Stephen Joseph Flemmi also known as "Jack from Boston", "Stevie", "Michael Fuclio" and "Shogun", was the eldest of two brothers Vincent Flemmi and Michael Flemmi born to first generation Italian immigrants Giovanni Flemmi and Mary Irene Flemmi. He was raised in the Orchard Park tenement located at 25 Ambrose Street in Roxbury, Massachusetts. It was the same neighborhood that Patriarca crime family capo Ilario Baione and Ilario Zannino were born and raised. His father Giovanni was a bricklayer who, according to fellow mobster Kevin Weeks, served in the Italian Army during World War I. His mother was a full-time homemaker who never lost her thick Italian accent and spoke only in broken-English. He was the stepfather of Deborah Hussey from his common-law wife, Marion Hussey. He stands at 5'8" and weighs 150 pounds with a slender build but earned a reputation as a tough guy with a hair-trigger temper. He had a natural dark tan and curly dark hair with deep set brown eyes. He is described by his girlfriend-mistress Marilyn DeSilva as mild mannered and personable. He was a childhood friend of to-be-State Police Lieutenant Richard J. Schneiderham who Richard grew to idolize along with his brother-in-law Massachusetts State Police Officer Thomas Duffy. and his lifestyle after enlisting in the State Police Department and began accepting bribes from him. His close friends included Winter Hill Gang member Edward Goss who would later work for the MCCA at the Under Common parking garage and Robert (Red) Conlin. Richard would later tell his son that if he ever had a problem Stephen could straighten anything out for him. His codename for Stephen was "Eric". He was raised as a child on the Roman Catholicism but later unofficially converted to Jehovah's Witness while incarcerated in 1981. He was a protege of brothers Walter, William and Edward Bennett during the Irish Mob Wars in 1964. He'd moved out of his estranged wife Jeannette's house and was shuffling from cheap apartment to cheap apartment to avoid being ambushed from the McLaughlin brothers. The need for constant mobility intruded on his gambling and loansharking rackets. He was suffering from depression about the separation from his wife, exhausted and suffering from extreme anxiety over the chance of being murdered. Flemmi earned himself a reputation during an encounter in a Roxbury, Massachusetts bar. The brawler was huge who stood half a foot taller than Stephen and was at least sixty pounds heavier. He reportedly said, "Hey, Flemmi, I hear your a real fucking tough guy. Why don't we find out how--" the man never finished his sentence. Flemmi punched him to the floor before the man could finish his idle threat. Witnesses at the bar swore he hit the loudmouth brawler five more times before he hit the floor. It was said that Stephen had fast hand reflexes.
After first being arrested at fifteen on a charge of "carnal abuse", and spending some time at a juvenile detention facility for assault, Flemmi enlisted in the U.S. Army at the age of seventeen, and served two tours with the 187th Airborne Regimental Combat Team. Stephen Flemmi served in the U.S. Army as a paratrooper during the Korean War and was honorably discharged in 1955. He was highly decorated, being awarded the Silver Star and Bronze Star for rescuing his friend James W. Lang in a bloody battle with the People's Volunteer Army in the Kumasha Valley in Korea. He later renewed his friendship with Lang after meeting him thirty-five years later at a paratrooper reunion in Norfolk, Virginia. On May 25, 1953 Mary told the FBI that Stephen enlisted in the U.S. Army paratroopers at Boston during January 1952. Since Stephen was underage, but had expressed a desire to entire the armed forces, his parents went before the Notary Public and signed an affadavit stating that Stephen had been born on October 10, 1932 and used the name of one of his childhood friends, Michael Fuclio, to enlist in the army but arrangements were made to have his name changed from Michael Fuclio, back to Stephen Flemmi. Although his mother Mary knew what she was doing was fraudulent, she later stated that her son was so persistent that they agreed to do it.
At his friend's urging, Steven became a prominent and popular member of the International Association of Airborne Veterans (IAAV) and travelled the world jumping out of planes with active paratroopers in South Africa, East Germany and Thailand. While a IAAV member he fraternized with military generals, sending them small gifts after returning to Boston. In 1993, he donated $3,000 to a Korean War memorial in Charlestown, Massachusetts 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." Flemmi earned the monicker, "The Rifleman" for his sharpshooting marksman skills he demonstrated in battle. The press later dubbed him "The Rifleman". He had remarkable marksmanship skills which he allegedly displayed when on February 4, 1980 he shot and killed twenty-four-year-old Steven Hughes, Junior as he was unloading groceries from his car in Charlestown from a nearby rooftop. Hughes Jr. had made remarks about seeking revenge on the Winter Hill Gang for Stephen and James J. Bulger machine gunning his father and namesake, Stephen Hughes Sr. in 1966.
When Flemmi returned to the United States, he and his brother Vincent Flemmi, joined the crew of Portuguese-American mobster Joe Barboza. Barboza possessed close ties to both the Italian-American Patriarca crime family of Providence, Rhode Island and the Irish-American Winter Hill Gang of Somerville, Massachusetts. Steven and Vincent were close. He was a prominent member of the Winter Hill Gang. He was also a close friend of the 1978 Blackfriars Massacre gunman, Vincent E. Solomonte. Flemmi also had a passion for raw foods.
He later involved his mother in he and Bulger's criminal activity. In the late 1980s James J. Bulger had come up with a way to establish a record of legitimate income, by continually flipping his properties. He would "buy" one of Kevin Week's lots or condominiums for $40,000, say, and then turn around and sell it to his mother Mary, or Kevin O'Neil. He would then give them a "mortgage", and they'd pay off the note, monthly. Mary Flemmi was particularly useful in Bulger's and Steven's money-laundering schemes because the FBI were always reluctant to hound somebody's mother, especially if they are over eighty years old. But by 1991, the newspapers had figured out their property-flip scam. In 1979 Stephen's mother had been mugged for a second time in Mattapan, Massachusetts, by a mob of fifty African-Americans, and a photo of her sitting outside her car, on the pavement, dazed and bloody, had appeared on the Regional Associated Press wire. This caused great frustation for Stephen. Her other son, Vincent Flemmi had also just recently died of an apparent overdose while in prison. He relocated his elderly parents from 98 Lennox Street to 832 East Third Street in South Boston, next door to William Bulger. His parent's home would later act as a meeting place for James J. Bulger, Stephen, their FBI Agents, H. Paul Rico, John Morris and John Connolly, and on occasion William Bulger for Sunday dinners. He also stored machine guns, artillery and the bodies of Debra Davis and John McIntyre underneath the home's sun porch. He moved his parents from 89 East Lenox Street to 32 East Third Street in South Boston, Massachusetts after his mother was mugged for the second time.
In 1967, when capo Illario Baione tried to persuade him to join the Patriarca crime family, he confided in H. Paul Rico that he "does not like the individuals as men, but it is possible that he will join it as Frank Salemme is impressed with these people and Salemme, after all, is his partner."
Steven was a close friend of John Martorano who Flemmi mentored to become a contract killer. Steven started out in organized crime under William (Wimpy) Bennett, who he would later murder. He was an occasional gambler who wagered on professional football, but was not a pathological gambler like other members of the Winter Hill Gang. Like James J. Bulger, he never did particularly like the blustery, alcoholic Patriarca crime family capo Illario Baione. Unlike his brother Vincent, who only cared about contract murders and wild parties, Steven was a businessman, always out hustling. Steven associated with the Patriarca crime family in the North End and the Winter Hill Gang in Somerville. He forged friendships around America with Korean war veterans who did not know of his criminal lifestyle. When Howie Winter went to prison in 1979 for fixing horse races, Steven would call his wife Ellen Brogna every day, or take her out to dinner.
By the 1960s he had two families to support with at least six children fathered by two women. At various points in his criminal career he owned a real estate dealership, an auto garage, a variety store and had even bought a funeral home in Roxbury, where he stored his fleet of vehicles. In 1967 with the help of his friend Frank Salemme and others, he murdered all three of the Bennett brothers, of whom Walter Bennett had given him a start in organized crime. By 1967. Flemmi was resisting overtures to become a made member of the Patriarca crime family, but he had no such qualms about being made by H. Paul Rico as a paid Top Echelon Informant. He was married to an Irish woman. Flemmi had been a fugitive since the fall of 1969. By early 1972, he was holed up in New York City, but wanted to return to Boston, and the FBI wanted him back.
Flemmi was considered the best kind of informant - an Italian hood who was trusted by the Mafia, but had no compunctions about informing on them. The problem was, he still faced a pair of outstanding arrest warrants, for the Wimpy Bennett murder in 1967 and for the car bombing of Barboza's lawyer, John Fitzgerald. The Bennett murder was disposed of quickly, when two of the other defendants were acquitted of the charges by a Suffolk County jury. Every few days, while he was a fugitive, Steven and his friend Frank Salemme would get together in Central Park. They would sit on a park bench and swap second-hand gossip about what was going on back in Boston. In 1972 Steven fled to Montreal, Canada.
He would later say that those were the best years of his life. On the witness stand, he later claimed, unconvincingly, that he didn't even want to return to Boston. He said H. Paul Rico made him return. Steven kept in tune of Frank Salemme's trial for the car bombing in the Boston papers. But the main witness against Salemme also testified that Steven was not present at the bombing. Then he vanished, not to be seen again for two years. In May of 1974 Rico told him it was safe to return to Boston. Once the charges against him were dismissed, Steven returned. He moved back with his mistress, Marion Hussey, in Milton, and was soon sleeping with her fifteen-year-old daughter Deborah Hussey fathered from a previous marriage as well.
In 1979 Steven's mother Mary was mugged for the second time in Mattapan, Massachusetts by a mob of fifty African-Americans, and a photo of her sitting outside her car, on the pavement dazed and bloody, had appeared on the regional Associated Press wire. This infuriated Stephen who remained close to his ailing mother over the years. He felt the need to locate his parents to a "nice" neighbourhood - an all-white neighbourhood. After consulting James J. Bulger, he was told that 832 East Third Street, next door to Bulger's brother William Bulger at 828, happened to be up for sale. Flemmi's parents' house eventually became a meeting place for James J. Bulger, Steven, John Connolly, Nicholas Guiardo and H. Paul Rico to meet.
In the early fifties he was married to an Irish-American woman named Jeanette who be became estranged with and later planned to legally divorce in 1980 and marry his girlfriend-mistress Marilyn DeSilva, but it is unknown if he ever followed through with the legal actions. Throughout his life, Stephen was a womanizer, polygamist and practiced incest with his three stepdaughters from two previous marriages, sisters Debra and Michelle Davis, and Debra Hussey. He began dating his stepdaughter Deborah Hussey. At the time she was twenty-six, ironically the same age as his girlfriend-mistress Debra Davis when she had been murdered. She was the daughter of Marion Hussey, Steven Flemmi's legal common-law wife. When he had returned from Montreal in 1974, Deborah was fifteen years old. Almost immediately he began having sex with her. At least one family friend blames the relationship with Stephem for Deborah Hussey's eventual slide into a life of drugs and prostitution. During her increasingly troubled teenage years, the friend said, she started exhibiting telltale signs of molestation- rebellion, alienation, self-hatred and self-medication with alcohol and drugs. "He just ruined her, he killed her as a person", the friend said. In her mid-twenties, Hussey reportedly made some attempts to straighten her life out, taking college courses and getting a steady job, which was arranged by Stephen at a cafe in Dorchester, Massachusetts. Law enforcement sources also say, however that she continued to get in trouble with the police over drugs and increasingly began dropping Stephen's name, attempting to get herself out of trouble. In late 1984, according to law enforcement sources, she began threatening Stephen that she was going to expose their sexual relationship. She disappeared just before Thanksgiving. For a while her mother had hopes that she had run off to California, but soon weeks turned into months and then years without a word. His close friend Frank Salemme would later say about Steven, "He was a womanizer. That was his MO all along, his money and his women, not necessarily in that order." Deborah had watched Steven eyeing her dark-haired thirteen year old sister, Michelle, whom he took to calling "Ava Gardner".
Looking for a change, Debra had started dating a Mexican on the side, a dangerous proposition, considering that one young man who had flirted with her, had already ended up dead, found shot in the back of the head in the Blue Hills Reservation. There was no way that Debra could end their relationship with Steven because she knew too much that could implicate him for many crimes. By the age of twenty-six she was fed up with her life as a moll in Steven's harem. One morning in September 1981, with Steven's parents gone for the day, Steven brought Deborah Davis back to the Flemmi's house in South Boston. James J. Bulger jumped on her and strangled her to death with a garrotte as Steven watched. The two then stripped her body, cut off her fingers and toes to prevent identification and wrapped her corpse in a plastic sheet. After dark they drove down to the marshes and buried her in the marshes alongside the Neponset River where they buried Thomas King back in 1975.
He later became the common-law husband of Marion Hussey. With Marion he fathered two children, Stephen Hussey and Robert Hussey, and two daughters. He also became the stepfather of two daughters including Debra, from a previous marriage. He bought Deborah Hussey a Jaguar when she turned sixteen, and later he set her up in an apartment in the Back Bay, even as he continued more of less living with her mother in Milton. By the age of seventeen, his stepdaughter had dropped out of high school and graduated from working as a waitress in a tough gin mill on Geneva Avenue in Dorchester to a stripper in the Combat Zone downtown. By 1984, his stepdaughter was out of control, willing to say or do anything. That fall, in front of her mother and family in the home on Blue Hill Avenue, Deborah Hussey personally confronted Steven and accused him of sexual abuse. Steven sputtered out a feeble, half-hearted denial, and Marion then threw Steven out of the house he had bought for her almost twenty years earlier. In March 1985, Steven took Deborah out shopping. James J. Bulger shot Deborah in the head and strangled her to death and with the help of Kevin Weeks interred Hussey's corpse under the porch of his parent's home.
Steven enjoyed the company of preteen females, of which there was a ready supply at nearby Cardinal Cushing High School, a now closed parochial school for girls on West Broadway a block or so east of Bulger's bar, The Triple O's. He would often pay off his victims' families with vacations, or expensive possessions, as did James J. Bulger. He found another girlfriend Debra Davis, at a Brookline, Massachusetts gas station, and when her father objected, he drowned mysteriously. He also is suspected of dating and murdering Deborah Hussey's sister, Michelle who was sixteen years old at the time of her disappearance. Unlike Debra Hussey, her body has never been found.
FBI Special Agent H. Paul Rico first met Stephen Flemmi investigating a bank robbery on State Street. At the time Flemmi was a tough, smart, scared and connected, exactly the kind of man the FBI needed to fulfill the latest edict handed down by J. Edgar Hoover. The previous autumn, the FBI director had been humiliated by his archrival, Attorney General Robert F. Kennedy and mafia turncoat Joseph Valachi.
On September 10, 1963, the director sent out a memo to all regional offices, demanding the recruitment of high-level informants from within the ranks of organized crime for his new Top Echelon Informant program. Rico figured Flemmi might be a possible candidate. Rico knew about the numerous attempts on his life, and he knew that information in the underworld was the true way to decisively change a gang war.
Critics of the FBI would later charge that Rico played a role in turning the tide to help Stephen. "Rico was giving Flemmi information that helped him eliminate his enemies," one lawyer close to the case said. "The FBI did not have jurisdiction over murders, so they dealt with their problems vigilante-style to take care of anyone who was going to be a problem to them." Years later Justice Department and FBI investigators launched a grand jury investigation of those allegations, trying to determine exactly what role H. Paul Rico played in Stephen's activities during the gang war. The only way Stephen would be saved as a potential Top Echelon Informant was if he switched allegiances.
Whether by design or whether it was just some happy accident for the FBI, he did, going to his old friend Illario Zannino and pledging to betray William, Walter and Edward Bennett. Flemmi also had his own reasons to dispose of the Bennett brothers, counting on the fact that he would be able to take over their territory after they were eliminated. Flemmi fed regular updates to H. Paul Rico about the activities of Illario Zannino, Boston underboss Gennaro Amguillo, and mob boss Raymond Patriarca in Providence, Rhode Island in 1966 and 1967. Rico promised that Stephen's identity would never be made public, he would be protected from prosecution and would never be expected to testify.
In court, Flemmi said that James J. Bulger approached him at the Lancaster Motors Incorporated in 1974 and told him he was talking to Connolly. Later, Bulger would tell Steven that John Connolly wanted to meet him, and that the introduction would be handled by Dennis Condon. He also became a close friend of FBI Special Agent Roy Morris, whose wife later testified about her husband, "He told me that Mr. Bulger and Mr. Flemmi really liked him, and that if there was anything he ever wanted or needed that they would help him out". They met in what Flemmi described as an obscure coffee shop in Newton, Massachusetts. It was a cordial get-together. Flemmi asked how Paul Rico was, and Condon said he was fine. It was Flemmi said, "like a transaction."
Every Friday night, at his Marconi Club in Roxbury, Massachusetts Steven would meet Frank Salemme's brother, John Salemme, and hand him $200 for Frank, who was still in state prison for the 1967 bombing of Joseph Barboza's lawyer. That was little enough money for Steven to pay, considering how much Salemme knew, and how tightly he was keeping his mouth shut. Steven was the owner of the Marconi Club in Roxbury. The Boston Police Department eventually dug up the restaurant's basement floor, looking for more entombed bodies but were unsuccessful.
In 1989 Steven started spending a lot of time with Frank Salemme, and his son Frank Salemme Jr. James J. Bulger knew that FBI Special Agent John Connolly had asked Steven to keep an eye on Salemme, but Bulger still did not appreciate Steven's "special relationship". He ordered Kevin Weeks to set up several new caches of weapons in South Boston, just in case "Stevie wasn't around", as he put it to Kevin Weeks. It wasn't that Bulger did not trust his old friend Steven; he didn't trust anybody, period. In 1994, when the FBI planned to indict Steven Flemmi and James J. Bulger on RICO charges, Steven seemed strangely unconcerned about the ongoing investigation.
Both Bulger and Flemmi had been a fugitive before, and Bulger had been captured after only a month or so. Steven, on the other hand, had no problem during his four years as a fugitive for the car bombing investigation. But at that time he had been protected by both by Patriarca crime family and the FBI. Steven appeared to have no understanding of how much the world had changed in twenty five years. As far as Steven was concerned, it was business as usual.
At the time of the investigation he had a teenage girlfriend who was pregnant, and he also traveled with a slightly older Asian companion by the name of Jien Fen Hu. One of his two sons by Marion Hussey was about to open a restaurant, Schooner's originally located on High Street. The restaurant would later be moved to its current location as of 2008 at 157 Nantasket Avenue in Hull, Massachusetts, an enterprise in which Steven was taking a great deal of interest in. The current Schooner's opened in 1990 and is not under management of Flemmi or his nephew.
FBI Special Agent John Morris ordered Stephen closed as an informant on September 23, 1982, a little more than a month after the John Callahan murder. His teletype to FBI headquarters on the subject, however, made no mention of the Roger Wheeler, Brian Halloran or John Callahan murders.
In the summer of 1994 Steven took his annual summer vacation to Le Plateau-Mont-Royal in Montreal, Canada, to visit old family friends. Steven may have been considered "a big man out on the street" but before 1994, he'd never spent a long period of time in jail. While incarcerated at the Plymouth County House of Correction, Kevin Weeks visited him regularly. They discussed Bulger and both agreed and hoped that he never returned. Steven also used Weeks to reach out to FBI Agent John Connolly. With Bulger gone, there were so many issues for Steven that arose, how to deliver money from the Winter Hill Gang bank account to John Martorano and what was to be done with the arsenal stashed under his mother's porch. Steven believed he had protection, but not immunity. But as 1995 faded into 1996, it began to dawn on Steven that no one was going to bail him out, figuratively or literally.
Steven took up with a burglar who was a Jehovah's Witness who would massage his feet in oil, Steven clad in only his underwear. When Steven was not attending Jehovah's Witness services, Steven began telling his and Bulger's secrets to fellow inmates and co-defendants- Frank Salemme, John and James Martorano and Rhode Island mobster Robert DeLuca. Silent for decades, Steven could not stop talking. He spoke of how Bulger allegedly wore a wire transmitter for many of his meetings with various FBI agents, and bitterly added that he was now furious that he did not obtain his own copies of these recordings.
Steven told them how John Connolly was like a son to William Bulger, and how Billy had joined them "plenty of times" at the Sunday afternoon get-togethers at his mother's house, allegations Billy would deny at the congressional hearings years later. In prison, Steven took to covering his bed with pictures of the Catholic saints. Many of the local inmates were from South Boston and knew the girls that Steven and Bulger had raped, and now many were looking for retribution. Steven had never directly admitted it, but most of his co-defendants had concluded early on that Steven and Bulger were both informants for the FBI. Steven was the hearing's star witness.
With his lawyer, they planned to prove through the testimony of his self and others, that he had indeed had protection from the FBI, Judge Wolf would have no choice but to throw out the entire indictment. But Steven's problem was that he couldn't really come clean. Without immunity, he couldn't admit to killings he hadn't been charged with. And by the time Steven took the stand, in August 1998, John Martorano had already started outlining the details of almost twenty murders he'd committed. Many of his murders had been done at the direction of Bulger and Steven, who had paid him more that $1 million during his years as a wanted fugitive between 1978 and 1995.To many questions about the murders Flemmi was involved in, he plead the Fifth Amendment.
In 1999 Mary Flemmi finally died, and two of Steven's illegitimate sons born by Marion Hussey decided to case the Winter Hill Gang's old headquarters on East Third Street. They discovered $500,000 in cash which they spent over a period of a six month shopping spree, as one of them later testified. The families of John McIntyre, Debra Davis, Brian Halloran, and both Wimpy and Walter Bennett all filed civil suits against the U.S. Government, claiming that the FBI's protection of James J. Bulger and or Steven Flemmi had resulted in the murders of their loved ones. In January 2003, Steven Flemmi's brother Michael, now a retired Boston Police Department officer, plead guilty to selling a load of Steven's stolen jewellery for $40,000.
The major witness against him was Steven's nephew, William St. Croix, formerly known as William Hussey, Steven's illegitimate son born to his common-law wife Marion Hussey who had been living with for nearly thirty years. St. Croix had turned against his father after learning that Steven and Bulger had strangled his half-sister, Deborah Hussey. In October 2003, Steven plead guilty in U.S. District Court in Boston to ten counts of murder. He made the decision as a part of a deal to reduce the sentence for his brother Michael Flemmi, the former Boston police officer, who is not scheduled to be released from prison until 2010.
In open court, prosecutor Fred Wyshak read aloud Flemmi's agreed-upon statement, and as Wyshak reached the paragraph about the 1981 murder of his girlfriend-mistress Debra Davis, one of her brothers stood up in court and screamed at Steven, "Fuck you, you fucking piece of shit!" In November, Steven's friend Frank Salemme led police to the Hopkinton's Sportsmen's Club located at 95 Lumber Street in Hopkinton, Massachusetts, where he said he and Steven had buried the bodies of Wimpy and Walter Bennett in 1967. After days of digging, the police abandoned the search, claiming that the topography of the area had been changed by the dumping of millions of tons of dirt from the Big Dig, the $15 billion public works swindle in downtown Boston that was now the subject of multiple federal and state corruption investigations.
On the same day Kevin O'Neil was sentenced to jail in Boston, Steven plead guilty in Tulsa, Oklahoma state court to murder World Jai Alai owner Roger Wheeler in 1981. He apologized to the Wheeler family and offered any assistance he could bring to bringing his friend James J. Bulger to justice. In November 2004, Frank Salemme at the age of seventy-one was arrested in Virginia after his indictment on charges of lying to the FBI about a 1993 murder. Steven acted as the main witness for the prosecution against him.
In April 2005, Steven was deposed in New York City by a group of lawyers representing the families of his and Bulger's victims who are now currently suing the federal government. Among other things, Steven testified that he and Bulger had been paying off six FBI agents in the Boston office. Those who could be reached issued denials. Flemmi also named Patrick Nee as the other gunman, along with Bulger, in the 1982 murders of Brian Halloran and Michael Donahue. Nee responded to The Boston Globe by calling Steven, a "punk" and that "He should do his time like the rest of us." He was also questioned at length about the 1985 murder of his step-daughter, Deborah Hussey but declined to comment from the advice of his lawyer.
In the early 1960s, a gangland war broke out on the streets of Boston after George McLaughlin, the younger brother of the Charlestown Mob's boss, groped the girlfriend of a ranking Winter Hill member. MacLaughlin was severely beaten in retaliation, leading his brother to demand that Winter Hill boss James "Buddy" McLean hand over the men responsible. When McLean refused, the McLaughlins later attempted to wire a bomb under his car and were disrupted by MacLean. More than 40 murders throughout the Boston area are believed to be linked to the resulting clash.
During the course of the war, the Barboza crew allied itself with Winter Hill and assisted in several contract killings.
In 1965, Flemmi was secretly recruited as a confidential informant by FBI Agent H. Paul Rico, giving the agency inside information about the Boston gangs. Flemmi allegedly used his informant status to get important members of the rival Charlestown Mob arrested and to protect his allies.
In 1967, James J. Bulger was released from Federal prison after serving a nine year sentence for robbing banks. After a few years of working as a janitor, he became an enforcer for South Boston mob boss Donald Killeen. After Killeen was murdered by an enforcer for the Mullen Gang, Winter Hill Gang boss Howie Winter mediated the dispute between Bulger and the remaining Killeens and the Mullens, who were led by Patrick Nee. Likely due to his talent for making money on the streets, Winter soon chose Bulger as his man in South Boston. Shortly afterwards, Bulger became partners with Flemmi.
At this time, the Boston FBI office tried to convince Bulger to become an informant, but he refused. Although he had followed Flemmi's example by 1975, how and why he did so continues to be disputed.
FBI agent John Connolly, who grew up with Bulger in South Boston, always claimed that he reached an agreement with Bulger during a late night meeting inside an unmarked car. According to Flemmi, Bulger became an informant on his own and quickly learned of his partner's secret as well.
In a conversation that Flemmi fully expected to be his last, Bulger allegedly told Flemmi that he knew his secret. Flemmi has insisted that he did not know at the time that Bulger was also an informant. Weeks, however, insists that Flemmi's story is untrue. He considers it too much of a coincidence that Bulger became an informant a year after becoming Flemmi's partner. He has written of his belief that Flemmi had probably helped to build a Federal case against him. He has said and that Bulger was likely "caught between a rock and a hard place;" supply information to the FBI or return to prison.
However, Flemmi and Bulger were quickly able to turn their informant status to their own advantage. John Connolly, who had been assigned to keep an eye on them, soon came to look up to Bulger and viewed him like an older brother. Federal prosecutors have since stated that Connolly discarded his moral compass, becoming, to all intents and purposes, a member of the Winter Hill Gang, allegedly supplying them with the names of informants and funneling bribes to at least one fellow agent.
In 1979, the U.S. Attorney indicted the leadership of the Winter Hill Gang, including boss Howie Winter, on extortion, gambling, and racketeering charges. Flemmi and Bulger were both listed as unindicted co-defendants; Connolly had convinced his FBI superiors that his two informants were too valuable to prosecute. At that time, Irish gangsters were not the Boston FBI's main concern; they wanted to destroy the Patriarca crime family. Then, as now, arrests and trials of Italian-American mobsters garnered far more of the publicity on which the FBI's funding depends. After the conviction of Winter and his associates, the leadership of the Winter Hill Gang devolved on Bulger, who chose Flemmi as his lieutenant. The pair moved the gang's headquarters to the Lancaster Street Garage in Boston's West End.
Bulger preferred dealing with his fellow natives of South Boston. Although Bulger had some dealings with Jerry Anguilo, the Patriarca crime family's underboss in Boston, he rarely spoke to the Italians personally, usually using Flemmi as a go-between. Through Vincent, he had become acquainted with his brother's handler H. Paul Rico, and as Vincent succumbed to heroin addiction in the late 1960s, Rico sought out Steven more and more often for reliable information.
In contrast Flemmi, who was full-blooded Italian, was considered a stand-up guy by La Cosa Nostra because of his tough-guy ways and talent for making money on the street. In fact, Flemmi was actually offered the privilege of becoming a Made man, as was Johnny Martorano, another Winter Hill Gang member. However, Flemmi turned down the offer from Anguilo and Ilario Zannino and stayed with the Winter Hill Gang.
At one point, Bulger and Flemmi took out a $200,000 loan from Anguilo. When Anguillo asked them about repayment, Bulger and Flemmi stalled him. Naturally, Anguilo was infuriated and a serious gang war looked imminent. However, Flemmi had already been describing the layout of the Anguilo's headquarters, which was inside a Prince Street tenement in the North End, Boston. In 1986, the FBI planted a bug in the building.
The second victim was John McIntyre, a thirty-two year old drug smuggler of mixed Irish and German descent. Like many of Boston's Irish Americans, he was also an avid sympathizer of the Irish Republican Army. McIntyre had informed on the Valhalla arms trafficking deal between the Winter Hill Gang and the Provos. Like Barret, McIntyre was lured to the house and killed in the basement. Bulger shot McIntyre in the back of the head with a .22 calibre rifle. However, Flemmi insisted that McIntyre was still alive and lifted McIntyre up by his hair. Bulger then pumped five or six more shots into McIntyre's face. According to Weeks, Flemmi then asked whether he could "autopsy" the corpse to "look inside," Bulger responded by ordering him to just bury the body. Bulger then laughed and told Weeks, "I told you Doctor Mengele was crazy." Weeks and Flemmi buried McIntyre's remains just like they had done with Barret.
Flemmi was enraged that Debra had been using drugs, working as a stripper in Boston's North End, and bringing African-American males to the house he shared with her mother in suburban Milton, Massachusetts along with drug dealers and other criminals. Flemmi lured her to James J. Bulger's mother's house next door to his and Bulger helped him to strangle her. After Bulger let go his hands, Flemmi declared that she was still alive and garotted her with a length of clothesline. Kevin Weeks was given the task of burying her. Six months after Hussey was killed, the house was sold. The three bodies were relocated to a gully overlooking the Southeast Expressway across from Florian Hall on Hill Top Street in Dorchester, Massachusetts.
Increasingly desperate, Flemmi reached out for Kevin Weeks, his and Bulger's trusted lieutenant in South Boston, to ask John Connolly for help. Weeks reported back that Connolly had said he was sorry, that he believed Bulger and Flemmi were getting railroaded, but there was nothing he could do. The previous August, Assistant United States Attorney James Herbert had gone to a magistrate judge, Lawrence Cohen, and filed a sealed motion to keep Stephen's informant status as a secret, saying there was nothing exculpatory that the other defendants needed to see. Cohen agreed, but ordered the government to at least give Flemmi an affadavit by Paul E. Coffey, a top FBI legal offical who, after a 1995 review of Flemmi's FBI informant files, had found that the FBI had "at least tactfully authorized" the gangster's participation in "illegal gambling and La Cosa Nostra policymaking."
So, in 1991 the FBI finally shifted its focus to the Winter Hill Gang. They began a five year investigation of Bulger, Flemmi, Weeks, John "Red" Shea, Kevin "Turtleneck Pants" O'Neil and many other prominent members of the Winter Hill Gang. In 1992 Shea and other members of his drug ring were indicted on Racketeer Influenced and Corrupt Organizations Act (RICO) narcotics trafficking charges. In 1994, Shea took a plea deal of twelve years in prison and was released on August 2, 2002. In 1995, Flemmi and Bulger were indicted in a large-scale RICO case Three days before this indictment was unsealed, the police picked up Flemmi for a minor Class E Felony. The idea was to have him in jail when the indictments came out and prevent any chance of flight. When Bulger heard that Flemmi had been picked up, he assumed the worst and took off. As of July 2008, Bulger has been on the run for over thirteen years.
Realizing that the FBI had him, the ever-practical Flemmi took a plea bargain. In exchange for a life sentence on his murder charges, Flemmi testified against his former associates in the Winter Hill Gang. In 1997, Flemmi finally revealed that he had been an FBI informant since 1965 and Bulger since 1975. No one could believe it.
After take a plea bargain, Flemmi told prosecuters that Weeks and O'Neil were now running the gang. In 1999, Flemmi gave information that helped indict Kevin Weeks and his lieutenant, Kevin "Turtleneck Pants" O'Neil. O'Neil took a plea deal for one year in prison. Weeks, facing life imprisonment, told the FBI where to find five of Bulger's murder victims. While it appears that Weeks flipped, some people theorized that Bulger told him to give up that information. Weeks was sentenced to five years plus time served (which was nearly a year by the time he was sentenced).
Flemmi and Weeks both testified at the racketeering trial of Flemmi former FBI handler, John Connolly. Having gained his reputation as a crime buster thanks to informants Flemmi and Bulger, Connolly now went to prison because of Flemmi. Connolly, age 66 in 2007, is scheduled for release on June 28, 2011.
Flemmi also gave the FBI critical information on the fugitive boss of the Patriarca crime family, Francis "Cadillac Frank" Salemme. Family boss since 1991, Salemme was indicted along with Flemmi and Bulger in 1995. In 1998, Flemmi tipped off the FBI to Salemme's hiding place. Salamme was captured, tried and sentenced to life imprisonment. Once he was sentenced, Salemme also decided to cooperate with the government against the Patriarca family.
Between Flemmi and Salemme there are 18 admitted murders from the two. In December 2006, Salemme was indicted at age of 73 on charges that he lied about the 1993 disappearance and presumed murder of, Westwood, Massachusetts nightclub magnate Stephen DiSarro. Flemmi testified that he and Salemme watched DiSarro being strangled in the Sharon, Massachusetts home of Salemme's ex-wife. Salemme has challenged Flemmi to a lie detector test and says that he knows nothing about DiSarro's whereabouts. So far, Flemmi and Salemme have admitted to 18 murders together.
In Spring 2003, the Boston Herald reported that Flemmi had implicated his first FBI handler, Paul Rico, in the death of a Tulsa, Oklahoma, businessman, Roger Wheeler. Rico had gone to work for Wheeler as a security chief after his retirement from the FBI in 1975. As Flemmi himself was involved in this crime, he was facing a possible murder conviction and death sentence. So once again Flemmi cut a deal with the Tulsa district attorney to testify against Rico.
He is the basis of Frank Costello's chief enforcer and contract killer "Arnold French" portrayed by Ray Winstone in the 2006 crime thriller film by Martin Scorcese. His character "Arnold French" reenacts the murder of his stepdaughter Debra Hussey, although in the film the character based on Debrah Hussey is said to be his wife. It shows a brief scene where he garrotes his character wife, the same way he murdered his stepdaughter.