Looking Back On Organized Crime In Boston

Ryan Henry

On a September night in 1981, Gennaro Angiulo sat in Francesco’s, one of his brother’s restaurants in the North End of Boston. In front of him sat a platter of pork chops. As he was dining, the doors of the restaurant burst open, reporters flooded the building and FBI agent John Connolly entered. Connolly personally arrested Angiulo, and as he was taken away in handcuffs, the sarcastic Mr. Angiulo yelled out to reporters and other diners, “I’ll be back before my pork chops are cold.” Angiulo never returned to finish his meal.

Francesco’s Restaurant: Gennaro Angiulo’s brother’s restaurant in the north end of Boston, the location of Gennaro’s arrest. Photo credit Boston Globe.

Gennaro Angiulo was one of Boston’s most prolific gangsters, he worked for La Cosa Nostra, a traditional Italian mafia, as an underboss in the Patriarca Crime Family. His successful racketeering made him very rich and powerful, in a time where it could be argued that these mobsters ran the streets and the underground world of Boston. A time when the city was run by James “Whitey” Bulger, Stephen “The Rifleman” Flemmi, Gennaro Angiulo, Howard “Howie” Winter, and many more. It was also a time filled with corruption down to the very core of the city by the dirty water. The countless murders, the destroyed lives, and the horrific fear these organizations instilled in people. But, it was also a time of the stories of the good men who broke down these criminal organizations and fought for justice in such a corrupt and broken system.

Gennaro Angiulo’s mugshot. Photo credit Boston Police Department.

However, it is not to say that these criminal organizations were completely abominable and animal-like. They had order, thus why this type of crime is referred to as organized crime. And this meant that the criminal hierarchy had rules and order, which controlled the chaotic crime-filled world. And when broken, these rules had consequences, it was a criminal society, but through the eyes of those involved, it was organized and fair. This is the reality of Boston’s underground in the ’60s, ’70s, ’80s, and ’90s, a world full of crooks and suffering, and a few good men who made the difference. I was fortunate enough to meet and speak with Phillip M. Vitti, former Boston PD undercover cop, and former head of the Boston police department’s organized crime unit. Vitti is also the author of his impressive memoir, The Passage, a tale of going undercover in Boston. He is an expert on organized crime and its workings. I also got to talk with Robert Long, another expert on the subject. Long is a private investigator, and a retired and well decorated Massachusetts State Trooper. During his lifetime he helped track and get intelligence on Bulger, and was a key part of that investigation.

A Criminal History

Organized crime can first be traced back to centuries ago, in 13th century India, when small gangs of criminals, bandits, and smugglers first arose. Although very basic, these gangs shared many characteristics with those of Boston’s gangs. They had a hierarchy and rules, and they worked as a group to commit crimes for monetary gain. However, Boston’s gangs were much more complicated and sophisticated than these ancient groups of thugs.

Advanced and large-scale organized crime began in Boston in 1916 when an Italian man named Gaspare Messina founded The Boston crime family, which later became the Patriarca Crime family, also known as the Boston Mafia. This mafia family fought with many other gangs over territory and rackets, a mafia power struggle ensued for many years, until Raymond Patriarca took control of the Patriarca Crime family in 1956 and made drastic changes. Patriarca ruled the mob for many years with an iron fist, expanding his operations all throughout New England, delegating power to various divisions throughout the area, and eventually handing off the Boston mob to a racketeer and Nahant resident, Gennaro Angiulo, making him an underboss and letting him rule over the Boston area. Soon after, in 1969, Patriarca was convicted and jailed. During his incarceration, Gennaro ran the day to day operations of the gang. Patriarca took control of the gang again in 1974 upon his release from prison. Patriarca died in 1984 of a heart attack, and from then on the famous gang dealt with a power struggle and a slow decline. Despite this, the crime group continued to keep a strong hold on Boston.

Raymond Patriarca: Mob boss of Patriarca crime family, he appointed Angiulo to underboss and gave him control of the Boston area. Photo credit William. L. Rooney–The Providence Journal
Gennaro Angiulo, donning a suit and tie.  Photo credit Boston Herald Archives.

Boston was also plagued by another unit of organized crime, the Winter Hill Gang, this gang was a rival of the Patriarca Crime family and ruled over the area north of Boston, specifically the Somerville and Charlestown area. This gang also birthed one of America’s most well known serial killers, James “Whitey” Bulger. Unlike the Patriarca Crime Family, which was Italian, the Winter Hill Gang was an Irish mob. This mob was founded in 1955 by James “Buddy” McLean, who ruled until he was killed in 1965. Soon after this Howard “Howie” Winter took over and ruled until he was jailed in 1978. After Mr. Winter, James Bulger, better known by his nickname “Whitey”,  took control of the gang until he fled Boston on the run from the FBI.

Organizing The Crime

These criminal organizations were businesses in every sense of the word. They were illegal and horrible, but at the most bare-bones level they often were, a very successful, functioning business venture. This type of crime was a very lucrative and sophisticated system. It was not disorderly, it had a structure, rules, and discipline. The structure generally followed a hierarchical system, at the top was the mob boss. The boss of the mob makes all major decisions, he maintains order in the gang, this boss is similar to the president of an organization and most of the money flows to him. The boss appoints an underboss, which is the second in command, some underbosses like Angiulo have lots of power, while others don’t have that much power. The main job of the underboss is to manage and run the day to day work of the mob and control the capos, also known as the lieutenants. These lieutenants either run a certain area that the mob controls or a particular racket. In Boston, the lieutenants were generally organized by the particular racket they ran. Each lieutenant is responsible for running their racket or area. They keep some of the money their racket makes and they give the rest to the boss and underboss. The lowest level of a mafia are the soldiers. Soldiers don’t make much money and don’t hold much power, they do the dirty work that needs to get done for the racket to be successful. The mob also has associates, people that work with the mob and are friendly with them but are not members of the mob.

Running The Rackets

Rackets are how the mob makes their money. Rackets are continuous criminal operations. There are many types of rackets, and the gangs of Boston’s underworld had all types of rackets. These rackets made serious money for the mafia. Some of the most well-known types of racketeering are protection rackets, fencing rackets, numbers rackets, horse race fixing, drug trafficking, human trafficking, theft and loan sharking. These were extremely lucrative ways for the mob to make tax-free money.

My family actually almost fell victim to a protection racket. A protection racket is a type of extortion in which a mobster tells businesses to pay them for protection from a danger. At the same time the mob is acting as the danger in the scenario. It is very similar in a way to a child paying a bully his lunch money in exchange for not being beat up. During Howard Winter’s reign over the Winter Hill Gang he went to my family’s restaurant and threatened my grandfather that if he didn’t switch his linen service to one tied to the mob, bad things would happen. My strong-willed grandfather refused to switch his service, the next day the WInter Hill Gang filled the building and began causing a scene in the barroom, even going as far as threatening staff members. My grandfather called the police and announced they were on the way, fortunately, the gang left. According to my father, the next day Mr. Winter arrived at the restaurant and shook my grandfather’s hand for being so strong-willed and not giving in to him, and we were not bothered by his gang again.

Howard Winter at a trial for attempted extortion in 2012, today Winter resides in the Boston area.  Photo credit Jonathan Wiggs–The Boston Globe.

Howard Winter was eventually arrested when one of his rackets failed, a horse fixing scheme as part of his illegal gambling racket, was discovered and he was arrested along with many other gang members, that’s when Whitey Bulger filled the gang’s power vacuum and began his rise to power. But while Howie ran the gang his rackets were very successful and the gang made a lot of money.

Howie Winters being escorted to his trial by multiple Massachusetts State Police Officers.  Photo credit Josh Reynolds– The Boston Globe.

These rackets were the main source of the mobs’ income. In order to run the rackets, the mob needed power, control, and intelligent people. Many people think gangsters were these brain dead, very large, and imposing figures. But these people were smart men, men who wore suits and lived their lives out in the open, and due to their wit and powerful stance, evaded capture.

A City With A Personality

Boston and the surrounding cities were an ideal society for organized crime, and a main reason why it was so hard to stop. The people of Boston lived in a world where they were surrounded by this crime. In this world where the criminals ran the streets, the people always got some of the rewards.

Part of the reason people didn’t rat out the local mobs was fear, but another major factor was Boston’s sit down, shut up, and mind your business mentality. During this time people lived in fear, if you spoke out against the mob you got “whacked” or murdered. Or worse, your closest family would be hurt or killed. Because of this fear, people stayed quiet and quietly enjoyed the few benefits the mob brought them.

In the famous gangster movie “Goodfellas” the mob steals a truck and sells cigarettes for dirt cheap to the citizens. Although this might seem like a fantasy, things like this happened all the time in Boston. One of the mobs most lucrative endeavors was their fencing rackets. A fencing racket is stealing items and selling them for lower than their worth. In this system the mob becomes rich easily, the citizens of the city get tax free goods for below market value, and big corporations get screwed over. They did this by hijacking trucks and then selling the stolen supplies to businesses and people on street corners. This was extremely profitable for the gangs and the people of Boston and the surrounding cities certainly didn’t mind the cheaper goods.

If the citizens of Boston weren’t fear-stricken and didn’t keep to themselves what they knew, these groups could have been taken down much quicker and Boston’s streets would’ve been much safer. But because of the mentality of the time, Boston was an ideal city for these groups to thrive.

Two Types of Law

Some people actually argue that the mob was a force of good. When the mob ran the cities it was very hard for children and teenagers to get drugs. The mob controlled the sale of drugs and usually would not sell to children, which was good for the youth of Boston and for their parents. Many also argue that the mob was good because of the unlawful but very cheap goods they made available to the public. Some also argue that the mob maintained order in a society with a government that followed a corrupt and inoperable system.

However, the people that argue these points are incorrect except for the partially true drug argument. As Phillip Vitti explained to me in our interview, the mob was an illegal business, it robbed the government of money by not paying taxes on its giant influxes of money. This alone was a primary reason to shut down these organizations.

The mob, in a way similar to that of terrorist organizations, used power to maintain their control. They did this through threatening, attacking, and murdering those who were against the mob or did not pay up to them. This method of getting power is very illegal for obvious reasons, which is another reason why terminating the mob was the proper thing to do. Any criminal organization that uses fear and illegal methods to get power and make non-taxable income should be stopped despite the small benefits they brought to the community.

Investigating a Dark World and The Importance of Intelligence

I was very fortunate to be able to interview two very intelligent and brave individuals, Phillip Vitti and Robert Long. Both of these men investigated and helped put a stop to Boston’s organized crime. Mr. Vitti was an undercover cop for the Boston PD for many years, he also eventually became the head of the Boston Organized Crime Unit in 1985. In this position he followed the gangs of Boston and gathered intelligence. Mr. Long is currently a high profile private investigator; but before this he worked for the state police as detective lieutenant inspector commander of the state police major crime unit. This unit was a specialized mobile strike force that focused on stopping major crime groups and criminals in Massachusetts. Eventually they were assigned to Winter Hill Gang and Bulger and worked with the FBI to build a case and bring justice to him and his gang. In my interviews with these two experts on the subject, I learned about the inner workings of Boston’s organized crime as well as the importance of stopping these criminals and ultimately how they are brought to justice.

These two men helped to bring many crime organizations down. Although they often were generally not the ones putting the handcuffs on these criminals, they were the ones who gathered intelligence on these criminals so they had proof in court and proof to make an arrest.

A survellance photo of a meeting between between Whitey Bulger and Stephen Flemmi taken by one of the many intelligence groups tracking these gangsters.  Photo credit FBI.

Intelligence is a vital part of these investigations. According to Mr. Vitti, the job of intelligence teams is to figure out what is happening and gathering information on these criminals so the police or the FBI can make arrests. Intelligence is obtained in many ways; following criminals, interviewing victims and people related to the crimes, and perhaps most importantly, bugging.

Bugging is the act of putting a recording or listening device in a location that will allow law enforcement to gather intelligence on those involved in these crimes. Unfortunately, as Robert Long explained to me, these bugging devices are extremely hard to get approved, in order to get permission for one, the law enforcement must prove they have exhausted all other efforts of getting intelligence before they are issued permission to implement these devices. Fortunately, because Long was able to get permission to place the first bug ever on James Bulger and Stephen Flemmi, these men were eventually captured, partially thanks to the bugs placed on them.

Robert Long.  Photo credit Bob Long Investigations Group LLC.

Without intelligence, there would be no cases against these criminals, and perhaps organized crime would still be running the streets today. So these two and the information they worked to uncover were very important aspects of the investigations against organized crime groups.

Unfortunately for these men, tracking these thugs was a dangerous task. It took serious guts to risk your life for this job. Both Vitti and Long explained to me how they never once regretted the job they took up. Vitti fell into the police force by chance and has never regretted it and Long always dreamt of joining the police force and every day on the job was a dream come true to him. They liked that they were bringing these low lifes to justice despite the dangers the job entailed. Long told me a harrowing story of being shot, and how even as the bullet pierced his skin he felt no regrets for taking on this career. Even with all the mobs’ power and the fear it instilled in people and the threats it made and fulfilled, people like these two stared evil in the eyes and fought these organizations for the good of the public.

Phillip Vitti with his book “The Passage”.  Photo credit Phillip Vitti’s Amazon page.

A Dirty Distrust

Unfortunately, sometimes it was the good guys fighting the good guys in this system. Intelligence was sacred information, and relationships between different branches of law enforcement were not good.

The FBI and the State Police had a very rocky relationship. Both organizations were very cautious in sharing information with one another about these organized crime gangs. These groups did not trust each other for the very valid fear of corruption. When this important intelligence got into the wrong hands the mobsters could get a step ahead and gain an edge. It would often help them in avoiding capture.

Due to this very cumbersome distrust, it was very difficult to collaborate information on organized crime groups and added to the many challenges that arose in the takedown of these gangs.

Today’s Underworld

Even in today’s world organized crime groups still exist. But after the hard work put in by people like Mr. Long and Mr. Vitti, groups like The Winter Hill Gang and The Boston Mafia have lost the stranglehold grip they held on the city. Currently, the organization’s most similar to the gangs of the 20th century are the small drug gangs run by young thugs. These small drug groups lack the sophistication, order, power, and rules of the groups like La Cosa Nostra. These gangs are also tiny in comparison, and will never rise to the level of these historical mobs. It can also be argued that we will never again see Boston’s streets plagued by the control of a mafia-like group because of the extreme amount of surveillance and new technology at our fingertips. A new crime group simply can’t gain that type of power anymore.

Whitey Bulger

In an article about organized crime, with the recent death of James Bulger, it seems fitting to include him. After the arrest of Howie Winter, Whitey Bulger filled the leadership role of the Winter Hill Gang, this increased Bulger’s power and with the decline of the Patriarca Crime Family, the Winter Hill Gang ran the streets.

James Joseph Bulger Jr., nicknamed Whitey for his light blonde hair, hated his nickname and much preferred being called Jimmy. He was born into poverty, growing up in a poor suburb of South Boston. As an adolescent, James was wild, committing many small crimes. He was able to avoid major consequences for these actions, and this made him feel invincible. At age 19 Bulger Joined the Air Force and despite an ‘honorable discharge’ after four years he had a large record of disciplinary issues, one of which was a rape charge in Montana. After his discharge he returned to a life of crime in Boston, climbing the ranks until he became the leader of the Winter Hill Gang.

During his time as gang leader, Bulger corrupted the FBI, becoming an informant in exchange for protection, in this exchange, his FBI wrangler John Connolly would tip him off about upcoming busts on his gang in exchange for information on other crime families and local rival gangs. This corruption is what kept Bulger safe from capture, and allowed him to successfully flee law enforcement and live on the lamb until he was captured. In court Bulger faced 48 different charges, these charges included 19 counts of murder, he pled not guilty to all charges.

James Bulger’s Mugshot. Photo credit Boston Police Department 1953.

Whitey Bulger is one of the most famous criminals of all time. He spent time in Alcatraz, and after the death of Bin Laden in 2011, was at the top of the FBI’s most wanted list. Before his capture, Bulger lived as a fugitive hiding out in Santa Monica for 16 years before he was finally arrested in 2011. Whitey Bulger was serving two life sentences for 11 murders before he met the same fate as his victims last month. His demise brought smiling faces to those who worked his cases. I asked Mr. Long about his reaction to Whitey’s murder and what it was like to be a part of his trial.

One of James Bulger’s Massachusetts State Police Department WANTED posters. Photo credit Massachusetts State Police.

Long was a part of Bulger’s trial and watched as Bulger was locked away, I was fortunate enough to be able to discuss this with him and talk about the emotions he felt as Bulger’s trial concluded. I asked him what it was like to witness the trial and see him be put away for good. To this he responded, ‘It was awesome. At first, I wanted him to get the death penalty, but then I thought that would be too quick, I wanted him to suffer, I wanted him to know what he’s missing every day. I wanted him to see the sun come out and not be able to go outside to enjoy it,  for the rest of his life.” And this was a very fitting punishment for Bulger for the things he did. Long then went on and described to me what this killer did to his victims, “He cut their fingers off so they couldn’t be identified, he pulled teeth out of people’s mouths before he murdered them. He did everything to them.” When I asked what his initial reaction was to his murder he told me, “I was elated by the way he was murdered, I know that might sound like a cruel and gruesome thought to have, but no not when I know what he did to other people, even innocent woman… and for him to die at the hands of his own was very fitting.” And it was a very fitting death indeed, an almost perfect ending to a life of chaos, “the life” caught up to him in the end, and he got what he deserved.

Whitey after his arrest in Santa Monica in 2011.  Photo credit Stuart Cahill of The Boston Glove via Associated Press.

On October 30th of this year, James Bulger sat in his wheelchair at Hazelton Prison. Mr. Bulger was serving his sentence in solitary confinement and was notorious for his disgusting and horrible behavior in prison. Bulger often threatened female prison staff with murder and other terrible things. Whitey faced discipline in prison for these actions, his days of getting away freely were over, he sat rotting in prison, in poor health, all alone, still as evil as the day he arrived. On this particular October day, Whitey would finally receive what many said to be a long overdue punishment for a life of sin. Two prisoners moved Bulger’s wheelchair out of security camera view and with a padlock inside of a sock beat the life out of Whitey until he was unrecognizable, his eyeballs displaced and his body disfigured, similar to how he left his countless victims during his criminal career.

A police photograph from the crime scene of one of Whitey’s gruesome murders. Photo credit U.S. Attorney’s Office.

But these men’s opinion on Whitey were far from unreasonable. Whitey was very different from other mobsters, In our interview, Mr. Vitti stated that, “Whitey Bulger was a psychopath, acting as a gangster. He made his money as a gangster, but he was more lethal and far more evil than a gangster, he was a psychopath”. The traditional Italian Mafia organizations like La Cosa Nostra had rules. These rules held the group to a certain standard, no mindless killings, no disfiguring of the dead bodies, no ruthless torture of their victims, and no selling of drugs to children, just to name a few. Whitey didn’t have rules, he was a cruel bloodthirsty killer without morals. Bulger’s killings were brutal, he always personally strangled the women he killed, and on one particular occasion, he tortured a man for countless hours before finally killing him with a machine gun. After he would commit these killings, he would rip out victims teeth and cut off their fingers so their families would be unable to identify them. This was an especially heinous practice and showed the insanity of the mob boss turned psychopath.

Whitey was a ruthless and tyrannical man who killed many, affected the lives of thousands, and struck fear into the hearts of millions. He was a low life in comparison to other bosses and underbosses of the era and was as, Mr. Vitti said in our interview, “A psychopath masquerading as a gangster.” Although some opinions may vary on his murder, one thing is certain, now that he is dead he can no longer harm anyone.

Bulger’s mugshot in 2011 after his capture.  Photo credit Bureau of Prisons.

Looking Back

Overall the mob was a terrible force, using fear to control and run the streets of Boston. Under the reign of mobsters, Boston lived in fear, but thanks to the actions of a few brave men who dove into the underworld and broke down these organizations the people of Boston can feel safe once more. If it had not been for the actions of these people the people of Boston would still be living in fear, hiding away from these “businessmen” keeping quiet and living a terror-filled life. Fortunately, good men like Mr. Long and Mr. Vitti put their lives on the line to uphold the law and what’s right, giving these gangsters what they deserve. So for this, we thank them and as always the brutality of these mobsters and their bold stature will remain in our memories forever.