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1900s - Chicago's Mafia of the early 1900s appears to have been led by several families from the Ciminna-Caccamo-Villafrati area of Palermo Province in Sicily. However, the Sicilian-Italian underworld was terribly fragmented until the Prohibition Era, and it may be a mistake to assign a citywide title of "boss" to any single individual in the early period.
1900 - Joseph Morici was considered by authorities to be an early boss of the Sicilian underworld in Chicago's Little Sicily, around North Union Street and Grand Avenue. Morici was from the Castelbuono area of Sicily and arrived in the U.S. in the mid-1880s. Sought by police following the the February 1901 murder of local Neapolitan leader Salvatore DiGiovanni, police found Morici a fair distance from home, at Milton Avenue in the Near North Side, where the intertwined Zagone, Dispenza, Spatafora and Nicolosi families were considered underworld leaders. Morici was acquitted of DiGiovanni's murder and continued for some time as a leading racketeer in the Little Sicily neighborhood, perhaps as a lieutenant of Mariano Zagona.
1900 - Mariano Zagone (1861 to May 7, 1909), originally from Ciminna, was regarded as the leader of a gang of blackmailers and counterfeiters in the Near North Side. He was arrested in 1901 for counterfeiting but not convicted. He married Biaggia Spatafora in Chicago on Oct. 5, 1902. Zagone became a wealthy cigar maker in Chicago. His home was 68 W. Oak Street, a fair distance from the congested neighborhoods inhabited by many of his fellow immigrants. He was targeted several times for assassination. He was shot to death in 1909 while at a saloon run by his in-laws, the Nicolosis, at 134 Gault Court (one block east of Milton Avenue). Joseph Nicolosi was suspected of involvement in the killing.
1909 - Rosario "The Heartless" Dispenza (Sept. 6, 1869, to Jan. 22, 1914) entered the United States in the early summer of 1899 at New York City and continued on to meet up with his brother-in-law (Spatafora, also from Ciminna) in Chicago. Dispenza - also spelled Dispensa - became a saloonkeeper at 147 Milton Ave., in an over-populated region known in the press as "Little Hell." (The address was affected by later renumbering to 1031 Milton Ave. and by a street name change to Cleveland Avenue. Buildings in the area were demolished long ago. Their replacements - the Cabrini-Green high-rises - have also been taken down.) He also operated a private bank. Dispenza appears to have succeeded Mariano Zagona as boss of the Mafia in the Near North Side. In 1909, New York-based Mafia boss of bosses Giuseppe Morello is known to have written to Dispenza about Mafia matters. During his reign, the intersection with Hobbie Street in front of his saloon was dubbed "Death Corner," due to the number of murder victims found there. The bodies of Rosario Dispenza and his banking partner Anthony Puccio were added to the total in January 1914. At the time, police noted that both Dispenza and Puccio were former business partners of Anthony D'Andrea, a Sicilian racketeer lately growing in importance.
1914 - Anthony D'Andrea (June 7, 1872, to May 11, 1921) gave up the priesthood to marry and at about the same time embarked on a life of crime. Originally from Valledolmo, he entered the U.S. in 1895, meeting family already settled in Buffalo. He studied to become a priest. Shortly after being assigned as pastor in an Independent Catholic parish in Chicago, he fell in love, stepped away from the church and married in the summer of 1899. A few years later, D'Andrea and his wife were arrested (one of the Nicolosis was later arrested as an accomplice) in a counterfeiting raid. The U.S. Secret Service believed that D'Andrea was part of a coin-counterfeiting network based in the New York area. He was sentenced to 13 months in prison. Upon his release, D'Andrea had greater stature in the Sicilian underworld in Chicago and became well connected to labor and government officials. D'Andrea is widely regarded as the most powerful Chicago Mafia boss following the murder of Dispenza. He became a political force and spokesman for the Sicilian colony in Chicago as he became president of the charitable United Italian Societies and of the fraternal order Unione Siciliana, following the Great War. While Unione Siciliana's outward business was insurance, its leaders beginning with D'Andrea were powerful Chicago Mafiosi. The Unione itself may have become a sort of mediating board for underworld factions in the Chicago area.
1920 - D'Andrea entered into a violent feud with established political figure John Powers and his allies. Shootings and bombings occurred. D'Andrea was blamed for the killing of a popular court official named Paul Labriola. As a number of D'Andrea men - including Angelo Genna - were arrested, D'Andrea announced that he was giving up politics. Authorities linked D'Andrea's 1921 murder to the political feud, but Mafiosi understood that betrayal by D'Andrea underling Joseph Laspisa was the cause.
1921 - Michele Merlo (Jan. 4, 1880, to Nov. 9, 1924) learned of the murder of his boss D'Andrea while he was vacationing in Italy. He returned to Chicago immediately and ordered the vendetta murder of Joseph Laspisa. Merlo set about the task of healing the differences between underworld factions in and around Chicago, and he became a widely respected regional boss with control of the Unione Siciliana and great influence over local labor unions. Merlo initially entered the U.S. at New Orleans with his parents around 1889. He settled in Chicago close to the turn of the century and quickly became a trusted aide to D'Andrea. Merlo's peaceful reign over the Chicago Italian underworld lasted only a few years. He died of natural causes in November 1924. Gang wars in Chicago erupted almost immediately.
1924 - Angelo Genna (1892 to May 26, 1924). Angelo Genna and his brothers earned respect in the Mafia (and earned their nickname as "The Terrible Gennas") through their fierce battles with the forces of local political boss John Powers. Angelo Genna was acquitted of the 1921 murder of Labriola and, with Michele Merlo, gained power within the Unione Siciliana. Upon the death of Merlo, Genna was recognized as the most powerful Sicilian Mafia leader in Chicago. But he did not have Merlo's diplomatic skills, and the Italian underworld fractured. Feuds began between Italian factions and between Italian and non-Italian gangs.
1924 - Angelo Genna was killed in his car on May 25, 1924. The vehicle crashed into a lamp post at Hudson and Ogden Avenues. Brother Michael Genna may have hoped to succeed his brother as local Mafia boss, but he was killed in a gunfight the next month. The remaining Gennas quickly lost their interest in the Chicago underworld and reportedly fled the city.
1925 - Joe Aiello (Sept. 27, 1890, to Oct. 23, 1930). Shortly after arriving in Chicago from upstate New York, Aiello and his family stepped to the leadership of the Windy City's Sicilian underworld. As non-Sicilian Capone grew in strength and attempted to take over the Unione Siciliana, Aiello resorted to violence and alliances with Chicago's other ethnic gangs.
1930 - Capone assassins killed Joe Aiello near the corner of West End and Kolmar Avenue on Oct. 23, 1930. The Aiello faction was essentially broken.
1902 - Vincenzo "Jim" Colosimo (Feb. 16, 1877, to May 11, 1920) is credited with initiating the organization that later became the Capone Outfit. Born in the Calabria region of mainland Italy, he traveled to the U.S. as a teen and settled with relatives in Chicago. Possibly through his marriage to Victoria Moresco, Colosimo became involved in organized vice. He ran saloons and brothels, likely participated in "white slave" trafficking, and involved himself in politics to provide protection for his businesses. As he became wealthy and well-connected "Big Jim," he was targeted by extortionists and brought young gangster Johnny Torrio from New York to provide him with protection. Torrio (or his step-father, Salvatore Caputo, who ran an illegal saloon behind his New York City grocery) may have been a relative of Victoria Moresco.
1910s - Johnny Torrio organizes a small group of gunmen to protect the interests of "Big Jim" Colosimo. Torrio becomes an active partner in some of Colosimo's enterprises. The two men are identified by authorities in 1914 as the primary rivals to the established figures in Chicago's old red light district. In 1917, Dale 'Babe' Winter began entertaining at Colosimo's cafe. Torrio brought young gangster Al Capone from Brooklyn around 1918 to assist him in managing Chicago rackets. Colosimo ended his marriage with Victoria Moresco in 1920 to wed young singer Dale Winter. Less than one month later, he was murdered at a restaurant he owned at Twenty-Second Street and Wabash Avenue.
1920 - Johnny Torrio (Jan. 20, 1882, to April 16, 1957) took over for the murdered Colosimo just as the Prohibition Era began. Torrio assembled a bootlegging gang in competition with existing underworld organizations in Chicago. Competition led to killings, negotiations and consolidation. Torrio's group emerged as the primary rival of the rum-running O'Donnell Brothers gang. Al Capone became Torrio's top lieutenant. Following Torrio's return from a trip with his wife to Europe, he was arrested as the owner of an illegal brewery. A competing gang boss Dean O'Banion was believed to have set up the arrest. O'Banion was shot to death a short time later. Torrio was sentenced to prison for his involvement with the brewery. Before beginning his sentence, he was ambushed in front of his home. Torrio was seriously but not fatally wounded. Police suspected O'Banion gangsters.
1925 - Alphonse Capone (Jan. 17, 1899, to Jan. 25, 1947). Torrio had been turning command of his operations over to Capone for several years, as he traveled extensively with his wife. Following the assassination attempt early in 1925, Torrio went into retirement. Capone's gang entered into a shooting war with Joe Aiello's Mafia and a North Side gang commanded by George "Bugs" Moran. About 1928, Capone gained Mafia recognition by being named as a capodecina under New York-based boss of bosses Giuseppe Masseria. Aiello and his allies were outraged, and the Masseria endorsement is one of the factors that led to the Castellammarese War. Aiello and Moran agreed to ally against Capone. On Feb. 14, 1929, Capone gunmen decimated Moran's gang in the St. Valentine's Day Massacre. Months later, Capone ended a rebellion in his Outfit with the murders of John Scalisi, Albert Anselmi and Joseph Guinta. Aiello was shot to death on Oct. 23, 1930. At the conclusion of the Castellammarese War in 1931, Capone was designated the leader of Chicago's united Mafia organization. He presided over the Windy City underworld only a short time. He was sentenced on Nov. 24, 1931, to serve 11 years in federal prison on an income tax conviction.
1932 - Frank Nitti (Jan. 27, 1886, to March 19, 1943). Nitti is generally believed to have taken over the day-to-day operations of the Outfit following Capone's imprisonment for tax evasion. (Some sources incorrectly state that Nitti took charge after the death of Capone, neglecting the fact that Capone outlived Nitti.) Nitti's rise to power could not have occurred before March 1932, as he was completing his own tax evasion sentence until then. Nitti's top lieutenant reportedly was Louis "Little New York" Campagna. They were assisted by Paul "Ricca" DeLucia and Anthony Accardo. Under Nitti's direction, the Outfit moved aggressively into labor racketeering. In the late 1930s, the Outfit took over the International Alliance of Theatre and Stage Employees. Through Nitti-ally Willie Bioff, it used its hold over movie projectionists to extort vast sums from motion picture companies. As the racket was exposed early in 1943, some in Chicago underworld leadership recommended the murder of Bioff to prevent him from providing information to investigators. Nitti refused.
1943 - Louis Campagna (June 27, 1900, to May 30, 1955). Nitti's trust in Bioff was misplaced. Bioff cooperated with federal investigators, triggering the end of Outfit control over the stage employees union and the end of Nitti. Just hours after a federal grand jury in New York indicted Nitti, Campagna, Accardo, Charles Gioe, Frank "Diamond" Maritote and Philip D'Andrea, Nitti committed suicide along railroad tracks at North Riverside, Illinois. Campagna appears to have briefly served as underworld leader while the court case was resolved.
1943 - The Chicago Outfit from 1943 on appears to have been controlled by committee, with day-to-day operations managed by a series of acting bosses. Paul Ricca (Nov. 14, 1897, to Oct. 11, 1972), who changed his name from Felice DeLucia following a prison term for murder in his native Italy, emerged as one of the more important committee members. Another leading figure was Anthony Accardo, (April 28, 1906, to May 27, 1992). Ricca was believed by the FBI to have assumed the role of regional representative to the Mafia's national Commission.
1947 - Following the parole of the Outfit leadership from prison in 1947 (after just one-third of their ten-year federal sentence), authorities perceived Accardo - who had avoided conviction in the union extortion case - as the top man controlling Chicago area rackets. This was likely done in consultation with Paul Ricca and other leaders.
1954-1955 - In the mid-1950s, the Outfit leadership apparently avenged itself upon those who assisted the government in the 1943 stage employees union investigation. Willie Bioff, Frank "Diamond" Maritote and Charles "Cherry Nose" Gioe were all murdered.
1956 - Samuel Giancana (June 15, 1908, to June 19, 1975). Accardo and Ricca faded into the background for a decade, as Giancana appeared to take the helm of the Chicago Outfit. The rise of Giancana coincided with Paul Ricca's conviction for tax evasion and his battle with U.S. officials over deportation. Giancana's term as acting boss was interrupted by a 1965 conviction for contempt of court and a prison stay of about one year. When released in 1966, Giancana left the United States, apparently in an effort to avoid further prosecution.
1965 - Sam "Teets" Battaglia (1908 to Sept. 7, 1973). During and immediately following Giancana's time in prison, Battaglia served as acting boss. Battaglia ran into his own trouble with the law in 1966. He was convicted of extortion and sentenced to 15 years in prison. (He was paroled in the summer of 1973 following a diagnosis of terminal cancer. He died 11 days later.)
1966 - Outfit operations continued to be managed behind the scenes by its leadership committee. Sources in this period pointed to Phil Alderisio, Jack Cerone and Fiore "Fifi" Buccieri as possibly occupying the acting boss position.
1967 - Anthony Accardo stepped forward from the shadows to assert his leadership over the Chicago organization. Federal investigators believed that he worked closely with the aging Paul Ricca in the management of Outfit rackets and personnel. The two underworld elder statesmen were said to be grooming Jack Cerone to handle the boss role.
1975 - Sam Giancana returned to Chicago in the 1974, likely as a result of U.S. pressure on Mexico. He was ordered to appear before Senate investigators in July 1975, but he would not live that long. Giancana was shot to death at his home in Oak Park on June 19, 1975.