Whitey Bulger America's Most Wanted Gangster and the Manhunt That Brought Him To Justice (2 page)

But the bulk of the book is based on the authors’ long and detailed knowledge of Whitey Bulger, the fruit of more than twenty-five years of reporting on his exploits, interviewing the FBI agents who protected him, the criminals who worked with him, the lawmen who hunted him down, and the families he destroyed. We have covered dozens of hearings and trials, from Boston to Miami to Los Angeles, and followed his story from Massachusetts to Florida to Ireland to Louisiana to California to Iceland. It is an account made richer by interviews with some of those who spent time in prison with Whitey and by the examination of thousands of pages from his prison file. It is a story bolstered by interviews with those whom Whitey and Catherine Greig met and befriended during their sixteen years on the run, from the bayous of Louisiana to a modest apartment complex a few blocks from the beach in Santa Monica. And it is a story underwritten by the institutional authority of the
Boston Globe
, which first exposed Whitey’s deal with the FBI and has driven understanding of the narrative of his life ever since.

More than anything, this book tries to capture the contradictions that fill in the silhouette that is Whitey Bulger—a man who considered himself a patriot even as he used murder and the threat of it to amass a fortune, a man who could fall asleep moments after killing someone but couldn’t watch a sick dog be put down, a man who held loyalty to be the highest moral value even as he traded damning information about friends to the FBI. There is great sweep and nuance to his story, but it is striking, in the end, how small Whitey’s world was, just a couple of miles, as the crow flies, from the soggy graves of Neponset to City Point, where Whitey regularly had dinner at the home of his politician brother. It is an epic tale with many characters, but one ultimately sketched on a very small canvas.

Shortly after his arrest in June 2011, Whitey was flown by Coast Guard helicopter from his jail cell in Plymouth, south of Boston, to the waterfront courthouse, giving him an aerial view of the shoreline. Those old graves had been dug up, the bodies exhumed, while Whitey hid in open view on the other side of the country. Now he was back in South Boston, his hometown, in chains, made to answer for those bodies and thirteen others. As he looked down from the helicopter, it may have dawned on him that he might still be in charge in his corner of this world if he had never stepped beyond those few square miles where all the shakedowns and killings were plotted and carried out, where Whitey first met his FBI handler, where, for all his misdeeds, he was embraced and not shunned by his brothers and sisters, his nieces and nephews, and his women.

Inside that narrow space, he was untouchable, protected by a tradition of neighborhood loyalty fostered on the stoops of that housing project in Southie, protected by the arrogance and corruption of an FBI and a Justice Department that tolerated murder as an acceptable price of doing effective law enforcement. His capture after a worldwide manhunt that was, by turns, intense and incurious, epic and inept, put the spotlight back on the life, the legends, the lies and the myths, on families protected and families ruined, on the neighborhood where loyalty was everything and where now, for him, it was nothing.

PART ONE

THE RISE

1

The Lessons of Logan Way

O
n the map of coastal Boston,
South Boston doesn’t look like anything special, just a stubby peninsula jutting out into the harbor, but in this case geography deceives. It is in fact a place apart, an island more than a peninsula, imbued almost since it was first settled with a proud separatism, an overweening sense of self. It might be a function of its having been so unwanted for so long. It might also be that for those who landed here, it was all they had, the first taste of security and possession and home.

Out of this place would come James “Whitey” Bulger. And from the shadows, he would one day rule it.

Before bridges connected it to the rest of the city in the nineteenth century, South Boston actually was an island at high tide, a place that was home to more cows than people. In 1673, James Foster, one of the Puritans who settled in the area, built the first house on Leek Hill, near the present-day intersection of E and Silver streets. By the start of the Revolutionary War, there were a dozen families living in what was called Dorchester Neck, but they fled as British forces flooded Boston. It was a bitter but timely retreat. The redcoats swept the Neck in February 1776 and burned down all the buildings. Within a month, this first incursion of unwelcome outsiders into Southie would be avenged when colonial forces used Dorchester Heights, overlooking the bay, to aim cannon at the enemy fleet.

Southie’s hilly topography afforded the rebels’ cannon, dragged to Boston from Fort Ticonderoga on Lake Champlain, an unobstructed shot at the warships below. The hasty, humiliating exit of the British fleet, the first victory for colonial forces under the command of General George Washington, helped give birth to the notion of Southie Pride, the sense that this place and the people who live there were special. The city still celebrates the memory of the British retreat on what is known locally as Evacuation Day, a secular holiday that happily coincides with St. Patrick’s Day, a holy day and occasion for garrulous celebration for the Irish, especially in Southie.

After the Revolution, succeeding generations built bridges to the peninsula, but paradoxically the connection to the mainland contributed to an even more insular attitude. Over the bridges came waves of new immigrants, changing the neighborhood’s demographics and its politics. In 1850, before those waves of newcomers arrived, a Democrat didn’t stand a chance in Southie, which was, like Boston generally and like much of the Northeast, a Republican stronghold. The antislavery party, the Republicans, were also in Boston the party of the old colonial families, the old money, and the Protestant power structure it supported. They were about to be overwhelmed. By 1900, after a huge influx of Irish, the situation reversed. The term South Boston Republican became an oxymoron, as Democrats took charge of the city; only one Republican was elected mayor after 1910, none after 1930. Though the neighborhood was in fact a blend of many immigrant groups, the Irish would dominate, in numbers and in moxie, and produce a string of leaders and notable souls.

James Connolly was Southie’s first well-known Irish son. Having studied his way to Harvard, he asked for a leave of absence to participate in the first modern Olympic Games in Athens in 1896. When Harvard denied his request, he simply dropped out and won the gold medal in the triple jump. When Babe Ruth was courting his future wife, Helen Woodford, a Southie girl, he was known to haunt the bars of Broadway, Southie’s main thoroughfare, but this was five years before he was sold by the Red Sox to the Yankees and became baseball’s biggest star. Helen lived on Silver Street, the same narrow, one-way side street Whitey Bulger would later live on with one of his girlfriends and her children.
¹

Southie was perhaps best known for producing priests and politicians. Cardinal Richard Cushing, who grew up in City Point—a relatively prosperous section near the tip of the peninsula—ran the Catholic Church in Boston for a quarter-century and presided over John F. Kennedy’s wedding, inauguration, and funeral. Cushing was born in a three-decker almost directly across from the East Third Street home where Whitey and his confederates killed and secretly buried three people. John McCormack, one of eight children born to immigrant parents near Southie’s gritty Andrew Square, was elected to the House of Representatives in 1928 and became its speaker in 1962.

But if politics, both in church and state, was the Irish strong suit, they weren’t bad at the rackets, either. Frank Wallace and his brothers led the Gustin Gang, named for a Southie street, for about a decade. Wallace’s demise in 1931 offered a cautionary tale about the threat from outsiders: He and an associate were shot to death in an ambush when they went over the bridge and into the North End, Boston’s Italian neighborhood, to discuss a bootlegging dispute with the ruthless characters who would later be known as the Mafia. The demise of the Gustin Gang established an Italian criminal supremacy in Boston that would go unchallenged for a half century, until another Southie gangster emerged to take them on. That gangster, Whitey Bulger, would become Southie’s most infamous product even though he was the sort that in Southie they call a blow-in.

James Joseph Bulger Jr. wasn’t born
in the neighborhood, or in Boston at all, but rather in Everett, the first city to the north. He only found his way to Southie, with his family, as a young child. His father, for whom he was named, was born in Newfoundland and, as an eleven-year-old, arrived in Boston with his mother, stepfather, and sister on the Fourth of July.
²
They settled in Boston’s North End, which for much of the second half of the nineteenth century was a prime destination of the Irish fleeing starvation and poverty. Whitey’s grandparents had come from Newfoundland, a common first stop for the famine Irish because it was cheaper than sailing directly to Boston or New York. The elder James Bulger stood 5 feet 6 inches and set the physical standard for the men of the family: slight and sinewy, but exceptionally strong. He was working as a seaman when he became a US citizen at age twenty-one, then worked as a laborer and as a young man found a job in a railroad yard. Somehow, he got his left arm caught between a pair of freight cars, and the doctor who examined him deemed the arm no longer of any use and cut it off at the elbow. His boss, less than sympathetic, paid him the wages due and fired him.
³
It was a devastating setback, particularly in that unforgiving era. James Bulger had little formal education and there was scant demand for one-armed laborers. He struggled for the rest of his life to find steady work, though no one remembers him complaining about it.

James Bulger was fitted with a prosthetic arm, but it was crudely made and he regularly stuck the wooden hand in his pocket.
⁴
Shy by nature, a man of few words, his accident made him even more self-conscious. Not so self-conscious, however, that he did not pursue women. He was in his forties and had previously been married when he met a young woman who lived in Charlestown, the neighborhood on the northern edge of Boston, across the street from the Navy Yard, where, no longer fit for physical labor, he had found a job as a clerk. Her name was Jean McCarthy. She was a fair-skinned, blue-eyed brunette with a sunny disposition that belied a certain toughness. Jean was the daughter of Irish immigrants, twenty-two years his junior, and very independent-minded. At some point, she decided she didn’t like her given name, Jane, and, thinking her middle name, Veronica, too pretentious for a Charlestown girl, settled on Jean.
⁵
When James Bulger asked her out, she didn’t seem to mind the age difference, or the missing arm.

They married and settled first in Everett, just north of Charlestown, and soon started a family. Everett was an industrial city, thick with factories and chemical and metal plants, and James Bulger scratched around for work as a watchman. The first two children were born in Everett: Jean, named for her mother, in 1928, followed sixteen months later by James, who was born on September 3, 1929, less than two months before the stock market crash that would send the nation spiraling into the Great Depression. He had his father’s name but his mother’s looks—light skin and sharp blue eyes. His mother took to calling him Sonny, even as he grew older and others called him Jimmy or, more rarely, Whitey, after his striking blond hair. It was a nickname he never liked much. As he got older, he asked people to call him Jimmy, and when those who didn’t know him well called him Whitey, he would correct or sometimes berate them.

After a few years in Everett, the Bulgers moved back into Boston, to Dorchester, the largest and most populous neighborhood in the city, and St. Mark’s parish. By the twentieth century, Irish and Italian immigration had turned Boston—for three centuries perhaps the most determinedly, and rigidly, Protestant city in the nation—into a Catholic haven, where the parish defined the social structure and the neighborhood. And within parishes, there was a social hierarchy based on when you’d arrived in town. St. Mark’s was home to many recent immigrants, but it was also the parish and church of established families, the children and grandchildren of immigrants, including the former mayor John “Honey Fitz” Fitzgerald, whose daughter Rose taught Sunday school at St. Mark’s. The Bulgers were newcomers and struggling, and their eldest son, Jim, didn’t seem to hold much promise of elevating the family name. Whitey struggled in first grade at St. Mark’s School. If the other kids tried to please the nuns, the Sisters of Notre Dame de Namur, an order founded to teach the poor, Whitey couldn’t be bothered. He was restless, unable to sit for long periods of time. When he was seven, the family moved into a triple-decker on Crescent Avenue in St. Margaret’s parish, the Dorchester neighborhood that bordered Southie. The Sisters of Charity who ran St. Margaret’s Grammar School had the same problems with Whitey. He was clearly intelligent, but the routine and regimen of school didn’t appeal to him. Sometimes he’d slip out unnoticed. Bill Bulger, in his memoir, said he believed his older brother was more naturally intelligent and a quicker thinker than him. “But he found school boring. His teachers, like my mother, often discovered that Jim was suddenly missing.”
⁶

Whitey was eight years old when, in 1938, the family moved to the neighboring parish of St. Monica’s in South Boston. The family had no roots in Southie, no relatives or close friends there. They moved for one reason only. They had been one of 1,016 families lucky enough, and poor enough, to be awarded a place in one of the grand experiments of Franklin Delano Roosevelt’s New Deal: public housing. The Old Harbor Village project, which opened that same year, was the first public housing development built in New England, and one of the first in the country. It consisted of one-, two-, and three-bedroom apartments in twenty-two squat, three-story brick buildings and one hundred fifty-two row houses, spread out over thirty-four acres in an area just south of Andrew Square. It was named for the body of water, sandwiched between Columbia Point and Castle Island, that surrounded much of Southie. The project bordered Southie’s old Hooverville, one of the shantytowns named derisively after President Herbert Hoover, whose name had become identified, in the minds of many, with the collapse of the economy.
⁷
The new development felt, to those lucky enough to win a place there, like a piece of heaven. For the Bulgers, home had been a series of cramped cold-water flats with drafty windows. Their new apartment was a giant step up.

By May 1938, there were five children in the Bulger household—Jean, 10, Whitey, 8, Bill, 4, Carol, 1, and John (Jack), a month old—which qualified the family for a three-bedroom apartment, No. 756, on the top floor of 41 Logan Way. It was just around the corner from St. Monica’s Church, a parish founded in 1907, mainly to absorb the overflow of immigrants who went to nearby St. Augustine’s. For the Bulgers, as for most of their neighbors, church life and home life were fused, for while the government provided housing, the church provided almost everything else. Beyond the touchstones of Mass and ritual, the parish fielded baseball and football teams long before there was anything like Little League or Pop Warner. Jean Bulger became active in the women’s sodality, or fellowship, at St. Monica’s and sent her kids to join in the various activities organized by the parish. They went willingly, all but Whitey. He had little interest in such things.
⁸
St. Monica was the patron saint of difficult children, and from an early age Whitey showed that he could have used her intervention.

It was no accident that one of the nation’s first public housing projects was built in South Boston. One of FDR’s key allies in getting the New Deal through Congress was John McCormack, an ambitious congressman from the district. Indeed, South Boston had been one of the strongest votes anywhere for Roosevelt and, in those devastating times, looked to him for help. The Depression had not just thrown millions out of work; it had crushed the housing construction sector. In 1935, McCormack told the
Boston Globe
that the Roosevelt administration was determined to step in and fill the breach left by the private builders. “I have no hesitancy in insisting that Government in an emergency do everything that can be reasonably done to relieve human suffering and distress,” McCormack said, as he helped sell the idea of public housing.

It was McCormack who told Roosevelt to consider not just the humanitarian but the political benefits of putting a housing project in Boston—where many Catholics, as the Depression wore on, were finding themselves drawn to the harsh xenophobia of Father Charles Coughlin, a Michigan priest who used his syndicated radio program to brand FDR his moral enemy and the nation’s. It went without saying that McCormack believed the development should be built in South Boston. “McCormack pointed out the softening of the South Boston vote in 1936 to President Roosevelt, warning him that the ‘sullen, discontented and bitter’ people who had gone out of their way to support Father Coughlin’s (preferred) candidates were obviously in need of greater federal assistance,” wrote Thomas O’Connor, a professor of history at Boston College.