Published January 14, 2008
This is a weekly series that profiles America's most wanted criminals.
In 1995, South Boston gangster James "Whitey" Bulger, the alleged leader of the city's notorious Winter Hill Gang — and an FBI informant — was tipped off that the feds were about to indict him on racketeering charges.
"He had planned for this to eventually happen," FBI Special Agent Richard Teahan said.
Since 1975, Bulger had been playing both sides: On the one hand, the FBI says he was responsible for at least 18 murders and ruthlessly guiding a crime organization more powerful than the Mafia; at the same time, he was ratting out his rivals to the FBI in exchange for protection against arrest and prosecution.
Bulger's criminal legend, which began with his first arrest in 1943 at the age of 14, was enhanced by the oddity of his South Boston family ties: Brother William, known locally as Billy, chose a different path and rose to become president of the Massachusetts State Senate and president of the University of Massachusetts.
Living across the street from the brothers Bulger was Stephen Flemmi, later known as "The Rifleman," who would join with Whitey Bulger in 1972 to take over what was left of a local group of street thugs known as the Winter Hill Gang.
By 1973, Bulger was running the rackets in South Boston and competing with the Providence, R.I.-based Raymond Patriarca crime family.
Soon after, Bulger struck his unholy alliance with the FBI that over time would unravel.
Bulger would become a criminal in need of an escape plan.
He had access to false identities, large sums of cash in safe deposit boxes in Florida, Ireland, England and Montreal, and could tap into a criminal network that would help him disappear.
When that day came, he packed his bags, grabbed his longtime girlfriend Catherine Greig and set off for a life on the run, leaving behind books and other evidence at his home for authorities to find.
More than 10 years later, he still eludes the law.
One of six children, Bulger started his criminal career at the age of 14 with a South Boston street gang known as the Shamrocks and built up a long rap sheet that included armed robbery, larceny and forgery.
He was sent to a juvenile reformatory and later tried to live on the straight and narrow by joining the Air Force. In spite of several arrests for assault and going AWOL, he was honorably discharged in 1952 and returned to Boston to resume his career in crime.
Bulger built a criminal resume that included serving nine years for bank robberies in the federal prisons at Atlanta, Alcatraz and Leavenworth.
The FBI says he is responsible for at least 18 murders, and is wanted on charges of racketeering (RICO), murder, conspiracy to commit murder, conspiracy to commit extortion, narcotics distribution, conspiracy to commit money laundering, extortion and money laundering.
He is also the oldest fugitive on the FBI's Most Wanted list, and ranked second behind terror mastermind Usama bin Laden.
Despite an intense international manhunt, Bulger and his girlfriend have remained at large, with reports of sightings around the world only adding to his legend.
In April 2007, a photo and 18 seconds of video surfaced of a person matching Bulger and his girlfriend's description.
"There are mannerisms and similarities that are making us key in on these people," Teahan said.
The April video shows a couple shopping in Taormina, a city on the island of Sicily.
The FBI dispatched agents to the area, but has been unable to positively identify the couple.
Bulger likes to read and visits libraries and historic areas. He's on atenolol, a heart medication, and usually walks for exercise. He also loves animals and uses disguises. He is known to carry a pocketknife at all times.
He's been known to use disguises and aliases. Those fake names include Thomas F. Baxter, Mark Shapeton, Jimmy Bulger, James Joseph Bulger, James J. Bulger, Jr., James Joseph Bulger, Jr., Tom Harris, Tom Marshall and “Whitey."
A task force set up to find Bulger is still investigating hundreds of tips from around the world, Teahan said.
The FBI is offering a $1,000,000 reward for any information leading to Bulger's arrest.