Chapter 1Old Harbor

Foreword

The Federal Bureau of Investigation did not fail to catch James Bulger.

It bought him, under a program built for exactly that purpose, and then paid what the program costs.

I want to put that at the front because everything in this book follows from it and because it is not the story most people carry. The story most people carry is about a corrupt agent: John Connolly, who grew up in the same housing project, who tipped off a murderer, who is serving time in Florida for it. That story is true and it is a very small part of what happened.

The Top Echelon Criminal Informant Program was created by J. Edgar Hoover in 1961 to penetrate La Cosa Nostra. Its logic is simple and, on its own terms, unanswerable: you cannot get inside a criminal organization without paying a criminal, and the further inside you want to get, the worse the criminal has to be.

That logic has no natural stopping point.

Chapter 5 of this book is not about James Bulger. It is about a man named Edward Deegan, shot dead in Chelsea, Massachusetts on March 12, 1965, and about four men — Peter Limone, Joseph Salvati, Henry Tameleo and Louis Greco — who were convicted of killing him at a fifty-day trial in the spring of 1968 on the testimony of an FBI informant, while the Bureau held documents in its own files showing that the testimony was false.

Two of them died in prison. The convictions were vacated in 2001. The government paid $101.7 million.

That happened seven years before John Connolly met James Bulger in a parked car.

The chapter is placed where it is, before the subject enters the arrangement, because it establishes the rule in advance. What the Boston field office did for Bulger between 1975 and 1994 was not an aberration invented by one agent for one gangster. It was the program working the way the program works, and it had already sent four innocent men to prison once.

That is the argument. Everything else is the evidence for it.

Seven chapters pass before he becomes an informant, and I want to say why that is not throat-clearing.

The reader has to see both the man and the machine before they meet in 1975, and the man is more interesting than the legend allows. He was not the most violent person in that world; the Killeen–Mullen war of the early 1970s ended not with him shooting his way to the top but with a negotiation at a bar in the South End, mediated by Howie Winter, which he walked out of as the man South Boston reported to.

He was better at politics than at violence. That is precisely why the violence lasted so long.

And he did not invent the arrangement he entered. Stephen Flemmi had been a registered Top Echelon informant since 1965, handled by an agent named H. Paul Rico. When Bulger moved up into partnership with Flemmi, he was joining something that already existed.

Three chapters in the middle of this book are murders and they are told from the victims' side, because the trial told them from the killers'.

The single hardest of them is Chapter 11. On the evening of May 11, 1982, on Northern Avenue on the Boston waterfront, Brian Halloran was shot dead in the street. Halloran had gone to the FBI earlier that year and told them Bulger had ordered a killing in Tulsa, and had asked for witness protection, and had not received it. What he received was a supervisor telling Connolly and Connolly telling Bulger.

Michael Donahue was thirty-two. He was a truck driver with three young sons and he had stopped to give Halloran a lift home.

That chapter is told from the passenger seat.

There is a chapter this book refuses to resolve and the reader should be warned about it now.

Debra Davis was twenty-six. She was Stephen Flemmi's girlfriend, she wanted out, and in September 1981 she disappeared. Flemmi testified that Bulger strangled her while he held her. Bulger said until his death that he had never killed a woman. Both of those accounts come from men who were selling something, and in 2013 the jury convicted on the Hussey killing and returned no finding on Debra Davis.

Chapter 14 lays out both accounts, names what each man bought with his version, and stops. It then gives the last word to her brother, who has spent forty years in courtrooms being told that the truth is unavailable.

I have also tried to take the case for the bargain seriously, and Chapter 17 is where that happens.

Connolly's position, then and now, is that Bulger's information made the Boston Mafia prosecutions possible: the bug at 98 Prince Street in 1981, the tapes that destroyed Gennaro Angiulo's organization, the induction ceremony recorded in Medford in October 1989, the first ever captured. If that is true, then this is a book about an immoral bargain that worked, which is a genuinely difficult thing to write about.

The chapter tests the claim against the trial records of those prosecutions and against Judge Mark Wolf's findings of 1999, rather than repeating it. What it concludes is in the chapter.

Two traps, named rather than dodged.

The first is the folk hero: the turkeys at Thanksgiving, the code, the drugs he supposedly kept out of South Boston. Chapter 15 disposes of that with the extortion record and with the arithmetic of what actually came into the neighborhood — a liquor store bought at a kitchen table with a pistol on it and a child in the room, bookmakers on a payment schedule, dealers taxed by the pound — and with Michael Patrick MacDonald's account of four dead siblings in one family.

The second trap is the mirror of the first, which is to treat him as a monster whose nickname explains him. It does not, and he hated it. He was an ordinary predator with a federal subsidy, and this book only works if Chapters 8 and 9 read as a plausible bargain made by intelligent people for reasons they could defend at the time.

Finally, the ending, which no previous book about him has.

Every standard account of James Bulger was written between 2000 and 2015. On October 29, 2018 the Bureau of Prisons moved an eighty-nine-year-old man in a wheelchair from a penitentiary in Florida to USP Hazelton in West Virginia, a facility already known for its homicide rate, and placed him in general population. He was beaten to death within about twelve hours.

The Justice Department's own Inspector General reviewed it and found staff misconduct, bad judgment and management failures, and no evidence that the transfer was arranged. Three men were indicted in August 2022. By the end of 2024 every murder count had collapsed into manslaughter, assault, or nothing.

No one has been convicted of killing James Bulger.

This book ends on the program rather than on the man, because the program is still operating, under the Attorney General's Guidelines, still buying information from people who kill.

He was the price. He was never the point.

Chapter 1 · Old Harbor

South Boston is a peninsula, and much of what has been written about the neighborhood follows from that piece of geography. It is joined to the rest of the city at its western end and surrounded by water everywhere else. Nobody passes through a peninsula on the way to somewhere else. Whoever is out on it is out on it deliberately, and the plainest fact about South Boston in the years this chapter covers is the one that describes the rest of the city rather than the neighborhood: the rest of Boston did not enter.

That has a consequence which is easy to state and easy to underrate. A place the rest of a city does not enter is a place the rest of a city cannot observe. There is no casual traffic through it, and therefore no casual witnesses to it, and therefore very little independent record of what happens on it beyond what the police write down after the fact and what the residents are willing to say. The archive of a closed neighborhood is thin by design, and it is thin in a particular direction: it preserves arrests and it does not preserve ordinary life. That asymmetry runs through everything in this chapter, and it will run through the rest of this book in a more consequential form, when the institution declining to write things down is not a newspaper but the Federal Bureau of Investigation.

In 1938 a family named Bulger moved onto that peninsula, into a development called Old Harbor Village. It was the first federal housing project in New England. That phrase deserves to be read slowly, because first is a claim about everything that came before it. Until Old Harbor Village there had been no such thing in this part of the country — no arrangement under which a government in Washington built apartments, held the title, and rented them to families who could not otherwise have had them. The Bulgers moved into an institution that was younger than the children moving into it.

It ran to a thousand-odd apartments. That figure is worth holding onto, because a thousand-odd apartments is not a building. It is a population. It is a census tract with a landlord. A federal housing project is, by construction, a place where a single authority decides who may live there and on what terms, and the consequence of that is a neighborhood in which the ordinary external markers separating one family from the family next door have been flattened. Nobody in Old Harbor Village had a better address than anybody else in Old Harbor Village. They all had the same address.

That is the physical fact from which this chapter's argument proceeds, and it is worth stating the argument now so that the reader can watch it be earned or fail to be: in a place where money cannot mark the difference between one family and the next, something else will. What circulated in Old Harbor Village was not money. It was standing — what could be said about you, by whom, and how reliably. A boy raised inside a closed system learns early that reputation is not a description of a person's assets. Reputation is the asset. Everything James Bulger later did with the FBI is a transaction in that currency, conducted at a scale the peninsula could not have imagined. But the arithmetic he was doing at the end was the arithmetic he was taught at the start, and this book will argue that the federal government eventually made him rich in the only coin he had ever recognized.

He was born before any of that. James Joseph Bulger Jr. was born on September 3, 1929, in Everett, Massachusetts, a city on the northern side of Boston, and the record of the Everett years is close to empty. It contains a date and a place. Almost everything else that has been printed about the household in that period reaches us through people interviewed long afterward, which is a problem this chapter will return to, because it is the central methodological condition of writing about this boy at all.

The father was James Bulger Sr. He lost an arm in a railroad accident, and after the accident he never worked steadily again. Those two sentences are the load-bearing facts of the household, and they are also very nearly the whole of what the available record establishes about the man. It does not fix the year of the accident. It does not name the railroad, or the yard, or the run. It does not say which arm, or how old he was when he lost it, or whether the injury preceded his son's birth or followed it. It does not record whether there was a settlement, and if there was, what it came to. Any biography that supplies those details is supplying them from somewhere, and this one will not.

What can be said without invention is what the loss of an arm meant for a man who had nothing to sell but his labor. The record does not establish what work he had been doing before the accident, so this book will not name it. It establishes the consequence, which is the part that mattered inside the apartment. "Never worked steadily again" describes a condition rather than an event: not a man who stopped working, but a man for whom work became irregular and contingent, and no longer the thing that organized the household's week. Whatever the Bulgers had been living on, it was no longer a wage arriving on a schedule. The route into Old Harbor Village ran directly through that fact.

The mother was Jean McCarthy Bulger, and the record says of her, in effect, that she held the household. That is a formulation the reader should be suspicious of, because it is the formulation that always attaches to the mothers in books like this one. Here it is what the available account supports and no more. She is not quoted. She did not write a memoir, give an interview that has come down to us, or testify. Her interior life, her view of her husband's injury, her view of what her son James was becoming — none of it is in the record this book is built from. She has been described by others, most of them writing after her son was famous, and description by others is what the file contains. A biography that puts words in her mouth is writing fiction. This one records that she was the fixed point of a household whose other adult had been broken by a railroad, and stops there, because that is where the evidence stops.

The move to Old Harbor Village came in 1938, the year James Jr. turned nine. The Boston City Archives hold public housing records for South Boston. They would establish the month the family was admitted, the apartment they were given, the number on the door, and quite possibly the terms. Those records have not been read for this account. Census returns would place the household in both locations and name everyone in it. They have not been pulled either. This is stated here rather than glossed over because the alternative — writing the scene as though the paperwork had been consulted — is the exact failure that produces the confident, unfootnoted childhood chapters that every previous book about this man has had to include. The year is what the record gives. The year is what this chapter uses.

What arriving in Old Harbor Village did to a nine-year-old is not recoverable and will not be reconstructed here. What can be described is the world he arrived into, because that world's structure is documented even where his experience of it is not. He came from a household with a disabled father and irregular income into a development where every household had been admitted on some version of the same showing. Whatever shame attaches to poverty is a comparative emotion; it requires a neighbor who is doing better. Old Harbor Village removed the comparison. A thousand-odd apartments on a peninsula, their tenants all tenants of the same landlord, all of them there because the private market had not worked for them, is a place where the question what does your father do stops being useful and some other question takes its place.

The question that took its place is the subject of this book. In a closed community with a flattened economy, the available distinctions are reputational. Who is reliable. Who talks. Who does not talk. Who can be counted on to do what he said he would do, and who cannot. Who will fight, and who will fight past the point where a reasonable person stops. These are not romantic categories and this book is not going to render them romantically; the register in which South Boston is usually written — the pubs, the code, the phrase carried in the subtitle of Dick Lehr and Gerard O'Neill's Black Mass (PublicAffairs, 2000) on its film tie-in edition, the Irish mob — is an aesthetic, and it is the aesthetic that turned the subject of this book into a folk figure. But strip the aesthetic off and the structural point survives it. Standing was the transferable asset. It could be accumulated. It could be spent. It could be destroyed in an afternoon, and once destroyed it could not be rebuilt, because everyone who would have to be persuaded had already watched.

The mechanism deserves to be spelled out, because it is what makes the neighborhood a system rather than a setting. Reputation is only an asset where it cannot be escaped. In a large city a man who has been discredited on one street moves to another and starts again; the information does not follow him, because there is no one carrying it. On a peninsula the information does not need to be carried. It is already at the destination. Everyone a boy in Old Harbor Village would ever need to deal with already knew what he had done and who his father was and what his brother was like, and there was no version of his life in which that stopped being true, because the geography would not permit an audience change. That is the closed system. It makes reputation permanent, and anything permanent becomes property. What a boy accumulates under those conditions is not a self-image. It is an estate.

Three brothers grew up in that apartment and went three different ways, and the three ways are the most useful single fact in this chapter, because they demonstrate that the peninsula did not determine the outcome. Jimmy went to the street. Billy went to the Massachusetts Senate. Jackie went to the courts.

William M. Bulger was born on February 2, 1934. He would become president of the Massachusetts Senate and hold that office from 1978 to 1996, and he would go from there to the presidency of the University of Massachusetts. Jackie Bulger's working life was in the courts. And James Jr. went the third way, into an economy the other two spent their careers looking at from the opposite side of a counter.

The temptation, and every book about this family has faced it, is to read the three careers backward as a single arrangement — to treat the Senate and the courts and the street as departments of one enterprise headquartered at one address in Old Harbor Village. That reading has a principal author. Howie Carr, the Boston Herald columnist, made it the argument of The Brothers Bulger (Warner Books, 2006), whose thesis is that the political power and the criminal power in this family were inseparable. Carr is an interested party with a long and public feud with the Bulgers, and his book is openly hostile, which does not make it wrong but does mean it cannot be cited as though it were a finding. It is an argument. Against it stands a fact that this book will state now and state again in its proper place, because it is the kind of fact that gets lost in the accumulation of insinuation: no evidence has ever been produced that William Bulger knew of his brother's murders or of the informant relationship. He was never charged with anything. What is true of the three brothers, on the evidence, is the ordinary and less satisfying thing: that they were raised together and diverged, and that the divergence began before anyone was in a position to profit from it.

There is a further reason to distrust the backward reading, and it is the reason this chapter has kept circling its own sources. Everything we possess about the boy in Old Harbor Village was collected after we knew what the man became. That is not a minor caveat. It is the governing condition of the material.

The relationship between James Bulger and the FBI was reported publicly in 1988, by the Boston Globe's Spotlight team. Every substantial account of his childhood was assembled after that date, by reporters and authors who went to South Boston knowing exactly what they had come to explain. The fullest published treatment of these years is Whitey: The Life of America's Most Notorious Mob Boss, by Dick Lehr and Gerard O'Neill, published by Crown in 2013 — the work of two of the Spotlight reporters, written for the trial. Nothing about the sequence discredits it. But it does describe what kind of evidence childhood recollection is when it has been gathered from neighbors who already knew, before the question was asked, what the boy from the next stairwell had grown up to be. Memory does not survive that intact. It reorganizes. The quiet child becomes ominously quiet; an ordinary fight becomes the early sign; the boy nobody thought about becomes the boy everybody had a feeling about. This is not dishonesty on anyone's part. It is what retrospect does, and it operates most powerfully on exactly the kind of detail that makes a childhood chapter readable.

The other body of testimony is worse for a chapter like this one, not better. A substantial literature about James Bulger was written by men who were inside the operation with him — enforcers, associates, rivals who later became partners. Every insider account of Bulger comes from someone who traded it for a sentence, a book advance, or both, and that is a reason to attribute each use of them rather than to discard them. But it is also a reason they cannot help here. Kevin Weeks, who wrote Brutal with Phyllis Karas (ReganBooks, 2006), is the closest thing the record has to a daily register of the enterprise. Pat Nee's A Criminal and an Irishman (2006) is the only full-length account from the losing side of the South Boston war. Neither of those books, and none of the others, is a book about a nine-year-old. The insider literature begins where this chapter ends. It describes a business, and the business had not been founded yet.

One document from inside the family predates the public break and is therefore a different species of evidence. William Bulger published a memoir of his life in politics, While the Music Lasts, with Houghton Mifflin, in 1996. Its value to a book like this one is not what it says but when it was written: it records the family's account of itself before that account had to serve as anyone's defense. It is a document of a narrative in its earlier state. This book has not read it against the housing records or the census, and does not represent it as corroborated. It notes only that it exists, that its date matters, and that a reader who wants the family's own telling should go to it rather than take this book's word for anything.

So the honest position on Old Harbor Village is this. We know where the family lived and roughly when they arrived. We know what the place was and how many apartments it held. We know what happened to the father's arm and what it cost the household. We know the mother held it together, on the authority of people who watched from outside. We do not know what was said in those rooms. We do not know what the boy thought about any of it. We do not have a diary, a letter, a school record quoted at length, or a single contemporaneous document written by or about him before he began generating a police file. Anyone who tells you otherwise is either working from archives this book has not opened or filling a silence with plausible material, and the second is far more common than the first.

That silence matters more here than it would in most biographies, because the childhood chapter of a criminal life is where the explanation is conventionally located. The reader arrives wanting Old Harbor Village to account for what came later — the project, the missing arm, the peninsula, the closed system, the poverty. It is a satisfying shape and it is available in every previous version of this story, and this book declines it. There were a thousand-odd apartments in that development. The other children raised in them did not become James Bulger. Two of the three brothers in this particular apartment went into public institutions and stayed there for their working lives. A childhood that produces a Senate president, a man who spent his career in the courts, and a man convicted of murder is not an explanation of the last of them. It is an argument that the childhood was not the variable.

The variable arrives later, and it does not arrive in South Boston. In 1961 the Federal Bureau of Investigation under J. Edgar Hoover created a program to place informants inside La Cosa Nostra — the Top Echelon Criminal Informant Program — on a premise that is not irrational and that the Bureau has never abandoned, since the program is still operating under the Attorney General's Guidelines today: that you cannot get inside a criminal organization without paying somebody who belongs to it. What that premise costs, when the person being paid is not merely inside a criminal organization but is running one, is the subject of this book. James Bulger did not invent that arrangement. He did not even find it. It was built, deliberately, by the government that would later list him for years among its ten most wanted fugitives, and it was waiting for him.

He came out of Old Harbor Village with what the place issued: a name that people on the peninsula knew, and an understanding of what a name was worth. The federal government would eventually pay more for that than anyone in South Boston could have. But the education was local, and it started here, in a thousand-odd apartments on a peninsula the rest of the city had no reason to visit, where money did not distinguish anyone and something else had to.