On the Cutting Edge

Growing up, Kevin Benedicto was taught to never take the importance of the rule of law for granted.

His grandfather was a lawyer in the Philippines, and his parents wound up fleeing their homeland due to the dictatorship of Ferdinand Marcos. “They really always instilled in me and my sister that they came here to give us a chance of a life in a country that’s governed by the rule of law,” Benedicto says. “It was the fairness and impartiality of our legal system and our society that led my parents to come here.”

Though he worked a few years as a teacher, it was ultimately that appreciation of the United States’ legal system that led him to law school in 2012. “I was so inspired by my students, but also that the story of a lot of issues in our society is about systems—and the way in which they can cause unfair outcomes,” he says. “A legal degree was really a degree in how to navigate complex systems.” 

Benedicto’s practice, first at Redgrave and now at Benedicto & Simonovich, focuses heavily on commercial litigation, artificial intelligence and e-discovery. “I love working at the intersection of law and technology, because it is always changing. Discovery is becoming more sophisticated,” Benedicto says. “Every exhibit in a trial is there because it was produced in discovery. Every statement that a witness said at a trial was first said at a deposition during the discovery phase.”

This means there’s rarely a dull moment. “Every day is different, and every month and every year,” he says. “[Having] the ability to jump in when your clients have the biggest problems that they haven’t been able to solve, and learning their industry … and then jumping to another client—a whole other industry and learning that field—I think there’s something really nice about helping clients … in a way that you get a lot of variety.”

AI, in particular, is a growing practice area for Benedicto, who counsels clients on best practices and also represents them in litigation stemming from AI. He notes that the law is being written in real time. “It’s building the plane as it’s flying,” he says. “The time for asking, ‘Is AI going to have an impact on legal practice, on our clients?’ has passed, because the answer is clearly yes.”

Now is the time, he adds, to ask how to deploy AI responsibly while maintaining protections like confidentiality and privilege. With Redgrave, he recently filed an amicus brief in the U.S. Court of Appeals for the District of Columbia Circuit on a privilege question. “You see more and more of these issues arising when parties are trying to get access to more potentially privileged documents. Or, as we’re seeing, what interactions with AI cause privileged projections to attach or not attach. Getting to be on the cutting edge of that issue was a real privilege.”

The skills he developed as a neutral serve him well in his volunteer role as a hearing officer for the Police Commission, the civilian oversight body of the San Francisco Police Department. Benedicto was appointed to the commission in 2022, having previously investigated SFPD’s use-of-force practices on a pro bono basis in 2015. “I spent about a decade working on building up this expertise on law enforcement and criminal justice reform,” he says, “working with departments and civil rights advocates around the country to improve their use-of-force policies.” 

During the 2020 election, Benedicto served as a voting rights fellow at the Lawyers’ Committee for Civil Rights Under Law. “There was just a ton of litigation,” he says. One case in Alaska centered on the state’s requirement that each absentee ballot be signed by a witness. “Since everyone was sheltering in place, and Alaska has the highest percentage of people living alone—and living hundreds of miles from their neighbors—the Lawyers’ Committee brought litigation to ensure that, under constitutional basis and emergency, some of those standards could be relaxed.” 

Another case dealt with a power outage in Virginia that knocked out voter registration servers just before the registration deadline. “We were able to work with the state attorney general and file a brief … to get the registration deadline extended 72 hours. In that time, 20,000 or 30,000 people were able to register.” 

After Election Day, he joined litigation across the country to ensure votes were properly counted and that the election itself was certified. “It was an incredibly rewarding but challenging experience to be able to work as a civil rights lawyer in voting rights at one of the most important voting rights-related periods in our history,” Benedicto says. “The power that lawyers have in our society to navigate these systems that are so opaque and so confusing—I think we often underestimate how much power that really is.” 

An uncle to four nieces and nephews, Benedicto says, “Everything I do, I’m looking at them. Whether it’s voting rights, criminal justice reform or work in private practice, to give them a society that’s just a little fairer, that has its guardrails, that they won’t have to fear, and that they know that their systems are fair and protected, is my motivation.”