From the Courtroom, to the Mayor’s Office, to the Hamptons Film Festival, Randy Mastro Helps Lead the Way to New Beginnings

Randy Mastro laughs when he recalls the night he saw the Oscar-winning film The Artist at the Hamptons International Film Festival 10 years ago. “I went to see the film because the programmers told me I should, but I had no idea it was in black and white and silent,” he says. “I remember sitting there as the film started, thinking it would never catch on. But by the end of the film, I was captivated. It remains to this day one of the most endearing, charming films I have ever seen.” The Artist went on to garner 10 Academy Award nominations, winning five, including Best Picture.

“The Hamptons International Film Festival continues to grow in stature,” Mastro says. “In fact, for the past 11 years in a row, we have screened the Academy Award/Oscar winner for Best Picture, including Nomadland last year.”

Mastro has a specific pride in the success of the Hamptons International Film Festival. For the past five years, he has co-chaired this major event. This year’s festival, which runs from October 7–13, marks its much-anticipated post-COVID return to theater screenings.

“We kept the festival alive last year with virtual screenings and drive-ins, but it is not the same experience,” says Mastro. “Now, we’re back!”

Mastro has been part of great comebacks before, both in government and in the private sector.

Over the past two decades, as a partner at the legendary Gibson Dunn law firm, he helped build that firm’s New York office into the powerhouse it is today. He has earned a well-deserved reputation as one of the nation’s top trial lawyers. And just last year, he convinced the U.S. Supreme Court to reopen churches and synagogues that Governor Cuomo had ordered closed because of COVID.

Perhaps the greatest comeback in which Mastro participated, though, was New York City’s in the 1990s. Mastro had been a trailblazing federal prosecutor targeting organized crime in the late 1980s. And in 1994, he again answered the call to public service — from Rudy Giuliani after his victory over David Dinkins to become the city’s 107th mayor. Mastro served as the mayor’s chief of staff and then as deputy mayor during a transformative period in New York City.

“Time magazine had just run a cover story calling New York City ‘The Rotting Apple,’” Mastro says. “We were seeing 2,000 murders a year, and we were a city in decline. So I answered the call. I felt it was my civic duty to help the city we all love.”

Mastro says that administration had three priorities: make New York City safe, improve quality of life, and make economic opportunities available to all New Yorkers.

“I had never been involved in politics. I’ve always been a lawyer representing clients, but the call to public service was profound, and my client was New York City,” he says.

The Giuliani administration made a difference, and the city showed dramatic improvement. There were historic decreases in crime, hundreds of thousands of private sector jobs returned to the city, and neighborhoods across all five boroughs improved. Mastro was the administration’s point person on so many initiatives, most notably, in taking on La Cosa Nostra at the Fulton Fish Market and in the private carting industry, eliminating the $600 million “mob tax” on waste hauling and subjecting himself to death threats from organized crime in the process.

“The historic changes that occurred could only have been accomplished through good government, professionalism, and non-partisanship, which are all principles that I hold dear,” Mastro says.

After four-and-a-half years in City Hall, Mastro returned to Gibson Dunn in late 1998. For the past 20 years, he has served on the firm’s Executive Committee. And he has headed Gibson Dunn’s firm-wide litigation practice group, which The American Lawyer has named “Litigation Department of the Year” nationally four out of its last six biennial competitions and a finalist six times in a row. Last year, the firm’s New York litigation group was honored by the New York Law Journal as New York’s “Litigation Department of the Year.”

In short, throughout his career, Mastro has proven to be an accomplished, effective leader who gets results.

The Mastro family has been part of the Hamptons community for the past 16 years, and he has long attended and supported the Hamptons International Film Festival. The festival was established in 1992 and is one of the most high-profile events in the film industry and on the East End every year.

Five years ago, Mastro’s involvement in the festival became complete when former chair and long-time friend Stuart Suna stepped down, and Mastro assumed the role, with Alec Baldwin as co-chair.

“It took two of us to fill Stuart’s shoes,” says Mastro. “I have especially appreciated working with Alec, who has done so much for the festival over the years.”

During Mastro’s tenure, the festival and the world have faced their biggest challenge — the COVID-19 pandemic. Undeterred, the staff and volunteers of the Hamptons International Film Festival worked hard to provide a satisfying event in 2020.

“It was very stressful, but we were able to do virtual screenings and drive-ins,” says Mastro. “I was very proud of our team, led by executive director Anne Chaisson and programming director David Nugent. We made sure everyone kept their jobs, we maintained our staff, and they never stopped doing their great work.”

Some of the most notable films of the last three decades, from documentaries to independent films to big studio blockbusters, have been screened at the festival. Over the years, Mastro has experienced the magic of the festival.

“The year we screened Searching for Sugar Man, I went to see the film without knowing anything about the story,” Mastro says about the 2012 documentary about folk music legend Sixto Rodriguez, who was thought to be dead for years. The South African filmmakers set out to find out how this revered performer died, only to find him alive and working as a laborer in Detroit, Michigan. “Just as that amazing film ended and I was thinking how incredible the story was, the screen rose, and behind it was Sugar Man himself, ready to perform. The audience went wild.”

Mastro also fondly recalls the day Julie Andrews was honored at the festival and her film, Victor/Victoria, was screened. “I am a huge fan, and she was so incredibly charming, so warm,” says Mastro. “That was a wonderful experience.”

This year, the festival will adhere to all COVID precautions. Proof of vaccination will be required to attend, masks will have to be worn indoors at screenings, and capacity will be limited at screenings and events.

Mastro is excited about the return of the festival. “This is something we give back to the community here,” Mastro says. “It’s a labor of love.”

He also continues to keep a close eye on New York City. He now chairs Citizens Union, New York’s preeminent, nonpartisan “good government” group that has been advocating for honesty, integrity, transparency, accountability and ethics in government for the past 125 years.

Unfortunately, he sees too many parallels between the New York City of today and the dark days of the early 1990s.

“This has been a tough time for our city. We’ve lacked the leadership we need,” says Mastro. “COVID is a major part of the problem, but it is not the only part. Public safety has become a major concern again. And we also need to do more to provide economic opportunity for every community in our city.”

Mastro says he believes that Eric Adams is “the right person at the right time to lead our City at this transformative moment. Eric has the experience, charisma, energy, compassion, and empathy necessary to turn things around here, and we desperately need that right now.”

“I am very hopeful for our city now that Eric Adams is poised to become our next mayor,” Mastro adds. “But we all have to do our part to bring New York City back. We all have to answer the call to help at this critical time.”

When the first film rolls at this year’s festival, Mastro will be thinking about resiliency — not only for the festival but also for the city he loves.

“Let’s get back to business and make this the greatest comeback we’ve ever had,” says Mastro.