Last news in Fakti

Capone on trial: The smile that disappeared in prison

Chicago boss expects a light sentence, but judge rejects the deal and sends him behind bars for 11 years

Sep 28, 2026 16:19 31

Capone on trial: The smile that disappeared in prison - 1

When Al Capone entered the federal courthouse in Chicago in October 1931, he did not look like a man expecting the collapse of his empire. In a yellowish suit, accompanied by his bodyguard, the gangster smiled at the jurors as if the trial were just another public performance. Just a few days later, the same man would receive one of the heaviest sentences ever imposed for a tax crime.

Alphonse Gabriel “Al” Capone was the most famous American gangster of the Prohibition era. In Chicago, he built a huge criminal organization that profited from illegal alcohol, gambling, prostitution, racketeering and bribery. His name was associated with numerous murders and a bloody war between gangs, but the authorities were unable to convict him of murder or of running the criminal network itself. In the end, he was arrested for something that seemed far more prosaic - unpaid taxes.

Capone believes he has made a deal

Federal agents prove that between 1924 and 1929, Capone received a net income of more than $ 1 million. However, he did not file tax returns and did not pay taxes. The investigation relies not only on witnesses, but also on accounting books, expenses and confessions that show the scale of his life.

On June 16, 1931, Capone pleaded guilty, convinced that he had negotiated a sentence of two and a half years. He defended his position with his usual self-confidence in front of journalists: “They asked me a question and I don't complain, but why don't they prosecute those bankers who took the savings of thousands of poor people and lost them in the bank failures?“

Judge James Wilkerson, however, refused to comply with the agreement. He declared: “The parties in a criminal case cannot agree on the sentence that will be pronounced.“ Then he added that it was time for someone to show the defendant that the federal court cannot be negotiated.

The smile and the silent signals

The trial begins in October. Capone was charged with 23 counts of tax evasion between 1925 and 1929. The prosecution turned his lavish lifestyle into evidence of wealth: $6,500 for meat, $8,000 for diamond buckles, expensive suits, silk shirts, horse racing bets, and lavish parties.

His demeanor in the courtroom was attentive but not entirely calm. At first, he smiled at the jurors. At the end, according to contemporary accounts of the trial, he sat with a frown, moved little, and passed notes to his lawyers, responding to reporters only in noncommittal tones. After the guilty verdict was pronounced, however, he smiled again—as if he thought that five convictions out of a total of 23 were not the worst possible outcome.

The judge did not leave the trial to chance. After information that Capone's men had a list of potential jurors and were trying to bribe or intimidate them, he changed the jury to one from another case. The jurors were kept under surveillance and locked up at night to prevent pressure on them.

A loaded revolver was found in the courtroom on the bodyguard Philip D’Andrea. Subsequently, Judge Wilkerson spoke of pressure on witnesses and behavior that posed a threat to the administration of justice. The official report of the tax agent Frank Wilson recorded that Capone stared at witnesses while they testified, and some of them suddenly began to “forget” important details.

The Verdict That Ended His Power

On October 17, 1931, the jury found Capone guilty on three felony counts of tax evasion and two counts of failure to file returns. According to the National Archives, they deliberated for nearly nine hours.

A week later, on October 24, Judge Wilkerson sentenced him to 11 years in prison, a $50,000 fine, and court costs. Capone must also pay about $215,000 in unpaid taxes, with interest. The main federal report on the case lists October 24 as the date of the verdict, although a later FBI report lists November 24. Archival materials from 1931 support the October date.

No reliably documented dramatic “last word“ of Capone at the sentencing has survived. What is remembered is his smile, his confidence that he had made a deal, and the line about the bankers, uttered before the court showed him who had the last word.

On May 4, 1932, Capone left by train for the federal penitentiary in Atlanta, and in 1934 he was transferred to Alcatraz. He was released in 1939, seriously ill and mentally altered. The man who once threatened witnesses and dictated the rules in Chicago did not return to a life of crime. His empire collapsed not from a bullet, but from five tax charges and a judge who refused to bargain.

Sources: Time