The Street-Fighting Lawyer Who’s Become Hollywood’s Dark Knight

In 2021, ESPN broadcaster Sage Steele was suspended following comments she made on a podcast, including calling parent company Disney’s vaccine mandates “sick” and questioning why Barack Obama considers himself Black when he was raised by his white mother. When she returned to her job, she felt she’d been sidelined from key on-air opportunities. So she dialed one of her closest friends, Chris Harrison, for advice. They’d gotten to know each other while co-hosting the Miss America pageant and the Scripps National Spelling Bee. He, too, had recently lost a big gig — as host of ABC’s The Bachelor, after defending a contestant accused of racism.

“Chris said, ‘I know who you need to talk to — my lawyer. He’ll be calling you momentarily,’ ” Steele remembers. “Within five minutes, Bryan Freedman was on the phone with me.” Steele left ESPN — she now has a podcast at Bill Maher’s Club Random Studios and will voice an upcoming animated series for conservative media outfit The Daily Wire — but was pleased by the settlement Freedman clinched. “He’s the kind of person you need if you’re David fighting Goliath,” she says. “Little me versus Disney? He’s the defender of what’s right. He fought for me when I didn’t even think I was worthwhile. He made me feel fearless when I was at my most vulnerable.”

Freedman, the divisive Hollywood attorney who’s referred to himself as a “pit bull” and is known for a rabidity and ruthlessness that can make even his fellow ferocious practitioners marvel in astonishment, has ascended as a powerhouse in recent years, becoming the go-to for alpha dogs who see themselves as the underdogs in a crisis.

He represented Kevin Spacey after the actor was accused of sexual assault and FKA Twigs when she alleged Shia LaBeouf abused her. Tucker Carlson, Chris Cuomo, Megyn Kelly and Don Lemon hired him when they were unceremoniously ousted from their networks. Dr. Dre’s ex-wife worked with him to get the music mogul to cough up spousal support. Freedman’s also been behind Gabrielle Union’s toxic workplace claim with America’s Got Talent, Jamie Lynn Spears in her war of words with sister Britney, and defended Diplo when the musician was accused of distributing revenge porn. Lately, he’s been a force in the “reality reckoning,” pushing a series of labor claims and putting Comcast and Bravo on the defensive as he publicly calls for network mascot Andy Cohen’s head.

After a long career progressing from the margins of entertainment litigation, the brighter spotlight has led to the resurfacing of a troubling legal allegation from Freedman’s past while he also defends his hardball tactics in and out of the courtroom. “If you fuck with my client, you get what you get,” he tells The Hollywood Reporter at his Century City office during an afternoon off from an ongoing trial in Santa Monica against Mattel; he’s suing on behalf of a production company that claims the conglomerate stole its idea for the show The Toy Box, which aired on ABC in 2017. 

Freedman’s reputation is comically menacing. On this June afternoon, across a wide conference room table, he’s mostly docile, on his best behavior with a PR rep by his side. But flashes of pugnaciousness can’t help but shine through. “If it serves my client’s purpose to be a zealous advocate, which I believe most of the time it does, then I will be a zealous advocate.” (Freedman also replied to questions about some legal matters in writing.)

His relentless go-for-the-jugular MO — in the press, via depositions, through court filings, during private dispute resolution — is, to his mind, rooted in hyper-competitiveness, along with childhood pain. “I have had a protective streak in me ever since I was a kid, where I really just wanted to help and protect people,” he explains. Asked more about it, he says, “There’s things I’d rather, while my mother’s alive, not get into, but everybody did the best they could with what they had. My sister killed herself a year ago. People have trauma. And so, I am a protector of people and try to do it in every way possible within the bounds of the law, hopefully thinking both inside and outside the box.”

Freedman, 59, whose family moved around the country a lot while he was growing up (his father was a pathologist who worked for a series of hospitals in different states), has been sober for 23 years. He now hosts recovery meetings at the $5.5 million Pacific Palisades home he’s lived in since the early 2000s and where he raised his kids with Denise, his wife of three decades. AA has informed the way he views the law, making him “think there is an opportunity for growth in every situation, whether it’s my client or someone else’s.”

Carlson had Freedman handle his 2023 exit from Fox News shortly after the network paid $787 million to settle a defamation suit brought by Dominion Voting Systems against the network. “Every time I read about Bryan, it’s like, ‘When are they letting him out of the cage?’ ” Carlson jokes. “He’s chewing on his own paw.” But he observes that persona may obscure another canine-like quality beloved by clients — loyalty: “If he takes you on, he’s not secretly working with the other side.”

“Like me, he’s sober,” Carlson says, “and I think that’s really a central part of his personality. It’s instantly recognizable to me, that he’s one of these people — and you cheapen it by describing it — but it’s his duty to help.” He recalls how Freedman encouraged him to reach out to Cuomo and Lemon when they, too, found themselves “at the bottom of the dogpile.” “And I did — even though I didn’t like them!” He pauses. “It speaks to his decency.”

Cuomo, another broadcaster who was abruptly terminated from his network — CNN discovered he had aided his brother, then New York Gov. Andrew Cuomo, amid a sexual harassment scandal — offers this about their mutual counselor: “When Freedman believes that he has a client who’s been wronged, it’s not just about relative equities,” adding, “The media business is uglier than most things, and in a very ugly world, he has a very uncommon sense of honor. There’s something beautiful about that. That’s what makes him stand out.” 

***

For many years, Freedman was a middle-of-the-pack player in the Hollywood legal world, which he entered decades ago. This followed an early stint at a stodgy firm doing commercial litigation after graduating from a lower-ranked law school. (His goal at the start of his career: “pay-back-your-
student-loan law.”)

At a practice he established with Michael Taitelman, a college buddy who specializes in real estate transactions — the firm has since expanded to 26 employees, including 15 lawyers — he handled workaday matters for the likes of gossip columnist Perez Hilton, production company Benderspink and, for years his main calling card, the talent agency UTA. His first claim to legal fame was winning a settlement in a defamation case against Courtney Love in 2011 when she went on a Twitter rant against his client, a boudoir-focused fashion designer named Dawn Simorangkir.

Then came a big break. In 2018, his client UTA recommended Freedman to Kelly, herself an ex-lawyer, for her acrimonious separation from NBC News after she’d made comments defending blackface. (The agency briefly held discussions about signing her after she’d fired CAA in the midst of the scandal.) “I was dealing with some dirty dogs,” she says, “and Bryan knew how to handle it. He wasn’t intimidated by their tactics or threats nor their constant leaks in the media.” After Kelly reportedly exited with her full $69 million contract intact, Freedman zoomed to the top of the industry’s crisis call sheet. In the years since, he’s repped Vin Diesel after the actor was accused of sexual assault by an assistant, The Bachelor host Chris Harrison during his departure from the show, Vanna White in her Wheel of Fortune salary dispute and Quentin Tarantino in a fight with Miramax over Pulp Fiction NFTs. (Freedman has previously also done work for THR’s parent company, Penske Media Corporation, as outside counsel — he says he ended the relationship so he could be a conflict-free voice for his Hollywood clients if they “wanted to go after” PMC — and unsuccessfully sued Los Angeles magazine when it was run by Maer Roshan, now THR’s co-editor-in-chief.) 

In fact, Freedman’s willingness to be the intimidator is a large part of his appeal among clients. He’s frequently compared to industry litigator Marty Singer, arguably Hollywood’s most mythologized living practitioner of performative aggression. However, those who know the two best say Freedman can be nastier. “Bryan is mean,” explains an attorney who admires and has worked with both. “Marty is loud and abrasive. But Bryan can be cruel. It’s worse when he’s an adversary.”

Brian W. Foster, creator of the popular Dungeons & Dragons web series Critical Role, learned what it’s like to go up against Freedman during his 2023 separation from his former fiancée, actress Ashley Johnson. Freedman filed a suit that was reported in the press in which Johnson and six other female plaintiffs — including Johnson’s sister — alleged sexual or physical misconduct by Foster, all of which he’s vigorously disputed or denied. 

Observes Foster: “Is Bryan Freedman effective? Yes. My life is proof. He’s a shakedown guy. That blitz? He’s destroyed my life and my family’s life.”

Freedman, who no longer represents the women, rejects this. “Foster need only look in the mirror to assign blame,” he says. “Any other interpretation is victim shaming and an attempt to further harass his accusers.”

The Wolf of Wall Street inspiration Jordan Belfort, who hired Freedman to sue the movie’s producers for purported fraud, says that Freedman’s theatrics serve him well. “The reputation makes people think twice,” explains Belfort, whose suit was settled. “It’s a big thing emotionally to people on the other side. They take it seriously.” 

Yet one seasoned litigator who’s had a history of dealings opposite Freedman believes that the bark can belie a lack of bite. “He knows how to create hype, which instills fear [in the other party], but there’s not a lot of substance — taking what, when you look into it, are small [grievances] and turning them into something untrue,” says this lawyer. “The business plan is about setting out narratives that are perceived as difficult by studios and production companies that don’t want negative press [in order] to secure settlements.”

For his part, Freedman’s response to such critiques ranges from dismissive (“sounds like they lost”) to earnest explications of his work as that of a mere servant, a vessel for his clients’ wishes. “I will morph into the need that my client needs,” he says. Still, it may be revealing that during a brief interlude about his passion for basketball — of his three sons, all in their 20s, one was a college phenom and another plays professionally in China — Freedman says that during his own high school playing days he “never was afraid to take the shot” but “was a better trash talker than probably a player.” 

Entertainment attorneys like Freedman almost always prefer to resolve conflicts through arbitration or mediation. Yet some critics point to the fact that he has scant record of victory in the most transparent and unforgiving forum, civil court, as proof that the core of his advocacy claims often don’t hold up. “Bryan Freedman isn’t considered a trial lawyer by my peers,” says Sanford Michelman, who represents Foster as well as axed MediaLink head Michael Kassan in a dispute against Freedman client UTA, which fired Kassan. (The case recently entered arbitration.) “In my experience with him, he is all hyperbole and no substance. We don’t take him seriously.” 

His satisfied star clients, though, share a different view. They see their lawyer as a fearless warrior and a wise tactician. “I absolutely adore him and would defend him to the end,” says Kelly. “He’s honest and has integrity and is brilliant and knows how to fight. He’s tireless. Once he’s on board for you, he’ll kill for you.”

Former Grammys CEO Deb Dugan (like Kelly, once a practicing lawyer) utilized Freedman to pursue a discrimination charge against the Recording Academy after she’d been fired amid alleged misconduct claims. “Like a perfumer has a nose for fragrance, he has a nose for foul play, especially when it comes to complex organizations where it’s hard to understand the inside,” she says. “He has a high sense of justice and operates with obvious intellect — but also a strong EQ.”

Freedman’s supporters describe a compassion that fuels his drive. “We did phone calls where he would just listen to me cry about my experience,” explains FKA Twigs, who employed Freedman to sue Shia LaBeouf for physical and sexual assault, a suit that was ultimately settled. (LaBeouf has since publicly apologized.) “He was the first person who didn’t interrupt me, who remembered everything. He supported my position when I was made to have no position in this industry. Bryan made me feel like I was brave, even through my tears. The woman I was then, I was broken, and he saw a strength in me.”

This tenderness, allies say, is lost in the caricature of Freedman — often bolstered by the attorney himself — as a cold-blooded legal terminator. “He’s where he is because of what people see, which is his advocacy, and also what they don’t, which is a warmth and emotion and humanity underneath,” says Mark Geragos, another high-profile litigator fond of rhetorical flourishes and campaigns waged in the media. The pair, who have known each other for years, have increasingly teamed on headline-generating cases, including advocating for Hunter Biden against Fox News.

***

In August 2023, a besuited Freedman appeared on TMZ Live. He and the equally controversial Geragos were doing the media rounds alleging systemic exploitation by Bravo and parent company NBCUniversal on behalf of current and former cast and crewmembers, including Bethenny Frankel and Brandi Glanville, on some of the network’s lucrative reality shows. Their crusading work has rocked the network and become pop culture grist, prompting SAG-AFTRA to issue a statement of support (“We stand ready to assist Bethenny Frankel, Bryan Freedman and Mark Geragos”), putting Bravo on-air ringmaster Andy Cohen on the defensive against unionizing reality talent (“You don’t go to school to be a reality star,” Cohen told THR on May 8) and seeing a stream of new business from high-profile unscripted figures.

During the TMZ Live hit, Freedman sought to underscore the claimed misdeeds by introducing a piece of purported evidence. This exhibit was an oversized piece of paper, ostensibly a binding agreement, with the header “Slave Contract.” The lawyer explained of the prop he held to the camera: “This is so bad, this is something I was provided with,” adding, “it says ‘slave contract,’ an actual slave contract. Like, you’re going to be able to have someone sign a slave contract?”

Harvey Levin, TMZ’s seen-it-all tabloid chief, responded with brows furrowed: “That’s an actual contract for a show?” Freedman — arms crossed, hair slicked back, palm trees framed in the window behind him — underscored, “That’s an actual contract between two people that allows filming and allows other things to happen and to be placed on a show.”

Yet in April, legal counsel opposing Freedman in a separate case contended the “slave contract” he waved around on TMZ was, as it happened, a document pertaining to a totally different legal dispute in which they were engaged, and that allegedly involved an actual BDSM relationship. They explained in a filing that the contract was “a sexual prop downloaded from the Internet and drafted mostly by” Freedman’s own client, who’d accused their litigant, a San Francisco CEO named Christian Lanng, of abuse.

Lanng, who’s since lost his job at the fintech platform Tradeshift, an enterprise that had been valued at $2.7 billion in a 2021 fundraising round, has named Freedman and his firm in a defamation and extortion action. “I’ve worked with a lot of attorneys over my decades as an entrepreneur, and even in the most high-stakes or contentious negotiations, I’ve never seen anything resembling my interactions with Bryan Freedman,” he says.

Lanng adds, “Freedman turned a settlement negotiation into a media circus. His actions got in the way of resolving grievances and protecting the financial position of investors, employees and other stakeholders of my company.” His attorney Christopher Frost believes that the TMZ incident was part of “an abuse of an attorney’s power.” NBCUniversal didn’t comment.

While Freedman declined to explain how or why the contract from the Lanng case ended up as a stunt in the wrong case on TMZ Live, citing “active litigation,” he dismissed the matter as “nonsensical.” (In court, he has offered a contorted legal rationale for its appearance.)

Lanng’s legal complaint against Freedman also alleges he and his firm “hired third parties to create deepfake stories” about him by developing sham websites and fake social media accounts “in an attempt to leverage a higher settlement.” In court, Freedman has denied the allegation, and he tells THR it “sounds like a spy novel about the CIA.”

***

Freedman has represented both those accused of sexual harassment and assault as well as survivors. One of his current docket dramas, alongside Geragos, is the legal consequence of the internet-shaking “Scandoval.” The lawyers are representing Vanderpump Rules castmember Rachel Leviss in her revenge porn lawsuit against former co-star and lover Tom Sandoval. 

Another ongoing dispute has brought Freedman himself briefly into the crosshairs. In March 2023, attorney Jeremiah Reynolds brought a motion for monetary sanctions against Freedman. He alleged Freedman filed a frivolous sexual assault claim and leaked it to favored media outlets to gain unfair advantage in a home renovation dispute between a couple Reynolds represented, director Sacha Gervasi (The Terminal, Hitchcock) and his wife, the heiress Jessica de Rothschild, and Freedman’s own client, the interior designer Diana Lands Nathanson, who was previously married to Freedman’s best friend, the former MGM head Michael Nathanson. Reynolds asserted that the allegedly false claim had impacted Gervasi’s career. The motion against Freedman was denied. Freedman: “Doesn’t that unequivocally establish that the [sexual assault] claim was not frivolous at all?” A trial is scheduled for 2025.

Freedman shrugs off the notion that he makes untoward use of what he refers to as “the media strategy,” at least compared to his peers. He insists that many cases never publicly surface because they’re successfully negotiated before that phase is reached.

Freedman himself has learned what it’s like to be on the business end of the media strategy. In 2022, former Nickelodeon actress and #MeToo activist Alexa Nikolas publicized court records of a sexual assault case that Freedman had settled for $40,000, without admitting liability, three decades earlier. (He was representing Nikolas’ ex-husband in then-ongoing litigation over abuse claims.) The documentation, reviewed by THR, details how the plaintiff — who first sued in 1986 — became drunk at a UC Berkeley party and met undergraduate Freedman and his frat brothers, who led her to their fraternity house where, she alleged, they sexually assaulted her in rapid succession. She was 17 years old at the time.

The plaintiff testified in a deposition about what she termed the “gang bang.” Afterward, she noted, “I had trouble seeing, because my eyes were filled up with tears.” The plaintiff also shared that she’d since been plagued by persistent nightmares in which Freedman was after her. “I was being chased, and I was hiding from him,” she said. The situation was reported on at the time by UC Berkeley’s student newspaper. Freedman later resigned as an officer of the campus student association.

After Nikolas resurfaced Freedman’s settlement, her activist group Eat Predators protested in front of his Century City office tower. Later in 2022, press outlets including Rolling Stone and Business Insider detailed the case, highlighting the attorney’s high-profile work on both sides of the #MeToo movement, from Kevin Spacey to FKA Twigs. For his part, Freedman remained mum.

The next year, however, the University of the Pacific’s McGeorge School of Law in Sacramento announced that Freedman, an alumnus, had established an entertainment law scholarship. It’s unclear whether Freedman informed McGeorge of his litigation when he applied. (He graduated in 1990, shortly before the assault settlement was finalized.) The law school tells THR it was unaware of the resurfaced allegation when it accepted his scholarship bequest and that, since alerted, it hasn’t distributed funds and removed videos of his speaking engagements from view. 

Likewise, the California State Bar won’t reveal whether Freedman notified it of his sexual assault case when he sought to join. “Moral character reviews are confidential,” it tells THR. Yet the organization also explains: “While we are unable to comment on standards that existed in 1991, speaking generally, we can say that today, serious allegations, including those involving sexual assault, would be given serious and appropriate consideration in the moral character review process.”

THR asked Freedman whether he disclosed his case to these institutions, and what effect, if any, he believes the accusation and settlement have had on his career and work. He declined to address them. In a statement, he said: “It has been reported that the matter was settled without any admission of liability on anyone’s part. It feels highly insensitive for any response to be used as a sword or a shield.”

In a May 30 filing in the Lanng case, Freedman’s side argued that “no one agrees to pay $10 million when they have done nothing wrong.” Questioned why, by the same logic, his 1991 settlement payment of $40,000 was not also a tacit admonition of culpability, Freedman writes THR, “I have consistently denied liability” and his own payout was covered “by my parents’ homeowners insurance company for a relatively nominal sum which the carrier believed was substantially less than the likely cost of litigation.”

Litigation is depleting for every party involved. The attorneys advocating for each side typically understand this most of all. But for Bryan Freedman it can also be invigorating.

“I can’t wait for the phone to ring, honestly,” he says at the end of THR’s time with him. “I have no idea who is going to call, what the case is going to be about, what I’m going to hear, what crisis or trauma someone is going through, and how I can help them. I feel the fire in my belly about wanting, with desperation, to help them in their situation.” 

Lachlan Cartwright contributed reporting.

This story first appeared in the June 12 issue of The Hollywood Reporter magazine. Click here to subscribe.