Organized Crime

  You can get much further with a kind word and a gun than you can with a kind word alone.  

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July 3,1921, Robert Vanella, his bride Sadie and his best man John Donato Torrio.

Torrio and Vanella had along history together.

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John Torrio

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Johnny Torrio (left)

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John "The Fox" Torrio (right) with his hitman.

CIRCA: 1936

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Torrio following his 1936 arrest for tax evasion.

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John Donato Torrio  was an Italian-American mobster who helped build the Chicago Outfit in the 1920s. It was later inherited by his protégé Al Capone. Torrio proposed a National Crime Syndicate in the 1930s and later became an adviser to Lucky Luciano and his Luciano crime family.

Torrio had several nicknames, primarily "The Fox" for his cunning and finesse. Considered one of the most influential personalities in American organized crime, Torrio impressed authorities and chroniclers with his business acumen and diplomatic skills.

The US Treasury official Elmer Irey considered him "the biggest gangster in America" and wrote, "He was the smartest and, I dare say, the best of all the hoodlums. 'Best' referring to talent, not morals". Virgil W. Peterson of the Chicago Crime Commission stated that his "talents as an organizational genius were widely respected by the major gang bosses in the New York City area". Crime journalist Herbert Asbury affirmed: "As an organizer and administrator of underworld affairs Johnny Torrio is unsurpassed in the annals of American crime; he was probably the nearest thing to a real mastermind that this country has yet produced".

EARLY LIFE: Torrio was born in Irsina (then known as Montepeloso), Basilicata, in Southern Italy, to Tommaso Torrio and Maria Carluccio originally from Altamura, Apulia. When he was two his father, a railway employee, died in a work accident; shortly after, Torrio immigrated to James Street on the Lower East Side of New York City with his widowed mother in December 1884. She later remarried.

His first jobs were as a porter and bouncer in Manhattan. While he was a teenager, he joined a street gang together with fellow James Street resident Robert Vanella and became its leader; he eventually managed to save enough money and opened a billiards parlor for the group, and from there grew illegal activities such as gambling and loan sharking. Torrio's business sense caught the eye of Paul Kelly, the leader of the infamous Five Points Gang. Torrio's gang ran legitimate businesses, but its main concern was the numbers game, supplemented by incomes from bookmaking, loan sharking, hijacking, prostitution, and opium trafficking. Al Capone, who worked at Kelly's club, admired Torrio's quick mind and looked to him as his mentor.

Capone had belonged to the Junior Forty Thieves, the Bowery Boys and the Brooklyn Rippers; they soon moved up to the Five Points Gang. Torrio eventually hired Capone to bartend at the Harvard Inn, a bar in the Coney Island section of Brooklyn owned by Torrio's business associate, Frankie Yale.

MOVE TO CHICAGO: Torrio was the nephew of Victoria Moresco, the wife and business partner of "Big Jim" Colosimo, who had become the owner of more than 100 brothels in Chicago. According to Laurence Bergreen, "Torrio is [also] described as Colosimo’s nephew, but in the absence of any evidence to confirm the relationship, it is more likely their kinship was spiritual rather than familial".

In 1909, Colosimo invited Torrio to Chicago to deal with extortion demands from the Black Hand. Torrio eliminated the extortionists and stayed on; he ran Colosimo's operations and organized the criminal muscle needed to deal with threats to them.

In 1919, Capone also left New York for Chicago at the invitation of Torrio. Capone began in Chicago as a bouncer in a brothel.

COLOSIMO MURDER: When Prohibition went into effect in 1920, Torrio pushed for the gang to enter into bootlegging, but Colosimo stubbornly refused. In March 1920, Colosimo secured an uncontested divorce from Moresco. A month later, he and Dale Winter eloped to West Baden Springs, Indiana. Upon their return, he bought a home on the South Side. On May 11, 1920, Torrio called and told Colosimo that a shipment was about to arrive at his restaurant. Colosimo drove there to await it, but instead he was shot in an ambush and killed. Frankie Yale had allegedly traveled from New York to Chicago and personally killed longtime gang boss Colosimo at the behest of Chicago Outfit friends Torrio and Capone. Although suspected by Chicago police, Yale was never officially charged. Colosimo was allegedly murdered because he stood in the way of his gang making bootlegging profits, having "gone soft" after his marriage with Winter. Al Capone has also been suggested as the gunman. Colosimo's ex-wife, unhappy with the financial arrangements of the divorce, is also theorized having arranged the murder.

RIVALRY WITH NORT SIDE GANG: Torrio headed an essentially Italian organized crime group that was the biggest in the city, with Capone as his right-hand man. He was wary of being drawn into gang wars and tried to negotiate agreements over territory between rival crime groups. The smaller Nort Side Gang led by Dean O'Banion (also known as Dion O'Banion) was of mixed ethnicity, and it came under pressure from the Genna brothers who were allied with Torrio. O'Banion found that Torrio was unhelpful with the encroachment of the Gennas into the North Side, despite his pretensions to be a settler of disputes. In a fateful step, Torrio either arranged for or acquiesced to the murder of O'Banion at his flower shop on November 10, 1924. This placed Hymie Weiss at the head of the gang, backed by Vincent Drucci and Bugs Morgan. Weiss had been a close friend of O'Banion, and the North Siders made it a priority to get revenge on his killers.

ASSASSINATION ATTEMPT AND HANDOVER TO CAPONE: In January 1925, Capone was ambushed, leaving him shaken but unhurt. Twelve days later, on January 24, Torrio was returning from a shopping trip with his wife Anna, when he was shot several times. After recovering, he effectively resigned and handed control to Capone, age 26, who became the new boss of an organization that took in illegal breweries and a transportation network that reached Canada, with political and law-enforcement protection. In turn, he was able to use more violence to increase revenue. An establishment that refused to purchase liquor from him often got blown up, and as many as 100 people were killed in such bombings during the 1920s. Rivals saw Capone as responsible for the proliferation of brothels in the city.

In late 1925, Torrio moved to Italy, where he no longer dealt directly in mob business, with his wife and mother. He gave total control of the Outfit to Capone and said, "It's all yours, Al. Me? I'm quitting. It's Europe for me". Torrio left a criminal empire which grossed about $70,000,000 a year ($997,500,000 in 2018 dollars) from bootleg booze, gambling and prostitution.

LATER YEARS AND DEATH: In 1928, Torrio returned to the United States, as Benito Mussolini began putting pressure on the Mafia in Italy. He is credited with helping to organize a loose cartel of East Coast bootleggers, the Big Seven, in which a number of prominent gangsters, including Lucky Luciano, Longy Zwillman, Joe Adonis, Frank Costello, and Meyer Lansky played a part. Torrio also supported creation of a national body that would prevent the sort of all-out turf wars between gangs that had broken out in Chicago and New York. His idea was well received, and a conference was hosted in Atlantic City by Torrio, Lansky, Luciano and Costello in May 1929; the National Crime Syndicate was created.

Torrio was charged with income tax evasion in 1936, and after several failed appeals, Torrio was sent to prison in 1939, serving two years. In 1940, property that Torrio co-owned with Vanella, Jack Cusick and Capone was sold at auction to satisfy Capone's tax delinquencies. After his release, he lived quietly until his death.

On April 16, 1957, Torrio had a heart attack in Brooklyn while he was sitting in a barber's chair waiting for a haircut; he died several hours later in a nearby hospital.

The media did not learn about his death until three weeks after his burial.

John Torrio in 1930.

(January 20, 1882 – April 16, 1957)

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After Colosimo died, his righthand man, Johnny Torrio, took control of the crime syndicate and went heavy into bootlegging. After barely surviving a hit by rival bootleggers in 1925, Torrio retired and Al Capone took over what came to be known as the Chicago Outfit. Courtesy of Library of Congress.

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Colosimo’s restaurant on South Wabash Avenue, where he met his second wife and where he was shot to death. The restaurant continued to operate as Colosimo’s for many years after his demise. William J. Helmer Collection / The Mob Museum.

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On May 11, 1920, Big Jim Colosimo was shot to death in his own restaurant, allegedly by notorious New York hit man Frankie Yale on orders from Johnny Torrio. No one was ever prosecuted for the murder. William J. Helmer Collection / The Mob Museum.

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Colosimo with his second wife, the singer Dale Winter. They had been married just a couple of weeks before he was killed. William J. Helmer Collection / The Mob Museum.

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Big Jim Colosimo (left) with his lawyer.

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Giacomo Colosimo , better known as Big Jim Colosimo, was an Italian-American mafia crime boss who built a criminal empire in Chicago based on prostitution, gambling, and racketeering. Immigrating from Italy in 1895, he gained power through petty crime and the heading of a chain of brothels. He would lead the Chicago mafia from about 1902 until his death in 1920. When prohibition went into effect in 1920, Johnny Torrio, an enforcer Colosimo imported in 1909 from New York, pushed for the gang to enter into bootlegging, but Colosimo refused. In May 1920, Colosimo left Chicago to marry his second wife, Dale Winter (he had deserted his first wife). After Colosimo returned to Chicago a week later, Torrio called him and let him know about a shipment arriving at his cafe. When Colosimo appeared at the cafe to wait for its delivery, he was shot and killed. The initial murder suspect was his new wife but no one was ever arrested for the murder. It was widely believed that Torrio ordered Colosimo's killing so that the gang could enter the lucrative bootlegging business. Torrio reportedly brought in New York colleague, Frankie Yale, to murder Colosimo. Al Capone has also been suspected as Colosimo's assassin. After his death, Colosimo's gang was controlled first by Johnny Torrio and then Al Capone. It became the infamous Chicago Outfit.

Three weeks after his marriage to the beautiful singer Dale Winter, James Colosimo remained giddy, and nervous. Known as “Big Jim” or “Diamond Jim” for his obsession with the gems, Colosimo reigned as boss of a whorehouse empire in Chicago’s Levee vice district. Celebrities, powerful pols and opera performers crowded his Colosimo’s restaurant, with a café-cabaret and separate late-night fine dining room.

On May 11, 1920, Colosimo and Winter set a date for dinner in the city’s fashionable and exclusive Loop area, along the shore of Lake Michigan. But Colosimo phoned Winter to tell her he’d be late, due to a sudden appointment. “Angel, just got a call,” he said to her. “Gotta meet a guy at the restaurant. It’s important.”

Colosimo had his chauffer drive him in his Pierce-Arrow to the restaurant that afternoon. Inside the still-closed restaurant, he asked a porter, Joe Gabrela, if he’d seen a man looking for him. Gabrela said no. Colosimo entered his office. Soon, Gabrela noticed a man in the dining room. “Mr. Colosimo’s in the office,” he told the man before leaving the room. Then the restaurant’s accountant noticed Colosimo exit the office. About a minute later, he heard a gunshot.

Colosimo had just peered out a windowed door to the large foyer of his café toward the street, when a gunman strode behind him and fired a .38-caliber revolver into the base of his brain, killing him instantly. The suspect fled, but Gabrela provided police with a detailed description. Chicago Police, acting on tips, shrewdly theorized that Brooklyn mobster-killer Frankie Yale did it. Gabrela did identify Yale in a photo lineup. But as things often wound up in gangdom in those days, his fear got the best of him. Taken to view a live police lineup in New York that included Yale, Gabrela declined to finger him. Practically everyone knew it was Yale, but lack of evidence meant no murder charges filed against anyone.

Johnny Torrio, Colosimo’s righthand man and Yale’s former saloon partner in Brooklyn, leapt into action. He organized an extravagant funeral for his dead boss that would serve as the template for future over-the-top, flowery send-offs for murdered mobsters of the 1920s. In a tribute to Colosimo’s political influence, mourners at the funeral inside his home included the all-powerful First Ward alderman and Cook County Democratic committee member Michael “Hinky Dink” Kenna, the second First Ward alderman “Bathhouse” John Coughlin, several other aldermen, a couple members of Congress, a state legislator and a few judges. About 5,000 people, some holding banners for the Democratic Party and street laborers union, trailed a hearse carrying Colosimo’s body in a $7,500 silver and mahogany casket to Oakwood Cemetery.

When people outside Colosimo’s brownstone watched Torrio enter Kenna’s waiting car, they realized who had moved in as Big Jim’s heir apparent in the First Ward. The Chicago Outfit was born.

Torrio most surely planned Colosimo’s assassination, enlisting Yale, his friend, former business partner and experienced hitman. His motivation to off his boss, acknowledged by history, came from his understanding that Prohibition, effective that January 17, clearly offered massive profits, based on his and Colosimo’s existing model of payoffs to police and local office holders to look the other way from Colosimo’s many prostitution houses in the area. Torrio read that the federal Prohibition enforcement agents would be political appointees, not subject to U.S. civil service rules. In other words, low-paid, low-skilled hacks, ripe for bribery and inattention to liquor smuggling.

But Colosimo, still in rapture with his new bride, disagreed with Torrio, fearing the prospect of federal law enforcement without the protection he was used to. Better to keep things the way they are locally, in the Levee and Loop, he thought. He nixed Torrio’s idea to make a major racket out of bootlegging.

However, it is rarely reported that Colosimo did in fact approve Torrio’s scheme to reopen closed breweries to make and sell illegal, real beer to underground merchants and barkeeps in Chicago. Earlier, before Prohibition, Colosimo invested $25,000 in a brewery operated by one of his saloon owners, Jake “Greasy Thumb” Guzik (one author claimed Guzik garnered his nickname for serving beer with his thumb in the stein). Still, this didn’t go far enough for Torrio. Just as he convinced Colosimo to expand the brothel business to the rising suburbs and towns bordering Chicago, he rightly predicted that unbridled bootlegging of beer and hard liquor would produce far more money — millions. Colosimo was dead set against going much beyond prostitution in Chicago and the suburbs, and his popular restaurant. For Torrio, to build this new domain, his shortsighted boss had to go.

Colosimo, born in 1878 in Palermo, Sicily, moved with his parents to the Windy City at age 1. He would not have reached his height as top pimp in Chicago – the nation’s brothel capital – without Hinky Dink Kenna’s well-paid protection. Hinky Dink and Bathhouse Coughlin represented the First Ward, when wards had two city alderman each, from the 1890s to the early 1920s. Two masters of influence and graft, Hinky Dink, thin, stoic and not quite five feet tall, and the floppish, flamboyant Coughlin, helped themselves to payments, not only from the vice businesses in the Levee, but on everything awarded by the city council in their ward – licenses, permits and utilities needed for hotels, banks, shops and clubs in the Loop as well as federal and state offices, the police, courts and jails. Colosimo, as Torrio after him, served at the pleasure of Kenna as his vice gang underlings and made sure he received his cut of the proceeds. Kenna let the illicit gambling operators and brothel madams run as long as they, as precinct captains, delivered him the votes to win elections.

Colosimo’s links to Hinky Dink started in the 1890s when Jim was an engaging young bootblack inside Kenna’s rowdy Workingman’s Exchange saloon. Kenna took a liking to the kid and later arranged for a city patronage job as a street cleaner. Colosimo ingratiated himself with Italian immigrants and got them to support Kenna. The boss in return promoted Colosimo to street cleaning supervisor. Colosimo organized his Italian men into a street cleaners union.

By the early 1900s, prosperous Chicago had been a bastion of illegal but tolerated prostitution for decades. Colosimo, with Kenna’s approval, made the move to the brothel business by marrying Victoria Moresco, a madam – six years older than Big Jim — of a pair of dollar-a-go whorehouses. Kenna elevated him to precinct captain to deliver the Italians to the polls. Colosimo was second only to Ike Bloom, the First Ward’s vice money bagman, in political power, under bosses Kenna and Coughlin.

In 1909, the dangers of Chicago vice life intruded on Colosimo’s rising stardom. Black Hand extortionists, by letter and then at gunpoint, demanded Colosimo pay them $50,000. He needed a bodyguard. Victoria knew someone who might be right for it – her cousin, Johnny Torrio (born in southern Italy in 1882), who co-owned a saloon called the Harvard Inn in Coney Island, Brooklyn, with Frankie Yale. They offered to pay Johnny’s expenses and put him up in their Chicago brownstone. Torrio, weary of years of gang wars in the New York area, decided to make the move, and sold his share in the Harvard to Yale.

Unsure of the calm, squat, chubby Torrio, Colosimo told him about his problem. Torrio, a veteran Black Hand-style extortionist himself in Brooklyn, assured Big Jim he had it covered. Driving a horse-drawn carriage with two Colosimo gunmen hiding inside, he lured the three extortionists one night with the promise of a payment. The gunmen stood up, shot and killed two of them and mortally wounded the third. Colosimo hired Torrio as his bodyguard. As time went by, Colosimo noticed Torrio’s talent for finances and leadership and delegated responsibility for managing prostitution houses to him as a “male madam.”

In the 1910s, Colosimo rose to vice boss and Kenna’s collector in the First Ward, thanks both to Hinky Dink’s sway with police, judges and prosecutors, and Torrio’s business acumen. With the Loop district’s thriving businesses and fancy residences, the First Ward developed into perhaps the richest area in the whole Midwest.

For Torrio’s headquarters, Colosimo bought a four-story building at 2222 S. Wabash Avenue. Torrio opened an office, a saloon – the Four Deuces – a gambling house and fourth-floor brothel. While there, his old friend Frankie Yale sent him a letter, asking if he could give a 19-year-old roustabout bar worker of his, Alphonse Capone, a job. The teen cut up a man in a fight and needed to leave New York. Torrio made Capone his front door bouncer and then, after seeing his violent side, his bodyguard.

By his death in 1920, Colosimo had unknowingly fathered the shell of an organization that Torrio, and Capone who succeeded Torrio in 1925, would transform into the Outfit, one of the most powerful crime syndicates in American history.

Big Jim Colosimo

(February 16, 1878 - May 11, 1920)

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Chicago Outfit Bosses

Giacomo Colosimo                       1910-1920 (Big Jim, Diamond Joe)

John D. Torrio                               1920-1925 (Papa Johnny, The Fox)

Alphonse "Al" Capone                 1925-1931 (Al Brown, Scarface)

Frank Nitti                                      1931-1943 (The Enforcer)

Paul Ricca                                     1943-1947 (The Waiter)

Anthony "Tony" Accardo             1947-1957 (Joe Batters, Big Tuna)

Salvatore "Sam" Giancana          1957-1966 (Mooney, Mo, Momo)

Samuel Battaglia                          1966-1967 (Teets)

Felix Alderisio                               1967-1971 (Milwaukee Phil)

Joseph Aiuppa                              1971-1986 (Joey Doves, Joey O'Brien)

Joseph Ferriola                             1986-1989 (Joe Nagall, Mr. Clean)

Samuel Carlisi                               1989-1996 (Sam Wings, Black Sam)

John DiFronzo                               1996-2014 (No Nose)

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As a Cubs ballplayer signs a ball for Sonny, McGurn turns and scans the crowd behind him with one hand reaching into his jacket, alarmed, perhaps, by the peanut vendor.

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McGurn sits on the right, directly behind Capone. Front and center is an embarrassed and uneasy Sonny Capone, and beside him in the dark suit is lawyer, state legislator and future congressman, Roland V. Libonati, one of Capone’s most steadfast apologists. The lady in the upper left corner seems to have just realized who is occupying the best seats in the park

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CIRCA 1920: Longtime Capone enforcer and bodyguard Jack McGurn “Machine Gun” is seen exiting a hotel phone booth at an unidentified location in Chicago.

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Al Capone goes to jail Rare film footage of Al Capone. It shows him turning himself in following his income tax conviction in 1931. He ended up doing six years on an eleven years bit.