Introduction
You likely know the Italian Mafia from cinema and history, but you rarely hear about the Irish American underworld. Popular culture ignores the foundational criminals who built the American mob long before the emergence of the Sicilian Cosa Nostra. You confront a hidden history of urban crime, political corruption, and labor racketeering that spans over a century and a half.
The Irish American underworld established the foundational patterns of organized crime in the United States over a century and a half, shaping politics, labor, and municipal corruption before fading into history.
The book traces this criminal lineage from nineteenth-century tenement slums through the prohibition era and into modern federal prosecutions. You will discover how historical trauma and urban survival forged a distinct underworld culture.
- How did Irish immigrants transform political machines into criminal empires?
- What role did Prohibition play in uniting Irish bootleggers with other ethnic mobs?
- Why did the post-war alliance between labor racketeers and politicians succeed?
- How did federal racketeering laws finally dismantle the Irish mob?
1. Birth of the Underworld and Tammany Hall
The American underworld was established by Irish immigrants decades before the arrival of Sicilian-transplanted Italian criminal traditions. While the FBI under J. Edgar Hoover initially denied the existence of the Mafia before aggressively pursuing La Cosa Nostra, the Irish Mob quietly maintained local operations. You discover a criminal lineage operating locally and integrating into the American system for over a century.
Irish immigrants laid the foundations of the American underworld by adapting rural resistance tactics to urban slums and seizing control of political machines like Tammany Hall.
The earliest progenitors of American gangsterism originated from rural secret resistance societies in 19th-century Ireland that used sabotage and violence against colonial oppression. Groups like the Whiteboys, the Ribbonmen, and the Molly Maguires used violence and sabotage to disrupt the colonial government in rural Ireland.
The Great Potato Famine, caused by a blight and politically mismanaged by British authorities, triggered mass starvation, death, and exile that shaped the Irish American identity. Regressive Corn Laws forced Ireland to export only potatoes, meaning the wipeout of the crop by Phytophthera Infestans between 1845 and 1855 devastated the population, leading to rampant disease, extreme desperation, and coffin ships. Ten years of famine left one million people dead and one million and a half in permanent exile from an island of eight million. An archdeacon in Kenmare witnessed people dying three a day without coffins and crawling out of homes on all fours, while a relief worker reported dysentery and rotting intestines.
Five Points in lower Manhattan became the world's preeminent incubator for gangs and criminal activity due to its horrific living conditions, overcrowding, and rampant tenement diseases. Charles Dickens described the harrowing conditions of Five Points and its rotting tenements in his 1842 book American Notes.
The nativist Know-Nothing movement arose in response to Irish Catholic immigration, combining religious bigotry and economic protectionism with violent political thuggery. William 'the Butcher' Poole, a leader of the Poole Association and Know-Nothing supporter, was shot and killed by Morrissey's henchmen in 1855. John 'Old Smoke' Morrissey established the prototype for the upwardly mobile Irish American mobster by combining street fighting prowess, gambling empires, and political influence. In October 1853, Morrissey defeated Yankee Sullivan in a brutal thirty-seven round bare-knuckle championship bout at Boston Corners to become Champion of America.
Irish immigrants integrated into the pre-existing Tammany Hall political structure, using ward systems and patronage to gain power and shape American municipal government. Irish immigrants worked their way into Tammany Hall like salmon swimming upstream, utilizing bully boys to police polling sites under the symbol of the Bengal tiger. Mob bosses forged a symbiotic relationship between the criminal underworld and the upperworld through political machines that utilized voter fraud and gang intimidation. In 1844, Isaiah Rynders delivered the presidency to James K. Polk through organized physical voter fraud and cohesive voting blocks.
You can trace how precinct operators manipulated elections through systematic disguise and multiple voting:
- Take a voter with a full beard to a barber to scrape off the chin-fringe for the first fraudulent vote.
- Vote the person a second time using side-lilacs and mustache.
- Return to the barber to remove the sides, allowing a third vote with just a mustache.
- Clean off the mustache for a fourth vote with a plain face.
By the late nineteenth century, notorious street gangs like the Whyos transitioned from political protection groups into organized criminal syndicates specializing in professional racketeering. A gangster price list found on a Whyo member included charges such as two dollars for punching, ten dollars for a broken nose and jaw, and twenty-five dollars for a gunshot wound in the leg.
2. Prohibition and the National Syndicate
Prohibition transformed Irish bootleggers into national syndicate leaders who partnered with multiethnic criminals before being marginalized by the rising Italian Mafia.
Illegal alcohol sales created an interconnected national network of bootleggers, corrupt officials, judges, and law enforcement. This market marked the peak glory years of the Irish Mob. New York and Chicago evolved into vast domains where speakeasy operators and corrupt federal agents enabled a new level of criminal enterprise.
William Vincent Dwyer organized a systematic operation to smuggle high-quality liquor into the United States. He purchased speedboats, seagoing rum ships, and warehouses, and secured protection by bribing U.S. Coast Guard officers. Enlisted U.S. coast guardsman earned a standard monthly salary of $126 a month during Prohibition.
Big Bill Dwyer operated out of midtown Manhattan offices and coordinated with suppliers in England, Canada, and the Caribbean to supply nationwide distribution networks. As leader of the Gophers gang in New York's Hell's Kitchen, Owney Madden survived multiple assassination attempts, prison stints, and violent turf wars. He was arrested by the police fifty-seven times in total.
When rival hijackers robbed his bootlegging shipments, Big Bill Dwyer recognized Owney Madden's power and brought him into a business partnership. Owney Madden and Big Bill Dwyer formed the Combine and opened the Phoenix Cereal Beverage Company under a government patent in 1924. They operated under the guise of legal near beer production while outputting illicit beer.
Police Commissioner Grover Whelan estimated the number of speakeasies in New York at 32,000. The Phoenix Cereal Beverage Company operated out of a massive red-brick building at Twenty-sixth Street and Tenth Avenue, producing Madden's No. 1 without interference. Systematic payoffs managed by Jimmy Hines, a Tammany Hall ward boss, ensured total protection.
To maintain profits, the Irish underworld strategically incorporated non-Irish criminal pioneers rather than maintaining an exclusive ethnic monopoly.
The Combine brought in Jewish gangsters like Arnold Rothstein and Meyer Lansky, and Italian mafiosi like Lucky Luciano and Frank Costello. When Big Bill Dwyer was convicted during the period of 1925-1926, Frank Costello stepped in and managed the daily operations of the Combine without disruption.
Chicago North Side boss Dean O'Banion resented Italian control over prostitution and encroachment on his territory. He sold his share of the Sieben Brewery to Johnny Torrio for $500,000. Immediately after the transaction, Chief of Police Morgan Collins raided the facility, confiscating 130,000 gallons of beer and arresting 31 bootleggers while O'Banion walked away on bail.
On November 10, 1924, three men entered Schofield's Florist Shop, pinned O'Banion's arms during a handshake, and shot him six times. The hitmen were posing as flower buyers. Al Capone ordered $8,000 worth of roses for Merlo's funeral, while Johnny Torrio ordered $10,000 worth of flowers. The funeral cortege to Mount Carmel Cemetery drew 15,000 mourners.
On February 14, 1929, gunmen disguised as police officers executed members of Bugs Moran's gang. They lined up six members of Bugs Moran's gang and another associate against a warehouse wall at 2122 North Clark Street and mowed them down with machine guns when the temperature was 15 below zero. The St. Valentine's Day Massacre shocked the public and turned opinion against the Volstead Act.
Over the weekend of May 13–16, 1929, thirty top-ranking mobsters checked into Boardwalk hotels to hold private summit meetings in penthouse suites. Attendees included Lucky Luciano, Frank Costello, Meyer Lansky, Al Capone, and Owney Madden. In 1929, Al Capone possessed an estimated personal wealth of $40 million and an annual income of $6 million.
The Atlantic City conference marked the beginning of a process where Sicilian, Italian, Italian American, and Jewish gangsters pushed Irish mobsters to the fringe. The emerging Syndicate argued that because the Irish already controlled police departments and political organizations, they should not also have an equal share in underworld profits.
3. Waterfront Rackets and the Kennedy Alliance
Post-war Irish gangsters entrenched themselves in labor unions like the ILA while patriarch Joe Kennedy leveraged underworld ties to secure political power for his family.
Longshoremen gathered twice a day hoping to be chosen by a hiring boss. To secure work, men had to form crews and pay bribes that funneled upward through stevedore companies, union officials, and corrupt politicians, anchoring the entire underworld economy.
In the Port of New York, the International Longshoreman's Association grew to 40,000 workers by the mid-1940s, serving as the glue for maritime criminal rackets. Total national membership of the ILA reached 100,000. Joseph P. Ryan ruled this organization as an autocrat for 26 years. Handpicked in 1927 and later named president for life by union agents rather than the general membership, Ryan doled out charters and protected notorious underworld figures who ran waterfront crews through intimidation and murder. Boss Joe operated on a modest annual salary of $20,000 alongside $7,200 in additional annual expenses.
Notorious enforcers like Eddie McGrath, Cockeye Dunn, and Squint Sheridan operated under Ryan's patronage until violent crimes and financial corruption brought down the union leadership. After murdering hiring stevedore Andy Hintz, Dunn and Sheridan were convicted and executed in the electric chair on July 7, 1949. Mae Hintz, the victim's widow and primary witness, fled in terror to Miami but was brought back under heavy guard to testify, sealing the fate of the killers. Before his execution, Dunn offered to expose the high-level political figures protecting waterfront rackets if his sentence was commuted.
Joseph P. Kennedy amassed his initial massive fortune during Prohibition as a top-tier whiskey baron through strategic smuggling networks and alliances with major organized crime bosses.
Leveraging family political connections and capital, Kennedy operated as an importer and wholesaler of foreign spirits, collaborating directly with syndicate leaders like Frank Costello, Owney Madden, and Al Capone. Kennedy supplied liquor to Al Capone's Chicago syndicate, utilizing shipments from Canada's Hiram Walker facility which quadrupled production to meet his demands. The adjusted total cost per case of bootleg Scotch along Rum Row reached $65. Cut Scotch was sold to bootleggers at $85 per case, yielding massive profit markups.
Despite his son Bobby Kennedy's anti-Mafia investigations, Joe Kennedy covertly relied on his historical underworld connections to secure labor and mob support for J.F.K.'s 1960 presidential campaign. Papa Joe arranged secret meetings with underworld figures like Johnny Roselli and Chicago mob boss Sam Giancana through intermediaries like Frank Sinatra, assuring them that a Kennedy administration would look favorably upon their legal troubles. Frank Sinatra flew to the Hyannis Port compound to initiate contact between Joe Kennedy and Sam Giancana, helping swing critical labor support in states like Illinois and West Virginia.
Sam Giancana and other mobsters agreed to help secure the election, expecting political protection and inside influence in return for delivering crucial primary and general election votes, such as in West Virginia and Illinois. In West Virginia, mob-controlled jukeboxes played Sinatra's High Hopes, and operatives spent $50,000 and distributed campaign cash. In Chicago, meetings between Joe Kennedy, Mayor Richard Daley, and Sam Giancana ensured manipulated pluralities that won the state. Carlos Marcello and Jimmy Hoffa contributed a secret $500,000 in cash to Richard Nixon's campaign.
Attorney General Robert F. Kennedy launched an unprecedented federal crackdown on organized crime, which the mob viewed as a profound betrayal. Despite the underworld's role in getting J.F.K. elected, Robert Kennedy aggressively targeted high-level mobsters, exponentially increasing Justice Department staff, wiretaps, and deportations. Federal agents snatched New Orleans crime boss Carlos Marcello off the street and illegally deported him to Guatemala in April 1961. The staff in the Organized Crime and Racketeering Section expanded from 17 to 63 attorneys, while illegal bugs and wiretaps nationwide increased from a few to more than 800.
New Orleans mob boss Carlos Marcello plotted the assassination of President J.F.K. as ultimate retribution for the Kennedy administration's persecutions. Believing that killing only the attorney general would invite relentless vengeance from the president, Marcello concluded that the president himself must be eliminated using a setup patsy, following traditional Sicilian methods. While talking to private investigator Edward Becker at Churchill Farms, Carlos Marcello used the Sicilian proverb about cutting off the head of a mad dog to explain why both the president and the attorney general had to be killed during his battle with the Justice Department, which cost $1 million in legal fees.
Young Irish immigrants and working-class kids in South Boston formed the Mullin Gang, engaging in sophisticated heists, dock thefts, and warehouse burglaries. Operating with a decentralized structure and strong neighborhood loyalty, the Mullin Gang, including figures like Pat Nee, specialized in safe-cracking, hijacking, and executing elaborate break-ins. Pat Nee and a six-man crew broke into Federal Liquor Distilleries by backing a truck against a fish company wall next door, hammering through the bricks, and leaving a mocking note inside the owner's desk. The crew took 40 minutes to break through the wall into the warehouse and less than an hour to clear out nearly every case of booze.
4. The Westies and Modern Gangsterism
Military service in major wars historically served as both an escape route and a psychological breeding ground for violent Irish-American gangsters. Men from tough neighborhoods returned from brutal conflicts with severe psychological scars, heavy alcohol problems, and specialized training in killing, which they applied directly to organized crime in gangs like the Whyos, Wild Bill Lovett's enforcers, and the Mullin Gang.
Mickey Featherstone volunteered for the Vietnam War, spent twelve months in Indochina, suffered a botched circumcision by army medics, and returned stateside with a severe alcohol problem and hair-trigger reactions that led to multiple killings. He had lied to enlist in the army in April 1966 at age 17.
The Italian Mafia systematically employed non-Italian, professional Irish contract killers to eliminate rivals without leaving obvious Mafia footprints.
To seize control of lucrative construction and labor rackets around major projects like the Javits Convention Center without starting a full-scale war, Mafia bosses like Fat Tony Salerno hired ruthless out-of-town or independent hitmen to take out Irish mob leadership piecemeal. The Jacob Javits Convention Center proposed 1.8 million square feet of floor space and cost $375 million. Joe 'Mad Dog' Sullivan, an escaped convict and hardened contract killer who was 36 years old when released from prison, was hired by Genovese family associates to assassinate Mickey Spillane's top right-hand men, including Tom Devaney and Eddie 'the Butcher' Cummiskey.
The Westies gang utilized gruesome body dismemberment to eliminate evidence and enforce absolute blood loyalty among members. Trained by figures like Eddie the Butcher who learned butchery in prison, Jimmy Coonan and his crew cut up murder victims, bagged the parts, and dumped them in the East River or around Ward's Island to prevent police investigations and force new recruits to cross an irreversible moral boundary.
Jimmy Coonan forced Mickey Featherstone to plunge a knife into the already dead body of small-time hood Rickey Tassiello to fully initiate him into the macabre ways of the Westies. Tassiello had originally owed $7,000 to Coonan's loan shark operation, an amount later adjusted to $6,000, with a remaining debt balance of $1,250 when he was snatched.
The Westies ultimately subordinated themselves to the Gambino and Genovese crime families to access big-ticket rackets, trading independence for wealth and protection.
Recognizing that local Hell's Kitchen rackets were minor operations, Jimmy Coonan forged alliances with powerful Mafia capos like Roy DeMeo and Paul Castellano, agreeing to clear all hits with the Italians and kick up a percentage in exchange for a cut of larger operations and protection. Following a formal sit-down at Tomasso's Restaurant in Brooklyn with Paul Castellano and other Mafia bosses in February 1978, Mickey Featherstone's weekly pay increased from $150 to $4,000 a week under a 10 percent cut arrangement.
Whitey Bulger leveraged a secret double-agent relationship with the FBI to systematically eliminate his Irish rivals and destroy the Boston Mafia. Through his childhood connection to FBI agent John Connolly, Whitey Bulger signed on as a Top Echelon confidential informant at age 46 in 1975, gaining government protection and immunity from prosecution while continuing to murder rivals, take over the Winter Hill Gang, and help bring down Boston's Angiulo Mafia family. When Whitey Bulger and his partner Steve Flemmi faced indictment in a massive race-fixing scheme that generated an estimated $8 million in profits, FBI agents Connolly and Morris intervened with the federal prosecutor to have their names dropped from the indictments under the pretext of their value as informants. Ultimately, 19 murders were attributed to the Bulger and Flemmi partnership.
Mickey Featherstone successfully overturned his murder conviction and became a government witness after discovering he was framed by his own gang. Convinced that Jimmy Coonan and Kevin Kelly framed him for the murder of Michael Holly using a disguised gunman and a rented car, Featherstone agreed to cooperate with prosecutors to avoid a life sentence of 25 years to life for Murder One. Billy Bokun confessed to Sissy Featherstone that he wore a thin eyeliner mustache and a wig to shoot Michael Holly, framing Mickey.
Federal prosecutors dismantled the Westies using comprehensive RICO charges that ended the century-long Hell's Kitchen Irish mob dominance. U.S. Attorney Rudolph Giuliani brought a massive federal indictment covering twenty years of extortion, loan-sharking, counterfeiting, gambling, and sixteen murders, securing guilty verdicts on all counts. Following Featherstone's cooperation, 10 members of the Westies were charged across 14 counts of racketeering conspiracy and 16 counts of murder and attempted murder, leading to arrests like Jimmy McElroy in Mesa, Arizona.
Whitey Bulger maintained absolute criminal impunity in Boston for decades through a corrupt, protective partnership with FBI agents. Bulger operated as a Top Echelon informant, utilizing FBI handlers John Connolly and John Morris to receive advanced warnings of investigations and eliminate rivals while murdering with impunity. Brian Halloran was murdered after attempting to inform the FBI about Bulger's role in the murder of World Jai Alai CEO Roger Wheeler, whose company had $1 million a year skimmed from it before Halloran was offered $20,000 to stay quiet.
Professional underworld assassinations were executed through highly compartmentalized, covert operations designed to minimize exposure for the primary hit man. Sheeran's contract killings involved being flown in, supplied with a weapon on-site, performing a quick hit, handing off the weapon immediately for destruction, and escaping via pre-arranged crash cars. When sent to Chicago by Jimmy Hoffa to paint a house, Sheeran completed the hit in about an hour using local backup to dismantle the weapon and divert police.
- Fly into the target city
- Receive the piece from local contacts on arrival
- Execute the target swiftly
- Immediately hand off the weapon to a designated operative for destruction
- Evacuate using crash cars positioned to block potential police pursuit
Jimmy Hoffa was lured to his death under the guise of a Mafia meeting where he was betrayed by people he trusted, an account beginning on page 441 of the historical record. Hoffa was told to meet mobsters including Russell Bufalino and Frank Sheeran at a restaurant in Detroit. Instead, he was diverted to a house where he realized he was set up, and Sheeran shot him twice in the back of the head behind his right ear. In July 2005, Frank Sheeran recalled shooting Jimmy Hoffa at a house in a placid Detroit neighborhood after arriving late to a meeting at the Machus Red Fox Restaurant on Telegraph Road.
Conclusion
The history of the Irish American underworld demonstrates how marginalized immigrant groups convert street-level survival strategies into institutional political and economic power. You can trace this trajectory from the nineteenth-century riots of the Five Points to the corporate suites of twentieth-century labor unions and national syndicates. The eventual decline of these criminal networks illustrates how federal law enforcement and generational assimilation dismantle ethnic-based organized crime.
To understand how illicit enterprises interact with legitimate political and economic systems, you can apply these historical lessons to modern governance:
- Recognize that political corruption often arises from social service deficits in immigrant and working-class communities.
- Analyze how criminal networks exploit legitimate labor unions and waterfront commerce to embed themselves in municipal economies.
- Observe that ethnic solidarity can protect illicit enterprises from law enforcement until federal investigative tools penetrate local loyalties.
- Note that successful assimilation ultimately disperses ethnic criminal syndicates into mainstream society and corporate structures.
10 Key Ideas
- Irish immigrants established the foundations of the American underworld by adapting rural resistance tactics to urban slums and seizing control of political machines like Tammany Hall.
- The Great Potato Famine triggered mass starvation, death, and exile that shaped the Irish American identity and fueled early urban criminal survival strategies.
- Prohibition transformed Irish bootleggers into national syndicate leaders who partnered with multiethnic criminals before being marginalized by the rising Italian Mafia.
- The Combine brought in Jewish gangsters like Arnold Rothstein and Meyer Lansky, and Italian mafiosi like Lucky Luciano and Frank Costello.
- Post-war Irish gangsters entrenched themselves in labor unions like the ILA while patriarch Joe Kennedy leveraged underworld ties to secure political power for his family.
- Joseph P. Kennedy amassed his initial massive fortune during Prohibition as a top-tier whiskey baron through strategic smuggling networks and alliances with major organized crime bosses.
- The Italian Mafia systematically employed non-Italian, professional Irish contract killers to eliminate rivals without leaving obvious Mafia footprints.
- The Westies ultimately subordinated themselves to the Gambino and Genovese crime families to access big-ticket rackets, trading independence for wealth and protection.
- Whitey Bulger leveraged a secret double-agent relationship with the FBI to systematically eliminate his Irish rivals and destroy the Boston Mafia.
- Federal prosecutors dismantled the Westies using comprehensive RICO charges that ended the century-long Hell's Kitchen Irish mob dominance.