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Prohibitions Most Notorious Gangsters



From 1920 to 1933 the 18th Amendment to the U.S. Constitution imposed a nationwide ban on the production, importation, transportation and sale of alcoholic beverages. This led to organized crime spreading like a cancer throughout the country. Click NEXT to view some of the eras most distinguished crime bosses.

Out Gunned

More often than not, police were hobbled by inadequate tools and training which made gangland clashes involving increasingly sophisticated weaponry of the prohibition era especially deadly.

Benjamin “Bugsy” Siegal

Siegal (February 28, 1906 – June 20, 1947) was a Jewish American mobster who was known as one of the most “infamous and feared gangsters of his day.” He became one of the first front-page celebrity gangsters. He was also a driving force behind the development of the Las Vegas Strip

“Big” Paul Castellano

Castellano (June 26, 1915 – December 16, 1985) was an American mafia boss who succeeded Carlo Gambino as head of the Gambino crime family in New York, the nation’s largest Cosa Nostra family at the time.

Ralph “Bottles” Capone

“Bottles” (January 12, 1894 – November 22, 1974) was the older brother of Al and Frank Capone. Ralph got his nickname “bottles” from running a legitimate non-alcoholic beverage bottling operation in Chicago.

Al Capone (Going To Court)

Al Capone (January 17, 1899 – January 25, 1947) entering the court room, surrounded by paparazzi.

Al Capone (In Court)

Capone would eventually go down for tax evasion. Capone was the co-founder and boss of the Chicago Outfit. His seven-year reign as crime boss ended when he was 33-years-old.

Al Capone (Leaving Court)

Capone leaving court surrounded by police, who were providing a security detail to keep Capone from being attacked or murdered.

Al Capone (On His Yacht)

Al Capone pictured during his heyday enjoying some fishing from his yacht.

Cracking Capone’s Safe

FBI agents surround Al Capone’s safe in suspense as it is cracked open…

Charles “Lucky” Luciano

Luciano (November 24, 1897 – January 26, 1962) considered himself the father of modern organized crime in the United States. He was the first official boss of the modern Genovese crime family.

Girl Bandits

Referred to as “Girl Bandits,” seen here being questioned by police officers after being busted for home burglary after a slew of break-ins. Jean Buttick, 15, and Anna Varich, 16, were caught red-handed while looting the bungalow of Louis Oehler in the 6100 block of South California Avenue on March 20, 1927

Clarence Darrow

Darrow (April 18, 1857 – March 13, 1938) pictured here in court, is an attorney who was well known for representing mobsters. He was a leading member of the American Civil Liberties Union. Clients included; Thrill killers Leopold and Loeb, Ossian Sweet and John T. Scopes.

Thrill Killers

Richard Leon (June 11, 1905 – January 28, 1936) and Nathan Leopold Jr.(November 19, 1904 – August 29, 1971) were nick named the “Thrill Killers.” In May 1924, they kidnapped and murdered 14-year-old Robert Franks in Chicago. Here they are getting a mugshot at ages 18 and 19.

Edward Dalton & De Gracy

Two deadly hit-men of the Bertelli mob.

“Diamond” Joe Esposito

Esposito (April 28, 1872 – March 21, 1928) was a prohibition era Chicago politician who was involved in bootlegging, extortion, prostitution, and labor racketeering with the Genna Brothers.

John Dillinger (With Prosecutor)

John Dillinger (June 22, 1903 – July 22, 1934) was an American gangster in the Depression-era United States. He operated with a group of men known by some as the Dillinger Gang or Terror Gang. He is pictured here with prosecutor Robert Estill. This image would become famous at the Crown Point, Indiana jailhouse.

John Dillinger (First National Bank Trial)

John Dillinger is responsible for the robbery of 24 banks and 4 police stations. Here he is being taken to court for the robbery of First National Bank.

John Dillinger (In Court)

John Dillinger in the preliminary hearing of a murder case. He is handcuffed to a Pierce Deputy Sheriff to prevent him from making a run for it. Dillinger would eventually be shot dead outside the Bio-graph Theater in Chicago, after watching a gangster movie.

Dutch Schultz

Schultz (August 6, 1902 – October 24, 1935) was a New York City-area German Jewish-American mobster of the 1920’s and 1930’s who made his fortune in organized crime-related activities, including bootlegging and the numbers racket.

Otille “Tillie” Klimek’s Husbands

Klimek (1876 – 1936) was a Polish American serial killer. Here, detectives are exhuming one of her deceased husbands. Following the death of her 3rd husband and the 4th husband becoming ill, police became suspicious of Otille who would poison her husbands and collect a hefty insurance payout when they died.

Frank Carbo

Carbo (August 10, 1904 – November 9, 1976) was a New York City Mafia soldier in the Lucchese crime family. With the passage of Prohibition, he began working as a hired gunman for several bootlegger gangs. During the 1940s, Carbo became a boxing promoter.

Frank “The Prime Minister” Costello

Costello (January 26, 1891 – February 18, 1973) is seen here giving testimony to the Kefauver Committee, a United States Senate Special Committee to Investigate Crime in Interstate Commerce.

George Francis Barnes Jr. “Machine Gun Kelly”

Barnes (July 18, 1895 – July 18, 1954) got his nickname “Machine Gun Kelly” from his favorite weapon, a Thompson submachine gun. His most infamous crime was the kidnapping of oil tycoon and businessman Charles F. Urschel in July 1933 for which he, and his gang, collected a $200,000 ransom.

George “Bugs” Moran

Moran (August 21, 1893 – February 25, 1957) was Al Capone’s biggest rival during the prohibition years. Moran’s hatred of Capone was apparent even to the public. Moran was disgusted that Capone engaged in prostitution. He would not increase profits himself by engaging in prostitution rings due to his Catholic religion.

George McManus

Seen here leaving the courthouse after his after being acquitted of murder charges for the murder of Arnold Rothstein.

Henry Hill Jr.

Hill (June 11, 1943 – June 12, 2012) was a New York City mobster. Between 1955 and 1980, Hill was associated with the Lucchese crime family. In 1980, Hill became an FBI informant, and his testimony helped secure 50 convictions.

Jack “Machine Gun” McGurn

McGurn (July 2, 1902 – February 15, 1936) was first introduced to Capone after his stepfather, Angelo DeMora, was assassinated by gang extortionists, and McGurn had methodically avenged his death by killing the three hitmen responsible.

“Crazy” Joe Gallo

Gallo (April 7, 1929 – April 7, 1972) was a celebrated New York City gangster for the Profaci crime family, later known as the Colombo crime family. Gallo initiated one of the bloodiest mob conflicts since the 1931 Castellammarese War and was murdered as a result of it.

Joseph Michael “Joe Cargo” Valachi

Valachi (September 22, 1904 – April 3, 1971) was the first Mafia member to publicly acknowledge the existence of the Mafia.

Meyer Harris “Mickey” Cohen (pictured on right)

Cohen (September 4, 1913 – July 29, 1976) was an L.A. based gangster who was head of the Cohen Crime Family. He also had strong ties to the Italian American Mafia.

Mary Wazeniak “Moonshine Mary”

Wazeniak, who had turned her La Grange Park home into a saloon was convicted of selling “fatal” moonshine after George L. Rheutan consumed a shot that she served him and later died.

James Morelli

Laying in the bed is Nick Kuesis, who is pointing to 20-year-old James Morelli who was found guilty of shooting him in the neck and in the murder of his brother, John Kuesis.

Joseph “Polack Joe” Saltis

Saltis (1894 – 1947) was an early prohibition gangster that controlled bootlegging on the southwest side of Chicago. Originally a Slovakian immigrant who had become a saloon owner in Joliet, Illinois, Saltis moved to Chicago with the announcement of the Volstead Act in 1920.

Salvatore “Mooney Sam” Giancana

Giancana (June 15, 1908 – June 19, 1975) was a Sicilian American mobster. From the early 1940s through the 1950s, he controlled most of the illegal gambling, illegal liquor distribution, and numerous other political rackets in Louisiana.

William Jack “Three Fingers” White

White (1900 – 1934) had been charged two times with police homicide. Here he is pictured with his attorney. In a 1935 letter to the FBI director J. Edgar Hoover, amateur investigator Frank Farrell identified White as the organizer of the St. Valentine’s Day Massacre.

Vito “Don Vito” Genovese

Genovese (November 27, 1897 – February 14, 1969) was an Italian-American mobster who rose to power during Prohibition as an enforcer in the American Mafia and would later become leader of the Genovese crime family.

Walter Smith

A cold-blooded murderer known for shooting people in broad daylight.

William Moore

A seasoned opium, morphine, and cocaine trafficker.

Albert “Mad Hatter” Anastasia

Anastasia (September 26, 1902 – October 25, 1957) one of the most ruthless and feared Cosa Nostra mobsters in United States history. A founder of both the American Mafia and Murder, Inc., Anastasia was boss of what would become the modern Gambino crime family.

Frank “The Enforcer” Nitti

Nitti (January 27, 1886 – March 19, 1943) was one of Al Capone’s top henchmen and was in charge of all strong arm and muscle operations. Nitti would later go on to succeed Capone as boss of the Chicago Outfit.

Meyer Lanskey

Lanskey (July 4, 1902 – January 15, 1983) was known as the “Mob’s Accountant,” a major organized crime figure that worked with his close associate Charles “Lucky” Luciano. He was instrumental in the development of the National Crime Syndicate in the United States.

Phillip Mangano

Mangano (13 April, 1898 – April 19, 1951) was a Caporegime and second Consigliere in the Gambino crime family. He was also involved with the International Longshoreman’s Association and in New York City politics.