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 wining author of Common Ground described the cause of the problem as “a feud within [Boston’s] 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, Raymond Flynn 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 society than people now living on the street where their grandparents grew up.

The View Through Lace Curtains

To both men, the behavior of Irish American politicians like Hicks, Flynn and Bulger was an embarrassment. 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 Garrity and Boston Busing

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. Judge Garrity was particularly harsh, and perhaps more than a little ignorant, in how he made final adjustments to the master plan for desegregation. It unnecessarily pitted the two most antagonistic neighborhoods in the city against each other. That ensured anything but peace would prevail when the buses began to roll into South Boston and Roxbury.

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’s 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.

Irish Immigrant Discrimination In Boston

Discrimination in Hiring — the Hostile Reception Irish Immigrants Received In Early Boston (links to Amazon.com page for “The Boston Irish, A Political History”)

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

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.

James Michael Curley, Mayor of Boston

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 Mayors Patrick Collins (1902–1905) and Hugh O’Brien (1885–1889)

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 betrayed their heritage and compromised their identity. It wasn’t long before leaders like James Michael Curley finally won election to office. They had a more combative approach and wrested power by whatever means necessary. 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 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 Mayors Hynes and Collins — Urban Renewal

Boston Mayors John B. Hynes (1950–1960) and John F. Collins (1960–1968)

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.

Finding a Balanced Approach

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 Politicians With Different Points of View

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. I think 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 city’s 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.

Read Another Post:   Whitey Bulger — How He Shipped Arms to the IRA

Whitey Bulger — How He Terrified Mayor Kevin White

Whitey Bulger — How He Beat the State Police

Remembering Kevin White

Home Page:  The Chieftains of South Boston

(This post authored by Steve Burke)

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The Wrong Color

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., and we’d wait around together for the day drivers to show up.

“So did your cousin get that job with the T?” Ed asked, while we were standing around killing time 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 that 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 cousin or neighbor or friend 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 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. I didn’t think it was 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.

Anne Boushay — The Story Behind Her Name

Anne Boushay and Essential Bakery

In 2006, 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 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. It worked for me. 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. Immigration officials who were too lazy to look at someone’s passport for the correct spelling would ask people to pronounce their name. It 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. There were Irish immigrants who were encouraged to drop the ‘O’ from their last name so it sounded more American. As the story goes, the Irish 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 two sequels, The Mahoneys of West Seattle and Ipswich, Mon Amour (due out late 2024, early 2025).

Remembering Kevin White

Kevin White — Boston Mayor 1968–1984

Michael Grecco/BOSTON HERALD — Boston Mayor Kevin White with a revitalized Quincy Market as a backdrop.

Kevin White 1929–2012

If you grew up in my Dorchester neighborhood, you loved hockey and you loved the Boston Bruins. My friends and I watched every game. The next morning at school, we’d critique all the key plays.

Did Gerry Cheevers earn a new scar for his goalie mask? Did Pie McKenzie win that last fight? Maybe Bobby Orr gave us another miracle by starting from behind his own net and skating up ice eluding, outmaneuvering and embarrassing every player on the other team, including their goalie, who would be the last man to bow to Orr’s grace and talent.

Bobby Orr and the Boston Bruins Won the 1972 Stanley Cup

Bobby Orr Holding the Stanley Cup in 1972

Winning the Stanley Cup

When the Bruins won the Stanley Cup in 1972, my friends and I piled into the back of a neighbor’s pickup truck and headed to City Hall Plaza to celebrate with 20,000 other fans. It was the only time my Dad ever gave me permission to play hookie. He was the business manager of the Boston school department and took education seriously. But he loved the Bruins too, so he understood when an exception should be made.

From the plaza that day, I may have seen Mayor Kevin White on the city hall balcony where a drunk Wayne Cashman was pulling off his socks and tossing them to a cheering crowd. After the celebration, I definitely saw a mark that Kevin White would leave on the city of Boston.

The City of Boston Celebrates the Bruins Winning the 1972 Stanley Cup

Celebrating the Bruin’s Victory in Downtown Boston

We had parked the pickup truck in the old Quincy Market. In 1972, it was still a dirty, smelly, unglamorous place where trucks unloaded meat, fruits and vegetables. In the next few years, the area would undergo a dramatic transformation. The makeover of Quincy Market brought in the charming cafes, shops and restaurants we all know today. Downtown Boston was turned into into a public space envied by other cities. It was all part of Mayor White’s vision for a new Boston.

Mayor Kevin White Turned Quincy Market into a Public Square

Quincy Market — It’s Come a Long Way Since It Was Built in 1742.

Making Boston a World Class City

On the way to turning Boston into a world-class city though, Kevin White had to deal with the busing conflict brought on by the Boston School Committee. Because committee members were elected, rather than being controlled by the mayor, White was in for a decade of frustration.

As I read various stories online this morning, I wanted to know where Kevin White grew up. His neighborhood. Back in the seventies, Boston was a collage of neighborhoods, each with its own personality and interests. None of the articles listed White’s neighborhood though. (My best guess would be West Roxbury.)

That lack of attachment to a specific neighborhood might have been one of Kevin White’s greatest assets in dealing with the busing crisis. Had he been from a neighborhood like Dorchester, Charlestown or South Boston, he would have been under tremendous pressure to fight against desegregation rather than make it work as best he could under difficult circumstances.

Desegregation Brings Tension

That’s not to say the he had an easy time. In an earlier post, I wrote about how threatened he felt by Whitey Bulger and his brother Billy. People in my Dorchester neighborhood and in South Boston truly hated the man, referring to him as “Mayor Black.” Because desegregation was enforced by the Boston Police department, cops became hated as well.

The annual St. Patrick's Day parade down Broadway in South Boston.

St Patrick’s Day Parade on Broadway in South Boston

On the St. Patrick’s Day after busing began, my friends and I watched the annual parade from the rooftop of Flanagan’s Market on Broadway in South Boston. I remember seeing a Boston cop lose control of his motorcycle. As it spun across the road, people applauded and cheered. The cop was OK, but he was screamed at and insulted from all sides until he managed to right the bike and ride it away.

As kids, we didn’t really understand the historic shift that was occurring and how Boston would never be the same after desegregation. Nor did we imagine what it must have been like for Kevin White to wake up every morning during those years and worry where the violence would erupt. And whether it would finally grow beyond the ability of the police to control it. We were kids. We cared about the Boston Bruins and Bobby Orr’s failing knees.

The Boston Globe has a pretty nice Kevin White photo remembrance here.

(This post authored by Steve Burke)

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Read Another Post:  Whitey Bulger — How He Shipped Arms to the IRA

Boston and Its Busing Problem — An Irish Family Feud

Whitey Bulger — How He Beat the State Police

Whitey Bulger — How He Terrified Mayor Kevin White

Home Page:  The Chieftains of South Boston

Whitey Bulger — How He Beat the State Police

Whitey Bulger Batted 3 for 3 Against Massachusetts’ Finest—the State Police

Whitey Bulger Beats the Massachusetts State Police

In 1980, Whitey Bulger Was Clever Enough to Foil State Police Surveillance

How do you beat the oldest state-wide police force in America? Whitey knew how.

The Massachusetts State Police force was founded in 1865 and currently has over 2,000 officers. But in 1980, they struck out in their surveillance attempts against Whitey and his underworld partner Stephen Flemmi.

State troopers were tipped off about a repair garage on Lancaster Street serving as Whitey Bulger’s new business headquarters. It was located near the North End, home to Boston’s Italian Mafia. The state police rented space on the third floor of a building across the street from the garage.

Whitey Bulger Conducting Business at Lancaster St Garage

Whitey Bulger and Stephen Flemmi Meet With Mafia Lieutenant Nick Giso.

The State Police Play a Waiting Game

Day after day, they watched various figures from Boston’s underworld entering and leaving the Lancaster Street garage. Over a course of six months, they documented the traffic and took lots of photos. Enough to convince a judge they should be allowed to place bugs inside the garage.

The first attempt failed when the microphone planted by the troopers picked up random noises but no voices. Strike two was when they placed another mike inside a couch cushion in Whitey’s office. The new plan might have worked if the next person to sit on the couch wasn’t Mafia henchman Vincent Roberto. Known as “Fat Vinnie”, he weighed over 400 pounds.

Vincent "Fat Vinnie" Roberto

Mafia Henchman Vincent Roberto, nicknamed “Fat Vinnie”, squashes a hidden mike

When Roberto sat down, he crushed the microphone. What the troopers across the street heard in their headphones was something like the roar of the crowd in nearby Boston Garden when the Celtics beat the L.A. Lakers.

Other failures involved interference from radio signals, causing the microphones to pick up an unintelligible jumble of noise. When the troopers finally succeeded in planting a microphone successfully, Whitey and his colleagues stopped conducting conversations in the garage’s repair bays. Instead, they’d all climb into a car and shut the doors before talking business.

Whitey Bulger and Boston Mafia Boss Harry Angiulo

Mafia Boss Harry Angiulo (left) Discusses Business With Whitey Bulger (right) at the Garage

When the troopers at long last began to pick up conversations, their excitement quickly faded to embarrassment. The comments they heard all went something like, “You want to make sure you obey the speed limit. The Massachusetts state police are very good at catching people who break the law. They’re very, very good at what they do…”

More Bugging Attempts Fail

It had gone on for months. And for all their hard work, the state police had nothing to show. Knowing that Whitey Bulger used a pay phone in front of a Howard Johnson’s restaurant in Dorchester to talk business, they sought permission to bug it. The very day that a court authorized the bugging of the phone, Whitey stopped using it.

Stephen "The Rifleman" Flemmi

Stephen “The Rifleman” Flemmi (State Police Surveillance Photo)

The state troopers tried one last time with a scheme to seize Stephen Flemmi’s car so they could install a secret micrphone inside. It failed when Flemmi flipped out, telling the troopers is was ridiculously clear they just wanted to bug his car because all their other efforts had failed.

Next at Bat: The DEA

The DEA proved equally unsuccessful. In 1984, they planted a bug in Whitey’s car, but he soon had a South Boston mechanic tearing apart his car door. Inside they found the bug. The DEA agents rushed to the shop to retrieve their expensive surveillance equipment. It was worth $50,000.

When the agents burst into the shop, Whitey greeted them with a smile. Holding one of the mike’s wires like a rat’s tail, he uttered his famous words, “Relax, we’re all good guys here. You’re the good-good guys. We’re the bad-good guys.”

Whitey’s quote revealed how he viewed his status with the federal government. He and Stephen Flemmi were both official FBI informants. As a result, Whitey believed he was working for the right side of the law. And that everything he did in the course of his business, no matter how crazy, was sanctioned by the government.

Whitey Bulger's Handler at the FBI Was Childhood Friend John Connolly

Special Agent John Connolly Was Whitey Bulger’s Handler at the FBI

FBI Tips Keep Them One Step Ahead

It was their status as FBI informants that allowed Whitey and Flemmi to always stay one step ahead of other law enforcement agencies. They were often informed of secret investigations and pending arrests. The FBI would have been aware of the state police surveillance in 1980, and Whitey and Flemmi were almost certainly being tipped off by Agent John Connolly.

Connolly grew up in South Boston and was a childhood friend of Whitey’s. It was Agent Connolly who tipped off Whitey and Flemmi in 1995 when they were about to be indicted. The warning allowed both men to flee, and extended Whitey’s federal holiday until just last year. Agent Connolly was convicted in 2002 for racketeering and obstruction of justice related to his relationship with Whitey and Flemmi.

(This post authored by Steve Burke)

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To read more about how Whitey Bulger beat the state police at the surveillance game, check out a good article in the Boston Globe’s Spotlight series: The Bulger Mystique.

Another in-depth article by the Boston Globe gives great insight into Whitey Bulger’s relationship with the FBI. 

Read Another Post — Whitey Bulger — How He Shipped Arms to the IRA

Whitey Bulger — How He Terrified Mayor Kevin White

Remembering Kevin White

Boston and Its Busing Problem — An Irish Family Feud

Home Page — The Chieftains of South Boston

Whitey Bulger — How He Terrified Mayor Kevin White

Whitey Bulger Terrified Mayor Kevin White

Kevin H. White, Mayor of Boston 1968–1984

Fear Was Whitey’s Greatest Weapon Against Mayor Kevin White

Even in 1975, Whitey Bulger had enough of a reputation to put the fear into Boston’s leading political figure — Mayor Kevin White. So much so, that the mayor was frightened out of his wits one night when leaving his gym in South Boston. Afraid that Whitey or one of his thugs would be waiting to kill him in the dark parking lot.

Mayor White admitted as much in a 1978 interview with WGBH TV’s Christopher Lydon. “I was never more scared in my life,” White said,  “…Whitey would be crazy enough to do it. And if they shoot me, they win all the marbles.”

Why was the mayor so afraid of Whitey Bulger? And why would Whitey want to kill him?

This was during school desegregation. Also known as forced busing, it had turned the whole city of Boston upside down. During desegregation, tempers were especially high. There were lots of protest marches, lots of violence and plenty of resentment.

Whitey Bulger In a Surveillance Photo With Stephen Flemmi and Kevin Weeks

Whitey Bulger With Colleagues Stephen Flemmi and Kevin Weeks On Castle Island in South Boston — DEA photo by Special Agent Mike Swidwinski.

Whitey Bulger’s Business Disrupted by Desegregation

South Boston was at the center of the storm. As the buses rolled into town, so did lots of cops. As a South Boston resident, Whitey Bulger was just as resentful as everyone else in his community. He also resented the police presence because it made it more difficult to conduct his business on the streets.

At the time, Whitey was part of a merger of different gangs, the Mullens, the Killeens and Winter Hill. To the police, they were referred to as the “Irish Mafia.” (Read more about the history of the gangs, and how Whitey ended up on top, in this ShortList article.)

J. Anthony Lukas writes about the mayor’s concern that the gangs would infiltrate an anti-busing march in September, 1974. In his Pulitzer-Prize winning book Common Ground, Lukas says White feared the gangs would draw weapons and shoot at the police if the march was stopped. There were also reports that the gangs were passing out weapons to kids in South Boston so they could join the battle as well. One rumor had Whitey Bulger preparing to blow up all the bridges into South Boston to keep the buses out.

Senator William Bulger vs Mayor Kevin White in the Busing Crisis

During Busing, South Boston Senator Billy Bulger Was No Friend of Mayor Kevin White

Billy Bulger’s Political World Disrupted by Desegregation

Another reason the mayor was terrified was because of Whitey’s brother Billy Bulger. The senator from South Boston was a fierce opponent of busing and one of Mayor White’s biggest political adversaries. The two had a very tense relationship. Kevin White was certain that if he ever crossed Billy Bulger, the senator would call on his brother Whitey to punish, even kill, him.

There’s no evidence that Billy Bulger ever asked his brother to do such a thing. But the fear was real enough for Mayor White. In a 1992 Boston Magazine article, he talks about a night he was called to meet at senator Bulger’s house in South Boston. The meeting was to take care of political business. But all the way there, the mayor feared that Billy had called him to South Boston where Whitey Bulger could kill him more easily.

Kevin White survived the years of desegregation, serving as mayor of Boston until 1984. And he survived any threats, real or imagined, from Whitey Bulger. Succeeding White as mayor was Raymond Flynn, the first South Boston politician elected mayor of Boston.

(This post authored by Steve Burke)

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Read another post — Whitey Bulger — How He Shipped Arms to the IRA

Whitey Bulger — How He Beat the State Police

Remembering Kevin White

Boston and Its Busing Problem — An Irish Family Feud

Home Page — The Chieftains of South Boston

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

The IRA Asks Whitey Bulger for 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.

The question came from the IRA back in the early eighties (Whitey’s mother was first generation Irish American.) The Irish Republican Army (IRA) had a specific request: a million dollars worth of hi tech weapons to be shipped across the Atlantic to aid the IRA in its efforts.

Whitey Bulger IRA Connection

In 1984 Whitey Bulger, Along With Pat Nee and Joe Murray, Schemed to Run Guns to the IRA. Photo by Detective Dick Bergeron.

Patrick Nee was Whitey’s colleague in Boston’s Irish Mafia. 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. They 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. There they were loaded onto tractor trailers 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 Valhalla Carried Seven Tons of Weapons from Gloucester to the IRA.

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 (Chapter 2—The Zugzwang). The name Valhalla has been changed to Avalon, but the spirit of the true-life story is all there.

(This post authored by Steve Burke)

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Read Another Post  Whitey Bulger — How He Terrified Mayor Kevin White

Whitey Bulger — How He Beat the State Police

Boston and Its Busing Problem — An Irish Family Feud

Remembering Kevin White

Home Page The Chieftains of South Boston