A November 1930 mugshot of Chicago gangster Al Capone
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October 17, 2014 10:30 AM EDT

Here’s a friendly regular reminder of why you should pay your taxes: Al Capone, the Chicago mob boss known for making the city’s bloody bootlegging business even bloodier, faced trial in 1931 — not for the dozens of murders he is suspected of engineering, but for the $215,000 in taxes he never paid on more than a million dollars in illegal earnings. Instead of a body count, prosecutors totaled the lavish expenditures that made Al Capone one of the flashiest figures of the Prohibition era.

According to the New York Times’ account of the trial, Federal Attorney G. E. Q. Johnson harped on the extravagance of Capone’s $135 suits and $27 silk shirts — which, “in the stress and passion of his talk,” the prosecutor sometimes referred to as $27,000 silk shirts. The expenses got bigger: $6,500 spent on meat to feed guests at Capone’s nightly poker parties, $8,000 on diamond belt buckles, $116,000 lost on horse races. The idea was that Capone’s expenses would prove that he had once had the money that had gone unreported.

The list went on, as TIME reported:

But when, on this day — Oct. 17 — in 1931, the jury returned their verdict, Capone was found guilty of only five of the 23 charges against him.

Both the prosecutors and defense attorneys were puzzled; Capone’s attorney, unsure what he was hearing, asked for the verdict to be read a second time. Capone, on the other hand, “grinned as though he felt he had gotten off easily,” despite the fact that the five counts still carried a potentially heavy sentence.

It’s unlikely his grin lasted through his sentencing hearing in November, since the 11-year term the judge imposed was then a record-breaking penalty for tax fraud. The costs of Capone’s years of extravagant living caught up with him behind bars, where he suffered from dementia related to late-stage syphilis. By the time he was released, his physician concluded that he had the mental capacity of a 12-year-old. He never returned to gang life, or — at least publicly — to Chicago.

Read TIME’s original coverage of Capone’s trial, here in the archives: Who Wouldn’t Be Worried?

Contact us at letters@time.com.

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