50 Fun Facts About Gangsters

Al Capone ran Chicago's bootlegging empire for years, but which crime finally sent him to federal prison?

Tax evasion earned Al Capone an 11-year sentence and a $50,000 fine in October 1931. Prosecutors had learned to prove a gangster's hidden income from his luxurious lifestyle.

Killers posing as a police raid shot seven men of Bugs Moran's gang in a Chicago garage on which holiday?

Valentine's Day 1929 became a byword for gangland killing, yet nobody was ever convicted of the murders. The likely target, Bugs Moran, was running late and never reached the garage.

Federal agents shot bank robber John Dillinger dead as he walked out of which kind of Chicago building?

A movie theater called the Biograph was showing the Clark Gable crime drama Manhattan Melodrama that night. John Dillinger tried to flee when agents closed in and was fatally shot.

Which newly opened federal prison took in Al Capone in 1934 and let him play banjo in the inmate band?

Alcatraz received Al Capone in August 1934, and good behaviour won him a place in its band, the Rock Islanders. The group gave regular Sunday concerts for the other inmates.

Which Las Vegas casino did mobster Bugsy Siegel take over and open in 1946, months before he was shot dead?

The Flamingo opened on December 26, 1946, struggled without a finished hotel and shut for weeks. A sniper killed Bugsy Siegel through a window in Beverly Hills the following June.

Which weapon, developed by a US Army general, became known in Prohibition gangland as the Chicago typewriter?

The Tommy gun, formally the Thompson submachine gun, was the work of Brigadier General John T. Thompson. Its use by Prohibition criminals made it famous, and the press shortened his name.

Thirty million viewers watched Geraldo Rivera open Al Capone's secret vault live on television, revealing what?

Dirt and empty bottles were all the walled-off room under Chicago's Lexington Hotel held in 1986. Geraldo Rivera admitted defeat on air and apologised to the audience.

A posse led by a retired Texas Ranger ambushed and killed Bonnie and Clyde on a rural road in which state?

Louisiana officers joined four Texas lawmen in the trap on Highway 154 in Bienville Parish on May 23, 1934. The bullet-riddled car later became a popular travelling attraction.

New York gambler Arnold Rothstein, nicknamed The Brain, was widely accused of fixing which sporting event in 1919?

The World Series of 1919 was thrown by Chicago White Sox players allegedly paid by Arnold Rothstein's agents. The Great Gatsby nods to the scandal through its gambler Wolfsheim.

Which Prohibition agent led the Chicago squad that a newspaper nicknamed the Untouchables for refusing mob bribes?

Eliot Ness combed the records of every Prohibition agent to build a team of about ten he could trust. He later spent years in Cleveland as the city's safety director.

Close friends called Al Capone Snorky, slang for a sharp dresser, but which nickname did the gangster loathe?

Scarface came from three knife slashes dealt by the brother of a woman Al Capone had insulted while working the door of a bar.

In which place was Al Capone born to immigrant parents who came from a small town near Naples?

Brooklyn was where Al Capone was born on January 17, 1899, and where he grew up. He only moved to Chicago, the city that made him notorious, in his early twenties.

Lucky Luciano won early release in 1946 for wartime help to the US Navy, provided he left for which country?

Italy took Lucky Luciano back after his organization promised the Navy intelligence from New York's waterfront. He died there in 1962, and his body was returned to the US for burial.

Bonnie and Clyde were killed with Clyde Barrow at the wheel of a V8 car built by which company?

Ford built the V8 that the posse riddled with bullets as it slowed on the road. A casino near Las Vegas bought the car in 1988 for about $250,000.

Which constitutional change banned alcohol from 1920 and handed gangsters like Al Capone a booming bootleg trade?

The 18th Amendment took effect in January 1920 and is the only one ever repealed, in 1933. Al Capone was estimated to earn $60 million a year from illegal liquor while it lasted.

Twins Ronnie and Reggie Kray became celebrity nightclub owners while running organised crime in which 1960s city?

London society embraced the Kray twins, who were photographed by David Bailey and interviewed on television. Both were sentenced to life imprisonment in 1969.

Which Teamsters union leader with alleged mob ties vanished in 1975 and was declared legally dead seven years later?

Jimmy Hoffa led the Teamsters from 1957 to 1971 and is thought to have been murdered in a Mafia hit. An autobiography he had been working on came out a few months after he disappeared.

Which Mafia code of silence forbids members from cooperating with the authorities, on pain of death?

Omertà goes beyond refusing to answer the authorities: it also demands turning a blind eye to the illegal activities of other people.

Which Mafia rank, popularised in English by the novel The Godfather, belongs to the boss's trusted adviser?

Consigliere is also an everyday title for city council members in Switzerland. In a crime family, the holder advises the boss and sometimes serves as the right-hand man.

Which New York crime boss was dubbed the Teflon Don after three high-profile trials ended without a conviction?

John Gotti was finally convicted in 1992 after his underboss, Sammy "the Bull" Gravano, agreed to testify against him. The earlier acquittals were later found to be tainted by jury tampering.

Which bank robber, born Lester Gillis, killed three FBI agents before dying after a 1934 gun battle near Chicago?

Baby Face Nelson owed the name to being a short man with a youthful appearance, though fellow criminals called him Jimmy. He killed more FBI agents than any other criminal.

Which woman did J. Edgar Hoover call the decade's most dangerous criminal brain after FBI agents shot her in 1935?

Ma Barker died beside her son Fred after an hours-long shootout in Florida. Those who knew her insisted she had no criminal role and that the label was invented to justify the shooting.

Which charity did Al Capone sponsor in a Chicago storefront during the Depression in an effort to polish his image?

A soup kitchen at 935 South State Street served breakfast, lunch and dinner to an average of 2,200 Chicagoans a day. On Thanksgiving in 1930 it fed 5,000.

Which untreated disease eroded Al Capone's mind so badly that he spent a year of his sentence in a prison hospital?

Syphilis, most likely caught while he worked as a brothel bouncer in Chicago, was diagnosed in his brain in 1938. Al Capone ended his sentence confused and disoriented.

Which New York prison up the Hudson put mob boss Lepke Buchalter and the Rosenbergs to death in its electric chair?

Sing Sing sent 614 men and women to the electric chair nicknamed Old Sparky before New York's death penalty ended. Lepke Buchalter went to it on March 4, 1944.

Anna Sage, the so-called Woman in Red, betrayed John Dillinger to federal agents in the hope of avoiding what?

Deportation to her native Romania went ahead anyway, despite the bargain Anna Sage struck with the FBI. She was a brothel keeper whom officials classed as an undesirable alien.

John Dillinger claimed he bluffed his way out of a supposedly escape-proof Indiana jail by waving what at the guards?

A wooden gun he said he had whittled was enough to cow the guards at Crown Point. Driving the sheriff's stolen car across a state line then made him a federal fugitive.

Which pastime did Bonnie Parker take up in a Texas jail and keep pursuing while on the run with Clyde Barrow?

Writing poetry gave Bonnie Parker "The Trail's End", better known as "The Story of Bonnie and Clyde". A handwritten poem was among the belongings the gang abandoned when fleeing police in Joplin.

In popular legend, Machine Gun Kelly coined which nickname for FBI agents as he surrendered unarmed in Memphis?

G-Men is short for government men. Machine Gun Kelly was arrested alongside his wife Kathryn, and both received life sentences for kidnapping an oil tycoon.

Which folk singer wrote a 1939 ballad that painted Oklahoma bank robber Pretty Boy Floyd as generous to the poor?

Woody Guthrie drew on the tale that the robber destroyed mortgage papers during raids, a story never confirmed. Oklahoma locals called Pretty Boy Floyd the Robin Hood of the Cookson Hills.

Where did gunmen, allegedly including Pretty Boy Floyd, kill four lawmen outside a railroad station in June 1933?

Kansas City's Union Station ambush killed four officers and Frank Nash, the prisoner the gunmen meant to free. A year later Congress gave FBI agents authority to carry guns and make arrests.

Which prosecutor, later twice the Republican nominee for president, sent Lucky Luciano to prison in 1936?

Thomas Dewey won a 30-to-50-year sentence on forced prostitution charges. Mob bosses had earlier vetoed a plot to kill him, fearing it would provoke an all-out crackdown.

Which associate of Lucky Luciano ran casinos in Cuba and fled to Israel in 1970 to escape federal charges?

Meyer Lansky was sent back to the US two years after arriving and was acquitted in 1973. He had been born Maier Suchowljansky in Grodno, then part of the Russian Empire.

Which bootlegger, born Arthur Flegenheimer, was shot in a Newark restaurant and left a legend of buried treasure?

Dutch Schultz spent his last hours in a stream-of-consciousness babble that a police stenographer took down in full. Treasure hunters have long searched the Catskills for his missing fortune.

Which enforcement arm of the National Crime Syndicate was run from a candy store until member Abe Reles exposed it?

Murder, Inc. was blamed for between 400 and 1,000 contract killings, and its most prolific killer alone was credited with over 100. It fell apart after former member Abe Reles turned informant.

The Purple Gang ran liquor across a river from Canada during Prohibition and came to dominate crime in which city?

Detroit sits directly across the water from Windsor, Ontario, which became a major smuggling point. One version of the gang's name credits a member who boxed in purple shorts.

Which Harlem nightclub, owned by bootlegger Owney Madden, hired Duke Ellington's orchestra as its house band in 1927?

The Cotton Club gave Owney Madden an outlet for selling his own beer during Prohibition. Its star performers were Black, yet the audience was whites-only with rare exceptions.

Which Chicago gang boss, nicknamed The Fox, handed control to his protégé Al Capone after surviving a shooting?

Johnny Torrio was shot several times outside his home in January 1925 and nearly died. He later proposed the National Crime Syndicate that tied America's big gangs together.

Chicago gang leader Dean O'Banion was shot dead in 1924 inside which business he used as a legitimate front?

A flower shop called Schofield's was his front, and he was a skilled arranger whose store became the florist of choice for mob funerals. He was clipping chrysanthemums when the gunmen arrived.

Which Manhattan street gang founded by Paul Kelly counted Al Capone and Lucky Luciano among its young members?

The Five Pointers took their name from a slum crossroads in lower Manhattan where several streets met. Their founder was born Paolo Vaccarelli and adopted an Irish-sounding name.

Which mob boss, dubbed the Prime Minister of the Underworld, had only his hands televised at a 1951 Senate hearing?

Frank Costello refused to let his face be filmed, a demand that backfired. The cameras stayed on his fidgeting hands and broadcast his nervous gestures live to a huge audience.

Which boss won the Castellammarese War in 1931, only to be killed months later on Lucky Luciano's orders?

Salvatore Maranzano declared himself boss of all bosses and ordered every Mafia family to pay him tribute, which provoked the rebellion that cost him his life.

Which Mafia boss wandered Greenwich Village in a bathrobe for decades, feigning insanity to dodge prosecution?

Vincent Gigante kept up the act for almost thirty years and earned the press nickname the Oddfather. He finally admitted in 2003 that it had all been a performance.

Which Chicago crime boss was recruited into a CIA plot to kill Fidel Castro and was shot dead at home in 1975?

Sam Giancana was killed shortly before he was due to appear before the Church Committee, which was investigating collusion between the CIA and the Mafia.

Which mobster's televised 1963 Senate testimony made him the first member to admit publicly that the Mafia existed?

Joe Valachi is credited with making the term Cosa Nostra widely known. He talked after killing a fellow prisoner he mistook for a hitman sent by his own boss.

Which early 1900s extortion racket sent Italian immigrants threatening letters decorated with skulls and nooses?

The Black Hand even squeezed the tenor Enrico Caruso, who paid a $2,000 demand. His reward, once the payment became public, was a stack of new threatening letters a foot high.

Which southern Italian region is home to the 'Ndrangheta, a crime syndicate that spread overseas with its emigrants?

Calabria forms the toe of the Italian boot. From the mid-20th century its clans followed emigrants across Europe and on to Australia and the Americas.

Which Caribbean capital hosted a week-long summit of American mob bosses at its Hotel Nacional in December 1946?

Havana gave the delegates a ready cover story: officially they were attending a gala party with Frank Sinatra as the entertainment.

Mob boss Albert Anastasia, nicknamed the Lord High Executioner, was shot dead in 1957 while relaxing where?

A barber's chair at Manhattan's Park Sheraton Hotel was where two masked gunmen caught Albert Anastasia. Nobody was ever charged with the killing.

Which ruling body did Lucky Luciano set up in 1931 so that Mafia bosses could share power and avoid turf wars?

The Commission replaced the single boss of all bosses with a committee made up of the heads of New York's leading families and the bosses of other cities.