Life on the Lam Works for Mythic Irish Mobster

After retiring at age 66, the old man abandoned his beloved South Boston for a lengthy vacation.

James “Whitey” Bulger had little alternative. Even if he stayed, the one-time head of Boston’s notorious Winter Hill mob was going away for a long time.

It was January 1995, and the nation’s last great Irish gangster faced indictment for the first time in three decades. A racketeering and extortion conviction would guarantee Bulger’s death behind bars.

And then, before the feds moved in, poof! Whitey Bulger vanished.

Six years later, he remains at large--a life on the lam that has both destroyed and remade his reputation. In absentia, Whitey Bulger has gone from stand-up guy to running man, from local Robin Hood to simple murderous hood.

Bulger, the lone senior citizen on the FBI’s 10 Most Wanted list, is said to be linked to 18 murders. The balding, bespectacled fugitive has logged a record six appearances on “America’s Most Wanted.” This month, he and an associate were charged with killing businessmen in Florida and Oklahoma; now he could face the death penalty.

There’s a $1-million bounty on his head; fellow FBI fugitives in his league include international terrorist Osama bin Laden and alleged Olympic Park bomber Eric Rudolph.

But neither of them ever shared a glass of wine with FBI agents, as Bulger did while serving as both federal informant and mob boss for some 20 years. And neither of them fled after receiving a tip from one of those agents, as Bulger allegedly did.

The FBI man, fellow Southie native John Connolly, has pleaded not guilty to his own racketeering charges.

Bulger, at age 71, remains two things: a free man and a source of embarrassment to FBI officials, who fight a perception in Boston that their pursuit of Bulger lacks a certain . . . enthusiasm.

“There’s still a huge debate about whether the FBI is sincere in its efforts to catch Whitey,” says Dick Lehr, co-author of “Black Mass,” an extraordinary book on Bulger’s reign.

Michael Davis, whose sister was one of Bulger’s alleged victims, has waited 19 years for the arrest of her killer. He complained last year when investigators stopped digging for bodies at a suburban mob graveyard without finding his sister Debbie’s remains.

“I just think they dug where they were pointed at,” he complained, citing an informant’s tip as opposed to any police work. His sister’s body was eventually found in October, buried in a shallow grave on the banks of the Neponset River in Quincy.

FBI officials acknowledge that the stepped-up Bulger manhunt--the reward was bumped to seven figures in November--is part law enforcement, part public relations.

“A group of people out there believe we don’t want to find him. It’s certainly not the truth,” says Supervisory Special Agent Tom Cassano of the Boston office. The search, he says, is the most intensive of his 30-year career.

The truth is that Bulger, still toting the knife that helped him carve his notoriety, is somewhere out there, financed by a national network of safe deposit boxes, each loaded with cash by Bulger in the late 1970s.

Unlike recidivist mobsters such as Sammy “The Bull” Gravano, Bulger lives clean. Traveling with longtime girlfriend Catherine Greig, he avoids the single misstep that could land him in jail.

His double life as mobster/snitch, coupled with his long flight from justice, is the stuff of movies. Already, Matt Damon and Ben Affleck are mentioned as possible leads.

“Bulger had an image that was mythic,” Lehr says. “What’s fascinating to me is the FBI’s role in creating and perpetuating that myth.”

*

In recent years, Bulger employed a variety of aliases: Thomas Baxter, Mark Shapeton, Tom Harris--the last a possible homage to the author who dreamed up elusive mass murderer Hannibal Lecter (Bulger’s wanted poster pops up briefly in the film “Hannibal”).

But Bulger is no literary figure. He’s an old-school mobster who did time on The Rock--Alcatraz penitentiary--before returning to his native Boston and a life of crime.

Arrested first at age 17, Bulger developed a fearsome reputation among the Irish and Italian gangs that shared Boston’s organized crime. The blond-haired thug ran with a gang called the Shamrocks.

“They’re all the same,” a Massachusetts state trooper once said of the local mobsters, “except some of them have their O’s at the beginning of their name, and some have O’s at the end.”

Bulger’s Alcatraz stay, part of a 9-year federal rap, was his last trip behind bars.

When Bulger returned to Southie in 1965, his brother Billy was the local state senator, helped into office by volunteers like John Connolly. Billy, who later became Senate president, now heads the University of Massachusetts.

Whitey followed a similar arc in his disparate career. He fell in with the Winter Hill gang, the Gaelic equivalent of a Mafia family. When bad luck befell its former leader--Bulger reputedly sprayed him with machine-gun fire--Whitey ascended.

Despite the violence, Bulger was often viewed as a benevolent rogue, as likely to buy a local kid an ice cream cone as to break somebody’s head. Southie’s own Robin Hood, folks in the insular neighborhood liked to say.

That would change.

In the fall of 1975, Bulger was recruited as an informant by a hotshot FBI agent--his brother’s ex-campaign volunteer, Connolly. They first met at midnight on Wollaston Beach near Southie. It was, prosecutors say, the meeting that changed everything.

Connolly had recruited a TE, a “top echelon” informant in FBI-speak, and he would protect his snitch. Within a year, authorities now say, Connolly accepted a bribe from Bulger: a diamond ring. By the end of 1976, an FBI informant was allegedly killed after Connolly tipped Bulger about the turncoat.

A pattern was established, authorities said: Bulger alerted Connolly to the crooked activity of his competition, and Connolly warned Bulger about government efforts to put him in jail.

“This was not a bank robbery, or bribing a public official one time,” Lehr says. “This is a history that spans the next 20 years.”

Over those two decades, according to federal indictments, the alliance turned Bulger into Boston’s most powerful mobster and Connolly into an FBI star.

Bulger and sidekick Steve “The Rifleman” Flemmi enjoyed a certain criminal carte blanche: shakedowns, extortion, drug deals, murder upon murder upon murder--all without prosecution, authorities said. Connolly’s tips to Bulger and Flemmi about three informants allegedly boosted the body count. All later were killed.

Their partnership ended when Connolly allegedly alerted Bulger to the impending 1995 indictment. Six years later, the FBI agent stands charged as just another Southie gangster, accused of racketeering, conspiracy and obstruction of justice. He remains free on bond, awaiting his trial.

It took until last year, with an informant’s help, to find some of the victims. Five bodies, including the skeletal remains of a man buried a few hundred yards from Bulger’s old home, were dug up.

The alleged Bulger-Connolly connection remains a touchy subject in the Boston FBI office. “We can’t talk about all the ongoing stuff,” says Gail Marcinkiewicz, a spokesperson.

But Bulger’s presence still lingers. Opposite the sixth-floor elevators in the FBI office, his wanted poster stares out from the wall.

*

The coming indictment sent Bulger south to New York City. Once there, he dumped his old identity and became a new man: Thomas Barrett.

Like Bonnie and Clyde on Geritol--or in his case, the heart medication Atenolol--Whitey and Catherine stay on the move. Sightings have come in from Louisiana, Mississippi, California, Wyoming, Iowa, Florida, New York. Tips still arrive daily.

In the summer of 1996, he evaded police in a New York City suburb. That same year, he visited a New Orleans bank and emerged with a cash-heavy briefcase apparently loaded from a safe deposit box.

“The thing that’s unique about Bulger is that he’s got sufficient funds to stay out of trouble,” says Cassano. How much? If Bulger is apprehended and convicted, he faces forfeiture of $10 million in assets.

Henry Wellman was Bulger’s landlord for six weeks in 1996, unwittingly setting the fugitive up in a two-bedroom apartment in the small fishing town of Grande Isle, La.

“Just an elderly guy with his wife, the grandfather type,” Wellman recalls. “A nice guy, stayed to himself.”

Bulger complained about the heat, went for nightly walks, and left as quietly as he arrived. Weeks later, Wellman and his wife, Barbara, were visited by the local chief of police. The FBI, he said, had questions about their tenants. Seemed the man was the head of Boston’s Irish Mafia.

Wellman recalls his response: “You gotta be kidding me.”

Bulger’s abandoned car, with gas receipts from Grand Isle, was found in New Jersey. Where Bulger headed from there was anyone’s guess.

It took four years for the next confirmed sighting: February 2000 in Fountain Valley, Calif., where Catherine had some work done at a local beauty parlor while Bulger waited in a car. That trail, too, went cold.

*

Whitey Bulger needs no disguise now.

Traveling with Catherine, who turns 50 next month, he sports sunglasses and a baseball cap. The once-feared gangster looks more grandfather than godfather, just another anonymous senior citizen.

“Go down to Florida,” Cassano says dolefully, “and you’ll see thousands of them.”

Despite Bulger’s amazing success, the odds of an arrest still favor the FBI. Since 1950, 458 criminals have made the 10 Most Wanted list. All but 29 were eventually taken into custody--an arrest rate of 94%.

Just last month, Oklahoma officials announced that they believed Bulger might be frequenting gay establishments and nudist colonies. They also said Bulger’s refusal to visit a dentist since fleeing Boston had left him with permanent bad breath.

While on the run, Bulger has tried to resurrect his Robin Hood role. The FBI has tales of Bulger buying appliances for acquaintances made on the road, or springing for a pet’s visit to the veterinarian.

Back in Boston, that image is forever lost. His crime spree far outpaces the work of “Boston Strangler” Albert DeSalvo, who killed 11. He’s accused of poisoning his beloved neighborhood with drugs. He killed with impunity. He turned on his friends.

“He was mythic. He was rock solid, the ultimate stand-up guy. And now he’s a rat. He’s been exposed,” Lehr says.

“The myth of Whitey Bulger is totally shattered now.”