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

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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 co-head 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.

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.

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.
There now exist three cuts of the film: Lonergan’s, one cut by a third party at the request of Gilbert, and a Martin Scorsese cut, which happened for still more complicated reasons. Each has been seen, tragically perhaps, by very few people. On the upside, Rosengart calls Lonergan a friend, and Matt Damon tells a story about the attorney in one of those Hollywood Reporter roundtables.

By 2011, Rosengart had joined the international firm Greenberg Traurig, and his clients have included Lena Dunham, Winona Ryder, Julia Louis-Dreyfus, Christopher Walken, Eddie Vedder, Keanu Reeves, and the Miami Heat’s Jimmy Butler, as well as Credit Suisse and Meta. “I’ve always been attracted to talented people, whether they’re brilliant hedge fund executives or studio executives or athletes or actors or actresses,” he says.

Sean Penn, for whom Rosengart got a National Labor Relations Board complaint dismissed earlier this year, tells me, “When we think about tough lawyers, they’re sort of performatively tough. His toughness is always grounded in that which I would identify with real strength. He knows the law he sees when people are trying to spin something, and it bounces off him and he keeps his head in it. He doesn’t get thrown. And he’s able to be stronger than, tougher than, the tough guys.”

Dunham says, “Unlike so many litigators, Matt isn’t too quick to action. He really analyzes and discusses before he makes any moves, and he’s deeply sensitive to the nuances of human behavior. To have someone like that in my life has been a massive gift.”

That might go toward explaining his work on Spears’s behalf. As Dunham put it to me, from her experience, Rosengart allows the client to “dictate their own desired outcome, which is what an attorney should do but often doesn’t. Britney’s voice had been dismissed for so long and his first job was to hear what she was saying. He did, and still does, refuse to be yet another man controlling her.”

In September of last year, California governor Gavin Newsom signed Assembly Bill 1663 into law, making conservatorships harder to get into and easier to get out of. It was a state-size win for the “dignity of risk,” a phrase with a long history in the self-advocacy movement. As Zoe Brennan-Krohn, staff attorney at the ACLU’s disabilities rights program, put it to me on a recent phone call, “In a guardianship or a conservatorship, the conservator is supposed to act in your ‘best interest.’ And dignity of risk is in some ways just recognizing that we don’t make choices in our best interest all the time.”

In our world, we allow adults “to make choices, even if [their] mothers don’t like them,” says Brennan-Krohn. Probate courts historically have had a tendency toward paternalistic overprotection when confronted with a person with disabilities, who probably, along with the elderly, are most at risk of court-ordered conservatorships. But “it really turns out that people don’t have better outcomes when they don’t have a choice. That the way that people actually best protect themselves from abuse or from harm or from manipulation is by having experience with saying what they like and what they don’t like, and having experience with that being taken seriously.”

No one could have predicted that a global pop star would become the face of this cause, not least of all Spears herself. As Brennan-Krohn puts it, “So much of Britney Spears as a person, of course, is extraordinary, and so much of her experiences in conservatorship is actually very, very typical.”

One of the provisions California probate law has now that it didn’t have before is an emphasis on “supported decision-making.” That means, in short, a person with disabilities can make decisions the way most people make them: by asking people they trust for advice. In this set-up, unlike in a conservatorship, decisions—from financial to physical—ultimately remain theirs.

An infuriating aspect of reading The Woman in Me, published last week, is understanding this kind of arrangement could have been an option and yet knowing that it wasn’t. The book produces an odd blend of relief and heartache in this regard. As a reader, you’re at once happy that her experience helped lead to some kind of reform, but also uncomfortable knowing it took 13 years to get there.

In the wake of Spears’s 2021 hearing, a bipartisan spectrum of politicians had rushed to stand by the performer. Florida representative Matt Gaetz was on the steps of the courthouse on the day Rosengart appeared in probate court on behalf of her—not so shocking, since Gaetz has a knack for appearing where more than one camera angle is promised. (As Rosengart ascended the courthouse steps, he heard the gentleman from Florida say, “Jamie Spears is a dick.”) Rosengart says the office of Pennsylvania Senator Robert Casey called him personally to discuss why there was no clear data on how many people live under conservatorships in the United States.

After Spears’s leaked testimony in June of 2021, Gaetz and a number of other House Republicans, including Georgia representative Marjorie Taylor Greene, invited her to testify before the House. Several months later, after she was released from her conservatorship, several Democratic House members asked Spears to speak. As something close to a moderate himself, Rosengart seemed to relish the bipartisan appeals, but he was true to his word about his client calling the shots. As Spears said herself, when she posted the latter invitation to Instagram months after she’d received it, “I was immediately flattered and at the time I wasn’t nearly at the healing stage I’m in now.”

While Spears could easily take credit for attracting a spotlight on the weaknesses in probate legislation and ushering in a very public reckoning for it, Rosengart doesn’t believe she set out to be the “poster child” for anything. As she herself said in her original court testimony, her dreams were pretty simple. Among other things, she wanted to drive in the car with her then boyfriend. She dedicates several paragraphs in the chapter about life after the conservatorship, detailing how it was like maneuvering a jet ski the way she wanted to.

Though Rosengart says there’s more to do at a federal level with regard to the probate law, he’s still focused on his client. (The issue was recently very publicly in the news again this summer, when former NFL offensive lineman Michael Oher, inspiration for the book and film The Blind Side, successfully petitioned to be released from a long-standing conservatorship.) There remain legal moles to whack in Spears’s life. Jamie Spears brought at least nine motions against his daughter after the end of the conservatorship, including an attempt to depose her. Rosengart handled the prenup prior to her yearlong marriage to Asghari and is now “quarterbacking the divorce situation.” He’s handling her exes, like Kevin Federline, who has posted old videos of Spears’s children (“bottom of the barrel stuff,” Rosengart says). He helped negotiate the terms of her duet with Elton John and her book deal.

Various particulars of the case have continued to play out in court, most notably around the question of who is on the hook for the elder Spears’s legal fees.

“Future legal proceedings,” he writes to me long after we’ve spoken, “at least the ones that are public, involve the efforts of her father and his many lawyers during and since the conservatorship to extract even more money from her, and accounting issues regarding his and others’ administration of the conservatorship over a decade, which involved enormous investigative work and reviewing tens of thousands of pages of materials.”

While the media environment around the case has cooled, it still has proven a reliable source of material for gossip sites including TMZ and Page Six, where both Rosengart and Jamie Spears’s attorney, Alex Weingarten, have been occasional headline subjects themselves. Weingarten declined to comment for this story.

As the postconservatorship back and forth continues in probate court, there are legal voices who have followed the case who take a more critical view. Adam Streisand, the lawyer who Spears attempted and failed to hire back in 2008, has watched from the sidelines, and thinks more aggressive tactics are warranted, especially against Spears’s previous, court-appointed attorney, Sam Ingham. In Spears’s memoir, Ingham is the “weird-ass lawyer” who was paid by the conservatorship. “How could he have been allowed to get away with it?” Streisand writes in an email. “Where was the lawsuit against him?” (Ingham did not immediately respond to a request for comment.)

Of any general criticism from onlookers, Rosengart says, “The lawyer’s role is to represent the client and the wishes of the client, not those of third parties. The conservatorship stripped Britney of certain fundamental rights and civil liberties. The goal, the task, was always to restore them and that’s exactly what we did, first by swiftly obtaining the court-ordered suspension of [Jamie] Spears and then terminating the entire conservatorship.”

Over the course of reporting this piece, I spoke with Rosengart over text, email, and the phone, in various time zones. (In part because he travels so much for work and in part because I was on vacation.) He was, in a word, relentless in every conceivable definition. Always genial, always with a sense of proportion, but nevertheless relentless. Any lawyer worth his weight in paperwork has a kind of easy relationship to correspondence, but it was clear to me why clients with résumés and disputes as diverse as Penn’s and Dunham’s took time to provide some nice words about their hired legal counsel to a magazine. It was clear why a woman like Spears, who has had, per her book, a hell of a time finding people she felt she could trust, would thank him in its acknowledgements. Accessing the dignity of risk does not mean, in Spears’s case, that one is completely exposed to a world that has not always treated her well. It means, at least in part, she gets to choose her lawyer.

After Spears’s success, a fresh round of accolades for Rosengart rolled in. (Attorneys, you may not be surprised to hear, honor each other a lot.) His alma mater Boston College Law School asked him to speak, and Trinity College of Dublin’s Law Society presented him with the Praeses Elit Award. He frequently begins sentences about his approach to law as well as successes in the courtroom with phrases like “not to be self-aggrandizing”—so much so that it becomes a small joke over several conversations. But he admits (“not to be self-aggrandizing”) to moments when he feels he can relate to his clients, especially those who practice their craft on the stage or screen. The feeling of performing in court is not unlike the feeling actors have when they are first in front of an audience. The people out there react to what they’re doing up here, and something blooms in their heart. He’s felt bemused when seeing CNN talkings heads discuss his choices, as they did in the Spears case. That can’t be too far from the surrealness that some of his clients must feel when their names and life stories are discussed with varying degrees of accuracy in the media.

“There is a skill set in terms of how one deals with celebrity clients as opposed to corporate clients. That’s just the reality of the practice of law,” he says. “The client should always be the star.… When you are behind the velvet rope, figuratively and literally, it’s because of the client.”

He talks about another meeting with Spears, one in Hawaii in the months after the conservatorship had ended. After they met and ate, they stood up to go, and they took a photo. Unbeknownst to him, she posted it to her Instagram. “This man has turned my life around,” she wrote in the caption, pointing out they were matching in their pink outfits. “Pssss Mathew Rosengart … I simply adore you !!!!”

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