Al Capone Trivia
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60 free Al Capone trivia questions with answers — history quiz, new questions added Aug 2026.
This Al Capone trivia quiz covers the most famous gangster in American history, from a Brooklyn barber's family to a Florida mansion with the mind of a child. The easy questions are the ones any true-crime fan knows: his nickname, his city, the crime that finally jailed him, and the island prison where he served his time. From there it moves into the rise: the Five Points Gang, the knife fight that scarred him, the mentor who handed him the Outfit at 26, the Cicero takeover, and the machine-gun ambush at the Hawthorne Inn. The harder end is for people who have read the biographies: the Pineapple Primary, the poisoned soup plot, the mayor who took a $250,000 contribution, the newspaper publisher who went to Hoover, the letter from Capone's own lawyer that sank him at trial, the judge who tore up the plea bargain, the banjo in the Alcatraz band, the hospital that turned him away, and the 30 million viewers who watched Geraldo Rivera open an empty vault. The questions stick to the documented record. Every answer was checked against encyclopaedia entries on Capone, the massacre, Eliot Ness and the vault broadcast before publishing, and the supporting sentence is stored with each question. If you enjoy this one, try our Prohibition, Chicago and 1920s quizzes next.
30 of 60 questions with answers and explanations. Play the quiz
Q 01In which New York borough was Al Capone born in 1899?
Brooklyn
Al Capone was born in Brooklyn on 17 January 1899, the fourth of nine children of Italian immigrants Gabriele and Teresa Capone.
Q 02What was Capone's famous nickname, which he loathed?
Scarface
Newspapers called him Scarface for the scars on his left cheek; Capone hated the name and preferred Snorky, his friends' slang for a sharp dresser.
Q 03How did Capone get the scars on his face?
Slashed by a man whose sister he insulted
Slashed by a man whose sister he insulted: Frank Galluccio cut Capone's face at the Harvard Inn after Capone insulted Galluccio's sister; Capone later passed the scars off as war wounds.
Q 04Which powerful Lower Manhattan outfit did the teenage Capone join?
The Five Points
The Five Points gang, Paul Kelly's Lower Manhattan outfit, took Capone in as a teenager; there Frankie Yale became his mentor and employed him at the Harvard Inn on Coney Island.
Q 05What was Capone's father's trade?
Barber
Gabriele Capone's trade was Barber: he ran his own barbershop after emigrating from Italy, while Al's mother Teresa worked as a seamstress.
Q 06Why was Capone expelled from school at 14?
Hitting a female teacher in the face
Expelled at 14 for Hitting a female teacher in the face, Capone never returned to school and instead took odd jobs in a candy store and a bowling alley.
Q 07Which one of Capone's brothers became a Prohibition agent in Nebraska under a different name?
James, as Richard Hart
James, as Richard Hart: the eldest Capone brother, Vincenzo, left home as a teenager, renamed himself Richard Hart and became a Prohibition agent in Homer, Nebraska, known as 'Two Gun' Hart.
Q 08Who was the mentor who brought Capone to Chicago?
Johnny Torrio
Johnny Torrio, whom Capone had known in New York, invited him to Chicago to work for Big Jim Colosimo's vice empire, which Torrio took over after Colosimo's murder in May 1920.
Q 09What was Capone's first job in Chicago?
Bouncer in a brothel
Bouncer in a brothel was Capone's first Chicago job, at the Four Deuces, a saloon, gambling den and brothel named for its address, 2222 South Wabash Avenue.
Q 10How old was Capone when Torrio retired and handed him the organisation?
26
Capone was 26: Torrio, shot and badly wounded by North Side gunmen in January 1925, handed him the organisation that March and withdrew from Chicago.
Q 11Whose murder in his flower shop in November 1924 set off the war with the North Side Gang?
Dean O'Banion
Dean O'Banion, boss of the North Side Gang, was shot dead among his flowers at Schofield's on North State Street on 10 November 1924; Hymie Weiss took over vowing revenge.
Q 12In which Illinois town did Capone base himself after taking over its elections?
Cicero
Cicero, just west of Chicago, became Capone's base after his gunmen terrorised its April 1924 town election; he ran the Outfit from the Hawthorne Inn there.
Q 13What did North Side gunmen do at the Hawthorne Inn on 20 September 1926?
Sprayed the restaurant with machine guns from cars
Q 21How many people were killed in the St Valentine's Day Massacre?
Seven
Seven men were lined up against the garage wall and machine-gunned by killers dressed as police: members of the North Side gang, their mechanic John May and optician Reinhardt Schwimmer.
Q 22Who was the intended target of the massacre, who was not among the dead?
Bugs Moran
Bugs Moran, the North Side boss, was running late and took the scene from down the street for a police raid, so he turned away and survived; he died in Leavenworth in 1957.
Q 23At what address did the massacre take place?
2122 North Clark Street
The SMC Cartage Company garage at 2122 North Clark Street was the North Siders' liquor depot; Capone's men had rented rooms across the street to watch it.
Sprayed the restaurant with machine guns from cars: a North Side motorcade fired about a thousand rounds into the Hawthorne Inn while Capone sat inside; he was unhurt, and Hymie Weiss was shot dead three weeks later.
Q 14Asked if he knew Rocco Perri, the northern neighbour's top bootlegger, what did Capone say?
I don't even know which street Canada is on
Capone's reply was 'I don't even know which street Canada is on'; the RCMP never found evidence he set foot in Canada, despite rumours linking him to Hamilton bootlegger Rocco Perri.
Q 15From which brewing family did Capone buy his Palm Island mansion in 1928?
Anheuser-Busch
Clarence M. Busch of the Anheuser-Busch brewing family sold Capone the Palm Island house in 1928 for $40,000; Capone died there in 1947.
Q 16How did rival Joe Aiello try to kill Capone at his favourite restaurant?
Bribing the chef to put prussic acid in his soup
Joe Aiello's plan was Bribing the chef to put prussic acid in his soup at Diamond Joe Esposito's Bella Napoli Café; the cook warned Capone instead, and Aiello's bakery was shot up in reply.
Q 17What bounty did Aiello eventually offer to anyone who killed Capone?
$50,000
Aiello's bounty reached $50,000; several out-of-town gunmen who came to Chicago to collect it were found shot dead instead, and Aiello himself was machine-gunned in October 1930.
Q 18Which Chicago mayor, elected in 1927, allegedly took a $250,000 contribution from Capone?
William Hale Thompson
William Hale Thompson, 'Big Bill', won back City Hall in 1927 on a wide-open, anti-Prohibition platform, and Capone's Outfit allegedly put $250,000 into his campaign.
Q 19Which of Capone's brothers was shot dead by police during the April 1924 town election?
Frank Capone
Frank Capone, Al's older brother, was shot dead by Chicago police detectives on 1 April 1924 while the gang was intimidating voters at a suburban town election.
Q 20Where was Capone when the St Valentine's Day Massacre took place in 1929?
At his Miami-area mansion
Capone was At his Miami-area mansion on Palm Island and that morning was being questioned by the Dade County solicitor, a neat alibi, yet he was widely assumed to have ordered the killings.
Q 24Capone allegedly beat three treacherous lieutenants with what before having them shot?
A baseball bat
A baseball bat, in the oft-told story of a May 1929 banquet at which Capone clubbed John Scalise, Albert Anselmi and Joseph Giunta before they were shot; some biographers doubt it.
Q 25Which newspaper publisher met Hoover in March 1929 to demand federal action against Capone?
Walter A. Strong
Walter A. Strong, a Chicago newspaper publisher, pressed the newly inaugurated Hoover in March 1929, and Hoover ordered the Treasury and Justice departments to concentrate on Capone.
Q 26Who dubbed the incorruptible Prohibition agents 'Untouchables'?
A Chicago Daily News writer
Charles Schwarz coined it; the squad included Eliot Ness.
Q 27For what offence was Capone jailed for a year in Philadelphia in 1929?
Carrying a concealed weapon
Carrying a concealed weapon: Capone and his bodyguard were arrested in Philadelphia in May 1929 and sentenced within a day; he served most of the term in Eastern State Penitentiary, released in March 1930.
Q 28Which unofficial body's list first named Capone 'Public Enemy #1' in 1930?
The Chicago Crime Commission
The Chicago Crime Commission, a citizens' body led by Frank J. Loesch, published its list of 28 public enemies on 24 April 1930 with Capone at the top.
Q 29Which Supreme Court case of 1927 confirmed that illegally earned income was taxable?
United States v. Sullivan
United States v. Sullivan (1927) held that a bootlegger's illegal income was taxable and had to be declared; Assistant Attorney General Mabel Walker Willebrandt pioneered the tax tactic.
Q 30What key piece of evidence sank Capone at his tax trial?
A letter from his own lawyer conceding his taxable income
A letter from his own lawyer conceding his taxable income: tax attorney Lawrence Mattingly, seeking a settlement in 1930, wrote that Capone earned about $100,000 a year in 1928 and 1929.