← Pocket Gerry
Gerald “Gerry” Finnegan
1970 – 2026
Dublin · Brookline · Waltham

Pocket Gerry is written in the voice and spirit of our dear friend Gerry Finnegan. If the memory of his warm, gravelly brogue still makes you smile, at least a bit, this page is for you.


I met Gerry on a dreary Thursday in April 2020. It was a crazy time. The city — the world — was shut. I bleached my mail, held my breath at the market, and ordered takeout often from the favorite neighborhood spots I couldn’t let be the latest victims of COVID-19.

Around that time, Encore Casino had just returned a thousand cases of Champagne, and Gerry was selling it out of his shop for almost nothing. A friend from my wine group put us in touch. I handed him a stack of cash and waited by my car. He came back with a stack of cases, and a question: “What are you doing tomorrow?”

It was a question I probably got a thousand times more from Gerry.

“Come by the store, we’ll open some good stuff.”

And boy did we!

Gerry came over from Dublin with a hundred dollars in his pocket and built a life around the Washington Square Tavern in Brookline and the remarkable people who found themselves on the other end of his pours.

Though he spent decades in the trade, rather than a wine professional, the best word for Gerry is amateur — in the old sense, from the Latin to love. He was a master of so many things, but never for any reason other than his love of them. Wine, mountain biking, the dogs, music/art/beauty, and the worst jokes you ever heard and could never retell.

He poured what he loved, because he thought it was the best. He introduced you to people the same way: not because they were important, but because he knew you’d love them. Humble, sharp, endlessly kind, quick to anger only at unfairness — and, in the best possible way, a bit like a bulldog puppy that got turned into a person.

Gerry died in February 2026, and if you found this website, you miss him as much as I do. I hope every turn of this app brings you joy, peace, and a reminiscence of our wonderful friend Gerry Finnegan.

Pour one for Gerry.
— Dan  (“Doctor Dan”)
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In loving memory of Gerald Finnegan