May 27th, 1981. Broad daylight, the Pier 4 restaurant parking lot in South Boston. Brian Howerin was sitting in a blue sedan. He was 41 years old. He had a wife. He had a heavy cocaine habit and he had a massive problem. He was talking to the Federal Bureau of Investigation. A car pulled up next to him.
Two men stepped out in heavy coats. They opened fire with a 30 caliber carbine and a silenced MAC 10 submachine gun. 21 bullets shattered the glass. Howeran died instantly, his blood pooling on the vinyl seats. The entire hit took exactly 18 seconds. This was not just another mob execution. Howerin was killed because he knew too much about the Winter Hill gang.
But the men who pulled the trigger were not just ordinary gangsters. One of them was completely protected by the federal government. He was a registered informant. This is the story of how the Italian mafia built an untouchable criminal empire in Boston only to be dismantled from the inside out.
From secret alliances in the North End to corrupt federal agents in high-rise offices. From millions of dollars in lone sharking to a hidden microphone that changed history. This is the rise and violent fall of the Patriarcha crime family in Massachusetts. But here is what the history books do not tell you. The federal government did not beat the mafia with superior detective work.
They did not win by playing by the rules. They beat the Italian mafia by partnering with a monster named James Whitey Bulier, handing him the keys to the city in the process. You have to understand how Boston operated back then. It was a city divided by invisible walls. The Irish ruled South Boston. The Italians ruled the North End.
And ruling over the Italians was a man named Raymond Patriarcha Patri AR Carr. He was 72 years old, walked with a slight limp, and wore dark tailored suits. He operated out of a vending machine business in Providence, Rhode Island, but his reach extended all the way to Maine. Patriarcha was old school. He demanded absolute loyalty.
He once ordered a man to kill his own son for stealing from the family. That was the level of fear he commanded. But Patriarcha needed a reliable manager in Boston. He found one in Janaro Yen NH. Oh, Jerry Anulo. Jerry was 41. He was a Navy veteran. He wore thick glasses, had a sharp temper, and possessed a brilliant mathematical mind.
Jerry was not a street thug. He was a businessman. But in 1960, he had a problem. He was running highly profitable illegal gambling operations and rival gangsters were trying to kill him to take over his territory. Jerry needed protection. The opportunity was clear. Raymond Patriarcha had the muscle, but he wanted more cash flow from Boston.
Jerry Andulo had the cash, but he needed Patriarcha’s reputation to stay alive. The inside connection was a sitdown in Providence. Jerry brought a briefcase containing $50,000 in pure cash. He offered it to Patriarcha as a tribute. The execution was simple. Patriarcha accepted the money and officially made Jerry the underboss of Boston.
Anyone who touched Jerry would now have to answer to the entire New England mafia. The money was immediate. With Patriarcha backing him, Jerry consolidated all gambling in the city. He was clearing $100,000 a week. But there was a problem. Jerry was arrogant. He thought he was untouchable. And arrogance in the underworld always comes with a ticking clock.
Jerry Andulo set up his headquarters at 98 Prince Street in the North End. It was a social club. The doors were heavy steel. The windows were bulletproof. Armed guards stood outside 24 hours a day. From this fortress, Jerry ran the city. He drank black espresso, smoked thick cigars, and counted mountains of cash.
He had three brothers who helped him enforce his will. They terrified the local merchants. Under Jerry, the Boston Mafia perfected the art of the shakeddown. Let us break down their vending machine scheme because it shows exactly how their minds worked. The opportunity was the hundreds of bars, restaurants, and social clubs operating across the city.
They all needed cigarette machines and jukeboxes. The inside connection was the liquor licensing board, which the mafia had heavily compromised through bribes. The execution was brutal. A mob associate would walk into a legitimate bar. He would tell the owner to remove their current vending machines and install the mafiaowned machines.
If the owner refused, the associate would make a phone call. The next day, the bar would lose its liquor license or a fire would mysteriously start in the kitchen. The money was staggering. They took 50% of every quarter dropped into every machine in Boston. We are talking about $500,000 a month in untraceable coins.
The problem was that this required hundreds of foot soldiers to collect the coins, making the organization highly visible to local police. But Jerry Andulo did not care about local police. He paid them off. He drove a Cadillac, wore expensive jewelry, and openly mocked law enforcement. He thought the rules did not apply to him.
He was making too much money. The crown jewel of Jerry’s empire was lone sharking. The opportunity was a severe economic downturn in the 1970s. Legitimate businesses in the North End could not get bank loans. The inside connection was the network of neighborhood butchers and bakers who knew exactly which families were struggling to pay rent.
The execution was predatory. A desperate restaurant owner would borrow $10,000 on a Tuesday. The mafia charged two points a week. That is 2% interest every 7 days. The money was absolute poison to the borrower. At two points a week, the borrower had to pay $200 every week just in interest. Over a single year, that is $10,400 in pure profit for the mob.
and the borrower still owed the original 10,000. The problem was inevitable. When the legitimate businessman eventually ran out of cash and missed a payment, the mafia took ownership of the business. They infiltrated the legal economy. Jerry Anulo thought he had conquered the world. He did not realize a trap was slowly closing around him.
And the trap was not being built by the police. It was being built by the Irish. Enter James Whitey Bulgar. Bulgar was 51 years old. He had piercing blue eyes, sllicked back blonde hair, and he did not drink or smoke. He spent his mornings working out at the gym and his evenings plotting murders.
He had spent 9 years in Alcatraz for bank robbery. While other inmates lifted weights, Bulger read military strategy. He viewed crime as a war. He led the Winter Hill gang in South Boston and he hated the Italian mafia. Bulier knew he could not beat the Patriarcha family in a straight street war. The Italians had too many soldiers.
They had too much money. So Bulier did something unprecedented. He decided to use the federal government as his personal hit squad. On a cold night in September 1975, Bulgar drove his car to Wallist Beach in Quincy. He parked facing the dark ocean. He was there to meet a man named John Connelly. Connelly was 35.
He was a rising star in the Federal Bureau of Investigation. But more importantly, Connelly had grown up in the exact same South Boston housing projects as Bulier. When Connelly was a kid, Bulgar had once bought him an ice cream cone and protected him from local bullies. Connelly never forgot it. He hero worshiped the gangster.
They sat in the dark car listening to the waves. Connelly pitched the FBI top echelon informant program. The opportunity for the FBI was massive. The federal government had declared war on the Italian mafia nationwide. They were desperate for inside information on Raymond Patriarcha and Jerry Andulo. The inside connection was Connelly himself, an agent willing to bend the rules to make his career.
The execution was a dark pact. Bulier would feed Connelly information about the Italian mafia’s operations. In exchange, Connelly would ensure the FBI looked the other way regarding Bulger’s own crimes. The money and power exchange was absolute. Bulier eliminated his Italian rivals without firing a single shot.
absorbing their territories and making millions of dollars. Meanwhile, Connelly received commendations, promotions, and envelopes stuffed with cash from Bulger. The problem was catastrophic. Connelly had essentially given a serial killer a license to murder anyone he wanted, as long as he occasionally provided a tip about an Italian bookie.
For the next 6 years, this toxic alliance thrived in the shadows. Bulier fed Connelly everything. He told the FBI about Italian safe houses. He told them about Italian gambling dens. He told them exactly who was kicking up money to Jerry Andulo. Jerry had no idea. He was sitting at 98 Prince Street, drinking his espresso, completely unaware that his every move was being telegraphed to the federal government by his Irish rivals.
He thought his men were getting sloppy. He thought he was having bad luck with the police. He never suspected a federal agent was orchestrating his downfall from a beach in Quincy. Here is where it gets interesting. By 1981, the federal government had enough circumstantial evidence to know Jerry Andulo was running Boston, but they did not have him on tape.
They needed audio recordings of Jerry ordering crimes. They needed to plant a bug inside 98 Prince Street. This was considered impossible. The social club was a fortress. But John Connelly had a secret weapon, Whitey Bulier. Bulier had a network of corrupt cops and street informants. He gathered the exact blueprints of 98 Prince Street.
He found out exactly what kind of locks were on the doors. He found out what time the cleaning crews arrived. He found out what time the armed guards took their coffee breaks. He handed all of this intelligence directly to John Connelly. January 19th, 1981. 3:00 a.m. The FBI blackag team approached 98 Prince Street.
The temperature was 12°. Snow banks lined the cobblestone sidewalks of the north end. Three agents stood in the freezing dark. They knew they only had a 30inut window. Because of the information Bulger provided, they knew exactly which door to target. The lead FBI lockpick expert went to work. His hands were shaking from the cold.
He had to remove his heavy gloves to feel the tumblers inside the heavy steel door. It took him 22 excruciating minutes to bypass the primary lock. They slipped inside. The smell of stale cigar smoke and spilled liquor hit them immediately. They moved silently across the room to Jerry Andulo’s personal desk.
They drilled a tiny hole in the baseboard behind the desk. They inserted a microphone the size of a dime. They ran the wire under the floorboards, connecting it to a telephone line that routed directly to an FBI listening post miles away. They cleaned up their dust. They relocked the door. They vanished into the winter night.
The next morning, Jerry Anulo walked into his office. He sat at his desk. He lit a cigar. He started talking. And the FBI heard every single word. For 3 months, the federal agents listened. They recorded over 800 hours of audio. The tapes were a gold mine. Jerry was caught on tape ordering beatings.
He was caught discussing lone sharking rates. He was caught bragging about bribing police officers. He even discussed the internal hierarchy of the Patriarcha family, laying out the entire organizational chart for the agents listening in their headphones. Jerry thought he could control the city forever. He could not. And on September 19th, 1983, the federal government finally closed the trap. 6:00 a.m.
Dozens of FBI agents swarmed the North End. They kicked in the heavy steel doors of 98 Prince Street. They rushed up the stairs. They found Jerry Andulo sitting in his pajamas. He was 64 years old. He looked up confused as federal agents slapped steel handcuffs on his wrists. The untouchable boss of Boston was being walked out of his own fortress in front of the entire neighborhood.
The immediate aftermath was devastating for the Italians. Jerry and his brothers were indicted on massive racketeering charges. The trial was a media circus. The federal prosecutors played the secret audio tapes for the jury. Hearing Jerry’s own voice ordering violence sealed his fate. In 1986, Jerry Anulo was sentenced to 45 years in federal prison.
The blast radius of this operation measured across the entire underworld. With Jerry gone, the Patriarcha family lost its grip on Boston. Their leadership was fractured. Their money streams dried up. The Italian monopoly on the city was completely broken. But that is not the crazy part. What happened next shocked everyone.
With the Italian mafia effectively destroyed, a massive power vacuum opened up in Boston. And James Whitey Bulier stepped right into it. Because he had helped the FBI take down the Patriarcha family, his federal handler, John Connelly, made sure the FBI never investigated Winter Hill. Bulier took over the Italian lone sharking operations.
He took over their gambling rings. He took over the drug trade. He ruled the Boston underworld for another decade, acting with absolute impunity. He murdered anyone who crossed him, knowing the FBI would cover his tracks. The federal government had essentially traded one mafia family for a much more violent Irish cartel. But history always demands a final payment.
Nothing stays buried forever. In 1999, the truth finally bled out. Honest federal prosecutors, completely separate from John Conny’s corrupted unit, began investigating the Winter Hill gang. They squeezed Bulger’s associates. The associates broke. They revealed the unthinkable truth. Bulier was an FBI informant and John Connelly was on his payroll.
The realization tore through the justice system like a shockwave. Warrants were issued. Whitey Bulier was tipped off by a corrupt agent and fled the city. He vanished into the wind, becoming one of the most wanted fugitives in American history. He spent 16 years on the run. John Connelly was not so lucky. The ambitious federal agent who thought he could control the underworld was arrested.
The hunter became the hunted. In 2002, Connelly was convicted of raketeering and obstruction of justice. A few years later, he was convicted of secondderee murder for leaking information to Bulger that led to the death of a businessman. Connelly was sentenced to 40 years in state prison.
Bulier was eventually captured in California in 2011. He was 81 years old, living in a rent controlled apartment with $800,000 hidden in the walls. He was sent to federal prison. In 2018, he was beaten to death by inmates in a West Virginia penitentiary. He was 89. Jarro Jerryo spent decades in a federal cell. The man who once ruled the North End from a bulletproof social club died in 2009 shortly after being released due to failing health.
This is the real story of the Boston Mafia. It is not a story of honor or loyalty. It is a story of tactical betrayal. Raymond Patriarcha and Jerry Andulo built an empire on fear and mathematics. They accumulated millions of dollars. They commanded armies of violent men. They thought their heavy steel doors and their political bribes made them invincible.
But in the end, they were destroyed because they failed to understand the true nature of their enemies. They thought they were fighting the police. They did not realize they were fighting a ghost. A ghost armed with a federal badge. The Patriarcha family traded decades of power for life behind concrete walls.
John Connelly traded his badge for a prison uniform. And Whitey Bulier traded his soul for temporary control of a city that eventually killed him. That is the inevitable grinding price of the life. Not the glory, not the money, just a cold cell, a violent end, and a legacy of absolute ruin.
