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Jay Boyarsky, a Palo Alto resident who currently serves as second-in-command at Santa Clara County District Attorney’s Office, is once again running to become a judge — this time in the neighboring San Mateo County.
Boyarsky is preparing for a June showdown against Brian Donnellan, a veteran prosecutor with more than 20 years of experience in the San Mateo County District Attorney’s Office. Both candidates have told this publication in interviews that they believe their decades of experience as prosecutors in their respective counties have positioned them well for the next step in their respective careers.
The June contest gives San Mateo County voters a rare opportunity to choose a judge. Superior Court judges serve six-year terms, but they routinely get retained during elections with no competition. The county’s current roster of candidates for the June 2 primary includes nine Superior Court judge seats. Only one of them lists more than one candidate.
In this case, Boyarsky and Donnellan are vying for a seat that opened because of the recent retirement of Judge Susan Greenberg.
But even though competitive races for judge are relatively rare, the June primary is Boyarsky’s second bid for an opening in two years. In 2024, he squared off with Johnene Stebbins to fill a Santa Clara County Superior Court seat that became vacant when Judge Vincent Chiarello retired. Stebbins, a former Santa Clara County deputy district attorney, prevailed in that race and assumed her new role in January 2025.
In recent interviews, both Boyarsky and Donnellan point to their strong local connections as an advantage. Donnellan was born in Ireland, and after a stint in Burlington, Vermont, moved to San Mateo County in 1983 to start fourth grade. His mother worked in municipal government in Vermont and then as a deputy treasurer in San Mateo, while his father was president of Notre Dame de Namur University in Belmont.
“I see both as having public-service-natured careers, and it was kind of implanted in me,” Donnellan said.
After several years in the airline industry, Donnellan enlisted in the U.S. Army and was deployed to Iraq in 2004 to work in logistics. In early 2005, he returned to San Mateo County and began his work at the district attorney’s office. Among assignments that he finds most meaningful is his work at Veteran’s Treatment Court, which helps connect veterans who get caught up in the justice system to critical services, he said.
“It matters a lot to me, and it also gives me perspective and insight in dealing with folks who are also dealing with substance abuse, PTSD and a myriad of problems that makes them ‘justice involved,’ ” Donnellan said.
He cited his strong connection to San Mateo County and his long list of endorsements from county judges, attorneys and politicians. That includes state Assembly member Marc Berman, U.S. Rep. Kevin Mullin and San Mateo County District Attorney Stephen Wagstaff, according to his campaign website. It also includes many of the Superior Court judges who would be his colleagues if he is elected.
Boyarsky, for his part, is undaunted by his opponent’s homefield advantage. For one thing, Palo Alto is at the northern edge of Santa Clara County and Boyarsky notes that he lives closer to the courthouse in San Mateo than the one in San Jose.
He also said he would not face the same types of conflicts of interest that a San Mateo County prosecutor like Donnellan would face as a judge on criminal cases.
“If someone comes from the District Attorney’s office and goes right to the bench, they’re typically conflicted from sitting on criminal matters for at least a year or two, especially if it’s a second-in-command like someone like me,” Boyarsky said. “Because I don’t practice in San Mateo County, there are no such restrictions. I wouldn’t be conflicted from handling criminal matters in San Mateo County.”
He also noted that the governor regularly looks to adjacent counties when filling a judicial appointment. Donnellan countered that he does not expect to have many recusals, if any, noting that his caseload represents just a tiny fraction of the many cases that San Mateo County judges face, which include civil, criminal and family court cases.
Boyarsky is hoping to counter Donnellan’s list of San Mateo connections with support from elected leaders in his own county. His supporters, he said, include U.S. Rep. Sam Liccardo and Santa Clara County District Attorney Jeff Rosen.
Boyarsky also pointed to his own extensive experience. He has been an attorney for more than 32 years and has appeared in front of more than 100 judges, he said. After graduating from U.C. Berkeley School of Law in 1991, he worked at the San Francisco firm of Steefel, Levitt & Weiss before joining the Santa Clara County District Attorney’s office, where he currently serves as chief assistant district attorney.
He cited in an interview his wealth of management experience in a position that oversees about 200 attorneys in the district attorney’s office.
“I would bring a lot to the bench and I want to serve,” Boyarsky said. “I want to contribute and I’m ideally suited.”
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