Frankie Yale – Forgotten Boss

Most discussions of Prohibition-era mob bosses focus on Al Capone, Johnny Torrio and Joe Masseria, the kingpins who thrived off booze and blood. Less remembered, but equally important was Frankie Yale, a murderous leader who straddled two underworlds and played a key part in the early Mafia.

Francesco Ioele, also known as Frankie Uale and Frankie Yale, was born January 22, 1893, in Longobucco, Italy. His family immigrated to New York about 1901.

Like most gangsters, Yale got an early introduction to crime. His future mentor, the flashy gangster John “Papa Johnny” Torrio, got him admitted to the Five Points Gang, the dominant street gang in Lower Manhattan.


Yale was renowned from an early age for his abilities as a street fighter and petty thief. He never shied away from violence: One of his earliest arrests, in 1912, was on suspicion of murder.

Torrio left Yale and New York for the Chicago underworld in 1909. But he imparted his approach to crime before he left: Yale, like Torrio, came to believe in business above all. The young man quickly set about real racketeering, infiltrating and dominating the ice delivery trade in Brooklyn.

He used the money from that scheme to buy a bar on Coney Island that he called the Harvard Inn. It had no connections whatsoever to Harvard or to anyone who had ever attended that school, but Yale liked the Ivy League feel of the name and hoped it would attract a classy crowd.

By now he had Americanized his Italian last name to Uale. Upon opening the Harvard Inn, he took the next natural step and started calling himself Yale.


It was through the Harvard that Yale came into contact with the second of his great underworld connections: Al Capone, who worked there as a bouncer. Scarface, as Capone hated to be called, earned that nickname at Yale’s bar one night when he insulted the sister of a patron and the patron cut him across the face. Capone eventually moved on from Yale’s bar to join Torrio in Chicago.

Yale and his gang dipped their fingers in several criminal pies. They carried out the Black Hand extortion scheme popular among Italian immigrants in the early 20th century, sending citizens letters that threatened physical harm unless money was paid. And they ran a set of brothels in the city.

Yale also engaged in protection and labor racketeering. As a front, he sold cigars and ran a funeral home across the street from his own house.

With the advent of Prohibition, Yale, like his friends, turned his sights to booze. He became one of the biggest bootleggers in New York.


Yale, like many larger-than-life gangsters, presented two sides of the same coin. On the one hand, he could be highly charming and showed a soft spot for the down and out. When a local deli owner was robbed, Yale paid him what he lost, and when a fishmonger lost his cart, Yale gave him $200 and told him to get a horse as well.

Murder of Big Jim

Frankie Yale (portrayed by Joseph Riccobene) walking away after murdering “Big Jim” in Boardwalk Empire.

On the other hand, Yale never hesitated to assault or kill when it suited his purposes. He was responsible for numerous murders in New York, and he was called to Chicago to handle at least two high-profile killings.

In 1920, Torrio and his acolyte Capone called Yale to the Windy City to assassinate Giacomo “Big Jim” Colosimo. He ran the city’s underworld, but Torrio wanted him out of the way so the Chicago Outfit could make more money in bootlegging. Yale was suspected in the murder but never charged.

Four years later, Yale returned to Chicago for another hit – this time at the behest of Capone, who had taken over the Outfit when Torrio retired. Yale and two other men allegedly walked into the Schofield Flower Shop on the North Side of Chicago and gunned down Capone rival Dean O’Banion.


Yale had his own share of enemies, and attempts on his life were frequent. Assassins tried to kill him twice in 1921, the first time while he was outside a banquet, the second while he was driving down a street in a car full of men. A third murder attempt came two years later, when hit men shot his chauffeur by mistake.

Rivalries within the New York underground were constant. Yale spent much of his time in conflict with the White Hand Gang, a group of Irish-American mobsters. The dispute came to a head in 1925, when the leader of the White Hands was killed at the Adonis Club in Brooklyn by Capone, who was in town, and men working for Yale.

At his peak, Yale was one of the most important gangsters of the day. The modern Mafia structure was still evolving, but Yale was one of the most powerful players in it. He was not, however, the most powerful, and he made the mistake of displeasing the man who was.

Yale smuggled Canadian whiskey during Prohibition, and he oversaw the trucks that shipped it on to Capone in Chicago. Capone began to suspect Yale was hijacking the trucks, so he sent a spy, who told Capone he was right.

Frankie Yale Murder

Police photo of Frankie Yale murder scene

The two tried to patch things up, but it didn’t work. On July 1, 1928, Yale received a strange phone call saying there was a problem with his wife at home. He ran outside and sped off in his Lincoln coupe.

He was ambushed by a Buick sedan with four armed men inside. The Lincoln had armor plating, but the windows hadn’t been bullet proofed, and Yale was killed by the gunfire. Capone was suspected in the murder, but no charges were ever filed. It was the first time a Thompson submachine gun was used in a New York Mafia hit.

Yale’s funeral was one of the most lavish in mob history. Thousands poured into the streets of Brooklyn to watch his coffin pass. His silver

Frankie Yale's Funeral Procession

Frankie Yale’s Funeral Procession

casket cost $15,000. It took 38 cars to carry his flowers. And two women showed up at Holy Cross Cemetery claiming to be his wife.

Frank Nitti – Feared Chicago Outfit Enforcer and Capone Predecessor


Francesco Raffaele Nitto, better known as Frank “The Enforcer” Nitti, followed Al Capone as leader of the Chicago Outfit in the years after Prohibition. He was boss more in name than fact, but he left a major stamp on the city’s Mafia organization by the time he killed himself to avoid prison time.

Nitti was born January 27, 1886, in Salerno, Italy, in the town of Angri. His parents were Luigi and Rosina Nitto, and he may have been a cousin of Capone, though this fact is disputed by historians.

Luigi died when Nitti was just two years old, and his mother was remarried to Francesco Dolendo. Nitti’s stepfather emigrated to New York in 1890, and Nitti, his mother, and his older sister followed three years later, when Nitti was seven. They settled in Brooklyn.

Nitti dropped out of school after the seventh grade, going to work as a pinsetter in a bowling alley, then as a factory worker, then as a barber. He left home at 14 when his relationship with Delendo went bad. Nitti started fencing stolen jewelry through his barbershop and became friends with Capone’s brothers and their gang, the Navy Street Boys.

Not much is known about Nitti’s life between 1910 and the start of Prohibition in 1919, when he began to make his name as a Chicago Mafioso under Capone. He left Brooklyn sometime around 1910 or 1911, and may have arrived in Chicago about 1913. He set up a barbershop there as a front for his criminal activities and made connections to figures in the Chicago underworld, including boss Dean O’Banion of the North Side Gang.

In 1917 Nitti married Rose Levitt in Dallas. They moved to Galveston, Texas, where he became a part of that city’s crime syndicate. After stealing money from two Galveston mobsters in 1918, he apparently fled back to Chicago and resumed his criminal enterprise there.

By this time both Capone and his mentor, Giovanni “Pappa Johnny” Torrio, had relocated to Chicago to work under Giancomo “Big Jim” Colosimo, boss of the city’s growing branch of the American Mafia, known simply as the Outfit. Eventually Nitti’s criminal success caught their attention.

Prohibition took effect in 1919, and Torrio had Colosimo assassinated so he could take over the Outfit and expand into the illegal liquor trade. Torrio and Capone were impressed by Nitti’s jewel theft and fencing ring, but they especially wanted a piece of his alcohol smuggling operation.

Nitti had a well-established network of smugglers who could bring Canadian whiskey across the border and into the city,

The destruction of alcohol at the start of prohibition in 1919

where he could distribute it to speakeasies. This made him invaluable to Torrio, Capone and the Outfit throughout the 1920s. Nitti started as a bodyguard for Capone, but he quickly rose through the ranks.

In the mid 1920s, tensions between Chicago’s two major bootlegging gangs erupted into open warfare. Dean O’Banion and his Irish-American North Side Gang, with whom Nitti had once worked, now competed against the South Side Outfit for control of liquor distribution in the Gold Coast neighborhood. O’Banion pulled a scam on Torrio, and Torrio retaliated by having O’Banion murdered.

The North Siders responded by trying to assassinate Torrio. He recovered but decided he’d had enough of the mob life. He handed the Outfit to Capone and retired. With Capone now boss, Nitti’s fortunes climbed. He also divorced Rose and married Anna Ronga, daughter of a Mafia doctor.

The violence and political corruption that marked Prohibition in Chicago eventually proved to be Capone’s downfall. By the end of the 1920s both local law enforcement and the federal government had decided he had to go. He was prosecuted for income tax evasion in 1931 and sentenced to 11 years in prison, marking the end of his reign.

Nitti also went to prison for failing to pay his taxes, but was only sentenced to 18 months. His time behind bars taught him he was severely claustrophobic and poorly suited to a life of incarceration.

On his release he took over the Outfit, at least as front man. In truth the organization’s day-to-day affairs were run by his underboss, Paul “The Waiter” Ricca, a close friend of Capone.

Police, emboldened by Capone’s downfall, immediately put the pressure on Nitti. He was almost killed during a raid in 1932 in which one of the police officers was paid $15,000 to murder him. Law enforcement would put a target on him for the rest of his life.

Prohibition formally ended in 1933, and the Outfit under Nitti turned its attention elsewhere: labor racketeering, prostitution and especially gambling. Nitti also began to focus on expansion, pushing the Outfit to take control of crime in parts of Wisconsin, Missouri, California and Nevada, where legalized gambling eventually became the mob’s most lucrative source of income.

But that expansion eventually brought Nitti down. In 1943, the federal government handed down a raft of indictments accusing Chicago mobsters of extorting the largest movie studios in Hollywood. The Outfit had used its control of unions to threaten labor unrest unless the studios paid out large sums. Nitti and Ricca were among those charged.

Police photo of Frank Nitti after committing suicide

Ricca blamed Nitti for the scandal and insisted he should be the one to go to prison for it. But Nitti couldn’t stand the idea of a return to the close confines of a cell, and he feared his fellow mobsters might kill him to keep him quiet. He may also have been suffering from terminal cancer.

On March 19, 1943, the day before he was scheduled to testify to a grand jury, two workers at a Chicago rail yard saw Nitti wandering the tracks. He was almost hit by a train, and the workers lost sight of him. They then spotted him sitting against a fence, where he proceeded to shoot himself in the head with a .32 caliber revolver.

Nitti was buried at Mount Carmel Cemetery in Hillside, Illinois. He lies near the gravesites of Capone, O’Banion and other Chicago mobsters.

Giacomo “Big Jim” Colosimo – Boss of the Chicago Outfit and Brothel Empire

Giacomo “Big Jim” Colosimo was an Italian immigrant Mafioso who got his start as a pickpocket and went on to build the Chicago Outfit, that city’s version of the American mob. He did it by pulling together a coalition of street thugs, pimps and extortionists to build a racket that has dominated organized crime in the Windy City for a century.

Colosimo’s success made possible the rise of bootlegging, which turned Chicago into a criminal’s paradise and, ironically, sealed his doom. He also gave birth to the careers of such future Mafia leaders as Johnny Torrio and Al Capone.

Colosimo was born on February 16, 1878, to Luigi and Giuseppina Colosimo in the small Italian town of Colosimi. The family emigrated to Chicago in 1895, when Giacomo was 17, and settled in the First Ward, a famously corrupt district that encompassed the city’s downtown. He took the name James after arriving.

Colosimo started his American life selling newspapers and shining shoes, but he soon moved on to petty thievery. Before long he rose in the criminal world and began organizing prostitutes. It was his work as a pimp that introduced him to his wife, a madame named  Victoria Moresco. They married in 1902 and opened a brothel together.

He also engaged in a uniquely Italian extortion scheme known as the Black Hand. Criminal immigrants targeted residents with threats of violence unless large sums of money were paid. Extortion letters were stamped with a hand in ink, giving the racket its name. This exposed Colosimo to a relatively organized part of the Chicago underworld, since Black Hands sometimes worked together.

Colosimo also got a legitimate job on the side. He worked alongside fellow Italian immigrants as a street sweeper and rose to become a foreman. He organized his co-workers into a social club that gave him even more influence among both his fellow immigrants and his fellow hoods. He also opened a pool hall that became a center of activity for street gangsters.

His brothel business was wildly successful and soon brought the attention of two key Chicago politicians, First Ward aldermen “Bathhouse” John Coughlin and Michael “Hinky Dink” Kenna. The two men, among the most corrupt in Chicago’s long history of political chicanery, controlled the city’s houses of prostitution. They first hired Colosimo as a Democratic Party precinct captain, then used him as a bagman.

Within a few years, Colosimo ran a network of 200 brothels and had his hands in gambling and other forms of racketeering. He was known as “Big Jim,” but his flashy dress and notoriety earned him another nickname that demonstrated his growing power: “Diamond Jim.”

Colosimo was now in charge of much of Chicago’s underworld, leading an organization that became known simply as the Outfit. The syndicate he created survives to this day and still bears his stamp. Though considerably weakened from its heyday, it continues to derive much of its income from gambling, as it did in his day.

But prostitution was always the center of Colosimo’s empire. At its peak, he even established a violent sex trafficking ring, known at the time as white slavery. Young immigrant women, often under age, were lured to Chicago with job offers, kidnapped, imprisoned, raped and sold to brothels or out-of-state pimps.

Colosimo’s power did not, however, fully protect him from his fellow Italian-American criminals. In fact it made him a target. In 1909 he received a Black Hand letter demanding money. Fearing for his life, he paid the extortionists. But this emboldened them, and they sent more letters.

Desperate for muscle to protect him, Colosimo turned to his wife’s nephew, Giovanni “Pappa Johnny” Torrio, a New York hood. Torrio owned a Brooklyn billiards hall that served as the gathering place for a criminal gang. Among the mobsters he had taken under his wing was Alphonse “Scarface” Capone, better known as Al.

Johnny Torrio came to Chicago to help his uncle and became his second in command. The two consolidated the

Giacomo “Big Jim” Colosimo with Giovanni “Pappa Johnny” Torrio

prostitution and gambling rackets and turned the Outfit into a criminal machine. Torrio also handled his boss’s extortion problem, murdering the Black Hands when they arrived to pick up what they thought was Colosimo’s latest payoff at a Chicago street corner.

By now Colosimo was one of the biggest names in the city. He had connections throughout the political world and owned a restaurant that attracted the rich and famous. Torrio kept the heat off, taking care of further extortionists and arranging the murder of a young woman who escaped Colosimo’s white slavery ring and threatened to testify against him.

But Colosimo and his underboss didn’t see eye to eye on the biggest criminal opportunity of the day, and their disagreement led to his downfall. Prohibition arrived in 1919, sending the distribution and sale of liquor into the hands of criminals. It was a perfect opportunity for the Outfit to make a fortune.

Colosimo, however, already made thousands on illegal alcohol from his restaurant and saw no need to risk federal attention by expanding further into bootlegging. This infuriated Torrio. Things got worse in 1921, when Colosimo divorced Torrio’s aunt, Victoria, and married a 19-year-old singer.

Torrio responded by putting a hit on Big Jim. At a meeting with leaders of the New York Mafia, Torrio asked for their support in making him the new boss of the Outfit once Colosimo was dead.

On May 11, 1921, Torrio called Colosimo and sent him to his restaurant to meet a supposed bootleg shipment. When Colosimo realized no shipment was coming, he became agitated and left. On his way out the door, he was shot dead by a gunman hiding in the coatroom. The assassin was never caught, though Frankie Yale has long been suspected.

A coroner depicting how Colosimo may have been shot.

Torrio quickly took the reins of the Outfit and built a massive network of speakeasies and liquor distribution. A few years later, after an attempt on his life, he handed the syndicate over to Capone, who built it into a genuine criminal empire.

Big Jim Colosimo left a major mark on Chicago, and the city rewarded him with a lavish funeral. There were 53 pallbearers, including congressmen and judges, and more than 1,000 members of the Democratic Party attended. The Catholic Church forbade burial on consecrated ground, not because of Big Jim’s crimes but because of his divorce.

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