The Brothers Karamazov, Set in South Boston

How the Novel Began

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

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

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

Dostoevsky’s Structure

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

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

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

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

The Brothers Karamazov Becomes The Brothers Mahoney

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

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

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

Matthew Mahoney and Buzzy Driscoll

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

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

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

Capturing the Time and Place

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

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

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.

Whitey Bulger and More…

Whitey Bulger Shipping Arms the IRA

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

Whitey Bulger and the IRA— 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.

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

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. 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 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.

Whitey Bulger shipped arms to the IRA in the fishing trawler The Valhalla.
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.

Whitey Bulger and More…

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