A mugshot photo of James McLean by US-amerikanische Bundesregierung – Wikimedia commons

20 Most Ruthless Gangsters in Boston


 

In the seedy underworld of Boston, where the streets are paved with the darkness of criminal enterprise, the ides of gangsters loom large. These ruthless men, with their cunning minds and iron fists, hold sway over the city’s illegal activities, from racketeering to drug trafficking.

Their power is maintained through a network of loyal associates, who stand ready to do their bidding at a moment’s notice. The threat of violence is ever-present, and those who cross these gangsters risk suffering the direst of consequences.

But even within this world of darkness, there are those who seek to challenge the status quo. These brave souls, who stand against the tide of corruption and oppression, often pay a heavy price for their defiance. Yet their efforts serve as a beacon of hope for those who yearn for a better, more just world.

In the end, the ides of gangsters in Boston represent both the worst and the best of human nature. They are a reminder of the terrible cost of greed and corruption, but also of the power of courage and compassion to overcome even the darkest of evils.

1. James McLean

A mugshot photo of James McLean by US-amerikanische Bundesregierung – Wikimedia commons

James “Whitey” Bulger, a notorious criminal figure in Boston, Massachusetts, was the head of the Winter Hill Gang. This group was involved in a range of illegal activities, such as extortion, racketeering, and murder. After being on the run for 16 years, Bulger was finally arrested in 2011 and was later found guilty of various charges, including being involved in 11 murders, extortion, and racketeering. As a consequence, he was given two consecutive life sentences in prison and died while in custody in 2018.

2. Whitey Bulger

James “Whitey” Bulger was a well-known and infamous gangster in Boston, Massachusetts, notorious for being the leader of the Winter Hill Gang. This criminal organization was involved in a wide range of illegal activities, such as racketeering, extortion, and murder.

Bulger’s notoriety was partly due to his brutal methods and willingness to use violence and intimidation to advance his criminal enterprise. He was renowned for his shrewdness and strategic planning, which enabled him to operate a vast criminal network while evading law enforcement for over a decade.

Eventually, Bulger’s criminal activities caught up with him, and he was captured in 2011 after spending 16 years on the run. His conviction on multiple charges, including racketeering, extortion, and involvement in 11 murders, confirmed his status as one of the most notorious and infamous gangsters in the history of the United States.

3. Howie Winter

Howie Winter is a former Boston mobster who was a prominent figure in the Winter Hill Gang, a criminal organization involved in numerous illegal activities in the Boston area. His reputation marked Winter’s involvement in the gang for being a shrewd and calculating leader, known for his ability to strategize and plan criminal operations with precision and skill.

Winter’s influence within the Winter Hill Gang was substantial, and he was considered one of the most powerful members of the organization. His leadership style was marked by a combination of charisma, authority, and cunning, which helped him to maintain control over his associates and instill fear in his rivals.

Despite his criminal activities, Winter was also known for his ability to maintain a low profile and avoid drawing attention to himself. He was a master of deception and subterfuge, using his intelligence and street smarts to outmaneuver law enforcement and other criminal organizations.

In the end, Winter was eventually arrested and sentenced to prison for his role in the Winter Hill Gang’s criminal enterprise. Despite his criminal past, Winter’s reputation as a skilled and savvy leader within the criminal underworld remains a part of his legacy.

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4. Joseph McDonald

Joseph McDonald was a well-known enforcer and mobster in the Boston area, associated with the Winter Hill Gang and the Patriarca crime family. He was notorious for his brutality and violent tendencies, feared by both enemies and some members of his own gang.

McDonald’s reputation as a violent enforcer was based on his readiness to use extreme force and intimidation tactics to accomplish his objectives. He had a short temper and frequently resorted to violence to settle disputes or maintain his authority within the gang.

Despite his vicious reputation, McDonald was also recognized for his business acumen and ability to make deals and generate profits for the criminal organizations he was associated with. He was often involved in illegal activities like racketeering, extortion, and drug trafficking, and was viewed as a significant player in the Boston criminal underworld.

McDonald’s criminal activities eventually led to his arrest and imprisonment for his role in the Winter Hill Gang’s illegal operations. His reputation as a violent enforcer in the Boston mob highlights the destructive nature of organized crime and the hazards associated with engaging in such criminal activities.

 

5. Johnny Martorano

Johnny Martorano was a notorious mobster and hitman in the Boston area, who was associated with the Winter Hill Gang and the Patriarca crime family. Martorano was known for his ruthless and violent nature, having been implicated in numerous murders and other violent crimes.

Martorano’s reputation as a hitman was built on his willingness to carry out violent acts without hesitation, using firearms and other weapons to execute his targets with brutal efficiency. He was known for his cold and calculating demeanor and was feared by both his enemies and his associates.

Despite his violent reputation, Martorano was also known for his loyalty to the criminal organizations he worked for and was considered a key player in the underworld of Boston. He was often involved in illegal activities such as racketeering, extortion, and drug trafficking, and was known for his ability to generate profits for the organizations he worked for.

However, Martorano’s criminal activities eventually caught up with him, and he was arrested and sentenced to prison for his role in the Winter Hill Gang’s criminal enterprise. His legacy as a ruthless and feared hitman in the Boston mob serves as a reminder of the destructive nature of organized crime and the dangers of engaging in such illegal activities.

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6. Patrick Nee

Patrick Nee was a prominent figure in the criminal underworld of Boston, having been associated with the Winter Hill Gang and the Patriarca crime family. Nee was known for his cunning and strategic planning, which allowed him to maintain a position of power within the criminal organizations he worked for.

Nee’s reputation as a shrewd operator was built on his ability to outsmart law enforcement and other criminal organizations, using his intelligence and street smarts to avoid detection and stay one step ahead of his rivals. He was also known for his ability to make deals and generate profits for the criminal enterprises he was involved in.

Despite his involvement in illegal activities such as racketeering, extortion, and drug trafficking, Nee was also seen as a charismatic and influential figure within the criminal underworld of Boston. He was known for his ability to inspire loyalty among his associates and was considered a key player in the criminal enterprises he worked for.

However, Nee’s criminal activities eventually caught up with him, and he was arrested and sentenced to prison for his role in the Winter Hill Gang’s criminal enterprise. His legacy as a shrewd and influential figure in the Boston mob serves as a cautionary tale of the dangers of engaging in organized crime and the destructive consequences it can have on individuals and society as a whole.

7. Stephen Flemmi

Stephen “The Rifleman” Flemmi was a notorious mobster in the Boston area, who was associated with the Winter Hill Gang and the Patriarca crime family. Flemmi was known for his calculating and strategic mindset, which helped him to rise through the ranks of the criminal underworld and maintain a position of power within the organizations he worked for.

Flemmi was also seen as a charismatic and influential figure within the criminal underworld of Boston. He was known for his ability to inspire loyalty among his associates and was considered a key player in the criminal enterprises he worked for.

However, Flemmi was arrested and sentenced to life in prison for his role in the Winter Hill Gang’s criminal enterprise. His legacy as a calculating and influential figure in the Boston mob serves as a reminder of the dangers of engaging in organized crime and the destructive consequences it can have on individuals and society as a whole.

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8. Stephen Tse

Stephen Tse, also known as Tse Chun-on or Chun-wah, was a restaurateur and leader of the Ping On syndicate in Boston’s Chinatown from the late 1970s to the mid-1980s. Tse was a prominent figure in the city’s criminal underworld, known for his strategic planning and ability to maintain his position of power.

Tse was jailed for 16 months in 1984 for refusing to answer questions after being subpoenaed by the President’s Commission on Organized Crime, which led to the decline of Ping On’s influence in Boston. Upon his release, Tse and his associates were forced to compete with rival groups, leading to a failed assassination attempt on two leaders who had openly defied him in 1988. This incident ultimately led to Tse’s arrest, extradition, and conviction in 1996.

9. Gennaro Angiulo

Gennaro Angiulo was a prominent figure in the Boston underworld during the mid-twentieth century, known for his involvement in organized crime. Angiulo established a vast criminal enterprise in the Boston area, controlling numerous illicit activities, including gambling, loan sharking, and extortion. He was highly profitable, and his shrewd business sense allowed him to make large sums of money.

Law enforcement officials eventually obtained evidence of Angiulo’s illegal activities and successfully prosecuted him and his associates, dismantling his criminal empire.

Despite his eventual downfall, Angiulo remains a notorious figure in the history of organized crime in Boston, serving as a reminder of the dangers of engaging in illegal activities.

10. George Jung

George Jung was a notorious American drug trafficker involved in the cocaine trade in the 1970s and 1980s. He used commercial airlines to transport drugs from Colombia to the United States and was known for his innovative approach to smuggling. Jung was a charismatic and ambitious individual who rose to prominence in the criminal underworld through his entrepreneurial spirit.

Jung’s involvement in the drug trade brought him immense wealth and allowed him to live a lavish lifestyle, but he was eventually caught and imprisoned for his illegal activities.

Despite his criminal past, Jung’s story continues to captivate audiences, with his role in popularizing the use of cocaine in the United States and his influence on popular culture.

11. Antonio Mirabito

Antonio Mirabito was a prominent figure in the American Mafia during the mid-twentieth century. He was involved in organized crime and known for his ability to navigate the complex web of criminal enterprises that operated in the United States during that period. Mirabito was able to amass a great deal of wealth and power through his criminal activities.

Mirabito was particularly well-known for his involvement in the illegal gambling industry, which was a major source of income for many Mafia organizations. He was also involved in other illicit activities, including loan sharking and extortion, which allowed him to exert control over many aspects of everyday life.

Mirabito’s criminal activities eventually caught up with him, and he was arrested and prosecuted for his involvement in the Mafia, serving as a reminder of the dangers of engaging in illegal activities and the importance of upholding the rule of law in the face of organized crime.

 
12. Frank Salemme

Frank Salemme is a former organized crime figure who was a prominent member of the Italian-American Mafia, also known as La Cosa Nostra. Salemme was reputed to have held leadership positions in the Patriarca crime family based in New England.

Salemme’s criminal activities were extensive and included extortion, racketeering, and conspiracy to commit murder. He was known for his ruthless tactics and his ability to maintain a low profile, often operating under the radar of law enforcement agencies.

Salemme’s criminal career came to an end when he was convicted of racketeering and obstruction of justice charges in 1995. He was sentenced to 33 years in prison and was released on supervised release in 2017.

Despite his notoriety as a criminal figure, Salemme’s life story is a fascinating study of the complex and intricate world of organized crime, where loyalty, secrecy, and violence are often the currency of success.

13. Kevin Weeks

He was a former associate of notorious organized crime boss James “Whitey” Bulger, who played a vital role in the criminal activities of the Winter Hill Gang, which was notorious for its involvement in racketeering, extortion, and murder. As a lieutenant, he supervised the gang’s illegal operations, including drug trafficking, loan sharking, and money laundering.

Weeks had a close relationship with Bulger, whom he considered a mentor and father figure. Weeks’ criminal career ended when he was arrested and charged with racketeering and extortion in 1999. He later cooperated with authorities and provided key evidence that helped secure Bulger’s conviction in 2013, highlighting the complexities of organized crime and the difficult choices that individuals face when confronted with the consequences of their actions.

14. Howie Winter

Howie was a former American organized crime figure, and was an essential member of the Winter Hill Gang, a criminal organization based in Boston. Winter was credited with co-founding the gang with fellow mobster James “Buddy” McLean in the late 1960s. Winter was involved in a range of illegal activities, including extortion, gambling, and drug trafficking, and had a reputation for violence and intimidation.

Winter’s criminal career ended in 1981 when he was indicted on charges of racketeering and conspiracy to commit murder. He was later convicted and sentenced to life in prison but was released in 2007 on medical parole due to his advanced age and poor health. Winter’s life story offers insights into the inner workings of organized crime and the complex relationships that exist between its members, as well as the ongoing challenges that law enforcement agencies face in their efforts to combat organized crime and bring its members to justice.

15. John Willis

He was a convicted murderer and American gangster, who was active in the Boston area in the 1970s and 1980s. Willis was a member of the notorious Winter Hill Gang, which was involved in a range of illegal activities, including extortion, racketeering, and murder. Willis was known for his violent and ruthless tactics and was allegedly involved in several high-profile murders in the Boston area. He was also reputed to have served as a hitman for the gang, carrying out contract killings on behalf of his bosses.

In 2003, Willis was convicted of the 1982 murder of Roger Wheeler, the former owner of World Jai Alai, and was sentenced to life in prison without the possibility of parole. Willis’ life story serves as a warning about the dangers of organized crime and the devastating impact it can have on both its victims and its perpetrators, as well as the ongoing challenges faced by law enforcement agencies in their efforts to combat organized crime and bring its members to justice.

16. Cornelius Shea

Cornelius Shea was an Irish-American labour leader and prominent figure in the late 19th and early 20th-century labour movement, who rose through the ranks of the Knights of Labor, a powerful union that represented workers in a range of industries. He was a charismatic leader with excellent oratory skills and an unwavering commitment to the rights of workers. Shea was a strong advocate for the eight-hour workday, fair wages, and improved working conditions for labourers.

He was involved in several high-profile labour disputes, including the 1892 Homestead Strike, where he served as a mediator between workers and management. However, Shea’s involvement with the Chicago-based Irish-American criminal organization known as the “Sons of the Molly Maguires” tarnished his legacy.

Shea was eventually convicted of conspiracy to commit murder and sentenced to life in prison, where he died in 1929. Shea’s life story reflects both the promise and the pitfalls of the labour movement and the challenges faced by those who sought to improve the lives of working-class Americans in the late 19th and early 20

17. Bernie McLaughlin

Bernie McLaughlin was an American gangster and one-time member of the Winter Hill Gang, a criminal organization based in Boston. McLaughlin was born in 1954 and grew up in the tough neighbourhoods of South Boston.

As a young man, McLaughlin became involved in the criminal underworld and quickly rose through the ranks of the Winter Hill Gang, where he became a trusted lieutenant of notorious mobster James “Whitey” Bulger.

McLaughlin was known for his role in the gang’s illegal activities, including extortion, drug trafficking, and money laundering. He was also known for his reputation as a tough enforcer and his ability to intimidate rivals and enemies.

Despite his criminal career, McLaughlin eventually turned against his former associates and became an informant for the FBI. His testimony was instrumental in bringing down the Winter Hill Gang and securing the conviction of several high-ranking members, including Bulger.

McLaughlin’s story is a compelling example of the dangers and complexities of organized crime, as well as the difficult choices that individuals must make when confronted with the consequences of their actions. His cooperation with authorities also sheds light on the important role of informants in bringing criminal organizations to justice.

18. Timothy Connolly

Timothy Connolly was a notorious American gangster and a trusted associate of the Winter Hill Gang’s leader, James “Whitey” Bulger. Connolly’s involvement in the gang’s illegal activities, including extortion, drug trafficking, and murder, resulted in his indictment and conviction in 1999 for racketeering, conspiracy, and obstruction of justice.

Despite being acquitted of conspiracy to murder a federal witness while in prison, Connolly’s criminal legacy remains a reminder of the dark underworld of organized crime.

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18. Joseph Barboza

Joseph Barboza, aka “The Animal,” was a feared enforcer for the Patriarca crime family in the 1960s and 1970s. Born and raised in a working-class Italian-American family, Barboza’s violent tactics included extortion, racketeering, and murder.

After becoming an FBI informant, Barboza helped bring down several high-ranking members of the Patriarca crime family, which led to his placement in the federal witness protection program. However, he was later murdered by members of the same crime family who discovered his cooperation with law enforcement.

20. James Martorano

He was a member of the notorious Patriarca crime family, who was involved in illegal activities such as extortion, racketeering, and murder. Despite his criminal involvement, Martorano became an FBI informant and provided critical information that helped convict several high-ranking members of the crime family.

Although his cooperation helped dismantle the organization, some criticized the authorities’ leniency towards him, given his past involvement in violent criminal activities. Nonetheless, Martorano’s story serves as a reminder of the dangers of organized crime and the importance of informants in dismantling criminal organizations and bringing their members to justice.

Finally, the gang problem in Boston is a complex and continuous issue that necessitates comprehensive answers. Boston has struggled with the presence of many gangs over the years, which has contributed to violence, crime, and social unrest in particular districts. To address this issue, a combination of law enforcement, community participation, and social programs focused at providing alternative avenues for at-risk kids has been implemented.

The fundamental causes of gang involvement, such as poverty, a lack of opportunity, and social marginalization, still exist, despite the fact that success has been made in many regions in terms of lowering gang-related activities and improving safety. A comprehensive strategy that integrates targeted law enforcement actions with investments in education, employment, and community resources is necessary to successfully combat gangs and create a safer and more prosperous future for all Boston residents.

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