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
His parents were immigrants from Angri, a small town near Naples.
Q 02What was Capone's famous nickname, which he loathed?
Scarface
His close friends called him Snorky, a term for a sharp dresser.
Q 03How did Capone get the scars on his face?
Slashed by a man whose sister he insulted
He later claimed the injuries were war wounds and hid the left side of his face from cameras.
Q 04Which powerful Lower Manhattan outfit did the teenage Capone join?
The Five Points
He was mentored there by Frankie Yale, who ran the Harvard Inn on Coney Island.
Q 05What was Capone's father's trade?
Barber
His mother was a seamstress.
Q 06Why was Capone expelled from school at 14?
Hitting a female teacher in the face
He then worked in a candy store and a bowling alley and played semi-pro baseball.
Q 07Which one of Capone's brothers became a Prohibition agent in Nebraska under a different name?
James, as Richard Hart
Ralph 'Bottles' Capone ran the bottling companies and was jailed for tax evasion in 1932.
Q 08Who was the mentor who brought Capone to Chicago in 1919?
Johnny Torrio
Torrio had himself been imported by crime boss Big Jim Colosimo.
Q 09What was Capone's first job in Chicago?
Bouncer in a brothel
It is thought to be where he contracted the syphilis that eventually destroyed his mind.
Q 10How old was Capone when Torrio retired and handed him control of the organisation in 1925?
26
Torrio quit after North Side gunmen shot him several times.
Q 11Whose murder in his flower shop in November 1924 set off the war with the North Side Gang?
Dean O'Banion
Torrio arranged the killing, and Weiss took over the North Siders vowing revenge.
Q 12In which Illinois town did Capone base himself after taking over its elections?
Cicero
His headquarters was the Hawthorne Inn.
Q 13What did North Side gunmen do at the Hawthorne Inn on 20 September 1926?
Sprayed the restaurant with machine guns from cars
Capone was unhurt and called for a truce that went nowhere.
Q 21How many people were killed in the St Valentine's Day Massacre?
Seven
The gunmen were disguised as police officers staging a raid.
Q 22Who was the intended target of the massacre, who was not among the dead?
Bugs Moran
He was the last survivor of the North Side gunmen.
Q 23At what address did the massacre take place?
2122 North Clark Street
The garage served as Moran's headquarters; Capone's men had rented a flat across the road to watch it.
Q 24Capone allegedly beat three treacherous lieutenants with what before having them shot?
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
The RCMP says there is no evidence he ever set foot on Canadian soil.
Q 15From which brewing family did Capone buy his Palm Island mansion in 1928?
Anheuser-Busch
He paid Clarence Busch $40,000 for the 10,000-square-foot house.
Q 16How did rival Joe Aiello try to kill Capone at his favourite restaurant?
Bribing the chef to put prussic acid in his soup
The chef told Capone, who had Aiello's bakery shot up with 200 bullets.
Q 17What bounty did Aiello eventually offer to anyone who killed Capone?
$50,000
At least ten gunmen tried to collect on the reward and ended up dead.
Q 18Which Chicago mayor, elected in 1927, allegedly took a $250,000 contribution from Capone?
William Hale Thompson
He campaigned on not enforcing Prohibition.
Q 19What was the 'Pineapple Primary' of April 1928?
An election day when Capone's bomber hit polling booths
At least fifteen people died; lawyer Octavius Granady was chased and shot.
Q 20Where was Capone when the St Valentine's Day Massacre took place in 1929?
At his Miami-area mansion
He was still widely assumed to have ordered it.
A baseball bat
Some biographers doubt the story; others think the Outfit spread it to burnish his reputation.
Q 25Which newspaper publisher met Hoover in March 1929 to demand federal action against Capone?
Walter A. Strong
Hoover directed all federal agencies to concentrate on Capone and his allies.
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
He served it in Eastern State Penitentiary and came out to find himself Public Enemy No. 1.
Q 28Which unofficial body's list first named Capone 'Public Enemy #1' in 1930?
The Chicago Crime Commission
It came a week after his release from prison in Philadelphia.
Q 29Which Supreme Court case of 1927 confirmed that illegally earned income was taxable?
United States v. Sullivan
Assistant Attorney General Mabel Walker Willebrandt is credited with the tax-evasion tactic.
Q 30What key piece of evidence sank Capone at his tax trial?
A letter from his own lawyer conceding his taxable income
The lawyer had admitted income of $100,000 for 1928 and 1929 while trying to negotiate a settlement.