The first time I met Isaac Fitzgerald, I accidentally walked into his birthday party at a bar that had been closed to the public for the occasion. Except you wouldn’t know it was a private event by the reception he gave me when I walked in the door. He didn’t know me any better than the other strangers walking down Grand St. that night, but as soon as I crossed the threshold, he made me feel like a friend. Though our paths have only crossed once or twice since then, he’s still genuinely happy to remake our acquaintance, and I can only imagine the love that he showers on his family and friends.
That’s the man he is today, but it could have gone much differently based on the stories that made up his youth and early adulthood. We’re all a sum of parts and experiences, and in his memoir, Dirtbag, Massachusetts, he lays out all the places on the map that led him here. From his start in a Boston homeless shelter to the fish-out-of-water experience of boarding school to big cities like San Francisco and New York, there was no shortage of fights and drinks in between.
Fitzgerald calls the book a confessional, an ode to his Catholic altar boy roots, and it does seem like he has a few things to get off his chest: a stint in pornography, low-level health insurance fraud, and smuggling medical supplies into Burma to name a few.
Then there are also the confessions that draw us closer to where he wants to be: his lifelong struggle to be comfortable in his body, his recognition of the traumas his own parents endured, and the decision that kids of his own aren’t in the cards. It’s in the retelling of his formative mistakes that he’s also able to see his progress.
Isaac’s story is by no means a blueprint or a parable with a tidy moral. It’s an account of someone who’s done stupid things, hard things, and loving things, and is now consciously steering toward a healthier destination.
We don’t typically crown unfinished journeys as success stories, but the beauty of this tale is its midway vantage point, a resting place where you can see how far you’ve come and know there’s a lot more still to go.
If you’re interested in buying Dirtbag, Massachusetts, find your nearest independent bookstore here or order it from Bookshop.org here.
Forgot to mention that Isaac has a great substack of his own: https://walkitoff.substack.com/
Thank you so much for these kind words, Jack! I so appreciate you taking the time to write about Dirtbag, Massachusetts. See you soon, I hope! 🙏🏻💚✨