How a national ban on alcohol turned a Brooklyn boy into the most feared businessman in America — and how a tax form finally caught him.
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Ten words wait for you in the story ahead. Work through the four short tasks below. Do the thinking first, then reveal — the answer only confirms what you worked out.
Read each situation aloud. What does the bold word mean here? Reveal only when you've decided.
Recall the word from its meaning (the first letter is there to help). Then reveal to check the word and see it used.
Decide how each word relates to the one in quotes, then reveal.
These words almost always travel with a partner word. Guess the missing partner, then reveal.
Read each part. After it, there's a quick comprehension check (try the questions from memory first), then one thing to discuss.
Alphonse Capone was born in Brooklyn, New York, in 1899, the son of Italian immigrants. He left school at fourteen after hitting a teacher, and drifted into the street gangs of the city. A knife fight in a bar left him with the scars that gave him the nickname he hated — "Scarface." As a young man he moved to Chicago to work for an older gangster, Johnny Torrio, and he learned fast.
His timing could not have been better. In 1920, a new law made it illegal to make or sell alcohol across the whole United States. Prohibition was meant to reduce crime and drunkenness. Instead, it created the greatest business opportunity organised crime had ever seen. People still wanted to drink; someone simply had to break the law to supply them. Capone and Torrio set about bootlegging on an industrial scale — brewing beer in secret, smuggling whisky, and supplying thousands of illegal bars, the speakeasies, across Chicago.
When Torrio was badly wounded and retired, Capone, still only in his twenties, took over. By the late 1920s his organisation was earning tens of millions of dollars a year. He controlled breweries, delivery routes and speakeasies, and he protected all of it through extortion and the systematic bribery of police, city officials and judges.
1. How did the law called Prohibition accidentally help criminals like Capone?
2. How did Capone rise to the top of organised crime in Chicago?
1. Banning alcohol did not stop people wanting it; it handed a huge, profitable market to whoever was willing to supply it illegally — the bootleggers.
2. He came to Chicago to work for Johnny Torrio; when Torrio was wounded and retired, Capone took over the whole operation while still in his twenties.
Capone was two people at once. To much of Chicago, he was almost a hero: he gave interviews, sat at boxing matches, and, when the Great Depression hit, opened a soup kitchen that fed thousands of the unemployed. He liked being seen as a generous businessman who simply gave the public the drink the government had wrongly taken away.
Behind that public face, his power rested on fear. Rival gangs competed for the same illegal markets, and the disputes between them were settled with guns. The most infamous episode came on 14 February 1929 — the St Valentine's Day Massacre. Members of a rival gang were lined up against a garage wall and shot dead by men, some dressed as police officers, who were widely believed to be working for Capone. Seven people were killed. Capone himself was far away in Florida, and nothing was ever proved against him, but the killings horrified the public and, for the first time, turned opinion firmly against him.
The massacre made Capone the most notorious criminal in the country. It also made him a problem the authorities could no longer ignore. The trouble was that fear worked: witnesses refused to testify, and bribery reached deep into the police and the courts. Everyone knew what Capone was; almost no one could prove a single thing in a courtroom.
1. In what ways did Capone try to appear as a "good" public figure?
2. What was the St Valentine's Day Massacre, and how did it change the way the public saw Capone?
1. He gave interviews, appeared at public events, and opened a soup kitchen for the unemployed during the Depression, presenting himself as a generous businessman.
2. On 14 February 1929, seven members of a rival gang were shot dead, by men some of whom were dressed as police; it was blamed on Capone's organisation and turned public opinion firmly against him, though nothing was proved.
For years the police had tried, and failed, to convict Capone of the violence everyone knew he directed. Witnesses were too frightened to speak; evidence disappeared. So the federal government tried a very different approach. If they could not prove the killings, perhaps they could prove something quieter and harder to hide: that Capone, a man living in obvious luxury, had never paid tax on his enormous income.
A team of investigators spent years piecing together records — bank deposits, spending, the paper trail of a business empire. In 1931, Al Capone was put on trial not for murder or bootlegging, but for tax evasion. The case was strong, the accounts were damning, and this time no amount of money could make the charges disappear. He was convicted and sentenced to eleven years in prison.
He served part of that sentence in Alcatraz, the island prison in San Francisco Bay built to hold the men no ordinary jail could control. But by then Capone was a fading figure. Years of untreated illness had damaged his brain, and by the time he was released in 1939 he was seriously unwell. He died in 1947, aged forty-eight, at his home in Florida — not in a gunfight, but quietly, his mind long gone. The most powerful gangster America had ever produced was finally undone not by a rival's bullet, but by an unpaid tax bill.
1. Why couldn't the authorities convict Capone of violent crimes, and what did they charge him with instead?
2. What happened to Capone after his conviction, and how did his life end?
1. Witnesses were too frightened to testify and evidence vanished, so the government proved instead that he had never paid tax on his huge income — the charge of tax evasion.
2. He was sentenced to eleven years, served part of it in Alcatraz, and left prison seriously ill; his health, damaged by long-untreated disease, declined until he died in Florida in 1947.
Capone's story is full of verbs followed by other verbs: he started bootlegging, he tried to bribe officials, investigators managed to convict him. In English, when one verb follows another, the first verb decides the form of the second — gerund (-ing) or infinitive (to do). There's no single rule; you learn the patterns.
Read the sentence and write the correct form of the verb in brackets.
1. For years the police failed (convict) Capone of any violent crime.
2. Running his empire involved (bribe) police, judges and city officials.
3. Frightened witnesses refused (testify) against him in court.
1. to convict (fail + infinitive)
2. bribing (involve + gerund)
3. to testify (refuse + infinitive)
Each sentence has a preposition. Write the correct form of the verb in brackets.
1. Capone was accused of (run) illegal bars and breweries.
2. For years there seemed to be no way of (prove) anything against him.
3. He was remarkably good at (avoid) arrest.
1. running (accused of + -ing)
2. proving (way of + -ing)
3. avoiding (good at + -ing)
Fill each gap with the correct form (gerund or infinitive) of the verb in brackets. Read it aloud once you're done.
Capone managed (build) a huge criminal empire, and for years he avoided (get) caught. He tried (appear) respectable, but the government kept (investigate) his finances. In the end, they succeeded in (convict) him of tax evasion.
managed to build (manage + inf.) · avoided getting (avoid + -ing) · tried to appear (try + inf.) · kept investigating (keep + -ing) · succeeded in convicting (preposition in + -ing)
Notice the mix: some verbs take the infinitive, some take the gerund, and every verb after a preposition takes the gerund.
Hold on to these patterns — you'll need them in the Speak tab, where you retell the whole rise and fall.
You've read the story and you have the words — so now the real thing is within reach. There's a full podcast episode that tells this story in much greater depth, in natural, real-speed English. It's optional: the lesson stands on its own without it.
From the Noiser podcast network. Hosted by historians, roughly 50 minutes. Open Spotify and search "Short History Of Al Capone" to find the episode.
Open the show on Spotify →This is the heart of the lesson — do all of it out loud. The timer is there to keep you going: fill the time with detail rather than escaping it.
Tell the story of Al Capone in your own words, as if to someone who has never heard of him. Move through the arc: the Brooklyn boy who moved to Chicago → how Prohibition handed him a fortune → the empire of bootlegging, speakeasies, extortion and bribery → the St Valentine's Day Massacre and his notoriety → the tax-evasion trial, Alcatraz, and his quiet end.
Chain your verbs carefully: use at least three of manage to, try to, refuse to, avoid + -ing, accused of + -ing, keep + -ing, and work in at least five key words (Prohibition, speakeasy, bootlegging, extortion, bribery, feud, notorious, convict, justice, tax evasion).
Prohibition tried to make society better by banning alcohol, and instead handed organised crime a fortune. Should a government ever ban something that large numbers of people want? Build an argument, using other examples you know — drugs, gambling, certain products — and decide where, if anywhere, a ban actually works.
Capone did terrible things, yet was jailed for tax evasion — a paperwork crime. Discuss a case where someone was caught, or escaped, not for the thing that really mattered but on a technical point.
Stuck for an idea? Pick one of these and run with it: