Boston History in the Novel

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.

Boston and Its Busing Problem — An Irish Family Feud

Why Did Busing Go So Wrong In Boston?

J. Anthony Lucas has perhaps the most interesting, and historically informed, answer to that question. The Pulitzer Prize winning author of Common Ground described the cause of the problem as a feud within the Boston Irish political family.

Students Being Bused In South Boston Under Heavy Police Escort
The Start of Busing In South Boston—
September, 1974.
Photo by Bettmann/Corbis.

On one side you had players like Arthur Garrity, the federal judge who oversaw school desegregation in Boston, and Senator Ted Kennedy, one of busing’s strongest supporters. On the other, you had politicians from neighborhoods like South Boston. Louise Day Hicks, Jim Kelly and Billy Bulger, to name a few, were fierce opponents of busing. Regardless of which side they were on, the major players named above had one thing in common: they were all Irish American. They had competing ideas of what that meant though, and busing would be the battlefield where those ideas played out.

Garrity and Kennedy were in favor of a desegregation solution that considered the city as a whole. They opposed an approach that would let each neighborhood determine whether and how they would participate in desegregation.

All Politics Is Local

Neighborhoods were at the heart of traditional Boston politics. Both of Ted Kennedy’s grandfathers rose to political power by practicing neighborhood politics. John F. Fitzgerald ruled as the boss of the North End, while P. J. Kennedy was the undisputed political chieftain across the harbor in East Boston.

However, by 1974 both Garrity and Kennedy had drifted far from their political Irish roots. Their families had achieved the American dream. They had climbed the socio-economic ladder. In doing so, they distanced themselves from their ethnic origins and cared more for the greater good of the city than people now living on the street where their grandparents grew up.

Shifting Values for the Boston irish

To both men, the behavior of Irish American politicians like Hicks and Bulger was an embarrassment. It was a reminder of how their ancestors conducted neighborhood politics but not the way Bostonians should behave in modern times. At least for those fortunate Bostonians who had “made it.”

It’s a common phenomenon. When somebody from a working class area succeeds economically and moves out, their relationship with the old neighborhood can get a little complicated. There might be some guilt about being successful, maybe a little resentment that others didn’t move up and move out rather than stay rooted in the old way of living.

Judge Arthur Garrity
U.S. District Judge Arthur W. Garrity, Jr.

How the Feud Begins

When it comes to feuds, the closer the family the harsher the fighting. In Boston, it was U.S. District Judge Arthur Garrity telling the Boston School Committee what they had to do. Garrity ruled in June, 1974, that Boston had deliberately maintained a segregated school system. Rather than having a federal plan developed for desegregation, he ordered the city to immediately implement a state board plan that paired the high schools of South Boston and Roxbury. That decision ensured that anything but peace would prevail when the buses began to roll into those communities three months later.

But you can’t have a serious feud without the other family members doing their own wrong. The Boston School Committee had years to address the desegregation problem. They had many chances to come up with a plan of their own that the federal courts would accept. They chose not to, and the reasons were simple. Committee members were elected. They represented the neighborhoods where they lived. Many were from neighborhoods with large Irish Catholic populations. They didn’t have to answer to the mayor or the city council. As the pressure grew for them to act and come up with their own desegregation plan, they instead chose a course of defiance. It played well with their constituents.

Committee members knew that Garrity was Irish American. It no doubt made them angry that one of their own was turning against them and forcing them to act against their neighborhoods’ interest. What followed was the messy busing crisis we know too well.

Boston Irish Receive a Hostile Reception

To get at the deeper source of the Irish American family feud in Boston, the roots of it, you might have to go back pretty far. As far back as, believe it or not, 1700. That’s when the Massachusetts General Court passed a law declaring that any Catholic priest found in Massachusetts would be sent to prison for life. If he escaped and was recaptured, he’d be put to death.

Discrimination in Hiring — Irish Immigrants In Boston

That’s an example of the hostile reception Irish immigrants would receive for the next 200 years. Other American cities would treat their Irish poorly as well. But the Protestant establishment in Boston was far more intense in its dislike of the Celtic swarm reaching its shores than cities like New York. It happened in the workplace, and it happened in the schoolhouse. Irish Catholic children attending public schools in Boston were forced to read from textbooks that insulted their heritage and their religion.

A Turning Point for Boston Irish Politicians

As a result of widespread discrimination, assimilation for Irish Americans in Boston was a lot more difficult. The Protestants resisted sharing political power as long as possible. With the Irish Catholic population increasing dramatically in the late 1800s though, one thing became clear. At some point the establishment would have to cede, or at least share, political power with the papists.

Boston Irish Mayor James Michael Curley
James Michael Curley (aka “The Rascal King) Elected Mayor of Boston in 1914.

With Rising Power Comes a Choice

This is when the split becomes apparent in the Irish community. After decades of abuse, some were calling for an adversarial approach to gaining political power. James Michael Curley was maybe the most famous Irish American to embrace that stance. He had a political personality that reflected the view of most Boston Irish. You take care of your own people first. You fight for your neighborhood. (This eventually led to a system of patronage that plagued city government into the twenty-first century.)

Again, opposing this neighborhood-centric approach to governing was the idea that those who govern should do so with an even hand to all. Regardless of where they grew up and how they identified in socio-economic terms, politicians should avoid favoritism of any kind, particularly to their friends and family. The good of the city as a whole should be considered above the interests of any particular neighborhoods.

One interesting anecdote retold by Thomas H. O’Connor in his book The Boston Irish: A Political History, illustrates neatly the difference in political philosophies.

As O’Connor tells it, a well-to-do Beacon Hill woman went campaigning for her school committee candidate, a Harvard graduate with a distinguished pedigree. Knocking on doors in an Irish neighborhood, she pitched her candidate to an Irish housewife, who asked, “Doesn’t he have a sister who works for the school system?”

The Beacon Hill campaigner answered, “I assure you, Madam, my candidate is not the sort of man who would use his position to advance the cause of his own sister.”

The Irish housewife replied, “Well, if the son of a bitch wouldn’t help his own sister, then why would I vote for him?”

Hugh O’Brien, the Peacemaker

That’s how most Boston Irish saw things, particularly the supporters of James Michael Curley. However, other Boston Irish politicians felt that they needed to work within the system that existed. Embrace the philosophy of the Puritan founders. Focus on the well being of the whole city, not just on the interest of those in your own neighborhood.

In 1885, the first Irish Catholic mayor of Boston was sworn into office. Born in Ireland, Hugh O’Brien ran on a platform of cooperation with a nervous Protestant establishment. He held true to his word and served four consecutive terms as a steady, reliable, impartial mayor. You could call it smart, or you could call it selling out.

Boston Mayors Patrick Collins and Hugh O'Brien
Boston Irish Mayors Patrick Collins and Hugh O’Brien

Patrick Collins was another Irish Catholic mayor who didn’t rock the boat. The Yankee Protestants admired his humble, industrious rise from poverty. Like O’Brien, Collins knew how to dress, walk and talk like a Protestant. He knew how to embrace the point of view of the establishment.

James Michael Curley, the Troublemaker

But Boston’s Irish community could only be so patient with leaders who they felt had turned their backs on their own people. It wasn’t long before leaders like James Michael Curley finally won election to office. They had a more combative approach and wrested power any way they could. Curley wasn’t above breaking the law. He once served time behind bars for helping a friend get a Post Office job by taking the exam for him.

It wouldn’t be the last time Curley served prison time. Rather than apologize for his tactics, Curley bragged about them. He was helping decent people start a career in a system that had long fought to keep them out. The majority of Boston Irish loved Curley for his defiance. They continued to elect him to office, and he did everything he could to help them out.

That’s a simple take on the split personality in Boston’s Irish community. But it shows how a neighborhood-focused philosophy began and how it continued well into the 20th century. Had the Protestant establishment been more accommodating in the process of assimilation, the political polarization might not have been so intense and might not have lasted so long.

Boston Irish Mayors Hynes and Collins — Urban Renewal
Boston Irish Mayors John B. Hynes and John F. Collins

Shifting Focus From the Neighborhoods

James Michael Curley’s neighborhood-focused approach persisted at the mayoral level until 1950. That’s when mayors John B. Hynes and John F. Collins took Boston in a very different direction for the next eighteen years. Both Irish American, they abandoned Curley’s ways and focused on rebuilding downtown Boston at the expense of its neighborhoods.

In downtown Boston, the old West End neighborhood tenements were torn down. The residents were promised housing in a modernized downtown core. Instead, the tenements were replaced with expensive high rise apartments that few of the former residents could afford. The plan was to do the same to Boston’s North End neighborhood. Residents there had seen what happened in the West End and organized to resist what the mayors referred to as “urban renewal”.

Boston's North End Neighborhood
Boston’s North End Neighborhood

Anyone who’s enjoyed a visit to Boston’s North End should be grateful to those who fought to keep the bulldozers and wrecking cranes away. If anything, the North End is now considered a gem in the city’s crown.

A New Generation of Boston Irish Politicians

Following Mayors Hynes and Collins were Kevin White and Ray Flynn. They took a more balanced approach, working to build Boston as a world class city while respecting neighborhood identity. Mayor White established “little City Halls” in various parts of the city. Not much more than trailers with a city seal painted on the outside, these neighborhood City Halls allowed people to get a permit or renew a license without having to venture downtown. A small but significant gesture.

Ray Flynn had the difficult task of healing the racial wounds from busing and building bridges across Boston’s different communities. He had the good of the city in mind. It cost him though. A resident of South Boston—in fact, the city’s first mayor who was actually from South Boston—Flynn would win election by carrying every neighborhood in Boston except his own. South Boston didn’t appreciate him putting its interests second to those of the larger city.

South Boston Political Foes — William Bulger and Ray Flynn
William Bulger and Ray Flynn, South Boston Political Foes

Bulger vs Flynn

Some would say it’s ironic that the mayor who fought so hard for South Boston during school desegregation fought against its interests when healing the city after busing.

In his memoir, While the Music Lasts, fellow South Boston politician Billy Bulger talks about Flynn as someone who was always holding his finger up to test the political winds. A politician who looked for ways to take more than one side on an issue, so that when the dust settled Flynn would be on the winning side, whatever side that happened to be.

Flynn would probably call it nuance, and a willingness to change with the times. Perhaps it’s a mix of all those motivations. One thing is certain: After busing, Boston needed to change. Flynn was able to bring the neighborhoods together and move the city forward. For that he deserves credit.

Historical Perspective

Bulger and Flynn might best represent in modern times (and maybe for the last time) the Boston Irish family feud. Bulger stayed true to his neighborhood’s interests and never put them second to anything. Flynn found a way to move up without moving out.

For more reading about the Boston Irish—The Boston Irish: A Political History is a sweeping look at the Irish American experience in Boston written by historian Thomas H. O’Connor. It can read as a text book at times, but it’s interesting and comprehensive. (link goes to Amazon.com, but the book is also available elsewhere).

To read more about Irish-American history and contemporary Irish issues, check out Mark Holan’s blog. He’s an Irish-American journalist living in Tampa, FL, and his blog has some very interesting posts.

Whitey Bulger and More…

Whitey Bulger Shipping Arms the IRA

How Whitey Bulger Terrified Mayor Kevin White

How Whitey Bulger Beat the State Police

Whitey Bulger and Billy Bulger: South Boston Brothers

Remembering Boston Mayor Kevin White