Organized crime in Chicago - AbsoluteAstronomy.com

The following is a timeline of Organized Crime
Organized crime
Organized crime or criminal organizations are transnational, national, or local groupings of highly centralized enterprises run by criminals for the purpose of engaging in illegal activity, most commonly for monetary profit. Some criminal organizations, such as terrorist organizations, are...

in Chicago
Chicago
Chicago is the largest city in the US state of Illinois. With nearly 2.7 million residents, it is the most populous city in the Midwestern United States and the third most populous in the US, after New York City and Los Angeles...

.

see also: Timeline of organized crime

Timeline of organized crime

This is a timeline of the history of organized crime.Note: Sources included are Carl Sifakis's The Mafia Encyclopedia, Herbert Asbury's The Gangs of New York and others. Online references also include Thomas P...

1910s

1910 - Chicago police arrest over 200 known Italian gangsters and known Black Hand
Black Hand (blackmail)
Black Hand was a type of extortion racket. It was a method of extortion, not a criminal organization as such, though gangsters of Camorra and the Mafia practiced it.-Origins:...

members in a raid in Little Italy. However, none are convicted as many of the notes of extortion threats cannot be traced to them.
1910 - Chicago racketeer James "Big Jim" Colosimo brings his nephew Johnny "The Fox" Torrio
Johnny Torrio
John "Papa Johnny" Torrio , also known as "The Fox", was an Italian-American mobster who helped build the criminal empire known as the Chicago Outfit in the 1920s that was later inherited by his protege, Al Capone...

, then with New York's Five Points Gang
Five Points Gang
Five Points Gang was a 19th-century and early 20th-century criminal organization, primarily of Italian-American origins, based in the Sixth Ward of Manhattan, New York City. Since the early 19th century, the area was first known for gangs of Irish immigrants...

, to Chicago to eliminate the Black Hand
Black Hand (blackmail)
Black Hand was a type of extortion racket. It was a method of extortion, not a criminal organization as such, though gangsters of Camorra and the Mafia practiced it.-Origins:...

due to their extortion demands. Within a month, ten Black Hand
Black Hand (blackmail)
Black Hand was a type of extortion racket. It was a method of extortion, not a criminal organization as such, though gangsters of Camorra and the Mafia practiced it.-Origins:...

extortionists had been killed.
March 15, 1910 - The Chicago Vice Commission, a civic organization to close the brothels and panel houses of the Levee district
The Levee
The Levee is a former red-light district in Chicago, Illinois, located near the intersection of Cermak Road and Michigan Avenue in the city's Near South Side...

, is organized.
January 1-March 26, 1911 - Thirty-eight Black Hand
Black Hand (blackmail)
Black Hand was a type of extortion racket. It was a method of extortion, not a criminal organization as such, though gangsters of Camorra and the Mafia practiced it.-Origins:...

victims are killed by Black Hand assassins, many by the unidentified assassin known only as Shotgun Man
Shotgun Man
Shotgun Man was an assassin and mass murderer in Chicago, Illinois in the 1910s, to whom murders of Black Hand extortionists were attributed. Most notably, Shotgun Man killed 15 Italian immigrants between January 1-March 26, 1911 between Oak Street and Milton Street of Chicago's Little Italy...

, between Oak Street and Milton Street in Chicago's Little Italy.
January 18, 1912 - Jim Cosmano, a major Chicago Black Hand
Black Hand (blackmail)
Black Hand was a type of extortion racket. It was a method of extortion, not a criminal organization as such, though gangsters of Camorra and the Mafia practiced it.-Origins:...

leader, is severely wounded in an ambush by Johnny Torrio
Johnny Torrio
John "Papa Johnny" Torrio , also known as "The Fox", was an Italian-American mobster who helped build the criminal empire known as the Chicago Outfit in the 1920s that was later inherited by his protege, Al Capone...

near the 22nd street police station. Cosmano had previously demanded $10,000 threatening to destroy Colosimo's Cafe.
1919 - Chicago Crime Commission
Chicago Crime Commission
The Chicago Crime Commission is an independent, non-partisan civic watchdog organization of business leaders dedicated to educating the public about the dangers of organized criminal activity, especially organized crime, street gangs and the tools of their trade: drugs, guns, public corruption,...

1920s

February 2, 1920 - Chicago labor racketeer Maurice "Mossy" Enright
Maurice Enright
Maurice "Mossy" or "Mossie" Enright was an Irish-American gangster and one of the earliest Chicago labor racketeers in the early 20th century....

is killed.
May 11, 1920 - Chicago gambling racketeer Jim Colosimo is gunned down outside his restaurant. The alleged killer was Al Capone
Al Capone
Alphonse Gabriel "Al" Capone was an American gangster who led a Prohibition-era crime syndicate. The Chicago Outfit, which subsequently became known as the "Capones", was dedicated to smuggling and bootlegging liquor, and other illegal activities such as prostitution, in Chicago from the early...

.
1923 - Al Capone
Al Capone
Alphonse Gabriel "Al" Capone was an American gangster who led a Prohibition-era crime syndicate. The Chicago Outfit, which subsequently became known as the "Capones", was dedicated to smuggling and bootlegging liquor, and other illegal activities such as prostitution, in Chicago from the early...

establishes his headquarters at the Lexington Hotel at the corner of 22nd Street and Michigan Avenue
Michigan Avenue (Chicago)
Michigan Avenue is a major north-south street in Chicago which runs at 100 east south of the Chicago River and at 132 East north of the river from 12628 south to 950 north in the Chicago street address system...

, in Chicago. He also gained control of the Chicago suburb of Cicero, Illinois
Cicero, Illinois
Cicero is an incorporated town in Cook County, Illinois, United States. The population was 83,891 at the 2010 census. Cicero is named for the town of Cicero, New York, which in turn was named for Marcus Tullius Cicero, the Roman statesman and orator....

, as a safe base of his illegal operations.
September 17, 1923 - George Meegan
George Meegan
George Meegan is a British long-distance walker best known for his unbroken walk of the entire Western Hemisphere from the southern tip of South America to the northernmost part of Alaska, in 2,425 days...

, a Chicago bootlegger allied with the Southside O'Donnell's, and Southside O'Donnell member George Bucher are killed by Frank McErlane
Frank McErlane
Frank McErlane was a Prohibition-era gangster. He led the Saltis-McErlane Gang, allied with the Johnny Torrio-Al Capone Gang, against rival bootleggers, the Southside O'Donnell Brothers. He is credited with introducing the Thompson submachine gun to Chicago's underworld...

.
April 1, 1924 - Frank Capone
Frank Capone
Frank Capone was a Chicago mobster who participated in the attempted takeover of Cicero, Illinois by his brother Al Capone's criminal organization.-Two brothers:...

, brother of Al Capone, is killed by policemen during the fighting which broke out while leading around 200 gunmen into Cicero during the 1924 Chicago elections in support of gangster-backed Republican politicians.
November 10, 1924 - North Side Gang
North Side Gang
The North Side family Gang, also known as the North Side Mob, was the dominant Irish-American criminal organization within Chicago during the Prohibition era from the early to late 1920s and principal rival of the Johnny Torrio-Al Capone organization, later known as the Chicago Outfit.- Early...

leader Dion O'Banion is killed when three unidentified men enter his flower shop, on the 700 block of North Clark Street
Clark Street (Chicago)
Clark Street is a north-south street in Chicago, Illinois that runs close to the shore of Lake Michigan from the northern city boundary with Evanston, to 2200 South in the city street numbering system...

, across from Holy Name Cathedral
Holy Name Cathedral, Chicago
Holy Name Cathedral, formally the Cathedral of the Holy Name, is the seat of the Roman Catholic Archdiocese of Chicago, one of the largest Roman Catholic dioceses in the United States. It is also the parish church of the Archbishop of Chicago...

, and shoot him several times. This begins a five-year gang war between the North Side Gang, under Hymie Weiss
Hymie Weiss
Hymie Weiss was a Polish-American mob boss who became a leader of the Prohibition-era North Side Gang and a bitter rival of Al Capone.-Early years:...

, and Al Capone's Chicago Outfit
Chicago Outfit
The Chicago Outfit, also known as the Chicago Syndicate or Chicago Mob and sometimes shortened to simply the Outfit, is a crime syndicate based in Chicago, Illinois, USA...

.
January 12, 1925 - North Side Gang members Hymie Weiss
Hymie Weiss
Hymie Weiss was a Polish-American mob boss who became a leader of the Prohibition-era North Side Gang and a bitter rival of Al Capone.-Early years:...

, George "Bugs" Moran
Bugs Moran
George Clarence Moran , better known by the alias "Bugs" Moran, was a Chicago Prohibition-era gangster born in St. Paul, Minnesota. Moran, of Irish and Polish descent, moved to the north side of Chicago when he was 19, where he became affiliated with several gangs...

, and Vincent "The Schemer" Drucci
Vincent Drucci
Vincent Drucci, also known as "The Schemer" , was an American mobster during Chicago's Prohibition era who served as a lieutenant under Dean O'Banion's North Side Gang and later as gang boss. Drucci was one of the few mobsters to ever be killed by a law enforcement officer...

attempt to kill Al Capone at a Chicago South Side restaurant, firing at Capone's car and injuring chauffeur Sylvester Barton, but leaving Capone unharmed.
January 24, 1925 - Weiss, Moran, Drucci, and Frank "Tight Lips" Gusenberg
Frank Gusenberg
Frank Gusenberg was a German-American contract killer and a victim of the Saint Valentine's Day massacre in Chicago, Illinois.-Early life:...

ambush Chicago Outfit leader Johnny Torrio
Johnny Torrio
John "Papa Johnny" Torrio , also known as "The Fox", was an Italian-American mobster who helped build the criminal empire known as the Chicago Outfit in the 1920s that was later inherited by his protege, Al Capone...

as he returns from shopping with his wife, shooting him several times, wounding him and his chauffeur Robert Barton. As Moran is about to kill the wounded Torrio the gun misfires and is forced to flee as the police arrive on the scene. Soon after this attack Torrio retires to Italy
Italy
Italy , officially the Italian Republic languages]] under the European Charter for Regional or Minority Languages. In each of these, Italy's official name is as follows:;;;;;;;;), is a unitary parliamentary republic in South-Central Europe. To the north it borders France, Switzerland, Austria and...

and was succeeded by his lieutenant, Al Capone.
February 9, 1925 - Johnny Torrio is sentenced by Judge Adam Cliffe to 9 months in the Lake County Jail, in Waukegan. The jail is chosen by Torrio's lawyers as a facility necessary for Torrio to receive proper medical treatment however it was actually chosen for Torrio's protection as the prison warden Sheriff Edwin Ahlstrom was in the pay of Torrio's organization. Torrio was later escorted by Capone out of the city after his release.
June 13, 1925 - "Bloody" Angelo Genna
Genna (crime family)
Chicago's Sicilian Mafia, also known as the Genna crime family, was a Prohibition era crime family in Chicago, United States. From 1921 to 1925, the family was headed by the Genna brothers, known as the Terrible Gennas. The Sicilians operated from Chicago's Little Italy and maintained control over...

is killed, possibly by members of the North Side Gang
North Side Gang
The North Side family Gang, also known as the North Side Mob, was the dominant Irish-American criminal organization within Chicago during the Prohibition era from the early to late 1920s and principal rival of the Johnny Torrio-Al Capone organization, later known as the Chicago Outfit.- Early...

or the Chicago Outfit.
November 13, 1925 - Samuzzo "Samoots" Amatuna
Samuzzo Amatuna
Samuel Sammuzzo "Samoots" Amatuna was a Chicago mobster and member of the Genna Brothers, who served as president of the Unione Siciliane.-Early life:...

, an ally of the Genna Family, is gunned down outside a Chicago West Side barber shop by the North Side Gang.
1926 - Al Capone and his crew try to kill Myles O'Donnell and William "Klondike" O'Donnell, leaders of the Westside O'Donnell Mob, in Cicero.
1927 - Al Capone's Chicago Outfit earns a yearly income of $108 million.
1927 - Sam Valante, recently hired by Joe Aiello
Joe Aiello
Giuseppe "Joe" Aiello was a Chicago bootlegger during the 1920s and early 1930s who had a longstanding, bloody feud with Chicago Outfit boss Al Capone.-Arrival in America:...

, is killed while arriving in Chicago.
August 24, 1927 - Green Ones members Anthony F. Russo and Vincent Spicuzza are killed in Chicago, supposedly lured there by the rival Cuckoos Gang in an attempt to murder Al Capone. Hours later Green Ones member Benjamin Giamonco is killed in a gunfight attempting to avenge their deaths.
April 21, 1928 - Illinois gangster Charles Birger
Charles Birger
Charles Birger was an American bootlegger during the Prohibition period in southern Illinois. His real name was Shachna Itzik Birger, and he emigrated to the United States as a child with his parents from the Russian Empire....

is executed for the ordered murder of West City, Illinois
West City, Illinois
West City is a village in Franklin County, Illinois, adjacent to the county seat of Benton, Illinois. The population was 661 at the 2010 census.- History :In the late 19th century, West City was a small settlement adjoining Benton on the west...

's Mayor Joe Adams.
July 25, 1928 - Aiello gang member Salvatore Canale is killed outside his home in Chicago.
September 7, 1928 - Capone's former consigliere
Consigliere
Consigliere is a position within the leadership structure of Sicilian and American Mafia crime families. The word was popularized by Mario Puzo's novel The Godfather , and its film adaptation...

and Unione Siciliane
Unione Siciliane
The Unione Siciliana was a Sicilian-American fraternal organization which eventually was rumored to have controlled much of the Italian American vote within the United States during the early twentieth century...

president Antonio "The Scourge" Lombardo
Antonio Lombardo
Antonio "The Scourge" Lombardo was an American mobster. He was advisor, or consigliere, to Al Capone and later President of the Unione Siciliana.-Biography:...

is killed. This could have been a motivating factor for the St. Valentine's Day Massacre
St. Valentine's Day massacre
The Saint Valentine's Day massacre is the name given to the 1929 murder of 7 mob associates as part of a prohibition era conflict between two powerful criminal gangs in Chicago: the South Side Italian gang led by Al Capone and the North Side Irish gang led by Bugs Moran. Former members of the...

.
1929 - Capone serves a brief sentence on a concealed weapons charge.
1929 - Tony Accardo
Tony Accardo
Antonino Joseph Accardo , also known as "Joe Batters" or "Big Tuna", rose from small-time hoodlum to the position of day-to-day boss of the Chicago Outfit in 1947, to ultimately become the final Outfit authority in 1972, until his death...

is made head enforcer for Capone's "Chicago Outfit".
January 8, 1929 - Unione Siciliane
Unione Siciliane
The Unione Siciliana was a Sicilian-American fraternal organization which eventually was rumored to have controlled much of the Italian American vote within the United States during the early twentieth century...

leader Pasquale "Patsy" Lolordo
Pasqualino Lolordo
Pasqualino "Patsy" Lolordo was an organized crime figure and head of the Chicago chapter of the Unione Siciliana a "front" organization for the Mafia, of which Lolordo was considered one of the most powerful capos during the late 1920s.Lolordo succeeded Antonio "The Scourge" Lombardo, an...

is killed in his apartment supposedly by Joe Aiello and members of Moran's North Side Gang.
February 14, 1929 - Four unidentified men, dressed as Chicago police officers, storm into a Near North Side
Near North Side, Chicago
The Near North Side is one of 77 well-defined community areas of Chicago, Illinois, United States. It is located north and east of the Chicago River, just north of the central business district . To its east is Lake Michigan and its northern boundary is the 19th-century city limit of Chicago,...

garage, at 2122 N. Clark Street
Clark Street (Chicago)
Clark Street is a north-south street in Chicago, Illinois that runs close to the shore of Lake Michigan from the northern city boundary with Evanston, to 2200 South in the city street numbering system...

, and murder members of George Bugs Moran
Bugs Moran
George Clarence Moran , better known by the alias "Bugs" Moran, was a Chicago Prohibition-era gangster born in St. Paul, Minnesota. Moran, of Irish and Polish descent, moved to the north side of Chicago when he was 19, where he became affiliated with several gangs...

's North Side Gang
North Side Gang
The North Side family Gang, also known as the North Side Mob, was the dominant Irish-American criminal organization within Chicago during the Prohibition era from the early to late 1920s and principal rival of the Johnny Torrio-Al Capone organization, later known as the Chicago Outfit.- Early...

and two gangster groupies. Known as the St. Valentines Day Massacre, the attack effectively ends the five year gang war between Capone and Moran.
May 29, 1929 - Thomas McElligot of the Westside O'Donnells is killed in a Chicago Loop
Chicago Loop
The Loop or Chicago Loop is one of 77 officially designated Chicago community areas located in the City of Chicago, Illinois. It is the historic commercial center of downtown Chicago...

saloon.

1930s

Taxi Wars of 1930s - rival gangs threw dynamite into the other rival's cabs.
May 1932 - Outfit namesake, Al Capone, began serving his 11-year sentence for tax evasion, in Atlanta, Georgia
Atlanta, Georgia
Atlanta is the capital and most populous city in the U.S. state of Georgia. According to the 2010 census, Atlanta's population is 420,003. Atlanta is the cultural and economic center of the Atlanta metropolitan area, which is home to 5,268,860 people and is the ninth largest metropolitan area in...

. He was out in six years for good behavior and because of declining mental and physical health.
February 4, 1935 - Thomas Maloy is killed by two blasts from a pair of gunmen while he drove down Lake Shore Drive
Lake Shore Drive
Lake Shore Drive is a mostly freeway-standard expressway running parallel with and alongside the shoreline of Lake Michigan through Chicago, Illinois, USA. Except for the portion north of Foster Avenue , Lake Shore Drive is designated as part of U.S...

near the Century of Progress
Century of Progress
A Century of Progress International Exposition was the name of a World's Fair held in Chicago from 1933 to 1934 to celebrate the city's centennial. The theme of the fair was technological innovation...

. FBI
Federal Bureau of Investigation
The Federal Bureau of Investigation is an agency of the United States Department of Justice that serves as both a federal criminal investigative body and an internal intelligence agency . The FBI has investigative jurisdiction over violations of more than 200 categories of federal crime...

agent William F. Roemer believed the two gunmen were Tony Accardo
Tony Accardo
Antonino Joseph Accardo , also known as "Joe Batters" or "Big Tuna", rose from small-time hoodlum to the position of day-to-day boss of the Chicago Outfit in 1947, to ultimately become the final Outfit authority in 1972, until his death...

and Gus Alex
Gus Alex
Gus Alex was a Greek-American mobster and high ranking member of the Chicago Outfit, who succeeded Jake Guzik as the Syndicate's main political "fixer".-Early life:...

.

1940s

March 19, 1943 - Facing extended incarceration for the extortion
Extortion
Extortion is a criminal offence which occurs when a person unlawfully obtains either money, property or services from a person, entity, or institution, through coercion. Refraining from doing harm is sometimes euphemistically called protection. Extortion is commonly practiced by organized crime...

of Hollywood film studios and being claustrophobic, Outfit boss Frank "The Enforcer" Nitti
Frank Nitti
Francesco Raffaele Nitto , also known as Frank "The Enforcer" Nitti, was an Italian American gangster. One of Al Capone's top henchmen, Nitti was in charge of all strong-arm and 'muscle' operations...

committed suicide.
1943 - The Hollywood extortion trial finds seven Outfit higher-ups (Paul Ricca
Paul Ricca
Paul Ricca, also known as "The Waiter" , was a Chicago mobster who served as the nominal or de facto leader of the Chicago Outfit for forty years.-Early life:...

, Louis Campagna
Louis Campagna
Louis "Little New York" Campagna was a New York mobster and a high ranking member of the Chicago Outfit for over three decades.-Early years:...

, Phillip D'Andrea, Frank Maritote, Charles Gioe
Charles Gioe
Charles "Cherry Nose" Gioe was a lieutenant in the Chicago Outfit criminal organization and a partner in the Hollywood extortion scandals of the 1930s....

, Johnny Roselli and Ralph Pierce) guilty and sentenced to 10 years each in Leavenworth Penitentiary.
1943 - Outfit boss Paul "The Waiter" Ricca
Paul Ricca
Paul Ricca, also known as "The Waiter" , was a Chicago mobster who served as the nominal or de facto leader of the Chicago Outfit for forty years.-Early life:...

meets Sam "Mad Sam" DeStefano
Sam DeStefano
Sam "Mad Sam" DeStefano was an Italian-American gangster who became one of the Chicago Outfit's most notorious loan sharks and sociopathic killers. Chicago-based Federal Bureau of Investigation agents such as William F. Roemer, Jr., considered DeStefano to be the worst torture-murderer in the...

in Leavenworth.
The Latin Kings criminal organization is formed. The alleged motivation for forming this group was an attempt to overcome the prejudices that Hispanic
Hispanic
Hispanic is a term that originally denoted a relationship to Hispania, which is to say the Iberian Peninsula: Andorra, Gibraltar, Portugal and Spain. During the Modern Era, Hispanic sometimes takes on a more limited meaning, particularly in the United States, where the term means a person of ...

s faced at the time.
1947 - Al Capone
Al Capone
Alphonse Gabriel "Al" Capone was an American gangster who led a Prohibition-era crime syndicate. The Chicago Outfit, which subsequently became known as the "Capones", was dedicated to smuggling and bootlegging liquor, and other illegal activities such as prostitution, in Chicago from the early...

dies on Palm Island, Florida
Palm Island (Florida)
Palm Island is a man-made island located in Biscayne Bay in the city of Miami Beach, Florida, United States, just south of Hibiscus Island. It is a residential neighborhood with relatively high property values, solely accessible by land via the MacArthur Causeway.-Education:Palm Island is zoned to...

.
1947 - In a stunning turn of events that could only mean someone did a political favor, the Outfit higher-ups who were each sentenced to 10 years in prison in the Hollywood extortion case get out of Leavenworth in 42 months. One condition of Paul Ricca's release from prison by the court was that he was banished from ever associating with the criminal element or face the rest of his prison sentence.

1950s

Nov.4, 1955 - Extortionist and informer Willie Bioff was blown to smithereens after getting in the driver's seat of his car, in his garage, in Arizona. He testified against his Outfit friends for a lighter sentence, in the, "Hollywood Extortion Case."
1956 - Political fixer Jake Guzik
Jake Guzik
Jake "Greasy Thumb" Guzik was the financial and legal advisor, and later political “greaser”, for the Chicago Outfit.-Early life:...

died of a heart attack.
1957 - Tony Accardo
Tony Accardo
Antonino Joseph Accardo , also known as "Joe Batters" or "Big Tuna", rose from small-time hoodlum to the position of day-to-day boss of the Chicago Outfit in 1947, to ultimately become the final Outfit authority in 1972, until his death...

retired from the day-to-day leadership of the Chicago Outfit
Chicago Outfit
The Chicago Outfit, also known as the Chicago Syndicate or Chicago Mob and sometimes shortened to simply the Outfit, is a crime syndicate based in Chicago, Illinois, USA...

and appointed Sam "Momo" Giancana
Sam Giancana
Salvatore Giancana , better known as Sam Giancana, was a Sicilian-American mobster and boss of the Chicago Outfit from 1957-1966...

to oversee these operations of the crime syndicate. However, Accardo remained a presence in the organization serving in an advisory capacity as consigliere
Consigliere
Consigliere is a position within the leadership structure of Sicilian and American Mafia crime families. The word was popularized by Mario Puzo's novel The Godfather , and its film adaptation...

on all major Outfit business and assassinations.
1958 - The Vice Lords
Vice Lords
The Almighty Vice Lord Nation is the second largest and one of the oldest street gangs in Chicago. Their total membership is estimated to be as many as 30,000...

criminal organization is founded in St. Charles
St. Charles, Illinois
St. Charles is a Chicago suburb in Kane and DuPage counties of Illinois, United States, and is roughly west of Chicago on Illinois Route 64. According to a 2004 census estimate, the city has a total population of 32,134. The official city slogan is Pride of the Fox, after the Fox River that runs...

Correctional Facility by a group of young thugs from 16th Street, on Chicago
Chicago
Chicago is the largest city in the US state of Illinois. With nearly 2.7 million residents, it is the most populous city in the Midwestern United States and the third most populous in the US, after New York City and Los Angeles...

's west side.

1960s

Sam Giancana
Sam Giancana
Salvatore Giancana , better known as Sam Giancana, was a Sicilian-American mobster and boss of the Chicago Outfit from 1957-1966...

allegedly "fixed" the 1960 presidential election in favor of John Kennedy, for Cook County
Cook County, Illinois
Cook County is a county in the U.S. state of Illinois, with its county seat in Chicago. It is the second most populous county in the United States after Los Angeles County. The county has 5,194,675 residents, which is 40.5 percent of all Illinois residents. Cook County's population is larger than...

.
The CIA conspired with a Chicago gangster described as "the chieftain of La Cosa Nostra and the successor to Al Capone" in a bungled 1960 attempt to assassinate Cuba
Cuba
The Republic of Cuba is an island nation in the Caribbean. The nation of Cuba consists of the main island of Cuba, the Isla de la Juventud, and several archipelagos. Havana is the largest city in Cuba and the country's capital. Santiago de Cuba is the second largest city...

n revolutionary
Revolutionary
A revolutionary is a person who either actively participates in, or advocates revolution. Also, when used as an adjective, the term revolutionary refers to something that has a major, sudden impact on society or on some aspect of human endeavor.-Definition:...

and dictator
Dictator
A dictator is a ruler who assumes sole and absolute power but without hereditary ascension such as an absolute monarch. When other states call the head of state of a particular state a dictator, that state is called a dictatorship...

, Fidel Castro
Fidel Castro
Fidel Alejandro Castro Ruz is a Cuban revolutionary and politician, having held the position of Prime Minister of Cuba from 1959 to 1976, and then President from 1976 to 2008. He also served as the First Secretary of the Communist Party of Cuba from the party's foundation in 1961 until 2011...

, the leader of that country's communist revolution, according to classified documents published by the agency. See also: Family Jewels (Central Intelligence Agency)
Family Jewels (Central Intelligence Agency)
The Family Jewels is the informal name used to refer to a set of reports that detail activities conducted by the United States Central Intelligence Agency. Considered illegal or inappropriate, these actions were conducted over the span of decades, from the 1950s to the mid-1970s...

, Operation Mongoose
Summerdale scandals, see: Chicago Police Department
Chicago Police Department
The Chicago Police Department, also known as the CPD, is the principal law enforcement agency of Chicago, Illinois, in the United States, under the jurisdiction of the Mayor of Chicago. It is the largest police department in the Midwest and the second largest local law enforcement agency in the...
1965 - Giancana thrown in federal prison for one year for a federal Contempt of Court
Contempt of court
Contempt of court is a court order which, in the context of a court trial or hearing, declares a person or organization to have disobeyed or been disrespectful of the court's authority...

citation, when he refused to testify to his or the Chicago Outfit's alleged criminal activity.
1966 - Giancana deposed as Outfit head, due to a lifestyle that brought heat and light on Chicago's underworld. He moved to Mexico
Mexico
The United Mexican States , commonly known as Mexico , is a federal constitutional republic in North America. It is bordered on the north by the United States; on the south and west by the Pacific Ocean; on the southeast by Guatemala, Belize, and the Caribbean Sea; and on the east by the Gulf of...

and oversaw the Outfit's international gambling operations.
Nov. 23, 1965 - The ultimate Outfit "fixer", Murray "The Camel" Humphreys
Murray Humphreys
Llewelyn Morris Humphreys , was a Chicago mobster of Welsh descent who was the chief political and labor racketeer in the Chicago Outfit during Prohibition...

suffers a fatal heart attack.
The Black Gangster Disciples criminal organization is formed on the south side of Chicago, in the 1960s, by uniting two separate gangs. The two gangs conjoined were The Supreme Gangsters, led by Larry Hoover
Larry Hoover
Larry Hoover was the leader of the Chicago street gang called Gangster Disciples.-Early life:...

, and The Devil's Disciples, led by David Barksdale
David Barksdale
David Barksdale , also known as King David, was the original leader of the Chicago-based street gang the Black Disciples....

.

1970s

Oct. 11, 1972 - Secret boss and ultimate Outfit consiglier, Paul Ricca
Paul Ricca
Paul Ricca, also known as "The Waiter" , was a Chicago mobster who served as the nominal or de facto leader of the Chicago Outfit for forty years.-Early life:...

, died of a heart attack.
April 14, 1973 - Outfit loanshark Sam DeStefano
Sam DeStefano
Sam "Mad Sam" DeStefano was an Italian-American gangster who became one of the Chicago Outfit's most notorious loan sharks and sociopathic killers. Chicago-based Federal Bureau of Investigation agents such as William F. Roemer, Jr., considered DeStefano to be the worst torture-murderer in the...

is shotgunned to death in his garage, allegedly by his brother Mario
Mario Anthony DeStefano
Mario Anthony DeStefano was a "made" member of the Chicago Outfit and a leading loan shark.Born Mario Antonio DeStefano, he later anglicized his middle name. DeStefano grew up in Little Italy, Chicago, with his brothers, including future "mob associate" Sam "Mad Sam" DeStefano...

and one-time Sam DeStefano protégé Tony Spilotro.
December 20, 1973 - Richard Cain
Richard Cain
Richard Cain was a notoriously corrupt Chicago police officer, made man in the Chicago Outfit and a close associate of Mafia boss Sam Giancana. Several conspiracy theorists have claimed that Cain was directly involved in the 1963 assassination of U.S. President John F...

, cop turned mobster, turned informant for William F. Roemer, Jr.
William F. Roemer, Jr.
William F. Roemer, Jr. was an FBI agent for 30 years. He is known for his battle against organized crime and being the most highly decorated agent in FBI history. After retirement he became a private attorney for businesses being muscled by the mob...

, is shot at Rose's Sandwich Shop on 1117 W. Grand Avenue
Grand Avenue (Chicago)
Grand Avenue is a major east-west arterial surface street in the city of Chicago and nearby DuPage County, although it deviates somewhat from Chicago's grid system, as it is diagonal west of Western Avenue. The street runs from the Kingery Highway Grand Avenue is a major east-west arterial surface...

. Suspects are Marshall Caifano and Joseph Lombardo
Joseph Lombardo
Joseph Patrick “Joey the Clown” Lombardo Sr. , also known as "Joe Padula," "Lumbo," and "Lumpy", is an imprisoned American mafioso and a high-ranking member of the Chicago Outfit crime organization...

.
June 17, 1975 - Former boss Sam Giancana
Sam Giancana
Salvatore Giancana , better known as Sam Giancana, was a Sicilian-American mobster and boss of the Chicago Outfit from 1957-1966...

was shot in the back of the head while cooking a snack of sausages and escarole in his Oak Park
Oak Park, Illinois
Oak Park, Illinois is a suburb bordering the west side of the city of Chicago in Cook County, Illinois, United States. It is the twenty-fifth largest municipality in Illinois. Oak Park has easy access to downtown Chicago due to public transportation such as the Chicago 'L' Blue and Green lines,...

home on his birthday. It has been debated whether it was the Outfit or CIA that murdered Giancana.
Aug. 9, 1976 - The decomposing body of Johnny Roselli, "Handsome Johnny", was found floating in a 55-gallon drum, in a bay near Miami. His legs were sawed off and shoved in the barrel with the body.
March 29, 1977 - Feared hitman Charles Nicoletti
Charles Nicoletti
Charles "Chuckie" Nicoletti, also known as "The Typewriter" "Chuckie Typewriter" , was a top Chicago Outfit hitman under Outfit boss Sam "Mooney" Giancana before and after Giancana's rise and fall.-Early years:...

was killed by three .38-caliber slugs to the head while waiting in his Oldsmobile at a Chicago-area restaurant.
1977 - Helen Brach
Helen Brach
Helen Vorhees Brach , was an American multi-millionairess widow whose wealth had come from marrying into the E. J. Brach & Sons Candy Company fortune; she endowed the Helen V. Brach Foundation to promote animal welfare in 1974....

, heiress to the Brach's
Brach's
Brach's Confections is a candy and sweets company which produces and invented many modern icons of the sugary world; it is headquartered in Dallas, Texas. In November 2007, Brach's Confections was sold to Farley's & Sathers Candy Company and the corporate office moved to Round Lake,...

candy fortune, disappeared. Suspects are Victor Spilotro
Victor Spilotro
Victor P. Spilotro was the older brother of Chicago Outfit mobster Tony Spilotro and Outfit wannabe brother, Michael. It was not until the 1980s that Victor started to get public attention.-Biography:...

and Curtis Hansen. Her body has never been found.
1978 - Jimmy "the Bomber" Catuara is found dead near his car at Hubbard Street
Hubbard Street
Hubbard Street is a road in Chicago, Illinois named for early settler Gurdon Saltonstall Hubbard. Where Hubbard Street passes over the Kennedy Expressway, the Expressway enters a tunnel made up of surface streets known colloquially as "Hubbard's Cave." Hubbard Street has three distinct sections....

and Ogden Avenue
Ogden Avenue (Chicago)
Ogden Avenue is an arterial street extending from the Near West Side of Chicago to Aurora, Illinois.The street follows the route of the Southwestern Plank Road, which opened in 1848 across swampy terrain between Chicago and Riverside, Illinois, and was extended to Naperville by 1851.The 1909 Plan...

. Bill Dauber
William Dauber
William "Billy" E. Dauber was a Chicago mobster, hitman and associate in the Chicago Outfit's South Side chop shop ring....

is suspect, who, at the bidding of his boss, Albert Tocco
Albert Tocco
Albert Tocco , also known as "Caesar" , was a high ranking member of the Chicago Outfit during the 1970s and '80s. He allegedly controlled the rackets on the South Side of Chicago, the south suburbs, and parts of Northern Indiana...

, was trying to take over Catuara's rackets
Racket (crime)
A racket is an illegal business, usually run as part of organized crime. Engaging in a racket is called racketeering.Several forms of racket exist. The best-known is the protection racket, in which criminals demand money from businesses in exchange for the service of "protection" against crimes...

.

1980s

1980s - Operation Greylord
Operation Greylord
Operation Greylord was an investigation conducted jointly by the Federal Bureau of Investigation and the IRS Criminal Investigation Division into corruption in the judiciary of Cook County, Illinois...
1980s - "Marquette Ten:" 10 police officers in the Marquette District convicted of taking bribes from drug dealers. Among those is Chicago police officer Thomas Ambrose, the father of former U.S. Marshall John Ambrose, who was convicted 20-years later of leaking information to the Chicago Outfit about federal informant, Nick Calabrese, who testified against top Chicago mobsters in the, "Family Secrets" trial.
January, 1986 - Joe Ferriola
Joseph Ferriola
Joseph Ferriola , also known as, "Joe Nagall," "Mr. Clean" and "Oscar," was an American mobster who helped run the Chicago Outfit, from 1985 to 1988, after Joseph Aiuppa and John Cerone went to prison for skimming Las Vegas casino profits.- Early life :Joseph Anthony Ferriola was a product of...

was appointed boss of The Outfit. With the approval of his top captains and consiglieri, Tony Accardo, he decided it's time to kill Anthony Spilotro
Anthony Spilotro
Anthony "The Ant" Spilotro was an Italian-American mobster and enforcer for the Chicago Outfit in Las Vegas during the 1970s and 1980s. His job was to protect and oversee the Outfit's illegal casino profits...

for causing a multitude of problems in Las Vegas
Las Vegas metropolitan area
The Las Vegas Valley is the heart of the Las Vegas-Paradise, NV MSA also known as the Las Vegas–Paradise–Henderson MSA which includes all of Clark County, Nevada, and is a metropolitan area in the southern part of the U.S. state of Nevada. The Valley is defined by the Las Vegas Valley landform, a ...

and in Chicago
Chicago
Chicago is the largest city in the US state of Illinois. With nearly 2.7 million residents, it is the most populous city in the Midwestern United States and the third most populous in the US, after New York City and Los Angeles...

.
June 14, 1986 - The bodies of Outfit enforcer, Tony Spilotro, and his brother Michael
Michael Spilotro
Michael Peter "Micky" Spilotro was the brother of Anthony "Tony the Ant" Spilotro and was an associate of the Chicago La Cosa Nostra organized crime organization referred to as "The Outfit".-Family background:...

, a small-time hood, were found in a shallow grave, in a cornfield, in Enos, Indiana. Due to authorities finding sand in their lungs, they were probably buried alive.
1989 - James Basile, a bookmaker, agreed to become a government informant, later identifying a "Mafia graveyard" in the suburban neighborhood of Hillside
Hillside, Illinois
Hillside is a village in Cook County, Illinois, United States. The population was 8,155 at the 2000 census.One notable landmark in Hillside is the Mount Carmel Cemetery. On the grounds of the cemetery are the graves of a number of organized crime figures, such as Al Capone and Dion O'Bannion...

.

1990s

1990s - Operation Silver Shovel
Operation Silver Shovel
Operation Silver Shovel was a major United States Federal Bureau of Investigation probe into political corruption in Chicago during the 1990s...
March 21, 1990 - Outfit gambling boss of west suburban Elmhurst
Elmhurst, Illinois
Elmhurst is a suburb of Chicago in DuPage and Cook Counties, Illinois. The population is 46,013 as of the 2008 US Census population estimate.-History:...

, Donald Angelini
Donald Angelini
Donald "The Wizard of Odds" Angelini was a mobster with the Chicago Outfit criminal organization who specialized in gambling operations....

, who had operated a highly successful sports betting
Sports betting
Sports betting is the activity of predicting sports results and placing a wager on the outcome.-United States of America:Aside from simple wagers such as betting a friend that one's favorite baseball team will win its division or buying a football "square" for the Super Bowl, sports betting is...

empire along with Dominic Cortina
Dominic Cortina
Dominic Cortina was a Chicago mobster and high-ranking member of the Chicago Outfit criminal organization, who oversaw gambling. His nicknames were "Big Dom", "Large", and "the Hat."-Chicago Outfit career:...

, is arrested and sentenced to prison.
May 27, 1992 - Tony Accardo
Tony Accardo
Antonino Joseph Accardo , also known as "Joe Batters" or "Big Tuna", rose from small-time hoodlum to the position of day-to-day boss of the Chicago Outfit in 1947, to ultimately become the final Outfit authority in 1972, until his death...

, Chicago's Boss of Bosses, died of congestive heart failure after almost 50 years at the helm of The Outfit.
September 1997 - Harry Aleman
Harry Aleman
Harry "The Hook" Aleman was a Chicago mobster who was one of most feared enforcers for the Chicago Outfit during the 1970s. Aleman got the nickname "Hook" from his boxing career in high school.-Early life:...

is retried for the murder of William Logan based on testimony by former Outfit attorney Robert Cooley
Robert Cooley
Robert Cooley is a former Mafia lawyer, government informant and author of the 2004 autobiography, "When Corruption was King."-Early life:...

and evidence showing the first trial was fixed. This is the first time in U.S. history someone has been retried for the same crime after being acquitted.
December 23, 1999 - Ronald Jarrett, a mob lieutenant to John "Johnny Apes" Monteleone of the South Side Crew, is shot while going to a funeral. It is the first hit in seven years.

2000 to present day

January 25, 2000 - Ronald Jarrett dies from the gunshot wounds he sustained in late 1999.
January 15, 2001 - William Hanhardt, former chief of detectives is indicted by a federal grand jury on charges of masterminding a ring of Outfit-related thieves who stole $4.85 million in jewels in heists across the nation.
November 20, 2001 - Anthony "the Hatch" Chiaramonti is shot outside a Brown's Chicken & Pasta
Brown's Chicken & Pasta
Brown's Chicken & Pasta, also known simply as Brown's Chicken, is a chain of fast food restaurants specializing in fried chicken. It is based in the Chicago Metropolitan Area.- History :...

in south suburban Lyons
Lyons, Illinois
Lyons is a village in Cook County, Illinois, United States. The population was 10,255 at the 2000 census.-History:Incorporated in 1888, Lyons is steeped in earlier historical roots. In 1673 French Explorer Louis Joliet and Jesuit missionary Father Pierre Marquette left Green Bay, Wisconsin by canoe...

.
Hired Truck Program
Hired Truck Program
The Hired Truck Program was a scandal-plagued program in the city of Chicago that involved hiring private trucks to do city work. It was overhauled in 2004 after an investigation by the Chicago Sun-Times revealed that some participating companies were being paid for doing little or no work, had...

scandal
April 25, 2005 - The U.S. Department of Justice's Operation Family Secrets indicts
Indictment
An indictment , in the common-law legal system, is a formal accusation that a person has committed a crime. In jurisdictions that maintain the concept of felonies, the serious criminal offence is a felony; jurisdictions that lack the concept of felonies often use that of an indictable offence—an...

15 Outfit mobsters and associates under the RICO Act
Racketeer Influenced and Corrupt Organizations Act
The Racketeer Influenced and Corrupt Organizations Act, commonly referred to as the RICO Act or simply RICO, is a United States federal law that provides for extended criminal penalties and a civil cause of action for acts performed as part of an ongoing criminal organization...

. Joseph "the Clown" Lombardo
Joseph Lombardo
Joseph Patrick “Joey the Clown” Lombardo Sr. , also known as "Joe Padula," "Lumbo," and "Lumpy", is an imprisoned American mafioso and a high-ranking member of the Chicago Outfit crime organization...

and Frank "the German" Schweihs
Frank Schweihs
Francis John Schweihs, aka "Frank the German" was an alleged hitman who had been known to work for The Outfit, the organized crime family in Chicago. He was under indictment in the Operation Family Secrets case for the crimes of racketeering and extortion...

evade the indictment and become fugitives.
January 13, 2006 - Joe Lombardo is apprehended in Elmwood Park
Elmwood Park, Illinois
Elmwood Park is a village bordering the northwest side of the City of Chicago in Cook County, Illinois, United States. The population was 25,405 at the 2000 census. The community has long maintained a large Italian-American population, with a more recent influx of Polish-American and Hispanic...

. FBI agents find him while a "person of interest
Person of interest
"Person of interest" is a phrase used by law enforcement when announcing the name of someone involved in a criminal investigation who has not been arrested or formally accused of a crime. The phrase was adopted by the media and widely disseminated, thus most law enforcement agencies have picked up...

" is under surveillance, most likely John "No Nose" DiFronzo
John DiFronzo
John "No Nose, Bananas, Johnny Bananas" DiFronzo is a Chicago mobster and the reputed boss of the Chicago Outfit.A former enforcer and caporegime, DiFronzo was convicted along with then-current Chicago boss Samuel "Black Sam" Carlisi on federal racketeering charges in 1993, however, the conviction...

, but this is yet to be confirmed.
April 17, 2006 - Former governor of Illinois
Governor of Illinois
The Governor of Illinois is the chief executive of the State of Illinois and the various agencies and departments over which the officer has jurisdiction, as prescribed in the state constitution. It is a directly elected position, votes being cast by popular suffrage of residents of the state....

George H. Ryan is found guilty of all 22 racketeering- and bribery
Bribery
Bribery, a form of corruption, is an act implying money or gift giving that alters the behavior of the recipient. Bribery constitutes a crime and is defined by Black's Law Dictionary as the offering, giving, receiving, or soliciting of any item of value to influence the actions of an official or...

charges against him.
June 14, 2006 - Former city clerk James Laski sentenced to 24 months in prison after admitting he pocketed tens of thousands of dollars in bribes as part of the Hired Trucking Scandal.
June 15, 2006 - A 26-year-old member of the Vice Lords
Vice Lords
The Almighty Vice Lord Nation is the second largest and one of the oldest street gangs in Chicago. Their total membership is estimated to be as many as 30,000...

on Chicago's West Side, is arrested. He may have information on where the supply of fentanyl-laced heroin is coming from which has already killed at least 60 people.http://www.suntimes.com/output/news/cst-nws-heroin16.html
August 31, 2006 - Mobster Anthony Zizzo disappears. His car was found in Melrose Park
Melrose Park, Illinois
Melrose Park is a village in Cook County, Illinois, United States. It is a "near-in" suburb of Chicago. The population was 23,171 at the 2000 census. Melrose Park has long been home to a large Italian-American population, though now it is majority Mexican-American. It was the home of Kiddieland...

, and there was no sign of foul play, because his body hasn't been found.
September 6, 2006 - George Ryan
George Ryan
George Homer Ryan, Sr. was the 39th Governor of the U.S. state of Illinois from 1999 until 2003. He is a member of the Republican Party. Ryan became nationally known when in 2000 he imposed a moratorium on executions and "raised the national debate on capital punishment"...

is sentenced to six-and-a-half-years in prison.
June 18, 2007 The trial for, "Operation: Family Secrets", begins.
September 10, 2007 - The Family Secrets trial's anonymous jury finds guilty verdicts on all counts of the five defendants. The five defendants were Joseph Lombardo
Joseph Lombardo
Joseph Patrick “Joey the Clown” Lombardo Sr. , also known as "Joe Padula," "Lumbo," and "Lumpy", is an imprisoned American mafioso and a high-ranking member of the Chicago Outfit crime organization...

, James Marcello
James Marcello
James J. “Little Jimmy, Jimmy Light” Marcello , also known as Jimmy "the Man" Marcello, is an imprisoned crime boss who was a front boss for the Chicago Outfit criminal organization in the 1980s, 1990s and early 2000s...

, Frank Calabrese, Sr.
Frank Calabrese, Sr.
Frank Calabrese, Sr. , also known as "Frankie Breeze," is a made man and a caporegime who ran major loansharking and illegal gambling operations for the Chicago Outfit. He is best known as a central figure in Operation Family Secrets and the subsequent Federal trial.-Early life:Frank Calabrese, Sr...

, Paul Schiro and Anthony Doyle.
October 2008 - Patrick Fitzgerald
Patrick Fitzgerald
Patrick J. Fitzgerald is the current United States Attorney for the Northern District of Illinois and a member of the U.S. Department of Justice Office of Special Counsel...

has former CPD
Chicago Police Department
The Chicago Police Department, also known as the CPD, is the principal law enforcement agency of Chicago, Illinois, in the United States, under the jurisdiction of the Mayor of Chicago. It is the largest police department in the Midwest and the second largest local law enforcement agency in the...

commander Jon Burge
Jon Burge
Jon Graham Burge is a convicted felon and former Chicago Police Department detective and commander who gained notoriety for allegedly torturing more than 200 criminal suspects between 1972 and 1991, in order to force confessions...

arrested on charges of obstruction of justice and perjury, with a trial date of October 29, 2009.
2009 - Joseph Lombardo
Joseph Lombardo
Joseph Patrick “Joey the Clown” Lombardo Sr. , also known as "Joe Padula," "Lumbo," and "Lumpy", is an imprisoned American mafioso and a high-ranking member of the Chicago Outfit crime organization...

and James Marcello
James Marcello
James J. “Little Jimmy, Jimmy Light” Marcello , also known as Jimmy "the Man" Marcello, is an imprisoned crime boss who was a front boss for the Chicago Outfit criminal organization in the 1980s, 1990s and early 2000s...

are sentenced to life imprisonment
Life imprisonment
Life imprisonment is a sentence of imprisonment for a serious crime under which the convicted person is to remain in jail for the rest of his or her life...

.
April 2, 2009 - Federal grand jury issued 19-count indictment for Rod Blagojevich
Rod Blagojevich
Rod R. Blagojevich is an American politician who served as the 40th Governor of Illinois from 2003 to 2009. A Democrat, Blagojevich was a State Representative before being elected to the United States House of Representatives representing parts of Chicago...

and his aides. The trial will be presided over by James Zagel
James Zagel
James Block Zagel is a United States district judge for the United States District Court for the Northern District of Illinois and a novelist.- Early life and education :...

. See also: Rod Blagojevich corruption charges
Rod Blagojevich corruption charges
Rod Blagojevich, former Governor of Illinois, is an American politician under investigation by the Federal Bureau of Investigation since 2005 for corruption. Blagojevich and his Chief of Staff John Harris were charged with corruption by federal prosecutor Patrick Fitzgerald...
April 28, 2009 - Deputy U.S. Marshal John T. Ambrose is convicted for leaking secret information to the mob about a protected witness in a federal organized crime investigation. He was originally charged with theft of U.S. Justice Department property, disclosing confidential information and lying to federal agents who questioned him about the leak. He was however acquitted of two charges of lying to federal agents.

Chicago Outfit

Al Capone
Al Capone
Alphonse Gabriel "Al" Capone was an American gangster who led a Prohibition-era crime syndicate. The Chicago Outfit, which subsequently became known as the "Capones", was dedicated to smuggling and bootlegging liquor, and other illegal activities such as prostitution, in Chicago from the early...

, Chicago Mafia leader
Mickey Cohen
Mickey Cohen
Meyer Harris "Mickey" Cohen was a gangster based in Los Angeles and part of the Jewish Mafia, and also had strong ties to the American Mafia from the 1930s through 1960s.-Early life:...

(Meyer Harris Cohen), Chicago Crime Syndicate member
William Daddano, Sr.
William Daddano, Sr.
William Daddano, Sr. , also known as "William Russo" and "Willie Potatoes," was a top enforcer and loan shark for the Chicago Outfit and a participant in some high-profile robberies.-Early years:...

(William Russo), Chicago crime syndicate enforcer
Sam Giancana
Sam Giancana
Salvatore Giancana , better known as Sam Giancana, was a Sicilian-American mobster and boss of the Chicago Outfit from 1957-1966...

(Salvatore Giancana), Chicago Crime Syndicate leader
Johnny Torrio
Johnny Torrio
John "Papa Johnny" Torrio , also known as "The Fox", was an Italian-American mobster who helped build the criminal empire known as the Chicago Outfit in the 1920s that was later inherited by his protege, Al Capone...

, Chicago Mafia Don and Chicago syndicate leader
Paul Ricca
Paul Ricca
Paul Ricca, also known as "The Waiter" , was a Chicago mobster who served as the nominal or de facto leader of the Chicago Outfit for forty years.-Early life:...

(Felice DeLucia), Chicago Outfit leader
Jake Guzik
Jake Guzik
Jake "Greasy Thumb" Guzik was the financial and legal advisor, and later political “greaser”, for the Chicago Outfit.-Early life:...

, "Chicago Outfit" financier
Frank Nitti
Frank Nitti
Francesco Raffaele Nitto , also known as Frank "The Enforcer" Nitti, was an Italian American gangster. One of Al Capone's top henchmen, Nitti was in charge of all strong-arm and 'muscle' operations...

(Francesco Nitto), Chicago Outfit enforcer and apparently Ricca puppet
Tony Accardo
Tony Accardo
Antonino Joseph Accardo , also known as "Joe Batters" or "Big Tuna", rose from small-time hoodlum to the position of day-to-day boss of the Chicago Outfit in 1947, to ultimately become the final Outfit authority in 1972, until his death...

(Anthony Accardo), Long-time Chicago Outfit de-facto leader

North Side Gang

Dion O'Banion, Chicago North Side Gang leader
Vincent Drucci
Vincent Drucci
Vincent Drucci, also known as "The Schemer" , was an American mobster during Chicago's Prohibition era who served as a lieutenant under Dean O'Banion's North Side Gang and later as gang boss. Drucci was one of the few mobsters to ever be killed by a law enforcement officer...

(Victor D'Ambrosio), Chicago North Side Gang
Hymie Weiss
Hymie Weiss
Hymie Weiss was a Polish-American mob boss who became a leader of the Prohibition-era North Side Gang and a bitter rival of Al Capone.-Early years:...

(Earl Wajciechowsky), Chicago North Side Gang leader.
George Moran, Chicago North Side Gang leader.

Chicago Mafia Leaders

Joey Aiello
Angelo Genna
Genna (crime family)
Chicago's Sicilian Mafia, also known as the Genna crime family, was a Prohibition era crime family in Chicago, United States. From 1921 to 1925, the family was headed by the Genna brothers, known as the Terrible Gennas. The Sicilians operated from Chicago's Little Italy and maintained control over...
Sam Cardinelli
Sam Cardinelli
Samuele Cardinelli [Salvatore Cardinella] was a Chicago mobster, extortionist, and leader of Cardinelli Gang during the 1920s....

Prohibition Gangs

Roger Touhy
Roger Touhy
Roger Touhy was an Irish-American mob boss and prohibition-era bootlegger from Chicago, Illinois. He is best remembered for having been framed for the 1933 faked kidnapping of gangster John "Jake the Barber" Factor, a brother of cosmetics manufacturer Max Factor, Sr...

, Chicago Prohibition gangster
Charles Birger
Charles Birger
Charles Birger was an American bootlegger during the Prohibition period in southern Illinois. His real name was Shachna Itzik Birger, and he emigrated to the United States as a child with his parents from the Russian Empire....

, Illinois Prohibition gangster
James M. Ragen
James M. Ragen
James Maxwell Ragen, Sr. was an Irish mobster and co-founder of the Chicago-based street gang and political club Ragen's Colts.-Biography:...

, Founder of the south side
South Side Irish
South Side Irish is the term that refers to the large Irish-American community on the South Side of Chicago, Illinois.-South Side Irish St. Patrick's Day Parade:...

Ragen's Colts
Ragen's Colts
Ragen's Colts was a chiefly Irish street gang which dominated the Chicago underworld during the early twentieth century. By the late 1920s and early '30s, the gang became part of the Chicago Outfit under Al Capone....

street gang and Chicago gangster.
Southside O'Donnell's
Westside O'Donnell's lead Myles O'Donnell with his younger brother William "Klondike" O'Donnell
Frank McErlane
Frank McErlane
Frank McErlane was a Prohibition-era gangster. He led the Saltis-McErlane Gang, allied with the Johnny Torrio-Al Capone Gang, against rival bootleggers, the Southside O'Donnell Brothers. He is credited with introducing the Thompson submachine gun to Chicago's underworld...

-Joe Saltis organization

Racketeers

Maurice Enright
Maurice Enright
Maurice "Mossy" or "Mossie" Enright was an Irish-American gangster and one of the earliest Chicago labor racketeers in the early 20th century....

, Chicago labor racketeer
Jim Colosimo, Chicago gambling racketeer