Chicago Outfit

The Chicago Outfit (also known as the Outfit, the Chicago Mafia, the Chicago Mob, the Chicago crime family, the South Side Gang or the Organization) is an Italian American Mafia crime family based in Chicago, Illinois, originating in the city's South Side in 1910. The organization is part of the larger American Mafia.
The Outfit rose to power in the 1920s under the control of Johnny Torrio and Al Capone, and the period was marked by bloody gang wars for control of the distribution of illegal alcohol during Prohibition. Since then, the Outfit has been involved in a wide range of criminal activities, including loansharking, illegal gambling, prostitution, extortion, political corruption and murder. Capone was convicted of income tax evasion in 1931 and the Outfit was next run by Paul Ricca. He shared power with Tony Accardo from 1943 until his death in 1972; Accardo became the sole power in the Outfit upon Ricca's death and was one of the longest-sitting bosses of all time upon his death in 1992.
Though it has never had a monopoly on organized crime in Chicago, the Outfit has long been the largest, most powerful and most violent criminal organization in Chicago and the Midwest in general. Unlike other Mafia factions such as the Five Families of New York City, the Outfit has been a unified faction since its conception. Its influence at its peak stretched as far as California, Florida and Nevada and it continues to operate throughout the Midwestern United States and Southern Florida, as well as Las Vegas and other parts of the Southwestern United States. Heightened law enforcement attention and general attrition have led to its gradual decline since the late 20th century, though it continues to be one of the major and most active organized crime groups in the Chicago metropolitan area and the Midwest.
The early years of organized crime in Chicago, in the late 19th and early 20th centuries, were marked by the division of various street gangs controlling the South Side and North Side, as well as the Black Hand organizations of Little Italy. In later years, the Outfit consisted of various street crews controlling different territories around Chicago including Elmwood Park, Melrose Park, Chicago Heights, Rush Street, Grand Avenue and Chinatown.
Big Jim Colosimo centralized control in the early 20th century. Colosimo was born in Calabria, Italy, in 1878, and immigrated to Chicago in 1895, where he established himself as a criminal. By 1909, with the help of bringing Johnny Torrio from New York to Chicago, he was successful enough that he was encroaching on the criminal activity of the Black Hand organization. Colosimo also "cultivated deep political connections" after "serving as a precinct captain in the organization of First Ward Alderman Couglin and Kenna, and later [became] the bagman (collector of illegal profits and dispenser of bribes) in the vice-laden Levee District, which afforded him with blanket political protection".
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 his wife, Victoria Moresco. A month later, he and singer Dale Winter eloped to West Baden Springs, Indiana. Upon their return, he bought a home on the South Side. On May 11, 1920, Colosimo was killed by a gunman waiting in the coat room of his restaurant, Colosimo's cafe. The killer was most likely Frankie Yale, fulfilling a contract commissioned by Johnny Torrio.
Torrio's organization was made up predominately of ethnic Italians but had a large contingent of members from other immigrant backgrounds. Torrio's gang also differed from the other Chicago gangs by recruiting from New York's underworld, regularly welcoming that city's ambitious criminals into his organization's ranks. Alphonse Capone had left New York for Chicago in 1919, likely under orders from mob boss Frankie Yale to leave town to avoid retaliation for previous violence they had committed in New York. Capone began in Chicago as a doorman at the Four Deuces club. By 1924, Capone's business acumen and shrewd intelligence had gained him a place as Torrio's right-hand man. Many rivals saw Capone as responsible for the proliferation of brothels in the city.
In 1923, William Dever was elected mayor of Chicago, and he began to crack down on Torrio's underworld activities within the city. Losing their political cover, the gang looked to the suburbs for a new base of operations. Torrio ordered Capone to lead a takeover of the town of Cicero, where he was able to corrupt city manager Joseph Z. Klenha. The gang set up dozens of brothels, speakeasies, gambling dens, and other businesses within the town. On April 1, 1924, Cicero municipal elections were threatening Kenha's leadership. Kenha appealed to Torrio and Capone for their support, which they responded to by terrorizing the opposition and voting public on election day. The gang guarded polling places, ensuring people knew the right way to vote and violently preventing entry to those who did not. They ransacked the local Democratic party campaign headquarters, forcibly detaining the election workers for hours. By that afternoon, the Chicago Police Department was ordered to step in to halt the violence by Cook County Judge Edmund J. Jareki. Seventy plainclothes officers, newly deputized as county sheriffs, descended on Cicero. Frank Capone, Al's brother, was killed that evening by detective sergeant William Cusack during an altercation on 22nd Street and Cicero Avenue. Charles Fischetti was also arrested at the scene. Kenha won the election, ensuring the Torrio-Capone gang's local immunity into the 1930s.
Torrio was wary of being drawn into gang wars and tried to negotiate agreements over territory between rival crime groups. The smaller North Side Gang led by Dean 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. The "Terrible" Genna brothers, as they were known, consisted of Peter, James, Angelo, Tony, Sam and Mike "The Devil" Genna. They were known for their ruthlessness and intemperate disposition. 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 Moran. Weiss had been a close friend of O'Banion and the North Siders made it a priority to get revenge on his killers.
At the end of 1924, the Torrio-Capone gang had between 300–400 members, while the North Side gang could count on around 200 soldiers.
In early 1925, the North Side began a string of retaliations for O'Banion's murder. First, in January 1925, Capone's car was shot up without him in it. Twelve days later, on January 24, Torrio was returning from a shopping trip with his wife Anna, when he was shot several times by North Side gunmen. After recovering, he effectively resigned and handed control to Capone, age 26 at the time. Torrio retired to New York and acted as an advisor to the New York Mafia in helping form the "Commission".
During the beer wars, the Capone gang's enforcement group was led by "Machine Gun" Jack McGurn, and included Tony Capezio, Claude "Screwy" Maddox, Sam "Golf Bag" Hunt, Frank Rio, and others. 1925–1926 were the most violent years of Chicago's "Beer Wars" in which 133 gangsters were murdered. On September 20, 1926, the North Side gang attacked Capone's headquarters at Cicero's Hawthorne Hotel, shooting hundreds of rounds and only narrowly missing Capone. Less than a month later, on October 11, North Side gang leader Hymie Weiss was gunned down with a Thompson in front of Holy Name Cathedral, allegedly by Jack McGurn. Weiss was succeeded by Vincent Drucci, a WW1 veteran and close friend of Weiss.
In 1928, the Capone gang was active in the violent Pineapple Primary election. Capone had previously donated $200,000 to Big Bill Thompson's corrupt mayoral campaign, and then used his gangsters to intimidate, assault, and bomb Thompson's political rivals in an attempt to keep the Republican party in power.
Capone was widely assumed to have been responsible for ordering the 1929 Saint Valentine's Day Massacre in an attempt to eliminate Bugs Moran, head of the North Side Gang. On that fateful and cold February morning, four Capone henchmen (two dressed as Chicago policemen) entered the S.M.C Cartage Company garage located at 2122 N. Clark St. Chicago, Illinois, to find seven men, which included five of Moran's soldiers, an auto mechanic, and a friend of the gangsters, awaiting a shipment of hijacked booze. All seven men were lined up against the wall in a mock police raid and shot to death. Moran escaped narrowly by accidentally arriving late to the meeting. Moran was the last survivor of the North Side gunmen; his succession had come about because his similarly aggressive predecessors Vincent Drucci and Hymie Weiss had been killed in the violence that followed the murder of original leader Dean O'Banion.
Capone was convicted on three counts of income tax evasion on October 17, 1931, and was sentenced a week later to 11 years in federal prison, fined $50,000 plus $7,692 for court costs, and was held liable for $215,000 plus interest due on his back taxes. Capone later died of heart failure as a result of apoplexy on January 25, 1947.
In 1931, head of operations Frank Nitti was also convicted of tax evasion and sent to prison; however, Nitti received an 18-month sentence. When Nitti was released on March 25, 1932, he took his place as the new boss of the Capone Gang. However, some historical revisionists claim that the real power in the Outfit was his underboss, Paul Ricca. Not only did Ricca frequently overrule Nitti's orders, but the leaders of the National Crime Syndicate dealt solely with him. Ricca would be the crime boss of Chicago, either in name or in fact, for the next 40 years.
Over the next decade, The Outfit moved into labor racketeering, gambling, and loan sharking. Geographically, this was the period when Outfit muscle extended to Milwaukee and Madison, Wisconsin, Kansas City, and especially to Hollywood and other California cities, where The Outfit's extortion of labor unions gave it leverage over the motion picture industry.
In the early 1940s, a handful of top Outfit leaders went to prison because they were found to be extorting Hollywood by controlling the unions that compose Hollywood's movie industry, and manipulating and misusing the Teamsters Central States Pension fund. In 1943, the Outfit was caught red-handed shaking down the Hollywood movie industry. Ricca wanted Nitti to take the fall. However, Nitti had found that he was claustrophobic, years earlier while in jail for 18 months (for tax evasion), and he decided to end his life rather than face more imprisonment for extorting Hollywood. Ricca then became the boss in name as well as in fact, with enforcement chief Tony Accardo as underboss—the start of a partnership that lasted for almost 30 years. Around this time, the Outfit began bringing in members of the Forty-Two Gang, a notoriously violent youth gang. Among them were Sam "Momo" Giancana, Sam "Mad Sam" DeStefano, Felix "Milwaukee Phil" Alderisio, and Fiore "Fifi" Buccieri.
Ricca was sent to prison later in 1943 for his part in The Outfit plot to control Hollywood. He was sentenced to 10 years in prison, along with a number of other mobsters. Through the "magic" of political connections, the whole group of Outfit mobsters was released after three years, largely due to the efforts of Outfit "fixer" Murray "The Camel" Humphreys. Ricca could not associate with mobsters as a condition of his parole. Accardo nominally took power as boss, but actually shared power with Ricca, who continued behind the scenes as a senior consultant—one of the few instances of shared power in organized crime.
Accardo joined Ricca in semi-retirement in 1957 due to some "heat" that he was getting from the IRS. From then on, Ricca and Accardo allowed several others to nominally serve as boss, such as Giancana, Alderisio, Joey Aiuppa, William "Willie Potatoes" Daddano, and Jackie "the Lackey" Cerone. Most of the front bosses originated from the Forty-Two Gang. However, no major business transactions took place without Ricca and Accardo's knowledge and approval, and certainly no "hits". By staying behind the scenes, Ricca and Accardo lasted far longer than Capone. Ricca died in 1972, leaving Accardo as the sole power behind the scenes.
During the 1960 presidential election, many claimed that the Mafia, and in particular, the Chicago Outfit, boosted candidate and future president John F. Kennedy. The strategy for boosting votes for Kennedy essentially ran through the Mafia-controlled unions, physically threatening those who did not vote for Kennedy. It was even said that Joseph Kennedy held a meeting with mob boss Sam Giancana before the election. Supposedly, the Kennedys and the Mafia agreed that if John were elected president, he would lighten the pursuit of authorities on the mob group. However, after the election, President Kennedy turned on Giancana. Theories say this is what led to his and Robert Kennedy's assassinations. Further, many believe the Outfit was involved in a Central Intelligence Agency–Mafia collusion during Castro's overthrow of the Cuban government. In exchange for its help, the Outfit was to be given access to its former casinos if it helped overthrow Fidel Castro in Operation Mongoose or Operation Family Jewels. The Outfit failed in that endeavor and faced increasing indictments under the administration of President John F. Kennedy.
The Outfit reached the height of its power in the early 1960s. Accardo used the Teamsters pension fund, with the aid of Meyer Lansky, Sidney Korshak, and Jimmy Hoffa, to engage in massive money laundering through the Outfit's casinos. The Outfit controlled casinos in Las Vegas and "skimmed" millions of dollars over the course of several decades. Most recently, top mob figures have been found guilty of crimes dating back to as early as the mid-1960s. It has been rumored that the $2 million skimmed from the casinos in the Court case of 1986 was used to build the Old Neighborhood Italian American Club, the founder of which was Angelo J. "The Hook" LaPietra. The 1995 Martin Scorsese movie Casino depicts The Outfit's activities in Las Vegas during the 1970s, where bookmaker Frank "Lefty" Rosenthal and made man Anthony "The Ant" Spilotro managed the Stardust, Fremont, Marina, and Hacienda casinos on behalf of Joey "Doves" Aiuppa.
The 1970s and 1980s were a hard time for the Outfit, as law enforcement continued to penetrate the organization, spurred by poll-watching politicians. Off-track betting reduced bookmaking profits, and illicit casinos withered under competition from legitimate casinos. Activities such as auto theft and professional sports betting did not replace the lost profits. In the 1970s and early 1980s, a series of over 20 murders resulted from the Outfit's takeover of car theft rackets on the South Side of Chicago and Northwest Indiana. During this period, known as the "chop shop wars", James "Jimmy the Bomber" Cataura, the head of the Chicago Heights crew, was tasked by Outfit leaders with seizing control of auto theft operations from a vast network of independent car thieves in the Chicago area. Cataura himself was a victim of the "chop shop wars" when he was killed in July 1978 amidst a power struggle within his own crew with underling Albert Tocco for control of the lucrative stolen car rings. The Outfit simultaneously waged a campaign to gain control over independent pornographic bookstores, massage parlors and strip clubs in and around Chicago, with several gangland-style murders being attributed to the "porn wars". Beginning in 1977, the Outfit engaged in a "loose alliance" with the Outlaws Motorcycle Club to control and share the profits from organized prostitution in Chicago.
Allen Dorfman, a key figure in the Outfit's money embezzlement operations, was investigated by the Department of Justice. In 1982, the FBI wire-tapped Dorfman's personal and company phone lines and was able to gather the evidence needed to convict Dorfman and several of his associates on attempts to bribe a state senator to get rid of the trucking industry rates. If Dorfman had succeeded, the Outfit would have seen a huge gain of profit. This was known as Operation Pendorf and was a huge blow to the Chicago crime syndicate.
Operation GAMBAT (GAMBling ATtorney) proved to be a crippling blow to the Outfit's tight grip on the Chicago political machine. Pat Marcy, a made man in the Outfit, ran the city's First Ward, which represented most of downtown Chicago. Marcy and company controlled the circuit courts from the 1950s until the late 1980s with the help of Alderman Fred Roti and Democratic Committeeman John D'Arco Sr. Together, the First Ward fixed cases involving everything from minor traffic violations to murder.
Attorney and First Ward associate Robert Cooley was one of the lawyers who represented many mafiosi and associates in which cases were fixed. As a trusted man within the First Ward, Cooley was asked to "take out" a city police officer. Cooley was also an addicted gambler and in debt, so he approached the U.S. Justice Department's Organized Crime Strike Force, declaring that he wanted to "destroy Marcy and the First Ward".
Cooley was soon in touch with the FBI and began cooperating as a federal informant. Through the years, he maintained close ties to Marcy and the big shots of the First Ward. He wore an electronic surveillance device, recording valuable conversations at the notorious "First Ward Table", located at "Counselor's Row" across the street from Chicago City Hall. The results in Operation Gambat (Gambling Attorney) were convictions of 24 corrupt judges, lawyers, and cops.
In February 1990, 20 members and associates of the Outfit's "Ferriola Street Crew", which was headed by Joseph Ferriola before being taken over by Ernest Rocco Infelice upon Ferriola's death, were indicted on various federal charges including murder, extortion and bribery following an eight-year FBI investigation.
Accardo died in 1992. In a measure of how successfully he had managed to stay out of the limelight, he never spent a day in jail (or only spent one day, depending on the source) despite an arrest record dating to 1922. Chicago's transition from Accardo to the next generation of Outfit bosses has been more of an administrative change than a power struggle, distinct from the way that organized crime leadership transitions take place in New York City.
Higher law enforcement investigations and general attrition led to the Outfit's gradual decline since the late 20th century. The Old Neighborhood Italian American Club is considered to be the hangout of Old Timers as they live out their golden years. The club's founder was Angelo J. LaPietra "The Hook", who was the main Council at the time of his death in 1999.
On April 25, 2005, the U.S. Department of Justice launched Operation Family Secrets, which indicted 14 Outfit members and associates under the Racketeer Influenced and Corrupt Organizations Act (RICO), including Joseph Lombardo, Nicholas Calabrese, Frank Calabrese Sr. and James Marcello. U.S. District Court Judge James Zagel presided over the Family Secrets trial. The federal prosecutors were Mitchell A. Mars, T. Markus Funk, and John Scully. Facing a life sentence, Nicholas Calabrese became the first "made" member of the Chicago Outfit to become a witness for the federal government. Calabrese gave information on 14 murders he was personally involved with and knowledge of 22 killings during the past 30 years.
As of 2007, the Outfit's size is estimated to be 28 official members (composing its core group) and more than 100 associates.
From 1996 to 2018, the Chicago Outfit was believed to be led by John DiFronzo. As of 2021, the Chicago Outfit is believed to be led by Salvatore "Solly D" DeLaurentis. On May 31, 2020, 24 year-old Bobby 'Boo Boo' English Jr. was murdered. The Cicero crew-affiliated 12th Street Players gang is suspected of ordering the hit. He was the son of Bobby "Taz" English, former boss of the 12th Street Players during the 1990s and early 2000s and currently in prison for attempted murder.
The street boss is a high-ranking member appointed to run the outfit's daily activities for the boss. The position was created to protect the boss from federal investigations.
The Outfit is notable for having had other ethnic groups besides Italians as high-ranking associates since the family's earliest days. A prime example of this was Jake "Greasy Thumb" Guzik, a Polish Jew, who was the top "bagman" and "accountant" for decades until his death. Others were Murray Humphreys, who was of Welsh descent, Gus Alex, a Greek, and Ken Eto (aka Tokyo Joe), who was Japanese-American.
Another well-known associate of the Outfit is Jewish New York City mobster Benjamin Siegel. Siegel was a childhood friend of Capone. Siegel's organization in Las Vegas and Los Angeles was an ally of the Outfit from 1933 to 1961 when the family boss, Mickey Cohen, was imprisoned and the family was decimated.
The Chicago Outfit has a long history of portrayal in Hollywood as the subject of film and television.
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