Organized crime has always had its famous names, the ones that became shorthand for the American underworld. But behind the headlines were other men and women who lived by the same codes, made the same money, and took the same risks. When their time ran out, they slipped quietly into the cracks of history.
Their stories once filled the front pages. Bootleggers, racketeers, loan sharks, and killers, each building an empire in the shadows. For a while, they ran cities, bribed cops, and made fortunes. Then the law caught up, the papers moved on, and what remains are fragments: yellowed clippings, police reports, bits of testimony, and stories passed around like urban legends.
These are five mobsters you have probably never heard of, but should have.
Frank McErlane's story ends in October 1932 inside a small hospital in Beardstown, Illinois. For four days, he fought pneumonia in a fever delirium, screaming for doctors not to let them take him for a ride. When it was over, the Chicago police called him the toughest gangster of them all.
He had earned that title. For a decade, McErlane was one of the most dangerous men in Chicago, a trigger-happy killer whose reputation for drunken violence terrified everyone around him, even other mobsters. During Prohibition, his own peers paid him hundreds of dollars a week to stay out of town. They preferred to buy peace rather than risk crossing him.
Frank McErlane was born in Chicago in 1894. By his late teens, he was already known to police. In 1922, he teamed up with Joseph "Polack Joe" Saltis to form the Saltis-McErlane gang on the city's South Side. They joined the powerful outfit run by Johnny Torrio and Al Capone, running bootleg beer and whiskey into neighborhoods south of downtown.
McErlane's name first hit the papers during the beer wars, the bloody battles for control of Chicago's bootlegging routes. He became notorious for his efficiency with a gun and his complete lack of hesitation to use it. He killed at least three men from rival boss Edward "Spike" O'Donnell's gang, helping the outfit secure its territory.
It was McErlane who first brought the Thompson submachine gun into the underworld, a weapon designed for soldiers, not street gangs. On September 25, 1925, he tried to gun down O'Donnell outside a drugstore at 63rd Street and Western Avenue. O'Donnell ducked behind a car as McErlane's burst shattered the storefront, spraying glass and splinters across the sidewalk.
A week later, on October 3, McErlane tried again at the Ragen Athletic Club on 52nd Street. He missed his target, "Dynamite Joe" Brooks, but killed an innocent bystander. The sound of that Thompson rattling through Chicago's streets would soon become part of the city's legend.
By 1926, the Saltis-McErlane gang had killed 15 people and robbed a mail train carrying $135,000. Witnesses refused to testify, terrified of McErlane's revenge. Even when police caught him, he slipped through on technicalities or silence. He survived at least a dozen assassination attempts, often leaving the scene wounded but alive.
When authorities proposed mental testing for him and his brother Vincent in 1927, they refused. The Chicago Crime Commission added his name to its public enemies list right under Capone.
McErlane's violence was not limited to the streets. In October 1931, drunk and armed with his Thompson, he opened fire on the back of a car carrying his common-law wife, Marian, and her two dogs. The bullets tore through the vehicle, killing her instantly. Police called it the most brutal killing they had ever seen.
He fled Chicago, hiding in Madison, Wisconsin, before surrendering eight weeks later. The evidence was overwhelming, but with no witnesses, the case collapsed. McErlane walked free again. His rap sheet by then included robbery, assault to murder, assault to kill, burglary, aiding a prison escape, and being an accessory to murder. But for all the blood on his hands, he never served time for killing anyone.
When he drank, he slipped into violent delusions. He once told police he had been attacked by an army of green snakes and pink elephants. Officers often found him roaming the South Side, firing his shotgun at invisible enemies.
His relationship with Marian had always been volatile. Once during a fight, she shot him in the leg, fracturing it. While recovering in a Chicago hospital, three gunmen burst into his room and opened fire. McErlane, bleeding from three new wounds, grabbed a pistol from under his pillow and shot back until they fled. He survived again, his legend growing darker each time.
By the time he turned 38, McErlane was nearly finished. He left Chicago behind, retreating to a houseboat on the Illinois River in Beardstown, where he lived with his mother. On October 4, 1932, he checked into the local hospital. Four days later, he was dead.
He was buried as a pauper in a cheap coffin. The family refused to announce the funeral's location, afraid his enemies might try to mutilate the body. Even in death, they feared Frank McErlane's reputation would draw trouble.
It happened on a cold night in Philadelphia, February 25, 1927. Mickey Duffy, known across the East Coast as the boss of beer, stepped out of his nightclub with his wife, Edith, and his bodyguard. The couple lived like royalty on the profits of bootleg beer, gambling, and extortion. But in the violent world of Prohibition, power never came without enemies.
As Duffy and his entourage reached their car, a large sedan sped past. From the window came the sharp mechanical roar of a Thompson submachine gun. Bullets tore through the night air. Duffy's bodyguard collapsed dead. A doorman fell gravely wounded. Duffy was hit five times but somehow survived. His wife, already inside their car, escaped unharmed.
From his hospital bed, Duffy clung to life. He would recover, but the clock was already running out. Four years later, he would be dead, killed not by rival gangs from Chicago or New York, but by men he trusted.
Mickey Duffy was born Michael J. Cusick, the son of Polish immigrants. He spoke and read Polish but changed his name to sound Irish, a common trick in those days to blend in with the city's rougher Irish wards. His criminal record stretched back to 1908. Over the years, he collected 28 arrests for robbery, assault, larceny, burglary, and attempted murder.
He even escaped from a New York jail in 1916 and remained on the run for a year before being caught in Philadelphia. In 1919, a judge sentenced him to three years in state prison for aggravated assault with intent to kill and carrying concealed weapons.
When he got out in 1922, Duffy did not change his ways. He picked up new arrests for robbery and assault, but money and intimidation always kept him out of serious trouble. By 1924, he had moved into bootlegging, buying breweries in Camden and Egg Harbor, distributing beer across New Jersey and Pennsylvania, and taking cuts from local speakeasies.
That same year, he opened the Club Cadix, a dance cafe in an upscale part of downtown Philadelphia. The place became a magnet for politicians, gangsters, and entertainers. Duffy, flushed with cash and protected by payoffs, stayed untouchable. A Philadelphia grand jury in 1928 even called him the king of Racketville, but they did not indict him.
With his partner Harry Mercer, Duffy expanded into extortion, shaking down truck drivers who hauled bootleg liquor and forcing them to pay for protection. The scheme made him one of the wealthiest racketeers in the city.
At home, Mickey and Edith Duffy lived like aristocrats. They bought a $65,000 Spanish-style villa in Overbrook, one of Philadelphia's wealthiest neighborhoods, a mansion reportedly paid for in 65 $1,000 bills. Inside, they spared no expense: ornate furniture, exotic birds, a cactus garden, and a state-of-the-art electric alarm system. Armed guards patrolled the grounds.
Duffy bought Edith a $30,000 diamond bracelet and a solitaire ring to match. He dressed like a movie star and called himself a modern Beau Brummell. The couple vacationed in Florida, stayed in hotel suites costing $1,000 a week, and hosted lavish parties attended by politicians and businessmen who did not ask too many questions.
By 1930, Duffy was making $10,000 a week and had half a million in the bank. He even paid his taxes, hoping to appear legitimate, but respectability stayed out of reach. When Duffy and Edith tried to adopt a child, an orphanage turned them down because of his criminal past. For all his wealth, he remained an outsider, a gangster in fine clothes.
By the summer of 1931, Duffy was nervous. He told police he had seen unfamiliar men loitering near his house. He moved into the Ambassador Hotel in Atlantic City and hired two armed bodyguards. The strain wore on him. He began using morphine to calm his nerves.
On August 30, 1931, Duffy met in his suite with his attorney, U.S. Congressman Benjamin Golder, to prepare for a racketeering trial scheduled in two weeks. After Golder left, Duffy shared lunch with two visitors, familiar faces and trusted associates. Later that afternoon, as Duffy lay down for a nap, the same men returned quietly to his suite. They fired several bullets into his head and slipped out without being seen.
News of the killing spread fast. Thousands turned out to watch the funeral procession at his Overbrook mansion. Edith Duffy inherited nearly $400,000 in cash and another $150,000 in property. Her husband's killers were unknown, and for years the case remained unsolved.
It was not until 1935 that investigators finally uncovered the truth. A Pennsylvania Bar Association probe into corruption exposed the rot that linked lawyers, police, and the underworld. Detective James Ryan concluded that two of Duffy's own men, Sammy Grossman and Al Scaly, had murdered him to take control of his beer empire.
But power in the bootleg world never lasted long. Grossman and Scaly grew reckless, expanding their operations with the 69th Street mob in New York. Before the year was out, hit men from that same mob gunned them down, taking the business for themselves.
It began on a strip of sand off the Texas Gulf Coast in the city of Galveston, a place once known for hurricanes, salt air, and something else entirely: vice. By the 1920s, Galveston had become the South's version of Las Vegas before Las Vegas existed. The men behind it were two Sicilian brothers from Palermo, Salvatore and Rosario Maceo.
Salvatore, known as Sam, came to the United States in the early 1900s, following his older brother Rosario, known as Rose. They were not Mafia men in the formal sense, but they came from a world where the Mafia's reach was everywhere.
In Galveston, they started small, two immigrant barbers trying to make a living cutting hair for a quarter a head. Rose ran a shop on Murdoch's Pier looking out at the Gulf of Mexico. Then in 1921, fate walked in for a haircut.
The customer's name was Dutch Voight, a local bootlegger and leader of Galveston's Beach Gang. He paid Rose $1,500 to stash a shipment of illegal liquor for a few days. It was more money than the brothers had ever seen at once. Soon after, Sam set up a soda stand on the pier as a front, and the Maceos stepped into the business that would make them rich and famous.
They played the game smart. Galveston's underworld was divided between two factions, the Beach Gang and the Downtown Gang, both disorganized and constantly fighting. Sam and Rose united the remnants of each and took control. From that moment, the Maceo brothers ran Galveston's rackets and would continue to do so until 1957.
Their empire began with bootlegging and quickly expanded. They opened a speakeasy called the Hollywood Dinner Club, offering gambling and high-class entertainment. Sam became the public face, smooth, charming, a natural host in fine suits. Rose stayed behind the scenes, handling enforcement and discipline.
In 1926, they took over a struggling Chinese restaurant and renamed it Maceo's Grotto. The following year, sheriff's deputies raided the Hollywood, smashing slot machines and roulette wheels. Within weeks, the club reopened. The Maceos did not back down. They paid off local officials, kept the liquor flowing, and expanded into bookmaking, prostitution, and gambling houses across the island.
The end of the pier became a key point for unloading liquor from Cuba. Trucks carried the shipments east to New Orleans and as far north as Cleveland. For the residents of Galveston, it was an open secret, an open city. The vice business brought tourists, jobs, and money. Few complained.
Sam Maceo became a local celebrity, the smiling face of Galveston's glittering nightlife. The Hollywood Dinner Club turned into the crown jewel of the Gulf Coast, a Moorish-style palace at the edge of the sea lined with palm trees and luxury cars. National acts like Guy Lombardo performed for wealthy visitors.
When a hurricane destroyed the Grotto in 1932, Sam rebuilt it as the Sui Jen, a Chinese-themed nightclub that attracted politicians, oilmen, and movie stars. Sam's charm went beyond business. He threw lavish Christmas parties for local families and orphans, sponsored boxing matches, and even owned Galveston's minor league baseball team, the Allstars. Newspapers called him the nightclub king.
To the public, he was more civic leader than crime boss. In a 1934 interview, Sam spoke with disarming honesty. "We break the law, but in a way that people like. We give them what they want." He believed Galveston's success depended on its openness to vice. "No resort can be a resort unless it's wide open. Otherwise, Galveston would be nothing."
But the good times did not last without trouble. In 1937, federal narcotics agents accused Sam of being part of a $10 million heroin ring, smuggling drugs from Europe to New York, then across the South. The charges made national headlines. Sam admitted knowing two of the accused but denied any involvement. In 1942, a jury acquitted him, and he walked out of court in New York with his wife, Edna, both in tears.
Free again, Sam built his masterpiece, the Balinese Room. Stretching out over the Gulf, it was an elegant private club with gambling tables, fine dining, and an ocean breeze through its doors. It became the heartbeat of Galveston nightlife. He also held stakes in other top spots: the Studio Lounge, the Western Room, the Turf Club, the Crystal Palace, and Murdoch's Pier.
The Texas Rangers raided the Balinese Room dozens of times, but Sam always stayed a step ahead. Electric buzzers warned the staff, who flipped the room into a legitimate cafe within seconds. When the Rangers burst in, they would find patrons playing dominoes and checkers instead of dice and blackjack. On any given night, you could see Frank Sinatra, Tony Bennett, or big band stars playing for the crowd.
By the late 1940s, the Maceos were expanding beyond Texas. They invested with Cleveland mobster Moe Dalitz in the Desert Inn in Las Vegas, one of the city's earliest casino resorts. It was a sign of how far they had come, from barbers on a pier to partners in the city that would redefine gambling in America.
In 1950, Sam opened a new restaurant downtown called The Corner, a polished oyster bar and tap room. But his time was running out. The next year, suffering from stomach cancer, he traveled to Johns Hopkins Hospital in Baltimore. He died there in 1951 from complications of surgery.
A few weeks later, the state of Texas finally took notice. Lawmakers launched a full investigation into Sam's finances and subpoenaed Rose and several associates. The results were staggering. The Maceos had operated the largest illegal gambling network in Texas. Between 1949 and 1950, they grossed $5.6 million, with $4.6 million coming from illegal gaming alone. Their organization employed 600 people and paid out a million in wages.
Colonel Homer Garrison Jr., the state's director of public safety, summed it up bluntly. "The people there in Galveston seem to think because they live on an island, they are immune from the laws of the state." It took new laws to finally end it: bans on slot machines and restrictions preventing phone companies from servicing bookie joints.
Rose Maceo died in 1954. Three years later, state raids and legal pressure closed what remained of their empire. The famous Balinese Room was sold to their relatives Anthony and Vic Fertitta. Anthony later moved to Las Vegas, working as a greeter at El Rancho Vegas. His descendants would go on to build one of the most successful casino empires in the city's history.
By the summer of 1934, the country was dry no longer. The long experiment of Prohibition had ended, and bars across America were opening their doors again. In Baltimore, a woman named Nettie H. Martin filed for a liquor license to serve beer, wine, and whiskey at a new restaurant downtown. To the clerks who processed the paperwork, it was a routine request. But to those who knew her past, it was irony at its sharpest.
Nettie Martin had spent years breaking every liquor law the United States ever wrote. Now she wanted to sell it legally. Fifteen years earlier, Nettie and her husband, George Martin, were already making headlines along the Mid-Atlantic coast. She had once run a beauty shop. He owned a used car lot. Together, they built one of the earliest organized bootlegging gangs on the East Coast, a network that started moving stolen whiskey before the Volstead Act even took effect in 1920.
Their story began around 1919, when officials in Virginia started hearing reports about a mysterious blonde woman running liquor shipments up and down the Richmond Highway. That woman was Nettie. Her husband, George, a stocky man with a hard face and a knack for planning heists, soon became the recognized leader of what reporters would call the Martin gang.
By 1921, the couple was operating as part of a larger criminal combine known as the Bootleggers Trust, a loose alliance of five major liquor gangs stretching from Virginia to New York. Together, they stole bonded whiskey, bribed officials, and pulled resources for lawyers and transport trucks. Each outfit had specialists: drivers, thieves, and men who could pose convincingly as government agents.
On September 9, 1921, the Martins pulled off their most daring job. Fifteen gang members and half a dozen trucks rolled up to the Outerbridge Horsey Distillery in Burkittsville, Maryland. George and several men flashed fake federal badges to the security guard, posing as Prohibition agents. Then, when the guard relaxed, George pulled a pistol and tied him up.
Nettie handled the books. As the men hauled away 1,100 cases of bonded whiskey worth about $200,000, she stood beside the trucks marking off barrels and keeping inventory. Witnesses later recalled seeing her supervise the unloading of the loot at a nearby barn.
The job made national headlines. It also drew federal attention. George, Nettie, and eight others were indicted, but the Bootleggers Trust had good lawyers. The charges against Nettie were dropped. George was acquitted.
Federal agents quickly linked the Martins to a string of other heists: $75,000 in whiskey stolen from the Standard Distillery in Baltimore and major robberies at Gwynnbrook and at the Fast Suns plant in Glen Rock, Pennsylvania. They became infamous for stealing legally bonded whiskey straight from government warehouses.
In one case, police found two drunk bootleggers stranded by the side of the road. Nettie arrived first, pulled two cases of stolen whiskey from their car before the law could find them, bailed the men out of jail, and returned the liquor to them later. It was a small act that showed the reach and loyalty of the Martin gang.
But the law was closing in. By late 1922, George had been arrested six times. When federal agents finally brought him in for the first robbery, he lost his temper and attacked one of them, a young investigator named Michael F. Malone, who would later become one of the most respected undercover agents in American history. For the assault, George earned 30 days behind bars.
The press loved the Martins. They were the perfect mix of glamour and crime. Nettie, described by reporters as a petite, pretty blonde of the flapper type, was often seen in stylish sports clothes and expensive jewelry, including a large diamond cluster ring. In print, she became the queen of the bootleggers. Her husband did not fare as well in the papers. They nicknamed him "The Face."
Prohibition agents called Nettie a daredevil driver. Once when officers tried to corner the couple in traffic, she slammed the accelerator and roared down a crowded Baltimore street, weaving through cars until she disappeared. George planned the robberies, Nettie scouted targets, mapped the getaway routes, and kept the trucks moving between Washington and Baltimore.
The York Dispatch wrote that the "mystery woman" succeeded in escaping the police dragnet and safely landed liquor into the hands of whiskey rings. In 1926, the law finally caught up. George was convicted in federal court for the Standard Distillery robbery and sentenced to two years in prison. Nettie waited for him, loyal as ever. And when he got out, the pair went right back to business.
By December 1928, the Martin gang was a shadow of its old self. But George was not done. That winter, he tried to rob a truck carrying government-approved liquor bound for diplomats in Washington. The plan fell apart fast. Nettie attempted to bribe the driver to keep quiet, but the man refused. George was sentenced to five years for assault with intent to rob. Nettie got 30 days for obstructing justice.
After that, their names vanished from the papers. The bootleggers who had once stolen millions in whiskey disappeared into obscurity. And then came August 1934. Prohibition was over. The speakeasies were gone, and America had moved on.
Nettie Martin, the same woman once chased by federal agents through the streets of Baltimore, filled out an application to buy and sell liquor legally at 117 North Utah Street. This time, the government said yes. The site today is a liquor store, the kind that once would have been her target. For Nettie Martin, the queen of the bootleggers, it was a full circle.
It was just before 11 p.m. on August 4, 1952, when Theodore "Teddy" Roe stepped out of his apartment on Chicago's Michigan Avenue. The summer air was heavy and still. He was about to climb into his car when someone called his name. Roe turned toward the voice. Two men opened fire with 12-gauge shotguns. Five blasts shattered the quiet.
When it was over, Roe lay bleeding on the sidewalk, struck in the head and chest by double-ought buckshot. He was taken to a nearby hospital, but the doctors could not save him. The king of Chicago's black numbers racket was dead.
Three days later, more than 6,500 mourners filled the streets around a Wabash Avenue church. Thousands more filed past his $5,000 open casket, a tribute to the man his neighbors called Robin Hood. He had given away money freely, forgiven debts, and handed out small loans to the poor. In his community, Roe was not seen as a criminal. He was a benefactor.
The police, less sentimental, caused an uproar at the funeral when they arrested his five pallbearers for questioning. They also rounded up nearly every major name in the Chicago outfit: Tony Accardo, Jake "Greasy Thumb" Guzik, Sam "Golf Bag" Hunt, Sam Giancana, Sam Battaglia, Leo Gianola, and Marshall Caifano. But none of them were charged. The murder went unsolved.
Detectives knew the motive. Roe's killing was part of a war for control of the South Side's numbers racket, a lucrative illegal lottery played mostly by working-class black Chicagoans. The outfit run by white mobsters on the West Side wanted it all. Most local bosses either surrendered or fled. Roe refused.
The irony was that Teddy Roe himself was half Italian. But on the South Side, he stood as a symbol of independence, a black racketeer who would not bow to the syndicate. He hired former police officers as bodyguards, carried a .38 with extra shells, and told the outfit to come and take his business if they could.
From 1945 to 1950, Roe and his partners, Edward P. Jones and three others, operated one of the biggest policy wheels in the city. Together, they made nearly $5 million in profits, running 16 or 17 games at a time, with 70 employees and 300 writers who collected bets from street corners and barber shops. In 1946 alone, their profits reached $1.1 million.
The roots of the business went back to the 1920s. During Prohibition, Al Capone made a quiet deal with South Side numbers operators, promising not to interfere with their gambling if they stayed out of his bootlegging rackets. For years, the policy game was one of the few major operations left in the city not under outfit control.
Edward Jones, Roe's older partner, had already made his fortune by the 1930s, but his downfall began when he grew too close to Sam Giancana. The two met while serving time together in 1939 at an Illinois prison. Jones bragged about his lottery operation, explaining how it worked, how thousands of people wagered nickels, dimes, and quarters on random numbers, and how the house always won. Giancana listened closely.
By the early 1940s, Giancana and his outfit bosses set their sights on the South Side. State investigators found that at least 66 policy wheels were running in the area, paying roughly $25,000 a week in bribes to cops and politicians. Jones, trying to keep peace, struck a business deal with the outfit to buy $2,000 jukeboxes for neighborhood taverns. But the city's political machine, tied closely to Mayor Edward Kelly and the Democratic Party, favored the mob's expansion. Jones began losing ground.
In May 1946, Giancana made his move. His men kidnapped Edward Jones and demanded a ransom of $250,000. Roe negotiated the price down to $100,000 and helped raise the money to free him. But the ordeal broke Jones's nerve. Facing a grand jury investigation, he and his brother George fled to their estate in Mexico.
Roe took over the business. He ran it from the Boston Club on the South Side, managing the main Idaho-Ohio policy wheel, one of the largest in the city. He sent the Jones brothers their share of the profits overseas and reinvested the rest in real estate and legitimate ventures. But his defiance put a target on his back.
That September, Giancana's gunmen stormed the Boston Club, spraying bullets through the windows. Roe escaped unharmed. Others were not so lucky. The outfit bombed the homes of the Italian-American Benui brothers, Julius, Caesar, and Leo, forcing them out of the racket. Big Jim Martin, who ran a black numbers operation on the West Side, gave up after his car was riddled with bullets. Roe stayed put.
In December 1950, he and Edward Jones were called to testify before the U.S. Senate's Kefauver Committee on Organized Crime. Under oath, Roe laid out how the policy game worked, explaining that it generated $12,000 per drawing twice a day, and that nearly 60 percent of South Side residents played. Their tax records showed almost $5 million in profits in five years.
Seven months later, Roe's defiance turned violent again. On June 18, 1951, four armed men tried to kidnap him on a South Side street. Roe and his bodyguard opened fire. When it was over, Leonard "Fat Lenny" Caifano, a ranking outfit member and the brother of enforcer Marshall Caifano, lay dead with a bullet through his head.
Roe claimed self-defense, saying the men had tried to take him. The jury agreed. His acquittal made him a folk hero in his neighborhood, the man who stood up to the mob and won. That victory sealed his fate. A year later, the outfit came back for him.
When Roe was gunned down in August 1952, outrage swept the South Side. To many in the black community, his murder was not the fall of a gangster. It was the loss of a man who had stood against an empire that bought everyone else.
But once he was gone, the outfit finally took control. They put local workers back on the payroll, made donations to churches and charities, and smoothed things over with cash. Within a few years, the policy racket became their most profitable enterprise, earning an estimated $150 million a year.
No one was ever charged for Roe's killing. In 1958, Chicago Police Lieutenant Joseph Morris testified before the U.S. Senate's rackets committee that he believed members of the outfit's Young Bloods faction, Giancana, Marshall Caifano, Battaglia, and William "Smokes" Aloisio, had carried out the hit.
For the city, it was another unsolved murder. But for the South Side, it marked the end of an era, the day the last independent king of the numbers was silenced, and Chicago's underworld became one empire under the outfit.