Book summary “Boston Mob”: summary

Introduction

You want to understand the grim mechanics of organized crime and the violent underworld of 1960s Boston. You look past Hollywood myths to examine the raw brutality that shaped the city's streets during a decade of unchecked gang warfare.

Marc Songini chronicles the bloody battles fought by independent gangsters, corrupt law enforcement officers, and Italian mafia dons. A brutal generation of independent gangsters, corrupt law enforcement officers, and Italian mafia dons fought for control of Boston in a bloody underworld war.

The book explores this descent into gang warfare, political pressure, and federal betrayal across six distinct phases. You will discover how violent operators rose through extreme brutality and how federal agents exploited underworld fractures.

• How did impoverished street enforcers build violent reputations?
• What triggered the brutal feud between the Winter Hill gang and the McLaughlin brothers?
• How did federal wiretaps and informants dismantle the New England Mafia?

1. Rise of the Enforcers

Extreme poverty and abusive childhoods forged violent operators like Joseph Barboza Jr., who rose to prominence through unyielding brutality.

You discover how early trauma shaped underworld figures. Joseph Barboza Jr. was born into a struggling Portuguese community on September 20, 1932. His childhood in New Bedford was marked by extreme poverty, a brutal criminal father, and an attempted suicide by his mother.

Childhood and Early Violence

You see how young Barboza quickly turned to street crime and explosive rage. He dropped out of school and joined local gangs, earning a notorious reputation as a brutal enforcer.

Barboza was arrested at age fourteen for damaging a streetcar signal. Authorities sent him to the Lyman Reform School, where he fought constantly and established his dominance through extreme violence.

The Animal and Barboza, Inc.

You trace the rise of a hyper-violent contract killer who spent half his life behind bars. Barboza weighed 185 pounds and possessed a Neanderthal look with broad shoulders sprouting straight from a big head.

His physical traits matched his terrifying moniker:

• an underbite resembling a barracuda with sharp, pointed teeth like fangs;
• palms that were padded rather than creased, resembling the paw of an animal;
• a resonant baritone voice that commanded fear.

During a brawl at a Nantasket amusement park, Barboza clamped his sharp teeth into an opponent's cheek and ripped the meat away when the man caught him in a bear hug.

He operated in New England as a thief, arsonist, extortionist, boxer, and assassin. He personally tallied his crimes at seventy-five stabbings, five hundred beatings, and twenty murders. He once boasted that murdering someone felt like sexual intercourse with Marilyn Monroe.

After being released from prison on May 8, 1964, at age thirty-two, Barboza underwent a surprising transformation. He married Claire Cohen, converted to Judaism by undergoing a circumcision at Beth Israel Hospital, and changed his last name to Baron.

He subsequently assembled a volatile crew of unstable misfits called Barboza, Inc. They established their headquarters at Chiambi's Grill in East Boston, recruiting men like Joseph Chico Amico, Nicky Femia, and Carlton Eaton. Locals were too terrified to make them leave the diner.

2. The Pax Patriarca and Angiulo Empire

Raymond Patriarca maintained a disciplined criminal empire from Providence while Jerry Angiulo managed a lucrative bookmaking network in Boston.

Providence Governance

Raymond managed his New England underworld empire from Providence with strict discipline. You saw him minimize open exposure and pragmatically align with various ethnic groups based on business utility rather than tribal background.

Raymond operated out of his shabbily furnished office at 168 Atwells Avenue in Providence and installed vending machines by threatening rivals with his top killer, John "Jackie" Nazarian.

Raymond operated legitimate fronts like National Cigarette Service and Coin-O-Matic to mask his criminal enterprises. He relied on 80 to 90 daily visitors, associates, and schemers entering Raymond's office to keep his syndicate running smoothly.

Raymond operated out of a modest house on Lancaster Street valued at approximately 35000 dollars in the 1960s. National Cigarette Service replaced 55 rival cigarette machines in just two months. Raymond claimed his late mother left him a nest egg of 80000 dollars in a cellar box to fund his vending enterprise.

Raymond's enforcer Jackie Nazarian killed bookie George "Tiger" Balleto in the Bella Napoli Cafe in front of twenty-two witnesses and strangled a witness with baling wire to prevent testimony.

The Angiulo Empire

Jerry Angiulo built a massive, highly lucrative bookmaking and loan-sharking empire by applying rigorous financial controls. You watched him manage mathematical odds management and strategic property investments from the North End and later Medford.

Jerry's parents married in a North End apartment in 1915. Jerry carried home 12,000 dollars upon his honorable discharge from the navy in 1946. Jerry and his brothers founded the Huntington Realty Trust in 1955.

Jerry kicked up an approximate annual dollar amount of 50,000 to Raymond Patriarca in the 1960s. Jerry boasted he could afford to buy out 300 Boston detectives out of 360.

The Angiulos maintained a round-the-clock operation taking bets on horse and dog races. They had an estimated quarter million dollars out on the street at one percent interest in the early 1960s.

3. The Somerville Charlestown Feud

A violent tavern brawl during Labor Day weekend triggered an unyielding gang war between the Winter Hill gang and the McLaughlin brothers.

Winter Hill Rise

Buddy McLean built a powerful working-class criminal network in Somerville centered around Winter Hill. He relied on sheer physical brawn, leadership, and community ties. Growing up hardscrabble in Somerville, McLean formed lifelong bonds with Howie Winter. He assembled a loyal crew operating out of local taverns. These men ran numbers, hijacked trucks, engaged in loan-sharking, and stole from the waterfront. McLean maintained a reputation as a fierce brawler and dedicated family man. He took 15 collars in 1960 alone. In August 1961, Buddy McLean, Bobo Petricone, and an MDC policeman named Russell Nicholson were involved in a massive brawl at Porter’s Diner on Mystic Avenue. The fight sent the sixty-five-year-old owner to the hospital.

The McLaughlin brothers from Charlestown built a violent criminal reputation through waterfront racketeering, armed robberies, and extreme brutality. They eventually clashed with established Boston underworld forces. Operating out of the Mystic Tower Tavern, the McLaughlin trio—Punchy, Bernie, and Georgie—utilized physical violence, loan-sharking, and labor union corruption. Volatile allies like the Hughes brothers and Thomas Ballou joined them in controlling local illegal activities. Bernie McLaughlin broke debtors' legs using sash weights wrapped in newspapers. Thomas Ballou slashed an ironworker's throat from ear to ear with a box cutter over a disputed bar seat. Edward 'Punchy' McLaughlin carried 38 entries in his police record. An emissary brought a weekly tribute of 3500 dollars from New York to Charlestown.

The Salisbury Spark

A brutal Labor Day weekend brawl in Salisbury, Massachusetts, triggered an unyielding and bloody gang war between Somerville and Charlestown. Georgie McLaughlin insulted a woman and fought Buddy McLean during a weekend trip. After receiving multiple beatings for his aggression, Georgie stabbed a local man in the face with a broken whiskey bottle. Red Lloyd and Billy Hickey responded by beating him nearly to death and leaving him in an alley. Georgie McLaughlin was beaten 25 times by Buddy McLean in their initial fight. He suffered severe injuries, including losing all but two teeth and having his scalp split. He spent 2 weeks in critical condition in the hospital and later refused police help, stating he would handle it himself.

Following the violent feud sparked in Salisbury, a dynamite bomb was planted on Buddy McLean's car but failed to detonate properly. Shortly after, Bernie McLaughlin was gunned down in City Square, Charlestown, in a meticulously planned two-minute execution. On October 30, 1961, at 12:30 A.M., Buddy's brother-in-law dropped off the family car. A cluster of dynamite was discovered hanging under the passenger side, intended to kill his wife and children. The next day at 12:35, a black sedan pulled up near Richard's Bottled Liquors. Bernie McLaughlin was shot dead by a gunman in a brown suit using a .38 caliber pistol that produced 5 muzzle flashes.

4. Gangland Executions and Betrayals

The escalating war demanded calculated ambushes, inside setups, and the systematic elimination of financial liabilities or rivals.

Thieves who robbed a mob-connected bookmaker faced extreme retaliation through elaborate and torturous murders orchestrated by rival factions. After Harold Hannon and Wilfred Delaney participated in a major robbery targeting an Everett bookmaker, they were hunted down, brutally beaten, and disposed of in Boston Harbor using specialized torture knots and drowning methods.

Hannon's waterlogged body was found near Logan Airport trussed with a piano-wire Chinese torture knot that caused him to choke himself when struggling, while Delaney's nude body was dumped near Charlestown.

High-Profile Ambushes

High-ranking gang members could be ambushed even in broad daylight despite heavy police presence and cover stories. Punchy McLaughlin sat in his car in a hospital parking lot under the guise of delivering confectionary items when two men dressed as rabbis approached him and sawed-off shotguns fired directly into his face and chest, nearly destroying his jaw.

On November 23, 1964, Frankie Salemme and Stevie Flemmi dressed as rabbis and ambushed Punchy McLaughlin in Brookline, leaving him for dead before he managed to survive after an eight-hour surgery.

Mob hits often relied on inside betrayals where a close associate of the target was manipulated into setting up the execution under the guise of a burglary. Conspirators recruited a trusted associate of the victim to orchestrate a fake bank burglary, allowing the killers to position themselves in an alley and execute the target from behind while he entered the building.

On March 12, 1965, Roy French set up his friend Teddy Deegan under the premise of a bank robbery in Chelsea, allowing Ronnie Cassesso, Romeo Martin, and Joe Barboza to ambush and murder Deegan in an alley at 9:30 P.M.

Internal Purges

Underworld partners and associates who became financial liabilities or suspected informants were systematically eliminated by their own peers. Underworld operatives facing mounting debts, pressure from failed scores, or suspicion of talking to law enforcement were lured into vehicles under false pretenses and executed at close range by trusted partners.

On July 8, 1965, Joe Barboza drove his partner Romeo Martin down a hill in Revere and shot him five times in the chest to eliminate a perceived liability.

Internal informants within mob-connected enterprises were quickly discovered and executed by their own co-conspirators under direct orders from Mafia leadership. When a series of dice games run by the Office were repeatedly robbed with clockwork precision, Jerry Angiulo traced the leak to Rocco DiSeglio and gave the other conspirators an ultimatum.

Rocco DiSeglio was fingering dice games for stickup men Richard DeVincent, Marino Lepore, and Bernard Zinna. After Jerry discovered the betrayal, the three co-conspirators drove DiSeglio to East Boston on June 15, 1966, and DeVincent shot him in the back of the head before dumping his body in Topsfield woods.

5. Law Enforcement and Top Echelon Informants

Federal agents exploited underworld fractures by recruiting violent criminals as informants to undermine syndicate stability.

Attorney General Robert Kennedy targeted organized crime aggressively after 1960. His actions shocked mob dons who had previously considered themselves protected under Democratic political ties. Bobby Kennedy utilized J. Edgar Hoover, the FBI, IRS audits, and public hearings to dismantle organized crime networks. His actions caused severe financial and emotional distress to Raymond Patriarca, who viewed the pressure as a personal vendetta.

Rhode Island State Police Superintendent Colonel Walter Stone publicly testified about Raymond Patriarca's immense power during Senate hearings, provoking outrage and public humiliation for the mob boss.

FBI Electronic Surveillance

Robert Kennedy's directive led the FBI to deploy aggressive electronic surveillance and bugging operations against New England mob leaders. Facing intense federal pressure, mob bosses like Raymond Patriarca and Jerry Angiulo grew paranoid about wiretaps and hidden microphones. Despite their security measures, agents successfully bugged the Coin-O-Matic building and Jay's Lounge.

FBI agents used a special water-cooled diamond-tip drill from New York to bore through fifty inches of concrete from the Shubert Theatre into the basement of Jay's Lounge to plant a microphone.

The operation relied on strict logistical support:

• 45 dollars for weekly rent for the FBI listening plant at St. Margaret's Home;
• 5368.75 dollars for total exact cost paid by the government to bug Jay's Lounge;
• 3.75 dollars for a leased line in the bugging operation.

Informant Networks

FBI agent H. Paul Rico utilized a Machiavellian approach to law enforcement by turning violent criminals into informants to fracture Boston gangs. Rico excelled at exploiting the cracks within the Winter Hill and Townie feuds by cultivating relationships with key figures like Francis Salemme and Buddy McLean. While gathering intelligence for J. Edgar Hoover, Rico sometimes provided tactical advantages to favored underworld factions to suppress rivals.

Rico met secretly with Frankie Salemme and provided Dorchester addresses of rival gang members to the Somerville crew to assist in their hunt.

Corrupt law enforcement officers frequently accepted bribes to ignore murders and protect underworld assassins. When Jimmy the Bear Flemmi stabbed a volatile ex-convict fifty times in the back inside a car, two patrolmen watched the crime happen without intervening because they wished to avoid paperwork, and later accepted a cash silence fee from the killer.

On December 27, 1964, Jimmy the Bear killed forty-one-year-old George Ashe in a borrowed Corvair in the South End, after which two patrolmen watched the murder and later collected a 2500 dollars silence fee from Stevie Flemmi.

6. The Fall of the Mafia

Joe Barboza's decision to turn government informant and subsequent federal wiretap discoveries crippled the New England Mafia leadership.

Barboza Turns Informant

Faced with a habitual-criminal indictment that carried an 80-year potential prison sentence, Joe Barboza decided to cooperate with FBI agents Paul Rico and Denny Condon. He offered to provide information on practically every gangland murder in the Boston area in exchange for protection for his family and a chance to strike back at his enemies.

On March 8, 1967, Joe met agents Paul Rico and Denny Condon at the Cedar Junction control room, where he baited his hook by offering vast inside knowledge of local murders in exchange for witness protection. He lost approximately 70,000 dollars in bail money at the Nite Lite and claimed to have suffered 20 double crosses.

The discovery of an FBI bug in Raymond Patriarca's office triggered extreme paranoia and chaos within the New England Mafia hierarchy. When court-ordered disclosures revealed that the FBI had covertly recorded operations inside Raymond Patriarca's headquarters, his aura of infallibility vanished. The underworld realized he had failed to outwit law enforcement, causing panic, recriminations among mob members, and severe nervous distress for Patriarca.

Raymond Patriarca became so paranoid about electronic surveillance that he stopped using the telephone entirely, turned office radios up to maximum volume, and installed an Anti Bug scrambler. A judge made 10 days worth of FBI bugging notes public on May 19, 1967. Henry Tameleo paid 23,000 dollars in legal fees for his various recent collars.

Witness Protection and Convictions

The federal government created a specialized witness protection framework, directed by John Partington, to shield cooperators and their families. Following a suggestion by Robert Kennedy after a funeral in Rhode Island, the U.S. Marshals Service established a program to give threatened mob witnesses and their families new identities and secure relocations. U.S. Marshal John Partington took charge of protecting Joe Barboza's family around the clock to ensure Joe would remain stable enough to testify.

John Partington personally moved into Joe's home in Swampscott and later coordinated complex, heavily guarded relocations to isolated locations like Thacher Island. John Partington joined the U.S. Marshals in 1962, and the distance between Joe's confinement in Barnstable and his family in Swampscott was 70 miles.

Federal authorities dealt a crippling blow to the New England Mafia by formally indicting and arresting its top leaders, including Raymond Patriarca and Henry Tameleo. Using information and conspiracy charges built largely around interstate travel and the murders orchestrated by the organization, the government issued warrants for key bosses. Despite attempting to go underground or evade capture, figures like Raymond Patriarca and Henry Tameleo were rounded up and brought to court.

Henry Tameleo was arrested outside the Wakefield Statler Hilton Motel where he had gone underground under the alias Henry Thomas, while Raymond Patriarca received his first collar in two decades in Providence. Bail was set at 25,000 dollars for Raymond Patriarca following his arrest, and Vinnie Teresa flew to British Antigua to pick up 7,200 dollars in casino-skim money.

Raymond Patriarca and his top associates were convicted on federal conspiracy charges, marking the beginning of the end for traditional New England mob dominance.

Following Barboza's testimony and federal prosecution pressure, Raymond Patriarca, Henry Tameleo, and Ronnie were found guilty and sentenced to prison. The convictions caused widespread panic in the Providence and Boston underworlds and opened the door for subordinates like Larry Baione to take over local operations.

In March 1968, after a brief jury deliberation, Patriarca and his co-defendants were found guilty, with Patriarca reacting by gripping the courthouse railing until his knuckles whitened. Raymond, Henry, and Ronnie received a 5-year prison sentence and 10,000 dollar fine, while bookies who took bets on a not-guilty outcome paid out 5 to 1 odds.

Conclusion

Unchecked violence, broken loyalties, and institutional corruption ultimately destroy every criminal syndicate. You can observe how the brutal enforcers, organized dons, and corrupt officials who dominated Boston all met the same fate through self-destruction or federal prosecution. Criminal enterprises offer no permanent security because their very foundation rests on exploitation and betrayal. When you study this underworld history, you recognize that power built on fear always collapses from within.

You must remember these practical rules when examining the limits of unlawful alliances:

1. Understand that criminal partnerships are temporary and transactional, ending the moment your survival threatens your associate.
2. Recognize that relying on corrupt protection offers no lasting immunity because legal systems eventually adapt to catch institutional decay.
3. Accept that extreme violence accelerates your demise by drawing intense law enforcement scrutiny and turning allies into informants.
4. Realize that hidden empires built on extortion and gambling carry an inevitable cost that far outweighs any temporary financial gain.

10 Key Ideas

1. Extreme poverty, abusive childhoods, and early trauma forged violent underworld operators like Joseph Barboza Jr., who rose to prominence through unyielding brutality.
2. Raymond Patriarca maintained a disciplined criminal empire from Providence while Jerry Angiulo managed a lucrative bookmaking and loan-sharking network in Boston.
3. A violent tavern brawl during Labor Day weekend at Salisbury triggered an unyielding and bloody gang war between the Winter Hill gang and the McLaughlin brothers.
4. The escalating war demanded calculated ambushes, inside setups, and the systematic elimination of financial liabilities or suspected internal informants.
5. Federal agencies exploited underworld fractures by deploying electronic surveillance and recruiting violent criminals as top echelon informants to undermine syndicate stability.
6. Corrupt law enforcement officers frequently accepted cash bribes to ignore murders and protect underworld assassins from criminal prosecution.
7. Faced with an 80-year prison sentence, Joe Barboza decided to cooperate with FBI agents Paul Rico and Denny Condon to secure protection.
8. The discovery of an FBI bug in Raymond Patriarca's office triggered extreme paranoia and chaos within the New England Mafia hierarchy.
9. The U.S. Marshals Service established a specialized witness protection framework, directed by John Partington, to shield cooperators and their families.
10. Raymond Patriarca, Henry Tameleo, and their associates were convicted on federal conspiracy charges following Barboza's testimony, marking the beginning of the end for traditional New England mob dominance.