Jerry Oshinsky: July 12, 1942 – April 9, 2024

Jerry Oshinsky, known professionally as one of the true titans of insurance coverage law, passed away on April 9, 2024, from complications related to Parkinson’s disease. I was privileged to work with Jerry at the very end of his life – because I am also a lawyer, sure, but mostly because I have the good fortune of being his son – and so when he needed help winding down his practice, the effects of Parkinson’s having started to take their toll, I was both saddened and honored to be able to step in and try to help. This, then, is my attempt to remember and honor Jerry Oshinsky as I knew him – as father to me and my sister, Ali, as father-in-law to Kim and Geoff, as grandfather to five grandsons, as husband of 59 years to his wife, Sandy, as brother-in-law to Sandy’s sister Chelle and her husband Andy, and as an irrepressible source of wit, wisdom, enthusiasm, generosity and curiosity to pretty much anyone lucky enough to cross his path at any point during his magnificent 81 years. 

The Jerry Oshinsky I knew, after all, was so much more than the sum of all his legal wins and accolades (of which, rest assured, there were very many). As you might expect, a lot has been written about my dad’s storied legal career and far-reaching influence; I will not try to improve upon or even repeat it here. If you want to know more about his legal career, I would point you to the bio on his website, this 2023 Lawdragon feature piece and lengthy interview, and this Chambers Associate interview from 2013, given when my dad was honored with a Chambers USA Lifetime Achievement Award. 

To his colleagues in the law game, Jerry Oshinsky was known as the “dean of the policyholders’ bar,” as respected and adored by his clients as he was feared (and, to be fair, also respected) by his adversaries. But to his five grandsons, Sam, Joey, Charlie, Jack and Mo, he was simply “Babu,” and wow did they ever adore him and love spending time with him – though I can’t imagine anything that could possibly match how much he loved and adored them, and what a pleasure it was to witness the joy that they brought him, something that only increased as they grew and began to find interests that were also interests of his. 

In me and my sister, my dad fostered a deep and life-long love of sports – both as participants (as you might imagine, family doubles matches could get pretty intense) and as spectators. Thanks to him, we got to see a Super Bowl (though please let’s not talk about the result), tennis at the U.S. Open, Stanley Cup hockey games (let’s go Caps!), NBA playoffs…and the list goes on and on. And his excitement to share this love of sports (and so many other things – music, wine, theater, travel) wasn’t limited to me and Ali – our Aunt Chelle will tell you that Jerry was like the brother she never had, and so many of our childhood friends have reached out to tell us the ways that he was like a second father to them, always happy to grab an extra seat or two at games or shows so we could bring them along for the fun. 

Once grandkids entered the picture, there was no length to which Babu would not go, no expense that Babu would not spare, to get to see his grandsons in their element, whether that was playing soccer or tennis or basketball or baseball or acting in a play or singing in a school concert or – really, if they were doing it, whatever it was, he wanted to see it. And because there was so much more he loved to enjoy – LA Clippers and Dodgers games, Messi on the soccer pitch, Hamilton on Broadway (four times!) – nothing made him happier than to get to share that love with his grandkids as well, taking them with him far and wide to watch games and see shows as often as he could. 

Indeed, Jerry was something of a “professional spectator,” though certainly not content to simply sit and watch a superb athlete in his youth, he was also quite the performer and entertainer himself, having studied acting and then acted in and produced dozens of plays and readings, especially over the past 20 years as he moved his practice from Washington, D.C. to Los Angeles and then Santa Barbara, California, a move that allowed him more time to hone his acting chops and even learn to play a little ukulele. I’ve lost count of the total number of ukes he ultimately acquired (definitely more than 10), but if you were to stop by to visit him at home in Santa Barbara in recent years, you would most likely find him in a living room chair, ukulele in hand, noodling away on some new tune he was trying to work out. Not even the steady, debilitating creep of Parkinson’s was going to completely deprive him of that pleasure. 

And no tribute to my dad would be complete without a proper mention of his adoration of and life-long commitment to his trophy wife (as he would always lovingly describe her), Sandy (also mom, as Ali and I know her, and Grammy, which is what the grandkids all call her). With their six-decade commitment to each another, my mom and dad provided a model for love, friendship, and interdependence that all of us in the family witnessed, learned from, and were better for. Without my mom supporting and managing so much of my dad’s life, my dad would have had a very different and far less successful legal career – something that was certainly not lost on my dad, and for which his gratitude was evident and frequently expressed. 

So now there is this gaping, Babu-sized hole in all of our lives. We will all have to come to terms with the loss in our own ways, something I know won’t be easy for any of us, given all of the changes that will take some getting used to – the empty seat at the kitchen table, the TVs not constantly tuned to English Premier League football or NBA games, Alexa not being asked to play show tunes, no ukuleles being plucked (ok, so maybe people aren’t so broken up about that one). We will be constantly reminded of his absence as we learn to get by with less laughter, less love, and a little more quiet in our day-to-day lives. 

For what it’s worth – and I do believe this helps – his was a peaceful and comfortable end, and it found him surrounded by his family in a room that was full of love, gratitude, laughter and music. In his final moments, he was serenaded by Neil Diamond, Jake Shimabukuro, the cast of Hamilton, and of course Don McLean’s “American Pie,” and I have little doubt that all the possible interpretations of that last one kept him busy right up until the end – and I sure hope that, wherever he is now, Buddy Holly, Richie Valens and the Big Bopper are there to entertain him, happy to have him singing along, and maybe even answering some of his lingering questions.