers
Forbes estimates that the pop star's net worth sits at approximately $60 million, with $56.5 million of that sum resting in business accounts and investment properties. According to the publication, her gross income is divided among a mix of agents, managers, lawyers, state and local taxes, and then her personal expenses.
Each year, Spears pays about $500,000 in child support to ex-husband Kevin Federline, plus millions in legal support and fees related to her conservatorship, Forbes said.
Editor's Note: This article has been updated to reflect Yahoo Finance's efforts to reach Jamie Spears' legal team in response to the conservatorship developments and Britney Spears' allegations
Alexandra is a Producer & Entertainment Correspondent at Yahoo Finance. Follow her on Twitter @alliecanal8193