Category Archives: The Story Behind the Characters

Boston History in the Novel

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History as Inheritance

Boston history runs in my blood. One side of my family made its start in the city a century ago and settled on Zeigler Street in Roxbury. The other half began in South Boston and Dorchester around the same time. They were all Irish immigrants. And they lived through the political power shift led by figures from James Michael Curley to John B. Hynes and finally Raymond Flynn. It brought the Irish from underdogs to top dogs at the local and state level.

I inherited that legacy, both the good and the bad. My own generation lived through the last of those years as the city continued to evolve. There were new cultural shifts and more immigrants from different parts of the world.

Our Common Ground: The T

One thing familiar to anyone who’s lived in the city over the last 100 years is the T. It’s the network of trains, trolleys and bus lines connecting the different neighborhoods. It spreads like a system of veins and arteries that flow underground, overhead and beneath Boston Harbor. It’s also been described as a hub with spokes. The different routes are color-coded in red, blue, green and orange.

An illustration of Boston's MBTA transit routes, including the Red Line, Orange Line, Blue Line and Green Line.
Whether it’s running well of breaking down constantly, people in Boston rely on the T to get where they’re going every day.

The T was used by my grandparents and parents to commute every day to work, and to visit relatives and friends. When I was about ten, my friends and I started finding ways to sneak into subway stations without paying. We’d explore the city that way, and sometimes get into some interesting trouble. As a teenager, I rode the Red Line from Ashmont Station in Dorchester to Boston Latin five days a week. After school, it was the Green Line that delivered me to a part-time job in Allston and to baseball practice near Cleveland Circle. In fall, the Orange Line took me to cross-country practice at Franklin Park.

Another thread running through the fabric of Boston history and my family history is sports. My dad played in an amateur baseball league until he was twenty. In one game at Fields Corner, he was jogging across the infield when he spotted Babe Ruth sitting in the stands. The retired Sultan of Swat was wearing his trademark raccoon coat to ward off the blustery winds of an early-spring day.

Sports in Boston History

My dad took the Red Line to work at 6:15 every morning, and I boarded a half hour later for school. Sometimes though, we’d travel the T together. We’d go to baseball games at Fenway, hockey games at the old Boston Arena, the Boston Garden and BC’s McHugh Forum. The first time we rode it to BU’s brand new Walter Brown Arena, he pointed across the street to Nickerson Field. It’s where Boston Latin played Boston English every November in the traditional Thanksgiving Day football game. “That’s used to be a baseball field where I watched the Boston Braves.”

A photo of Fenway Park in Boston, taken from the stands near home plate.
Built in 1912, Fenway Park is a landmark familiar to generations of people who have lived in Boston.

Every neighborhood of the city had its own character. That’s what I learned after I finished college and moved out of Dorchester. Through my twenties, I shared apartments in the Back Bay, Roslindale, Somerville and Brighton. To pay the rent, I was a sandblaster, painter, chimney sweep, and a residential and industrial roofer. I waited tables at a Northern Avenue restaurant called Jimbos, worked at a downtown company called Pilot Executive Software, and memorized the tangled layout of Boston streets while driving a taxi.

The Many Takes From Street Level

When you work as a cabdriver in a city, you know a lot, more than just the best routes to the airport during rush hour. You learn everything going on in the different neighborhoods, down to specific streets. You become a scholar of the whole culture and its many subcultures.

Waiting at a cab stand for my next fare, I liked to scan that day’s Boston Globe. I’d read about the latest political drama playing out on Beacon Hill or at City Hall. Billy Bulger was often the main character in those stories. His brother Whitey would sometimes compete for the same space on page one with his latest underworld schemes. The media liked to refer to Whitey as the head of the Irish mob. It was maybe too grand of a title, but he certainly was a major player in the New England drug trade and other rackets.

Irish American Whitey Bulger
In 1984 Whitey Bulger Schemed With Pat Nee and Joe Murray to Run Guns to the IRA.

Through the Lens of a Writer

That was around the same time I began to consider a future as a writer. Not that my writing consisted of much more than some journaling and a few attempts at short stories. But I could imagine a grand storytelling canvas on which Boston’s local dramas could play out.

Those dramas included school desegregation in the 70s. I write more about that in a post titled Boston and Its Busing Problem. It was a time when South Boston politicians like Billy Bulger, Louise Day Hicks and Jim Kelly were resisting change and stirring up animosity. There were some, like Ray Flynn, who opposed busing but spoke out against racial rhetoric and violence. For refusing to join the more militant group, Flynn’s car was firebombed and his family received death threats.

I followed the lives of those major figures when I moved to Seattle in the 90s. It continued when I returned east to attend the MFA program at Columbia University in New York City. In my thesis workshop, I sketched a narrative landscape that would become my first novel—The Chieftains of South Boston.

Pulling From Many Sources of Boston History

After coming up with a general plot structure, I began the heavy research. Next to the building that housed Columbia’s Graduate School of the Arts was the School of Journalism. My ID gave me access to their library and its LexisNexis research system. I dug up every detail I could about historical events during the 70s and 80s. After printing stacks of pages, I highlighted, hole-punched and organized them into 3-ring binders.

I did the same with newspaper stories available on microfilm at the New York Public Library in Midtown Manhattan, and later at the State House Library in Boston.

In addition, I pored over several books, including the following.
Common Ground
The Boston Irish: A Political History
The Rascal King: The Life and Times of James Michael Curley
South Boston: My Home Town
Black Mass
All Souls: A Family Story From Southie
Valhalla’s Wake
The Brothers Bulger
While the Music Lasts: My Life in Politics
The Bulger Mystique
How the Irish Became White

Some of the scenes were informed by the memories of people in my family, like my dad. He once told me about the time in his his teens when he worked at the Boston Public Library. Cardinal O’Connell would stop by occasionally. According to my dad, O’Connell would be dressed in formal ceremonial garb with purple robes flowing, and he would stride through the place as if on parade.

That was in contrast to Cardinal Cushing, who succeeded O’Connell. Cushing was much preferred by Boston’s working class community. They considered him the salt of the earth in contrast to O’Connell, who was caught up in the trappings of his office. I found a couple of places to slip those figures into the novel.

The Bulger Brothers as Inspiration

I pulled other relevant piece of Boston history into the narrative, and every major Boston player. Beyond the Bulger brothers and other South Boston players, there were leading figures across the city. Among them were the Angiulos, who ran the Italian Mafia out of the North End. Also John Connolly, Whitey’s childhood friend and handler at the Boston FBI field office. And politicians like Ray Flynn, mayor of Boston and Billy Bulger’s sometimes ally, sometimes opponent. They competed for the title of South Boston’s most influential leader.

The Bulger Brothers: Billy Ran the State House, Whitey Ran the Irish Mafia
The Bulger Brothers: Billy Bulger Ruled the State House— Whitey Bulger Ruled the Irish Mafia

Certain historical events were easily adapted to the Jimmy Mahoney character. There was Billy Bulger’s unexpected rise to Senate president, his press-conference-turned-debate with Mayor Raymond Flynn in front of the State House, and the way Bulger twisted the arm of Governor Dukakis, who was running for the White House, to end Boston’s garbage disposal crisis on terms favorable to Bulger.

I did the same when building the character of Francis Mahoney. I pulled in details and plot lines from the world of Whitey. One was the triangle trade of drug dealing and the shipping of arms to the IRA. Then there were the various murders attributed to Whitey, his complicated relationships with the Italian Mafia and the FBI, and the destruction of lives in South Boston when Whitey unleashed a flood of drugs into the neighborhood, all the while pretending to be its protector.

My Personal Boston History

My first-hand experiences enter into the story in different places, like witnessing the chaos and racial strife of school desegregation, and attending games and concerts at Boston Garden. There’s also the character Buzzy Driscoll, who earns a living as a Boston cab driver. Those details are drawn directly from my time behind the wheel.

Then there were occasional visits to South Boston itself. In one scene, Matthew Mahoney recalls watching the Saint Patrick’s Day parade from the roof of Flanagan’s Supermarket on Broadway. That was what I did at the age of fourteen with a handful of buddies. We shimmied up a pole at the back of the building, then watched the parade from our comfortable perch.

A photo of the front Flanagan's Supermarket on East Broadway in South Boston from back in the 90s.
Flanagan’s Supermarket on East Broadway in South Boston back in the 90s.

There are plenty of other places in the novel where my memories inform the book—too many to list, really. Overlaying those details is my intimate knowledge of the Irish American working class culture in that particular place, during that particular time.

I finished The Chieftains of South Boston fifteen years ago. When I look back at the details of the story now, it’s not always easy for me to distinguish between the actual history of the place and my fictional rendering of it.

The Brothers Karamazov, Set in South Boston

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How the Novel Began

The Chieftains of South Boston was born in a graduate seminar I took while earning my MFA at Columbia University, with a little help from Dostoevsky’s The Brothers Karamazov.

One seminar assignment was to sketch out a novel. Over the course of a few weeks, we were supposed to refine our concept so that we’d have some sort of structure to use if and when we chose to leap into the writing of a book-length work of fiction. A crutch, if you will, against the doubt and fear that grip a writer launching into the unknown.

I began with a set of characters from the world in which I grew up. They were mostly politicians, some from South Boston. The milieu was the 70s during the turbulent time of desegregation in the city, when I came of age. I ended up with life-based characters floating in an undefined soup of story.

Dostoevsky’s Structure

The professor leading the seminar made a very useful suggestion: Select a novel I admired and copy its structure. Use it as a way to organize my ideas and feelings around my milieu. I wouldn’t need to follow the structure for the entire novel, but rather use it as a point of departure to get my story off the ground. At some point in the writing, probably early on, the story would assume a life of its own and I could lose the crutch.

I’d recently read The Brothers Karamazov by Dostoevsky and was really gripped by it. The story is a family drama involving a cruel father, Fyodor Karamazov, and his three sons. The older brothers, passionate Dmitri and philosophical Ivan, hate their father. The youngest, Alyosha, is a novice monk who doesn’t share his siblings’ feelings. Instead, he tries to guide his father toward redemption and a spiritual path.

There’s also a half-son, Smerdyakov, who has his own reasons for hating his father. When Fyodor is murdered, it appears that Dmitri is guilty. Ultimately, it’s revealed that Smerdyakov has committed the act.

The book covers for The Brothers Karamazov and The Chieftains of South Boston
Screenshot

The Brothers Karamazov Becomes The Brothers Mahoney

That’s the basic structure I took from The Brothers Karamazov. I lined up my main characters this way:

The Karamazov family would be the Mahoney family living in South Boston. The Dmitri character would be Francis Mahoney, head of the Irish mob. Ivan would be Jimmy Mahoney, the politician poised to become president of the state Senate. The two of them would be inspired by the famous South Boston siblings, Whitey Bulger and Billy Bulger.

Even as I began applying it to The Chieftains of South Boston, I found myself changing the structure in small ways. The biggest shift came with the third brother. Matthew Mahoney would not be like Alyosha. Instead, he would join his brothers in hating their father Salty Mahoney. The opening chapter would be from Matthew’s point of view (the second chapter would be from Francis’, and the third from Jimmy’s). The subsequent chapters would weave all three together.

Matthew Mahoney and Buzzy Driscoll

Matthew would be the most accessible character in the novel, the one through which the reader would experience the heart of the story. His brothers, on the other hand, would be larger than life. The reader wouldn’t have access to what schemes Francis and Jimmy were plotting in their respective worlds until events unfolded. With Matthew, the reader would know more than he does and would be aware of the traps he was about to step into. Again, this brings the reader closer to his perspective.

In The Brother Karamazov, the identity of Smerdyakov as the half-son is revealed early on. In The Chieftains of South Boston, the identity of Buzzy Driscoll as the half-son of Salty Mahoney is withheld until later in the book. It’s important that Matthew not know that Buzzy, his best friend from childhood, is his half-brother. Francis is aware of the fact, and Jimmy suspects it.

The murder of Salty Mahoney occurs at the end of the first chapter. All evidence points to Francis as the culprit. As with Dmitri, Francis is guilty of many things in his life as a mobster but not this particular crime.

Capturing the Time and Place

After the initial setup, the novel took its own course, guided by the main characters, and the energies and conflicts within them. All of it was filtered through the zeitgeist of the mid 70s and late 80s, and through the platzgeist of Boston during those years.

Side note: As I was developing the story in a thesis workshop, my advisor asked me if I’d ever read Freud’s writing on parricide. I told him I hadn’t. He paused before suggesting I not read any of it, presumably so it wouldn’t taint the experience I was having as I played out the drama in my creative bubble.

Anne Boushay — The Story Behind Her Name

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Anne Boushay and Essential Bakery

Anne Boushay is not a name that I composed from an online list or from anybody I’ve ever known. It was a serendipitous discovery in 2006, when I quit my full-time job and began writing the first draft of The Chieftains of South Boston. I wrote twice a day, mornings at Essential Bakery on E. Madison St and afternoons at various cafes, including The Victrola on 15th Ave. It was at Essential Bakery where Anne Boushay’s last name came to be.

Essential Bakery, Madison Valley
My morning writing spot— Essential bakery on E. Madison St. in Seattle.

Deciding on the name ‘Boushay’ took longer than I expected. With most characters in the novel, I’d settle on a name right away. Occasionally, I’d go through a couple of options before the name felt right and true. It’s a strange thing how writers come to land on names for their characters. It’s not really logical. At least not for me.

With Anne, I found the first name easily. For her last name, I struggled to discover one that would match her character and her backstory, one that captured a feeling about who she was (the women who inspired her character is another story.)

The Bailey Boushay House

I finally solved the puzzle one rainy Monday morning in March. I was staring out the window of the bakery. Across the street was the Bailey Boushay House. It’s a facility that provides care to patients with HIV/AIDS as well as end-of-life care for people with ALS and other complex conditions. The name was spelled out in big letters.

Anne Boushay name inspiration
The Bailey Boushay House — inspiration for Anne Boushay’s name.

I had never heard the name Boushay, so I tried it out. Anne Boushay. The sound seemed to work for me. And it suggested some creative possibilities for family history.

As a last name, Boushay is fairly rare. I found very few references to it online. So I used it as I started writing chapter one. Later in the story, I introduced a history of the name in Anne’s family. Boushay would be the phonetic spelling of the French name ‘Boucher.’ That kind of mutation happened occasionally to immigrants arriving in America. Rather than look at someone’s passport for the correct spelling of their name, an immigration official might ask someone to pronounce it. The phonetic verison would then be spelled out in official documents in a way that seemed logical to the American ear. Which is how many name variations came into being.

Dropping the “O” and Taking the Soup

Usually it was unintentional, but not always. Here’s a story I’ve heard, which may or may not be accurate. It’s about Irish immigrants who were encouraged to drop the ‘O’ from their last name so it sounded more American. As the story goes, the immigrants were enticed by the offer of a free bowl of soup. In Irish-American neighborhoods, someone named O’Leary might say to someone named Leary, “So your family took the soup.”

Anne’s grandparents emigrated from France and arrived in America during Prohibition. At that time, a Frenchman by the last name of Boucher was notorious for running illegal liquor from Canada into New York and New England. To avoid association with the rumrunner, Anne’s grandparents didn’t protest the misspelling of their name but adopted ‘Boushay’ as part of their new American identity.

In The Chieftains of South Boston, Anne Boushay isn’t aware that her family name changed. But the subject is explored further in the sequel, The Mahoneys of West Seattle.