A “Lost Cause” Finds His Way: On Isaac Fitzgerald’s “Dirtbag, Massachusetts: A Confessional”

“I WAS BORN of sin,” writes Isaac Fitzgerald, “a mistake in human form, a bomb aimed perfectly to blow up both my parents’ lives.” The product of a fling between two restless, bookish, devoutly Catholic divinity students who were already married, “just to different people,” Fitzgerald internalized his origin story as shameful transgression.

Fitzgerald’s debut memoir, Dirtbag, Massachusetts: A Confessional, is about stories he inherited and sometimes invented, stories he dodged or clung to or performed, often in self-destructive ways, until he began to confront himself. This negotiation between received “truths” and capital-T Truth is the work of every memoir, one could argue, but Fitzgerald’s project of openhearted self-interrogation still feels refreshing in a culture where men are socialized to bury their pain, or worse, turn it back on the world as misplaced resentment.

In 12 linked essays, Fitzgerald tracks his coming of age from his early years in Boston and the depressed town of Athol, Massachusetts — “a hill town surrounded by river towns, all of them now emptied of hill people and river people” — to a scholarship ride through boarding school, to his adventures in biker bars and queer artistic spaces in San Francisco and New York City, where he began to find his tribe.

His parents stayed together, but the union was wracked by emotional and financial strain. The family spent Fitzgerald’s early years in Boston’s South End, where they lived in a halfway house run by the Catholic Worker while his mother did admin for Cardinal Bernard Francis Law — described as having “one of those big slabby Boston faces,” an image that had this Boston resident laughing in recognition. Fitzgerald learned bar tricks from guys in soup kitchens and tagged along to his mother’s cathedral job, leading to at least one close call with a priest. But it’s a time he nonetheless remembers fondly. “I was poor but cared for […] nobody told me I was supposed to be miserable,” he writes.

When the author and his mother moved to North Central Massachusetts, next door to his judgmental grandmother, things went south. His father, who stayed behind for work, began another not-so-secret affair in the city. In her despair Fitzgerald’s mother used young Isaac as a sounding board, openly threatening self-harm and recklessly oversharing. At one point, she wondered aloud if she should have aborted him. “I didn’t react,” he writes, after describing heat rippling off the road. “I just stared at the glistening blacktop, wishing the waves were real and the water below so deep it could swallow up the entire car, taking us along with it.”

His father, after rejoining the family, beat Fitzgerald in the shower. “I learned that these things — her sadness, his anger — were mine as well,” Fitzgerald writes. “I claimed my inheritances.” His shame soon gave way to adolescent rage and escapism, though his parents’ love of books and faith in learning also stuck with him. “Your parents’ obsessions can so often become your obsessions,” he observes, “especially if your parents themselves are hard to hold.”

Fitzgerald’s radar for story has served him well in the literary world: he co-founded The Rumpus and did stints at McSweeney’s and Buzzfeed, earning a reputation as a buoyant managing editor and shepherd of fearlessly honest writing. More recently, he authored the children’s book How to Be a Pirate (2020) and has charmed viewers as an infectiously stoked recommender of books on NBC’s Today show. He doesn’t dwell on those professional highlights in his memoir, however. Instead, he keeps his eye on his journey of personal reckoning.

Amidst the pain, Fitzgerald is entertaining and often funny as he reveals how his anger and hunger for validation found risky outlets. Seduced by the 1999 film — and Brad Pitt’s turn as “manic pixie dream boy” Tyler Durden — he and his friends started a “fight club,” pummeling each other to beat back feelings of worthlessness: “The mood was bloodthirsty and cheerful; usually we were rooting for both [participants]. No winners or losers, just the guy who stayed up and the guy who went down.” As with the bars he’d haunt later, he sought spaces where violence buzzed in the air, but felt controlled.

In another essay, Fitzgerald chronicles his missionary work with the Free Burma Rangers, who smuggle humanitarian aid across the Thai border. Despite some good deeds — including a charming sequence where he playfully rounds up kids for eye exams — he ultimately looks back on his zealous risk-taking with skepticism. “[B]y putting myself in illegal and sometimes dangerous situations,” he writes, “I got to have my white-boy adventure-tourism cake and eat it too.”

And yet, despite the tough guy trappings — the motorcycles, the tattoos, even a brief turn as a porn extra — Fitzgerald is chronically nice. At Zeitgeist, the biker bar that became his spiritual home, he is scolded for being too friendly to patrons, who expect a rougher edge. At the aforementioned porn shoot, he worries about hurting the female director and star, who nudges him, “[Y]ou can choke harder next time.”

Fitzgerald’s charm opens doors, but he recognizes it as the mark of an abuse survivor and explores its downsides. In “When Your Barber Assumes You’re a Racist, Too,” he grapples with his trouble speaking up when other men, noting his Proud Boy–esque haircut, expect him to validate their casual racism and misogyny. “I was plunged into so many moments from the Telling on Oneself Hall of Fame that I started to wonder if there was something about me that made these dudes want to talk about the worst shit on their minds,” he laments.

Through it all, Fitzgerald presents himself as an earnest work in progress — a salvaged “lost cause” in the mold of Saint Jude, the apostle whose name was regrettably similar to the traitor Judas Iscariot’s, and whose image is inked on the author’s arm: “I loved him […] because I loved rooting for the underdog and witnessing the miracles that can bloom out of low expectations. The miracle of even trying when failure and ignominy haunt your steps.”

Eventually, his steps lead him back to his family of origin, despite years of distance and the scars. In “High for the Holidays,” a vignette-style essay that artfully suggests tensions between the lines, he describes a trek up Mount Kilimanjaro with his half-sister and his father, with whom he shares a cramped tent and whom he struggles to forgive, even as the family gels anew around his half-siblings’ kids. “There had been no great conversation,” he writes. “We just walked up a mountain together. One foot in front of the other. Either me looking at his back or him looking at mine. He was a different man and I was a different boy. Polé, polé. Slowly, slowly.”

At times, the essays in Dirtbag, Massachusetts fold back on themselves in ways that can feel recursive. But this is what trauma does: it refuses to go away; it demands revisiting. In their casual, looping trajectories, some of Fitzgerald’s essays seem to mimic active processing, like a heart-to-heart over beers. It takes a great deal of trust to commit one’s shames — and more than that, the shames of others — to the page with honesty. Messily, lovingly, Fitzgerald lays it bare.

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Dorian Fox is a writer and freelance editor whose essays and articles have appeared in Brevity, The Rumpus, Gay Magazine, SmokeLong Quarterly, McSweeney’s Internet Tendency, Creative Nonfiction’s “Sunday Short Reads,” and elsewhere. He lives in Boston and teaches writing courses through GrubStreet, Pioneer Valley Writers’ Workshop, and Creative Nonfiction Foundation.