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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 Wrong Color

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It was back in the’80s when I drove a taxi in Boston for a short time. I worked for someone who owned three cabs, and I would show up for my evening shift at a parking lot next to City Hospital in the South End. There were two other guys, Ed and Tommy, whose shifts started at 4 p.m. We’d usually stand around bullshitting while waiting for the day drivers to return with our cabs.

“So did your cousin get that job with the T?” Ed asked one day.

“No,” Tommy said. “He was the wrong color.”

The bleak parking lot where I heard the discussion about The Wrong Color.

A 2007 Google Street View of the parking lot where drivers exchanged cabs.

The three of us were White, and we all knew what being the wrong color meant in that context. Tommy was blaming the MBTA’s hiring guidelines for his cousin, who was also White, for not getting the job. In Tommy’s eyes, the job his cousin deserved to get was instead given to a person of color.

Affirmative Action and the White Community

The MBTA had recently implemented a diversity policy. It dictated a certain percentage of jobs should go to women and people of color. It was referred to as affirmative action. The term was thrown around a lot back in the ’70s and ’80s, and almost never in a positive way among the White people I knew. Even organized labor fought against the change, as detailed in this legal case.

An MBTA affirmative action case involving women and people of color.

The way Tommy saw it, his cousin would have gotten the job if the old system of hiring for government jobs hadn’t been changed. Part of that old system was patronage. If you were the one looking for work, you’d turn to a friend for help. It might be a cousin or neighbor whose sister or uncle worked in some agency like the MBTA or the DMV.

They’d put in a good word for you, with maybe a case of beer, tickets to a Bruins game or a certain sum of cash thrown in. Then, a week or two later a letter shows up congratulating you on your new position. There might be proficiency tests that you’d have to pass, a union to join and a background check that had to come back clean. But once those were taken care of, someone putting in a good word and a gift could seal the deal.

The History of My People in Boston and Patronage

When I wrote The Chieftains of South Boston, I included the history of how Irish immigrants in Boston were discriminated against by the Protestant Yankee elites. They controlled government at every level. It took generations for the Irish to wrest control of power. When they did, they made sure to take care of their own when it came to patronage. It happened at agencies like the police department, fire department, city hall, the state house and so on. “To the victor go the spoils” applies to the worlds of war and politics.

Taking care of their own meant helping not only fellow Irish Americans but other people considered White back then. In my community, that included all kinds of hyphenated Americans, but it did not include the Black community. It also didn’t include women. Irish American culture at that time was heavily influenced by the Catholic Church, an organization that has always struggled with the concept of gender equality.

The Cost of Ignoring History

When a group maintains such systematic control over government institutions for three or four generations, it’s easy for those people to develop a sense of ownership and entitlement, while also being blind to it. The Black community in Boston has never achieved anything close to the institutional power enjoyed by their White neighbors.

I can remember a time back in the ’70s when my reaction to affirmative action was similar to Tommy’s. It didn’t seem fair. I felt like I could be be penalized when applying for a job because of my skin color. It was the feeling of being cheated because I was White.

At the time, I was oblivious to my own people’s history and how it put me in a place that made life a whole lot easier than it was for many others. Learning the history changed everything for me, although it didn’t happen overnight. It took years.

Boston and Its Busing Problem — An Irish Family Feud

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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

Whitey Bulger and the IRA — An Irish American Who Gave Back … Sort of.

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Updated June 7, 2026

The IRA Asks Whitey Bulger for a Favor

Whitey Bulger and the IRA had an interesting relationship back in the eighties. Like a lot of conspiracies involving the underworld, it began with someone requesting a favor.

If you’re Irish American, ask yourself this—what have you done for Ireland lately? Now imagine you’re Whitey Bulger, and it’s the IRA doing the asking. This is how a scheme began between Whitey Bulger and the IRA.

The favor was requested by the Irish Republican Army (IRA) back in the early eighties. They believed Whitey would be sympathetic to their entreaty because his mother was first generation Irish American. The IRA was very specific in what they were asking for: a million dollars worth of hi tech weapons to be shipped across the Atlantic to aid the IRA in its cause.

Irish American Whitey Bulger and the IRA schemed to deliver ship arms by boat. Photo shows Whitey discussing the matter with a henchman.
In 1984 Whitey Bulger Schemed With Pat Nee and Joe Murray to Run Guns to the IRA.

Patrick Nee was Whitey’s colleague in Boston’s Irish mob. He was also an Irish immigrant and enthusiastic supporter of the IRA. Although not as excited as Nee about supporting the organization, Whitey agreed to partner with Nee and Joe Murray of Charlestown because he saw an opportunity to make a buck.

It was Whitey’s idea to set up a sort of triangle trade. When the IRA asked for weapons, Bulger asked for help in securing the funds necessary to purchase the weapons. The IRA contacted an Irish American admiral in the U.S. Coast Guard. An IRA sympathizer, the admiral made sure no Coast Guard boats were patrolling certain waters off Boston on certain nights.

Whitey’s Trade Plan: Drugs for Money, Money for Weapons

Ships laden with bales of marijuana rendezvoused with small craft, which then ferried the drugs to a wharf in Chelsea. Once there, they were loaded onto tractor trailer trucks for distribution throughout New England.

The operation created an impressive cash flow for Whitey Bulger. As a result, he maintained it long after securing sufficient funds to purchase the weapons. Because the IRA became insistent, Whitey finally turned off the cash spigot and finished obtaining the weapons. He arranged for everything to be shipped to Ireland on a fishing trawler named the Valhalla.

The fishing trawler The Valhalla was how Whitey Bulger and the IRA schemed to deliver weapons.
The Valhalla Carried Seven Tons of Weapons to the IRA, thanks to Whitey Bulger.

In 1984, the Valhalla left Gloucester, Ma, loaded with seven tons of munitions, including assault rifles, hand grenades and Redeye surface-to-air missiles.

The weapons never reached Ireland though. An informant within the IRA’s senior leadership spilled the beans, and the shipment was intercepted by the Irish Navy.

Everyone Loses, Except Whitey Bulger

There were a lot of losers in the operation, including the IRA and the crew of the Valhalla when they returned to Boston. Whitey Bulger and his partners were the only winners. Their drug-smuggling scheme let them leave the game with some serious money.

That’s the short, simple version of the tale. It gets more complicated when you take in different versions of the story from different players. For example, Patrick Nee believed that Whitey Bulger was the one who tipped off the CIA about the weapons shipment. Supposedly to enhance his own standing as an informant.

To read more, the Irish Times has a good post that takes you deeper into this story, with all its interesting details.

That’s just a quick look into Whitey Bulger’s triangle trade with the IRA. I found the whole story interesting enough to weave it into a chapter of my novel The Chieftains of South Boston (Chapter 2—The Zugzwang). The name Valhalla has been changed to Avalon, but the spirit of the true-life story is all there.

An Interesting Follow-Up

For a couple of years in the late 1980s, I lived in Gloucester. Neighbors of mine told me an interesting story that relates to all of this. They had been renting a house on East Main Street, either 101, 103 or 109. A driveway ran behind the houses and onto a short pier.

These neighbors described a time not too long before when they were woken in the middle of the night by the sound of a truck moving along the driveway and onto the pier. They watched as a group of men unloaded crates from the truck before carrying them onto a fishing trawler, which was the Valhalla, they said.

They didn’t know the significance of that delivery at the time. It was only later they put the pieces together. But it would have been the perfect way for Whitey to to take care of business. Do it away from the main piers along Rogers Street, and do it in the dead of night.

We never how how a seeming unimportant incident might one day turn out to be a notable event in some historical narrative.

More Posts About Whitey Bulger

How Whitey Bulger Terrified Mayor Kevin White

How Whitey Bulger Beat the State Police

Whitey Bulger and Billy Bulger: South Boston Brothers

Boston and Its Busing Problem — An Irish Family Feud

Remembering Boston Mayor Kevin White