- The Washington Times - Saturday, July 8, 2006


By Howie Carr

Warner Books, $25.95, 352 pages


After reading “The Brothers Bulger,” Howie Carr’s tale of the life of James “Whitey” Bulger, Beantown’s most vicious gangster, and his brother Billy, the most powerful politician in Massachusetts, I’m somewhat baffled: Given Whitey’s brutal nature and his willingness to use violence against virtually anyone who posed a threat to his criminal enterprises, how has Mr. Carr, a columnist for the Boston Herald and radio talk-show host, managed to live long enough to tell this fascinating story?

This isn’t an idle question. In March, Kevin Weeks, one of Whitey’s top criminal lieutenants, told CBS Television’s “60 Minutes” that he went to Mr. Carr’s home planning to shoot him to death, but decided not to after seeing him leave the house with his child.

While there is no way to know for certain whether Weeks is telling the truth, it’s certainly plausible: Mr. Carr presents evidence in the book that Whitey and his gang had intimidated other members of the press, and he makes clear that they had no ethical compunctions about killing. Fortunately, the author survived to tell this remarkable story.

For more than a decade, James “Whitey” Bulger, who fled Boston in 1994 after starting his reign of terror in the 1960s, has been a fixture on the FBI’s Ten Most Wanted list (behind only Osama bin Laden), with the focus of the search in Europe, where there have been repeated Whitey sightings over the past decade.

What made Whitey an especially dangerous hoodlum were the men on his team: his criminal partner, Stevie “The Rifleman” Flemmi; brother Billy, an attorney and politician who rose to become president of the Massachusetts Senate (making him arguably more powerful than most governors he served with) and later became president of the University of Massachusetts and John “Zip” Connolly, the crooked Boston FBI agent who grew up with the the Bulgers in South Boston and used his law-enforcement position to help Whitey carry out his crimes and eliminate his mob rivals.

Mr. Carr’s story starts in the 1920s with James and Jean Bulger, who had six children. James “Whitey” Bulger was born on Sept. 3, 1929, and brother Billy on Feb. 3, 1934. The brothers’ lives could hardly have taken more different paths. Billy was the studious sort who wanted to better himself and get out of the bleak housing projects the family lived in. As a child, Billy’s idea of disobedience was sneaking a flashlight under his pillow so he could read after bedtime.

Whitey, on the other hand was a budding sociopath who was destined to be a career criminal. He began in 1943 with larceny, soon advancing to assault and battery and robbery. Mr. Carr suggests Whitey, who was bisexual, made money by robbing men he met in gay bars on Boston’s skid row.

During adolescence, his idea of fun was maiming other youths while pinning the blame on someone else. In one incident, when Whitey was about 18, he was driving Billy and another youth home from the beach, when they saw a child named O’Hara riding his bike. When Billy mentioned in passing that he disliked young O’Hara, Whitey tried to run him off the road. “Jimmy,” Billy said. “I just said I didn’t like him. I didn’t say kill him.” As the boy sped through a stoplight trying to get away, Whitey smiled at his younger brother. “We’re not going to kill him,” Whitey said. “When he gets to Broadway and barrels out into the street, the bus’ll kill him.”

Many young hoodlums do in fact “grow out of it,” but not Whitey. In 1955, he fell in with a recently released ex-convict, becoming a bank robber. The following year, Whitey would be convicted of armed robbery, serving nine years in various federal penitentiaries. Whitey would later regale fellow gangsters who complained about Massachusetts prisons with tales of his time at Alcatraz.

A favorite story of his was the one about how a hulking black inmate began making sexual advances to a smaller white convict, describing in graphic detail how he planned to rape him. Terrified, the white guy made a scythe-type weapon in the prison shop, and just before the evening lockdown, hid at the top of a stairwell he knew the black guy would climb.

When the latter reached the top of the steps, the white convict emerged from the shadows and cut off the black convict’s head with the scythe. “The inmates listened in their cells as the head bounced down the stairs one step at a time like a bowling ball,” Mr. Carr recounts.

After leaving prison in 1965, Whitey spent the bulk of the next three decades making himself the most powerful gangster in New England.

Using his connections with Connolly; his FBI agent colleague John Morris; H. Paul Rico, a rogue veteran FBI agent; and Flemmi; Whitey either murdered or engineered the arrest and conviction of every Boston-area organized-crime figure who stood in his way, most prominently, Boston Mafia boss Gerry Angiulo and members of the Winter Hill Gang — a non-Mafia mob that Whitey hooked up with after getting out of prison.

Mr. Carr describes scores of murders that Whitey was responsible for. When he was attempting to take over a company called World Jai Alai, he needed to find out what Peggy Westcoat, a cashier knew about skimming of profits. One day in December 1980, two men broke into her Florida house, hanged her boyfriend, tortured Westcoat and threw her into the garbage disposal after she told them what they needed to know.

Later, with the help of Rico (who had left the FBI and was World Jai Alai’s vice president for security), Whitey arranged the murder of Roger Wheeler, the 55-year-old millionnaire owner of the firm. In 1981, Whitey strangled to death 26-year-old Debbie Davis, Flemmi’s girlfriend, because she was breaking up with Flemmi and knew too much. In 1985, Whitey, Weeks and Flemmi strangled to death Deborah Hussey, the daughter of Flemmi’s common-law wife; they were afraid that she would tell police that Flemmi had sexually molested her when she was 16.

In many instances, however, Whitey’s ferocious reputation was sufficient to intimidate people into yielding to his demands. Chapter 13 of the book, describing how Whitey forced Steven Rakes to sell his liquor store to him, is chilling, as is the story of how Richard Bucheri, a real-estate developer in Quincy, was taken for $200,000 by Whitey, who threatened to kill Bucheri after he made the mistake of advising a neighbor who was feuding with Weeks over the location of a fence.

For years, Billy claimed not to be in contact with Whitey and professed ignorance of his criminal activities. This was undermined by the fact that from 1979 on Flemmi’s family owned a home, where Whitey’s gang used to convene, next door to Billy, and the fact that relatives of gangsters repeatedly ended up on the public payroll — something over which Billy exercised iron-fisted control.

All of the above barely scratches the surface of what’s in this book. In the end, changes in the FBI and the U.S. attorney’s office led to the collapse of Whitey’s criminal enterprises and resulted in his flight to avoid prosecution. And Billy gave disastrous congressional testimony that led to his removal as president of the University of Massachusetts. Gov. Mitt Romney helped seal his fate.

Joel Himelfarb is the assistant editor of the editorial page of The Washington Times.

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