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RIP Captain Pepa

 

This month, I’m sharing something a little more personal. I recently lost my father-in-law, Larry—Pepa to us—and below is the eulogy I had the privilege of delivering at his funeral. His life reminded me that some of our greatest lessons in leadership come simply from how we live, love, and show up for others.

 

When I think of Larry—who he was to me, and who he was to so many people — a few things immediately come to mind: his deep love of family, the way he always showed up for the people he loved, his art, his laugh, and, of course, how to enjoy a vodka martini – straight up, two olives.

I first met Larry in 1998, at his home on Fresh Ponds Road, about six weeks after Brad and I started dating. In that first meeting, Larry said, “Why don’t I build a house behind this house so you and Brad can move in and start having a couple of kids?” That’s not exactly how he said it but it went something like that and … It was music to my ears.

Larry and I were both ready to move this relationship along – we just had to make sure that Brad was on board.

And so he was and on June 25, 2000, Brad and I were married, and from that day on, Larry took me in. And I never, for even one second ever, felt like an outsider or an in-law. I simply felt like part of Larry’s family.

And then, about a year after we were married, on August 3, 2001, Ari was born, and Larry became Pepa—not just to Ari, but to me, too.

Like many other New Yorkers close to the scene at 9/11, Brad, Ari, and I had to leave our home in New York City and move in with Pepa and Grandma in East Brunswick, New Jersey. Brad would head back into New York City for work each day, and I could tell Pepa was very excited to be home with Ari and me.

I’d wake up each morning to freshly cut cantaloupe and brewed coffee, and then Pepa, Ari and I would take our daily ride into Princeton to see Pepa’s mother (Ari’s great-grandmother) Nani. We’d hang out at her house on Bank Street, and then the four of us would head out for lunch. And if I were lucky enough, Aunt Eunice would join.

So, for the first few years in New Jersey, besides Brad and Ari, I spent my days with Pepa, Nani, and sometimes Aunt Eunice. And they were all the family and friends I needed. I was perfectly content.

In fact, I often referred to Pepa as my best girlfriend in Princeton – which always made him laugh that great, familiar Pepa laugh.

Over the last 28 years, Pepa became my family, my friend, and someone I knew I could always count on.

One day, walking in NOLA, I saw a painting I loved. Pepa took a picture of it, and about a month later, he gave me his own painted version that proudly hangs in our hallway.

And quite a few years, in 2011 when I mentioned that our living room felt a little dull, a week or so later he gave us a beautiful, colorful painting of the Italian Riviera, based on a picture he had taken while visiting his grandson, Joey. It still hangs above our fireplace protected by me from a large flat screen TV.

That was Pepa. He listened. He remembered. And he found a way to let you know he was thinking about you.

His paintings are treasures to our family. And now I see another little piece of Pepa in Gabi’s paintings—not only in the same circular signature she inherited from him, but in her talent as an artist. It’s a talent that began with Pepa’s dad, Mor Nani, was passed down to Pepa, and now lives on in Gabi. L’Dor V’Dor.

I also remember Gabi coming home from preschool one day and declaring that Pepa was her favorite person. And I have to say, I was perfectly happy – actually thrilled – to relinquish that title to Pepa.

And when my dad passed away fifteen years ago, I said, “Pepa, you now have big shoes to fill.” And without missing a beat, he said, “I accept.”  … I knew I could say that to him. And I knew he meant it.

There is a beautiful idea in Jewish tradition that one way we can honor someone who has died is by carrying forward some of their best qualities—by letting the way they lived influence the way we live.

There are so many things about Pepa that I hope to carry forward—his gentleness, the way he listened, his love of family, and, of course, the way he always showed up.

But there is one other thing I’m going to do in his honor.

Pepa had a passion for sailing, and those in our family who sailed with him affectionately called him The Captain.

So even though I went to sailing camp for four years as a kid—and, embarrassingly, spent the entire time playing tennis and refusing to sail because I was afraid of the eels in the water—I’m finally going to learn how to sail.

Pepa, I promise: the next time Brad asks me to take sailing lessons or go on a sailing trip, I will say yes.

Thank you, Pepa. You loved me. You loved Brad, and you taught Brad—and all of us—by example how to be a wonderful parent. You loved Ari and Gabi. And you loved your whole family deeply—your children, their spouses, your grandchildren, your nieces and nephews. We all knew how much we mattered to you.

Okay, so you didn’t love Bear (our ten pound Cavapoochon). In fact, you hated her. Oh well. No one’s perfect.

But you taught me what it means to be family and how to show up for the people you love.

Just like you did. I love you, Pepa.

Your memory will be for a blessing and live on in all those who knew and loved you.

Lawrence (Larry) Bailey, 95, born in 1931, a beloved husband, father, grandfather, passed away September 25, 2026 (14 Tishrei 5787).

Click here for Larry’s obituary.