Feature Articles

December 2004
Ten Years On The Lamb And The Question Still Remains: Where's Whitey?

By David Kales, Journalist, Editor, and Free-Lance Writer

David Kales has been a journalist, editor, and free-lance writer for over forty years. His journalist experience includes Newsweek, Forbes, INC magazine, and foreign correspondent for the Hearst Newspapers, covering the Vietnam War and Southeast Asia. He has written several books, including "All About the Boston Harbor Islands." "The Phantom Pirate" is his first work of fiction.

     Rumors circulate in Boston three or four times a year of Whitey sightings. Whitey refers to James "Whitey" Bulger, Boston�s notorious gangster, who after being indicted for racketeering and murder, has skipped town and been on the lam since 1995.

     The FBI, supposedly wants Whitey so badly that the agency has put him on its Ten Most Wanted List, right after Osama bin Laden, and posted a $1 million reward for his capture.

     The latest rumor circulating this November in Boston has it that Whitey wants to give himself up. Whitey watchers think Bulger is dying, so he wants to surrender and arrange for a family member to collect the $1 million reward on his head. The deal would also include some kind of blanket immunity for everyone who�s helped him during his decade on the run.

     Law enforcement officials in Boston say that there is no truth to news reports that Bulger is trying to negotiate a deal to end his life as a wanted man. "There wasn�t any negotiations concerning Bulger�s surrender," said one law enforcement official. "These are just street rumors."

     The question still remains: Where�s Whitey? Who is this "most ruthless gangster and feared crime boss to ever come off the streets of Boston"? How has he managed to elude law enforcement authorities for a decade?

     I�ve tried to answer these questions in a book I�ve just published called "The Phantom Pirate�Tales of the Irish Mafia and the Boston Harbor Islands."

     I had been thinking about writing a book about Whitey Bulger for several years. In fact, I started writing a non-fiction book about him. But I turned it into fiction, historical fiction if you will. As I say in the book: "Some readers would no doubt recognize this man and many people in his world. So the names of the characters in this story have been changed to protect the dead and those who could become the dead."

     Literary flair aside, in truth, this story of the life and crimes of Whitey Bulger is so rich in lore, legend, and myth that it is better told as fiction, where I could use the different voices of characters�gang members, co-conspirators, fellow mobsters, lawmen, victims, and seanachies (Irish storytellers)�to spin their tales about him. As the author, I could weave them into a credible story.

The Phantom Pirate

     In my book, Whitey Bulger is called James Freney. "For twenty-five years, a man named James Freney ruled the Boston underworld, controlling illegal gambling, loan sharking, and drug dealing in Boston, up and down the East Coast from Maine to Rhode Island. He was the Don of Boston�s Irish Mafia. They say that he even sat at the table with the Five Families of New York when La Cosa Nostra was big. The FBI credits him with murdering twenty-two people, but who knows how many more bodies he�s dumped into Boston Harbor?"

     "Freney went on the lam in 1995 when he found out that he was going to be indicted for racketeering and murder, and the FBI, along with every other law enforcement agency across the country, is still looking for him. The FBI has put Freney on its Ten Most Wanted List, right behind Osama Bin Laden, and posted a $1 million reward for his capture.

     "Although his story has been reported for years by newspapers and television in Boston and across the nation, providing many facts about his life, little is certain about the myth and mystery that shroud him. We are not even sure whether he is still alive. But dead or alive, his ghost haunts the present, and is doomed to haunt the future. Time, in the end, is the best storyteller.

     " The setting�the Boston Harbor Islands�is real. The intersection where characters and setting meet is imaginary. But it could have happened this way."

Boston�s Two Mafias

     In researching the book, I discovered the rich and gritty history of organized crime in Boston. The city�s underworld was ruled by two Mafias�the Italian Mafia, and what was to become under Whitey Bulger, the Irish Mafia.

     As I say in the book: "Ever since Prohibition in the 1930s, the Irish gangs had always been subordinate to the Italian Mafia. The Irish tried to take control of bootlegging operations in Boston Harbor from the Italians, but when two leaders of the Kelsey gang out of South Boston went to the North End to dictate their terms, they were murdered. The Irish retreated to South Boston and it would be many years before they again challenged the Italians for control of Boston Harbor.

     "After Prohibition, the Italian Mafia grew stronger, more organized, disciplined, and regimented than the Irish gangs. They had capos, soldiers, and consiglieres. The Irish gangs were smaller, undisciplined, constantly feuding with each other, and were headed by strongmen�smart and cunning dictators. But if the top man got knocked off, it usually spelled the gang�s end.

     "When illegal gambling replaced alcohol as the prime criminal activity, the Italians remained on top of the business. They controlled the bookies. The bookies, in turn, were protected by the cops, who were paid off by the mob. They say the mob�s tentacles extended everywhere, even to Beacon Hill, where a bookie ran an illegal betting line from the Massachusetts State House.

     "The Irish gangs survived as subcontractors to the Mafia. They became the enforcers, the hitmen, the leg-breakers for the Mafia when the Italians didn�t want to use their own guys. They survived because they took money from the Italians, and put it on the street as loan shark money."

     "So here�s the picture. The Italians are on top of Boston�s underworld. The Irish gangs operate pretty much independently, ruling like princes in their principalities of Dorchester, Roxbury, Charlestown, Somerville, and South Boston, but for the most part minding their own business and staying out of the way of the Italian mob, living in peace among themselves�until Labor Day, 1961."

The Irish Gang Wars

     That�s when the Irish gang wars began. "When Freney (Bulger) was paroled from Alcatraz and returned to South Boston in 1965, the streets were bathed in the blood of Irish gangsters. The back alleys, car parks, and wastelands of Somerville, Charlestown, Roxbury, Dorchester, and South Boston had become killing fields in what some say was the bloodiest gang war in American history. There were already fifty dead and, with Freney back in town, there were more to come."

     After the Irish gang wars petered out, Bulger consolidated his power in the Winter Hill Gang, the largest Irish gang, and in less than a decade, built the organization into a powerful Irish Mafia.

     It was also during this period that an infamous secret deal was struck between Bulger and the FBI�a deal which was to alter the criminal landscape in Boston and ultimately lead to the fall of the Italian Mafia in Boston and New England.

     Back in the 1970s, the FBI was waging a crusade across the country against the Italian Mafia on orders from Attorney General Robert F. Kennedy and FBI chief, J. Edgar Hoover. In Boston, the bureau thought the best strategy to break up La Cosa Nostra in this town was to pit the Irish gangs against the Italians, divide and conquer the underworld.

The Informant

     How do you divide and conquer the underworld? Recruit informants to tip off the FBI to Mafia moves. Find out how the Mafia operates. The FBI recruited Whitey Bulger as a TE (top echelon) informant.

     According to many law enforcement officials, Bulger�s biggest tip to the FBI was informing the agency about a Mafia induction ceremony. This enabled the FBI to secretly record the ceremony on video tape. The tape showed a secret meeting of the who�s who of the big bosses in the New England Mafia. It was the first time an inside look of Mafia operations had ever been recorded. It was the first big step in taking down the Mafia in Boston and New England.

     In "The Phantom Pirate," I tell the story about what happened to Boston�s two Mafias. By the year 2000, organized crime in Boston was history. The Italian Mafia has become a shadow of its past. Feuding capos, vying for power, have torn the organization, already weakened and demoralized from the stunning 1998 revelation that their allies in crime�Winter Hill Gang leaders, Whitey Bulger and Steve Flemmi�were in cahoots with the FBI to bring them down.

     Since that time, scores of capos, soldiers, and associates have been put behind bars, many of them for life. Decimated by racketeering indictments, the New England Mafia has been unable to recruit new wiseguys.

     As one law enforcement agent put it: "The Mob may not be dead yet, but it�s dying. Quite frankly, who in his right mind in the twenty-first century would get involved with the Mafia."

     By the turn of the 21st century, the Irish Mafia was no more. Indictments handed out by law enforcement decimated the higher ranks of the Winter Hill gang. The revelation that Whitey Bulger was an informant for the FBI and on the lam, served a crushing blow to the gang. Leaderless and undisciplined, gang members began to rat on each other, leading to more indictments, more gang members going to prison, or into the Witness Protection Program. The Winter Hill gang, Whitey Bulger�s gang, has collapsed.

     Today, Boston Irish gang leaders are either dead, in jail, or in the Witness Protection Program (though several are out of jail now having received reduced jail sentences in exchange for turning states evidence).

     Only one person got away�a fugitive from justice for ten years�James "Whitey" Bulger.


     The Boston bureau of the FBI is hardly in a position to boast about its victory over organized crime in the city. True, the Italian Mafia is now only a faded imitation of its former glory days. And what constituted the power behind the Winter Hill gang, and later Bulger�s gang, has disappeared.

     But the FBI is under siege. A growing number of plaintiffs are still seeking damages totaling $2 billion from the federal government, stemming from the FBI�s relationship with organized crime bosses. At least ten suites were filed under the civil portion of the Racketeer Influenced and Corrupt Organization (RICO) Act, the same federal law used against the Mafia and organized crime figures.

Where�s Whitey?

     Over the years, Whitey Bulger has been sighted with his female companion Catherine Craig all over the US�New York, California, Iowa, Louisiana, Florida and in the Caribbean. In 2002, the manhunt expanded overseas. Whitey Sightings were reported in London, Manchester, Brighton, Oxford, Hastings, and on the Isle of Wight in the United Kingdom; in Dublin, Ireland, and as far away as France, Italy, Spain, and Greece.

     After a decade on the run, why hasn�t Whitey been caught?

     Some people say the FBI doesn�t want to capture him. If Whitey were caught, they think, he could provide embarrassing information about FBI agents and their relationship with criminal informants. As one law enforcement official put it: "The FBI doesn�t want this loose-lipped old gangster (Bulger is now 75) turned informant anywhere near a witness box."

     Others think Bulger is dead. Maybe buried in the Meadow Lands

     "He�s alive. We�ll catch him," said a Boston FBI agent."We�ve tracked down 1600 leads since 2002. Our agents have traveled to twenty-five countries, including Greece and the Caribbean pursuing these leads. It�s a matter of time and luck. But we�ll catch him. The FBI has caught 445 out of the 475 top ten fugitives ever listed."

     But so far, all these leads have led to tracks that have vanished.

     So where is Bulger now? My guess he�s alive and staying in an IRA safe house in Dublin or in some little village nestled in the Irish countryside.

     But there�s another question you might want to ask: Where�s Whitey�s money? He�s has had to finance his ten years on the run. How has he bankrolled his flight? The answer to these questions may be found in "The Phantom Pirate�Tales of the Irish Mafia and the Boston Harbor Islands."

David Kales has been a journalist, editor, and free-lance writer for over forty years. His journalist experience includes Newsweek, Forbes, INC magazine, and foreign correspondent for the Hearst Newspapers, covering the Vietnam War and Southeast Asia. He has written several books, including "All About the Boston Harbor Islands." "The Phantom Pirate is his first work of fiction.

Past Issues

Copyright © 1998 - 2004 PLR International