The Winter Hill Gang

Topic: BusinessBusiness Operations
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Last updated: March 30, 2019

For a long time, the streets of America had been controlled by organized crime syndicates. While some of these organized crime groups operate in depressed localities, others have legitimate business operations that they use to mask their criminal operations. The Boston-based Winter Hill Gang is one such group that has even connected with one of the most powerful government agencies to protect them from their operations.

The Irish Gang WarThe Winter Hill Gang became influential in the 1960s. For the most part of its history, Boston had been controlled by two major organized crime groups: the Italian Mafia and the Irish gangs. Two such Irish gangs were the Winter Hill Gang, which was then led by James “Buddy” McLean; and the McLaughlin Brothers.It so happened that on Labor Day in the year 1961, while enjoying their outing at Salisbury Beach, a drunk George McLaughlin had initiated what turned out to be a war between the two gangs. When George was apparently rejected by a girl who was with a Winter Hill man, it was rumored that he bit her breasts, from which her escort and other Winter Hill men beat George until he was unconscious and dumped him outside a local hospital. George’s brother and leader of the McLaughlin Gang, Bernie, demanded McLean a few days later that the men who had beaten their brother to be surrendered to them to be punished, which McLean rejected. The McLaughlin’s regarded this as an insult. Weeks later, McLean’s wife’s car was found wired with dynamite.

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McLean retaliated by gunning Bernie a month later. Soon, bodies were dropping in a series of attacks and counter-attacks from the gang members. The number of dead Irish-American gangsters has easily reached fifty, until the Italian Mafia got into the way.

Irish gangs were under the subordination of the Italian Mafia, in that while Irish gangs maintained independence on their criminal operations, most of them are under the payroll of the more powerful Italian Mafia, especially when the Mafia did not want to use their own men as hitmen. Irish gangs also had the tendency to stay out of the Mafia’s way as much as they can. At first, The Italian Mafia watched with amusement the war between the Winter Hill Gang and the McLaughlin Brothers. Soon enough, however, Italian Mafia operations were in jeopardy.

The McLaughlin’s began to harass bookmakers to obtain funds to pay for their gunmen. These bookmakers were, however, under the protection of the Mafia. The killings had also urged the cops to pick up gangsters on sight, including Italians. Henry Tameleo, under the orders Raymond Patriarca who was then a leading member of the Angiulo Italian Mafia, organized in 1965 a peace conference between the Winter Hill Gang and the McLaughlin Brothers. McLean and his followers arrived at the conference unarmed but the McLaughlin, on the other hand, kept their guns inside paper bags. This prompted Tameleo to cancel the peace talks, and Patriarca ordered that the McLaughlin’s be wiped out.Change of LeadershipThe Irish Gang War had resulted to the death of at least fifty gang members on both sides, including James McLean (Reppetto 249).

He was succeeded by Howie Winter who brought stability back to the Winter Hill Gang. Winter became the second most powerful gangster in Massachusetts, next only to Gennaro Angiulo (Bloom 82). He established ties with the Italian Mafia from which he remitted $20,000 a week to Angiulo for a share of gambling and loan sharking money. His leadership, however, was short-lived.

In 1979, he and other members of the Gang were convicted of fixing horse races. He was replaced by James “Whitey” Bulger and Stephen “The Rifleman” Flemmi, both were included in Winter’s indictment but was revoked after the FBI intervened with the case.Bulger grew up in South Boston where he committed petty thefts as a youngster.

This soon turned into a full-scaled bank robbery from which he spent 9 years in various federal prisons including the Alcatraz. He was supposed to be serving a total of 20 years but was released 11 years earlier when he agreed to participate in LSD experiments designed to explore the possibilities of mind control with the use of the drug.FBI ProtectionBulger and Flemmi’s indictment did not pursue at the time when Winter was charged with fixing horse races because of the protection they enjoyed from having an arrangement with the Federal Bureau of Investigation.

They became two of the top informants used by the FBI to pin down what the FBI perceived to be a more serious threat to national security. Bulger has also more to gain from working for the Feds: it allowed him to eliminate the competition.In 1975, FBI agent John Connolly approached Bulger and offered him a deal.

Bulger was to become an informant against the Italian Mafia La Costa Nostra. Connolly would then protect the Winter Hill Gang against state and federal prosecution from their criminal operations, including murder.Connolly would provide Bulger information about wiretaps and pending investigations which allowed Bulger to prepare and protect himself. As a result, Bulger and Flemmi were able to control and dominate the criminal activities in New England States. The Boston Globe reported: “Jimmy Bulger and his partner in crime, Stevie Flemmi, ended up using the FBI to take down the New England Mafia so that they could have a monopoly in the crime business. He was sort of the way ahead of his time. He was the Bill Gates of the criminal world” (Bloom 83).

The Boston Mafia ScandalThe deal between Connolly and Bulger, at first glance, worked both ways for them. Connolly needed information to bring down one of the most notorious Mafia, Bulger needed the protection of the FBI for their criminal operations. Stich explains that “Connolly would receive promotions and bonuses for having helped bring about the downfall of the Italian Mafia and Bulger would benefit by taking over their criminal activities” (“Those Ugly Americans” 229). Furthermore, having recruited Bulger to be an FBI informant earned Connolly a reputation from his peers. He had already received awards for his successes in having developed informants against the New England Mafia. While early FBI attempts to recruit Bulger proved to be unsuccessful, Connolly’s success in closing the deal with Bulger was “a real feather in his cap” (Bloom 85).A deeper look on the deal, however, reveals that Bulger has more to gain.

While the information that was provided by Bulger was relatively minor, the information that Bulger was provided for was most definitely immense for their operations. It gained him immunity from prosecutions from any criminal operations and, as already specified, allowed him to control and dominate the criminal world, at least in New England. To ensure his continued protection, Bulger provided Connolly with financial benefits and Winter Hill mobsters continually send bribes to Connolly and his supervisor, John Morris (Stich, “Those Ugly Americans” 229).Aside from providing information about wiretaps and pending investigations to protect Bulger, Connolly also provided Bulger with information about FBI informants against the Winter Hill Gang (Stich, “Terrorism against America” 97). Stich explained that the information Connolly provide “permitted the Winter Hill gang to murder many government informants—with the full knowledge of the FBI agents and the Justice Department in Washington—including FBI Director J. Edgar Hoover” (“Terrorism against America” 97).

The relationship will prove to be disastrous for the image of the government agency when the Winter Hill Gang’s association with the FBI was exposed by the media. Some claim that the FBI had for decades contrived with various criminal organizations (Stich, “Those Ugly Americans” 225). David Burnham had commented about the FBI, stating that: “The FBI’s improper, often illegal, political investigations had the blessing of the nation’s highest elected officials and were not the work of rogue agents or a rogue agency” (Stich, “Those Ugly Americans” 228).

It is a fact that the FBI receives its directives from Washington, D.C. Boston based FBI followed a national policy to destroy the La Costa Nostra which they perceive to be “the most powerful organized crime group in the United States” (Bloom 84). This prompted Boston FBI agents to use the Winter Hill Gang to pursue and find evidence to prosecute the La Costa Nostra.What really is disturbing is that the FBI-Bulger relationship was more than just the provision of information in exchange of protection. It was a social relationship. Connolly, Morris, and other FBI agents frequently dined together, and even exchanged gifts throughout the relationship (Bloom 87).

Having been exposed, however, Connolly and others were charged with, among others, protecting known murderers, providing them with confidential information, racketeering and obstruction of justice. The trial also exposed that the FBI Director, Hoover, and the Justice Department in Washington had known about the relationship between Connolly and the high ranking members of the Winter Hill Gang. It was also revealed that high federal officials have known the protection enjoyed by Bulger and his gang from various criminal offenses, including murder which had even led to the conviction of three innocent fall guys (Stich, “Those Ugly Americans” 230). In 2002, Connolly was finally convicted “of four counts of corruption” (Stich, “Those Ugly Americans” 231). He “was found guilty of racketeering, bribery and alerting New England mobsters to impending indictments” (Stich, “Those Ugly Americans” 231).Analyzing the ScandalWhile it could be true that Connolly was the one who initiated the relationship between the FBI and the Winter Hill Gang, it is apparent that Bulger and his associates were the ones who benefited primarily from the deal. On the other hand, Bulger had no reason to be an FBI informant and make a deal with them. Aside from being the leader of a powerful gangster in New England, Bulger already had also powerful political connections.

Bulger was regarded to be “the most powerful man within Southie” (Bloom 85). His younger brother, William Bulger, had at one time been the President of the State Senate and “was generally considered the second most powerful politician in the state” (Reppetto 252). Nevertheless, his connection with the FBI made him the top figure in New England, the undisputed “king of the hill.” His connection with the FBI allowed him to operate virtually without competition or opposition. Thus, while the FBI could have benefited from the information that Bulger and his gang gives, it is apparent that Bulger was using the FBI for his own purposes, not the other way around. Bulger even had at one time commented that “you can’t survive without friends in law enforcement” (Bloom 85).After the ScandalRevelations on the FBI’s association with top gang members had resulted to the Winter Hill Gang without a leader.

Gang members are often undisciplined, which would ultimately contribute to its decline. As members began to rat on each other, it was possible to indict more members, hence, members began to pour either into prison or into the Witness Protection Program.Escaping ConvictionBulger and Flemmi would of course not escape indictment. Top members of the Winter Hill Gang, like John Martorano and Kevin Weeks, proved to be valuable in pinning down Bulger and Flemmi. Martorano, who confessed to be responsible for at least 20 killings, testified against Bulger and Flemmi in exchange for a reduced sentence.

But even until the end, Connolly had protected Bulger from conviction by sending information before investigations could progress. It had also allowed Bulger and Flemmi to escape in some other country to avoid trial. Flemmi was apprehended in 1995 for a minor felony before their indictment. The FBI had listed Bulger among their Ten Most Wanted criminals. Up to date, Bulger remains a fugitive.


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