“His equanimity in the face of chaos was amazing, as was his ability to break a tense moment with an apt wisecrack,”  said Luanne Sacks, a friend and attorney who worked with him.

As much as he will be remembered as an astute litigator with a sharp wit, Jay’s personal life was as bountiful as his professional career. In 1989, he and Mary settled in Corte Madera in the shadow of his favorite Mount Tamalpais. He, too, was a life-long 49ers and San Francisco Giants fan. While his musical taste evolved, it was his early affinity for the Grateful Dead and its members that led him to attend scores of their concerts. Jay tackled even mundane tasks with the same curiosity he applied to his work. During the pandemic, when the nation’s restaurants were closed, he researched pizza makers and found one in Italy who could make and deliver his and Mary’s favorite pies.

At his core, Jay was an adventurer. He enjoyed mountain biking in Lake Tahoe with his daughter, Kelsey, cliff jumping in Hawaii, playing recreational league softball with his friends and braving Northern California’s chilly waters to swim at Stinson Beach. The family’s cabin in Lake Tahoe became a place for summer and winter retreats. Jay, too, was a creature of sentiment and habit; on the first day of family vacations he would play Bob Dylan’s “New Morning” to celebrate the moment with his wife and daughter. 

In 2015, the trio took a 17-day trip to Ireland and Scotland where the family explored their Irish heritage. Like so many other escapades, Jay researched the itinerary and planned it with zeal. When they got to their hotel room in Edinburgh, he pulled back the window curtain and surprised his wife and daughter with a majestic view of Edinburgh Castle high atop Castle Rock.  “He would get so excited to show us something,” Kelsey said. He coaxed the two to drive through the Burren, a desolate landscape in western Ireland etched by weather and age, to show them Poulnabrone dolmen, a Neolithic tomb he had read about.

Closer to home he was equally as intrepid. The family made not one, but two attempts at Jay’s urging to navigate the Alakai Swamp Trail on Kauai, one of the island’s most challenging hikes. There, they scrambled over rocks and slipped on muddy boardwalks until they reached Kilohana Lookout on their second try. “He loved pushing the envelope on adventure and taking his family along,” Mary said.

Jay is survived by Mary, Kelsey, his sister, Kerry Highland, his mother, Sara Connolly, and a large extended family.