East Hampton Town Justice Race Pits Two Local Attorneys With Deep but Different Legal Backgrounds

East Hampton Town voters will be asked next month to elect a new town justice for the first time in a decade, as veteran Justice Lisa Rana has chosen not to run for another term on the town bench.

Two local attorneys with deep but very different legal backgrounds are running for the single seat — one of the town’s two justice positions — with the top vote-getter to serve a four-year term.

Brian Lester, the Republican candidate, and David Filer, the Democratic Party’s nominee, were both born and raised East Hampton, each from families with roots in the area since the 1600s. Both graduated from East Hampton High School and then went away to college.

But from there they followed very different, and each unique in their own right, paths to becoming local attorneys and, now, landing on the November 7 ballot.

Lester, 51, graduated summa cum laude from Westchester University. He had worked as a traffic control officer in the summer since high school and aspired to be a police officer, so after graduation he enrolled in the Suffolk County Police Academy, graduated as the class valedictorian, and began working as a police officer for East Hampton Village.

But his high scores on the LSATs while an undergrad had also landed him scholarship offers to the law program at Hofstra University.

“I couldn’t turn down an opportunity to go to law school when it was pretty much paid for,” he said this week.

But he kept his part-time position on the village force, working weekends through law school — from which he graduated with distinction — and then when he joined a local law firm. While most young attorneys aspiring to someday wade into the lucrative world of criminal defense do a turn in a district attorney’s office shortly after graduating from law school, Lester never did.

“I got to see it from the other side instead,” he said. “I learned it from the perspective of what’s expected of the police and how criminal cases are made.”

For the first decade of his legal life, he handled primarily civil litigation cases, not criminal, for Caleca & Towner. He is now a partner in Tarbet & Lester in East Hampton.

In 2007, he merged his two careers when he was offered to become the village’s prosecutor in the Town Justice Court on code violation summonses, parking tickets and zoning matters — a position he still holds, and one that he says has prepared him to move to a seat on the other side of the dais.

“My experience in this court makes me the right choice — I’ve been in this court every week for 16 years, I know what’s going on and how it works. I know the criminal prosecutions, but also the small claims and zoning. I’ve seen all the various judges and seen the different styles.

“The justices in East Hampton do a good job of listening to the people that come before them,” he added. “Even on minor matters like parking summonses — they want to be listened to, and it’s important that we do that.

“The best justice is someone who knows the law, listens to the defendants and victims, and has compassion.”

Lester says that as one of the town justices, he would press for the town court to resume evening sessions — something that had been done years ago by Justice Catherine Cahill, but was dropped because it was deemed economically inefficient. But, he says, the dockets were much smaller then than they are now, and with people busier than ever and having to work harder to remain in the community, the benefit to those tied into court business would be substantially greater today than ever before.

“For things like small claims, for instance, someone often has to take the day off of work to defend or pursue a small claims case,” he said. “That may deter someone who should bring one from doing it, or puts an extra burden on someone defending themselves that they aren’t going to get [reimbursed for]. I think it’s worth looking at again.”

His opponent, Filer, 61, left East Hampton High School about 10 years earlier for Lynchburg College in Virginia. After brief turns selling insurance for the Cook Agency, earning a master’s degree in education and teaching grade school in Virginia, he landed at Brooklyn Law School and, soon after graduating, on the prosecution team for famed Manhattan District Attorney Robert Morgenthau — where he would work for 16 years.

As one of the D.A.’s veteran prosecutors, he handled major crimes, primarily violent ones, and then the complicated work of the Sex Crimes Unit. He concluded his career in Manhattan as the director of the Prosecution Clinic, which worked with third-year New York University law students on real-life criminal prosecutions in the city’s courts.

In 2018, with his son entering middle school, Filer moved his family back to East Hampton and went into private practice with a childhood friend, Rick Whalen. Their firm, Whalen Filer PLLC, is based in Amagansett. Filer served as legal counsel to OLA of Eastern Long Island, the Latino advocacy and support organization based in East Hampton, for two years.

“Most of my career has been in public service, and I gave all that time to New York City, so I feel like now it’s time to do that for my hometown,” Filer said. “I have this tremendous experience with the criminal justice system. For 16 years, I prosecuted criminal cases, thousands and thousands of cases.”

In the Town Justice Court, Filer says, a judge’s temperament is perhaps the most important component to the proceedings the members of a local community will experience.

“It’s all about temperament — I’ve worked with many judges over the years, all of whom were good with the law, but some, somehow, lost respect for the people in front of them,” he said. “It’s one thing to follow the facts and apply the law in a balanced and unbiased way, which all judges must do, but as important as that is how you treat people. Court is where the law hits people in the face. Court is a frightening place.”

The justice system in general, he says, needs to improve its resources and methodology for dealing with people with mental illness or addiction issues — and often both — and needs to find better ways to help those charged with crimes find a path back to the straight-and-narrow so that they do not become repeat, or chronic, offenders.

As justice, he said he would like to see the local courts improve their communication to those coming through their doors about services available to them — from domestic violence counseling, to addiction treatment to the rights of a tenant being evicted.

The Town Justice Court has done a good job of adjusting to the growth and change in the community in the decades since he graduated from East Hampton High School, he said, but needs to grow in practical ways to deal with the changing faces of those in the audience.

Filer said that as a justice, he would focus on respect and compassion for those before him — when appropriate.

“I’m a law and order guy — with my experience, I have no tolerance for violence — but everyone needs a fair shake,” he said. “Some people need help, some need jail. And some need a second chance.”