How Britney Spears’s Lawyer Mathew Rosengart Helped Regain Her Right to Risk

Britney Spears’s case was not a typical one for attorney Mathew Rosengart. It was a matter of probate law, and he had never pursued a probate conservatorship case. He could not, prior to summer 2021, give you directions to the probate courtroom in the Los Angeles County Superior Court system. He did not know the insular group of lawyers or the judges that populated it. But Rosengart had followed Spears’s life and career, and the conservatorship that had grown to govern both, for years. He’d listened, like so many, to the pop star’s desperate and powerful plea that June before Judge Brenda Penny: “Ma’am, my dad and anyone involved in this conservatorship, and my management, who played a huge role in punishing me when I said no—ma’am, they should be in jail.” He had read a series of articles on the pop star’s circumstances, including reporting in The New Yorker and a piece by Human Rights Watch. He understood, as even casual observers were then beginning to understand, that an adult woman with one of the most familiar faces on the planet had not been allowed to hire her own lawyer. This was a civil liberties case, he thought. He figured he could learn probate law.

“One of the things that, candidly, bothered me, just as a citizen, is that shortly after the conservatorship was created in 2008, the father and the business manager who was hired on her behalf, whom she did not have a say in, sent her on a grueling world tour,” Rosengart told me recently during one of several conversations we had in which he spoke extensively about the Spears case. “So on the one hand, you supposedly have this woman who’s so incapacitated that she cannot make any decisions for herself. On the other hand, she becomes an earner for the conservatorship.”

Soon after the hearing, the litigator and pop star sat down in her pool house to talk on July 10, 2021. (“Not,” he says, “that I remember that date.”) Rosengart impressed upon me that he prefers to do this with all his clients, not just the world-famous ones—to sit down with the person he’s going to potentially work with to make sure there’s a connection.

“My whole thing with her was that she would call the shots as a client,” he says. “Because for 13 years prior to that, she could not call the shots.”

The story of Spears’s decade-plus under the legal control of her dad and a court-approved business manager, Lou Taylor, has been everywhere again these last few weeks as the performer’s much-anticipated memoir, The Woman in Me, was published. That there is such a memoir to discuss would have been inconceivable for the 13 years Spears spent living under the court-mandated arrangement—a once semi-obscure legal mechanism that she helped turn into an object of bipartisan concern. Spears’s case led directly to a September 2022 reform of California state’s probate conservatorship law that makes it more difficult for a person to be put into a conservatorship, and easier for a person to get out of one.

Still, the story of how it happened bears repeating: In 2008, after a period of public indignities that included two psychiatric holds, her father, Jamie Spears, petitioned the LA court to place her under a conservatorship, which he would oversee. The state of California ceded her decision-making power over all manner of life choices to appointed guardians. Spears, she writes in her book, couldn’t drive or have a cup of coffee without the permission of one of her handlers. Visitation with her two sons with ex-husband Kevin Federline were highly regulated. As she told the judge in June 2021, she couldn’t decide to have a baby with her then boyfriend and now ex-husband, Sam Asghari; a therapist put her on lithium, which she’s said she did not like. She was compelled to work, while her father, the cohead of the conservatorship, collected a percentage of her earnings.

She writes in the memoir that she had tried to quietly fight the conservatorship after it was first implemented, but, “After being held down on a gurney, I knew they could restrain my body any time they wanted to. And so I went along with it.”

As the conservatorship wore on, there were murmurings from a group of Spears fans who believed that she was trying to call for help by posting hidden messages on Instagram. The following was expansive, and they grew in number under the hashtag #FreeBritney, support of which exploded after Spears herself spoke in court about her own situation. Besides the longtime #FreeBritney evangelists and advocates, journalists and congresspeople turned attention to her situation, as did a QAnon contingent obsessed with the case—a woman stripped of her rights, and forced to work, maps easily onto their trafficking fixation.

Mathew Rosengart, outside of Stanley Mosk Courthouse in Los Angeles on Wednesday, Sept. 29, 2021.By Alex Welsh/The New York Times/Redux.

Many wanted to help; Rosengart was one of the few people in a position to do so. After the June 2021 hearing, Spears was finally allowed to hire a lawyer of her own choosing. In that meeting in the pool house, as Spears writes in her book, she and Rosengart agreed to remove Jamie Spears from the conservatorship as a first step toward dissolving it completely. It proved to be a sound strategy. Excising her father from the conservatorship, Rosengart says, meant he was no longer protected by attorney-client privilege and would expedite the entire process.

“Had I simply filed a petition to terminate the conservatorship in July or August or September of 2021, we might still be litigating the issue,” Rosengart says. “The docket moves very, very slowly.”

Before the September 2021 hearing that would decide whether Jamie Spears would be removed, Rosengart had arranged for Spears to go to Tetiaroa, the Tahitian atoll owned by the Marlon Brando estate, so that she could be out of LA and hopefully relax a little. She was there when he called her with good news.

“I got to her before she read about it,” he says, “I got to make that phone call and that’s one of the most satisfying moments I’ve had in my career.”

In the immediate aftermath of the conservatorship’s end, Rosengart became something of a folk hero to Spears’s vast coalition of fans. As Spears’s die-hards saw it, rarely in the world is there so obvious an injustice so resolutely rectified. To them, he was suddenly “Rosengod,” replacer of inadequate legal counsel, slayer of bad dads, freer of pop princesses locked in their Thousand Oaks towers. Select photos from his professional and social past, most available through Google search, were collaged into artful memes and shared widely.

“It was complex,” Rosengart tells me about the sudden and specific renown. This is perhaps not entirely how the longtime attorney anticipated the public apex of his career thus far would look. Rosengart grew up on Long Island, the younger of two boys. His father, a well-regarded local doctor, died of a heart attack when he was a teenager. Almost immediately, his brother was on a track to become a top heart surgeon. Rosengart, without the same inclination toward science and medicine, chose law. He attended Tulane, and then Boston College Law School, where he distinguished himself enough to earn a coveted clerkship with future US Supreme Court justice David Souter, who was then serving on the New Hampshire Supreme Court. From Souter, who would become a lifelong friend and mentor, he found a touchstone that would ground him over the next decades of adversarial litigation. “I learned so much from him in terms of how to conduct yourself as a lawyer and how to conduct yourself as a human being,” Rosengart says, recalling the judge’s pious sense of what’s appropriate—to the point where the justice would pay for and apply his own stamps rather than letting the office mailroom pick up the tab.

After his clerkship, Rosengart began at the Justice Department. There, he worked on cases both high profile—prosecuting Indonesian businessman James Riady for campaign finance violations over donations to former president Bill Clinton—and low—Rosengart remembers standing up to a supervisor who wanted to pursue a life sentence for a crack cocaine dealer under the era’s “three strikes” mandate. It was where he learned almost everything he knows about being a lawyer, from how to work with witnesses to how to synthesize information and present it to a judge or jury.

By 2001, Rosengart moved to the private sector, and half a decade later, he’d traded New York for Los Angeles to continue building his practice in the corporate and entertainment space. He noticed some differences. At the Justice Department, he tells me, you are representing the United States of America, and your marching orders are to “do justice.” When you’re representing, say, Meta, or what have you, it’s “an honor, but it’s usually about money going from one pocket to another.” Entertainment law was an ego-driven (and lucrative) field to be sure, but if there was a hint of a justice angle to a case, Rosengart was apt to find it. Kenneth Lonergan was his first headline-grabbing client in the field, when the writer-director hired him to go tit for tat with financier Gary Gilbert, who helped mire what The New York Times would call Longergan’s “thwarted masterpiece,” Margaret (2011), in postproduction hell over the edit. A settlement took six years. Rosengart deposed Matt Damon for it, and, because the case was so personal and often intense, he and Longergan wouldn’t speak for a day or two. Then: “I’d wake up…to a long email from [Lonergan], which would be brilliant and funny and would suck me back in,” Rosengart says.

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