Al Capone Trivia
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58 free Al Capone trivia questions with answers — history quiz, new questions added Oct 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 58 questions with answers and explanations. Play the quiz
Q 01In which New York borough was Al Capone born in 1899?
Brooklyn
Brooklyn: though his name is tied to Chicago, Capone was a New Yorker, the fourth of nine children of Italian immigrants, and only moved west at about 20.
Q 02What was Capone's famous nickname, which he loathed?
Scarface
Scarface came from the scars on his left cheek; Capone hated the name and tried to keep that side of his face away from the cameras, while his friends called him Snorky.
Q 03How was the young Capone's left cheek marked for life?
Slashed by a man whose sister he insulted
Slashed by a man whose sister he insulted: Frank Galluccio cut him three times at the Harvard Inn, the Coney Island bar where he worked; Capone later passed the marks off as war wounds, though he never served.
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
Barber: Gabriele Capone cut hair for a living while his wife Teresa worked as a seamstress, and nothing in their law-abiding household hinted that a son would become America's most notorious gangster.
Q 06What ended Capone's schooling at the age of 14?
Hitting a female teacher in the face
Hitting a female teacher in the face got Capone expelled, or in another telling he quit after the principal beat him for it; either way he never went back, and drifted into odd jobs and street gangs.
Q 07What job did Capone's eldest brother take in Nebraska under the name Richard 'Two-Gun' Hart?
Prohibition agent
Prohibition agent: James Vincenzo Capone left home in his teens, took the surname of cowboy film star William S. Hart, and was raiding stills around Homer, Nebraska, while his brother built a bootleg empire.
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 in Big Jim Colosimo's vice empire, which Torrio took over when Colosimo was shot dead in 1920.
Q 09What was Capone's first job in Chicago?
Bouncer in a brothel
Bouncer in a brothel: Capone started at the bottom of Big Jim Colosimo's vice business, but was soon managing the Four Deuces, a speakeasy, gambling den and brothel under one roof.
Q 10After handing Capone the Chicago organisation in 1925, his wounded boss left for which country?
Italy
Italy: shot several times by North Side gunmen that January, the boss quit, left the 26-year-old Capone in charge and moved back to the country of his birth, staying about three years.
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 was among his flowers when a visitor gripped his hand in greeting and two gunmen opened fire; Hymie Weiss took over the North Side Gang and swore revenge.
Q 12In which Illinois town did Capone base himself after taking over its elections?
Cicero
Cicero, just west of Chicago, became the gang's base because a reforming mayor had taken office in the city in 1923; Capone's gunmen then terrorised the suburb's 1924 election to keep its town hall friendly.
Q 13What did North Side gunmen do at Capone's Hawthorne Inn headquarters in September 1926?
Machine-gunned it from passing cars
Q 21How many people were killed in the St Valentine's Day Massacre?
Seven
Seven men were lined up against a garage wall and shot by gunmen posing as police: five North Side gangsters, a mechanic who worked for them and an optician who liked their company.
Q 22Who was the intended target of the St Valentine's Day Massacre but escaped it?
Bugs Moran
Bugs Moran was running late, saw what looked like a police raid at the garage and turned away; days later he told reporters, 'Only Capone kills like that.'
Q 23At what Chicago address did the St Valentine's Day 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.
Machine-gunned it from passing cars: a North Side motorcade raked the inn's restaurant while Capone sat inside. He was unhurt and proposed a truce, but Hymie Weiss was shot dead three weeks later.
Q 14About which country did Capone joke that he didn't even know which street it was on?
Canada
Canada: asked by a Toronto reporter whether he knew Ontario bootlegger Rocco Perri, Capone said he didn't even know which street Canada was on, though Canadian suppliers were shipping whisky to his gang.
Q 15In whose name was the title to Capone's Palm Island estate put when he bought it in 1928?
His wife's
His wife's: a go-between put up the deposit and the deed went to Mae Capone, but the estate still told against him, because prosecutors used it at his tax trial as proof of income he had never declared.
Q 16How did rival Joe Aiello try to have Capone killed at his favourite restaurant in 1927?
Prussic acid in his soup
Prussic acid in his soup: Aiello offered the chef of the Bella Napoli Café a small fortune to poison Capone, but the chef told Capone instead, and gunmen wrecked Aiello's bakery in reply.
Q 17Chicago's violent 1928 'Pineapple Primary', when Capone's men terrorised voters, took its name from slang for what?
A hand grenade
A hand grenade: 'pineapple' was the slang of the day, and the name stuck because bombs marked the whole campaign, thrown at polling places and at the homes of candidates.
Q 18Which Chicago mayor, nicknamed 'Big Bill', won back City Hall in 1927 with Capone's backing?
William Hale Thompson
William Hale Thompson promised a wide-open town and hinted he would reopen the saloons his reforming rival had shut, and Capone's money, put at $200,000 or more, helped pay for the campaign.
Q 19Which of Capone's brothers was shot dead by police during a 1924 town election?
Frank Capone
Frank Capone was gunned down in the street by police sent out from Chicago after the gang's gunmen began terrorising voters at the polls; the gang's candidates won all the same.
Q 20Where was Capone when the St Valentine's Day Massacre took place in 1929?
At his Miami-area mansion
At his Miami-area mansion: Capone was wintering in Florida, a ready alibi, yet press and public blamed him at once. He was never charged, and the case stayed unsolved.
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 banquet at which Capone clubbed John Scalise, Albert Anselmi and Joseph Giunta before they were shot; some biographers doubt it ever happened.
Q 25Which US president told his Treasury secretary in 1929 that he wanted Capone in jail?
Herbert Hoover
Herbert Hoover, in office only weeks, was answering the public outcry over the St Valentine's Day Massacre; his Treasury secretary, Andrew Mellon, set the tax investigators on Capone.
Q 26Which federal lawman led the Chicago squad that the press nicknamed the 'Untouchables'?
Eliot Ness
Eliot Ness and his men earned the name by refusing bribes while they raided Capone's breweries, but it was the Treasury's tax investigators, not Ness, who sent Capone to prison.
Q 27Two years before his tax conviction, what offence put Capone in a Philadelphia jail in 1929?
Carrying a concealed weapon
Carrying a concealed weapon: police picked up Capone and his bodyguard as they left a Philadelphia cinema, and by the next day both had been sentenced to a year in prison.
Q 28Which Chicago citizens' group first named Capone 'Public Enemy No. 1' in 1930?
The Chicago Crime Commission
The Chicago Crime Commission listed the city's worst gangsters, Capone first, to keep the light of publicity on them; the FBI later took up the phrase for its own most wanted men.
Q 29In the 1927 case that opened the way to try Capone, a bootlegger claimed which amendment excused him from filing tax returns?
The Fifth
The Fifth: Manley Sullivan argued that declaring his bootleg profits would incriminate him, but the Supreme Court ruled that he still had to file, and that let prosecutors charge gangsters with tax evasion.
Q 30Which document became the most contested evidence at Capone's 1931 tax trial?
A letter from his own lawyer
A letter from his own lawyer: seeking a settlement, Lawrence Mattingly wrote that Capone had earned up to $100,000 a year, and the judge admitted it over the protest that a lawyer cannot confess for his client.