Sean Penn Salutes Attorney Mathew Rosengart With Varietys Power of Law Award: He Still Practices His Dignity of Indignance

Sean Penn hailed his longtime lawyer Matthew Rosengart as a dedicated crusader for justice Wednesday at the Variety Power of Law breakfast in Beverly Hills, presented by City National Bank, where he presented Rosengart with the Power of Law award.

Penn noted Rosengart’s major accomplishment of helping the “Free Britney” movement triumph last November by guiding pop superstar Britney Spears through the maze of ending the restrictive conservatorship arrangement that had been in place for her since 2008.

“By extracting a young woman named Britney Spears from a disturbingly antiquated conservatorship, he did much more than inspire the memes of fans in finding justice for this high-profile client,” Penn said at the event, held outdoors at the Four Seasons Hotel.

Penn praised his legal eagle for managing to stay very involved in his life and CORE non-profit that aims to provide disaster and humanitarian relief around the world, despite being in the thick of an all-consuming case that drew worldwide attention.

“He remained the constant and active general counsel for my organization, CORE,” Penn said. “For those of us who have Matt on our side, we all feel we were the only fight on his card. He’s extraordinary.”

Moreover, despite his success as a partner and principal shareholder at Greenberg Traurig, Penn emphasized that Rosengart is dedicated to work that helps those who need muscle the most.

“He still practices his dignity of indignance on behalf of the big and the small, both as a litigator and as a friend,” Penn said.

Rosengart was clearly moved by the high praise as he took the stage. “There’s something very surreal about being handed an award by Sean Penn,” he joked.

On a more serious note, Rosengart said he was prompted to reflect on his work for Spears (though he did not say her name) when he was asked recently to make a speech at Harvard Law School. He was unsure of what to say until he reached out for guidance to a fellow lawyer and friend.

That friend told Rosengart, “You have changed somebody’s life at a time when law is under siege. You’ve taught your profession that lawyers can do great things, lawyers can help people and law is a noble profession,’” Rosengart said. “That got my thinking about the profession… It really is a high calling. It’s an honor to do the job.”

Rosengart, a former Justice Department trial attorney and federal prosecutor, represents a number of high-profile clients, including Julia Louis-Dreyfus, Steven Spielberg and Keanu Reeves. But he stepped into a huge spotlight last year when he was named the new attorney for Spears in her conservatorship case against her father, Jamie Spears. The conservatorship was terminated in November, but her legal battle is ongoing. In October, Rosengart was also hired by Facebook/Meta in advance of an upcoming TV program about the company.

With Rosengart as his attorney, Penn sued Lee Daniels in 2016 for $10 million, alleging that Daniels defamed Penn while speaking to The Hollywood Reporter, which quoted him comparing domestic abuses allegations against “Empire” star  Terrence Howard to Penn’s marriage to Madonna. The two eventually reached a settlement.

Recently, Penn has made headlines for filming a Vice documentary in Ukraine during ongoing conflict, before returning to the United States at the beginning of March. Last week, he was quoted saying he was was thinking about “taking up arms against Russia,” and said he is continuing to shoot the documentary.

Rosengart also serves as general counsel for Penn’s nonprofit organization Community Organized Relief Effort (CORE). Penn founded the org following the 2010 Haiti earthquake, and it has since expanded globally. Most recently, CORE has worked to combat the COVID-19 pandemic and has established a presence in Poland to aid with the Ukrainian refugee crisis, which Rosengart is working with on a pro bono basis.

Variety‘s Legal Impact Report, which features the best in entertainment lawyers, has included Rosengart in its ranks for a number of years. In April 2021, Rosengart told Variety, “The pandemic has not slowed down my practice at all … In fact, for whatever reason, things are busier than ever with two trials coming up in the next six months.”

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