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Whitey & The FBI

Sidekick’s double-dealing career worthy of master spy

Shephen “The Rifleman” Flemmi.

AP File Photo

Shephen “The Rifleman” Flemmi.

Stephen "The Rifleman’’ Flemmi has always been the sidekick, the guy with the colorful nickname barely mentioned in organized-crime stories that kept the spotlight on his notorious partner, Whitey Bulger.

But in many ways, the soft-spoken Flemmi was the main man while he operated in the shadows.

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By the time Bulger turned FBI informant in 1975, Flemmi had already been talking to the bureau for a decade.

In just one example of how he juggled conflicting interests, Flemmi tipped off the FBI about the permanent disappearance of a gangster during the 1960s gang wars. Later, he was charged with murdering the man, a case for which he has yet to stand trial.

When Bulger and Flemmi teamed up in 1974 as enforcers for Somerville’s Winter Hill gang, it was Flemmi who was the feared killer in the underworld.

And it was Flemmi who first straddled both gangster camps -- the Italians in the North End and the Irish in Somerville. He so ingratiated himself with Mafiosi like Raymond Patriarca in Providence and Ilario Zannino in Boston that they courted him to become a Mafia soldier.

Even Winter Hill gang leader Howie Winter admits he was fonder of the fun-loving Flemmi than of the antisocial Bulger.

"I thought the world of Stevie Flemmi,’’ said Winter during a telephone interview from prison. "He was a man’s man.’’

Flemmi’s long career has been a story worthy of a master spy -- liked by many, but known by few.

A former paratrooper who served in Korea, he forged friendships around the country with veterans who had no idea he was a gangster. He had a cadre of wise guy friends who didn’t know he was an informant -- one who was actually informing on them. And he socialized with FBI agents, who said they trusted him with their lives, despite his reputation as a killer.

"He was a fun guy to be around and he was a real gentleman,’’ said Winter’s wife, Ellen Brogna, of Millbury. "Stevie would do anything to help you.’’

In fact, when Winter went away to prison in 1979 on race-fixing charges and again in 1992 on drug charges, a sympathetic Flemmi would call Brogna to make sure she was OK, or to take her out to dinner.

But at the same time he was consoling Winter’s wife, Flemmi was leaking information to the FBI about Winter’s activities, according to FBI reports.

"He never represented himself as having an evil side,’’ Brogna said. "I always saw one side of him, the kindness he showed to me.’’

The revelation last year that Flemmi moonlighted as an FBI informant for 30 years was initially greeted with disbelief by Flemmi’s underworld friends.

"It was the most difficult thing to believe,’’ said Brogna. She said she recently wrote to Flemmi in jail, where he is awaiting trial on racketeering charges, urging him to call her. And he did.

Despite stacks of FBI documents indicating he snitched on his friends, Brogna said Flemmi assured her "things aren’t what they appear.’’

Flemmi was born June 9, 1934, the first child of Italian immigrants, Giovanni and Mary Flemmi, who raised three sons in the Orchard Park housing project in Roxbury. His father worked as a bricklayer.

Flemmi’s childhood friends included Frank Salemme, still the reputed leader of the New England Mafia, who sits in a jail cell awaiting trial in the same racketeering case as Flemmi.

After being arrested at age 15 on a charge of "carnal abuse,’’ and spending some time at a juvenile detention facility for assault, Flemmi enlisted in the Army at age 17, serving two tours in Korea with the 187th Airborne Regimental Combat Team. He was highly decorated when honorably discharged in 1955. Like other soldiers in his squad, Flemmi was dubbed "a rifleman.’’ But unlike the others, he took the nickname home with him.

Although short -- 5-foot-8 -- and slender, Flemmi had a reputation as a tough guy who wouldn’t hesitate to shoot.

When rival gangs from Somerville and Charlestown started killing each other in the 1960s, FBI Special Agent H. Paul Rico recruited Flemmi as an informant. His code name was "Jack from South Boston’’ in the early days. Later, the FBI referred to him as "Shogun.’’ He was deemed an underworld comer by Rico, "if he survives the gang war.’’

Although he was being wooed by mob capo Zannino in 1967 to join the Mafia, Flemmi confided to Rico he "does not like the individuals as men, but it is possible that he will join it as Salemme is impressed with these people and Salemme, after all, is his partner.’’

But Flemmi’s partnership with Salemme was about to end. In 1969, they were charged with planting a car bomb that tore off Attorney John E. Fitzgerald’s leg and nearly killed him. The motive for the January 1968 attack was that Fitzgerald was representing a notorious hit-man-turned-informant who was testifying against the local mob hierarchy.

Both men went on the lam, but only Salemme was captured and convicted of the Fitzgerald bombing. He spent 15 years in prison. Flemmi surrendered in 1974 after a witness recanted and all charges against him were dropped. Last year, Flemmi revealed that Rico alerted him it was safe to return to Boston.

"He hooked up with Whitey and they did well together,’’ Salemme confided about Flemmi to a fellow Mafiosi during a bugged conversation at the Logan Hilton in December 1991.

For Flemmi, life had never been better. As partners, Flemmi and Bulger expanded their criminal enterprise while running from meetings with wise guys to dinners with FBI agents.

In the 1990s, Flemmi began investing in real estate, buying up property in Boston’s Back Bay. And he soon expanded his social circle, joining veterans groups and raising money for Korean War memorials.

James W. Lang, a retired winery worker from British Columbia, who served in the same company with Flemmi in Korea, was shocked to learn Flemmi is charged with murder, loansharking, and extortion as part of a federal racketeering indictment.

"He’s a very mild person,’’ Lang said. "He doesn’t really get excited, but when he says something, he means it. I’ve never seen anyone so sincere.’’

Thirty-five years after Flemmi and Lang helped rescue a wounded soldier during a bloody battle with Chinese soldiers in the Kumwha Valley in Korea, they renewed their friendship at a paratrooper reunion in Norfolk, Va.

At Lang’s urging, Flemmi joined the International Association of Airborne Veterans and traveled the world jumping out of planes with active paratroopers from various countries in a show of good will. In 1989, Flemmi jumped in South Africa, the following year he jumped in East Germany and Thailand, and in 1991, Israel. He fraternized with generals, sometimes sending them small gifts after returning home.

When Lang couldn’t afford the South African trip, Flemmi gave him $1,000. Flemmi also donated $5,000 in 1993 to a Korean War Memorial in Charlestown, where his name is inscribed on a granite bench reading, "In memory of the paratroopers who made the supreme sacrifice on the battlefields of Korea.’’

Lang, who thought Flemmi earned his living as a liquor store owner, added: "Steve is just a terrific humanitarian.’’

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