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Al Capone convicted of tax evasion on Oct. 17, 1931

October 17, 2016

Eighty-five years ago today — Oct. 17, 1931 — a federal jury in Chicago convicted gangster Al "Scarface" Capone of tax evasion. He was sentenced to 11 years in prison, ultimately ending up in fabled Alcatraz.

Al Capone mug shot_US DoJ_tax evasion arrest

Al Capone's U.S. Department of Justice mug shot, taken four months before his tax eviction conviction on Oct. 17, 1931.

Keep that in mind if you're thinking of blowing off today's extended filing deadline for getting your 2015 tax return to the Internal Revenue Service.

All these years later, the IRS and Treasury still proudly point to Capone's conviction. It was T-men who put one of the most brutal criminals in U.S. history behind bars for tax evasion, not for his other crimes. 

Those suspected but never proven offenses included the rumored killing at least four men himself and ordering 1929's brutal St. Valentine's Day Massacre.

Doing time for tax crimes: The key to Capone's conviction was his refusal to pay taxes on his illegally earned income. His Prohibition era crime syndicate reportedly pulled in around $100 million a year, the largest portion from bootlegging, with added illegal income from gambling, prostitution and racketeering.

Chicago Tribune Al Capone conviction headline

Capone's hometown paper gave his tax conviction plenty of play.

Capone was sentenced to 11 years behind bars and fined $50,000. At the time, it was the harshest sentence ever delivered for tax fraud.

Over the years, the IRS has continued to go after tax evaders, both regular folks and celebrities, but none has captured the public fancy as much as Capone did and still does all these decades later.

In fact, tax evasion has even been used by crooks against each other.

Capone not alone: Waxey Gordon was another gangster who profited during Prohibition through alleged bootlegging and illegal gambling. 

Gordon's million-dollar operation included many trucks, buildings, processing plants and employees, but his business front could not account for the ownership and cash flow.

When Gordon had a falling out with fellow mobsters, including Benjamin "Bugsy" Siegel of Murder, Inc., Gordon's peers, perhaps learning from the Capone trial, provided authorities with evidence that led to Gordon's conviction in 1933 and imprisonment for 10 years on tax evasion.

So, yes, it true. There is no honor among thieves.

Comparing convictions: Gordon served his 10 years for his tax crimes, but he ended up on the wrong side of the law again after his release. In 1951, Gordon was arrested for selling heroin to an undercover police officer, was convicted and, due to his long criminal record, was sentenced to 25 years in Alcatraz, where he died of a heart attack on June 24, 1952.

Capone had earlier come out somewhat better than Gordon, at least in terms of time served. Scarface was released early from Alcatraz in 1939 for good behavior. But he spent his final year in the island prison in a hospital, suffering from syphilis.

Plagued by health problems for the rest of his life, Capone died in 1947 at age 48 at his home in Palm Island, Florida.

A Capone cornucopia: If you're interested in more about Capone, a new book, "Al Capone: His Life, Legacy, and Legend" by Deirdre Bair, will be available on Oct. 25. Bair, a National Book Award-winning biographer, worked with Capone's family in producing this latest story of Public Enemy #1.

You also can check out Deirdre Marie Capone's personal reminiscences of "Uncle Al Capone," which was published back in 2012.  Ms. Capone claims in her book that the IRS basically set up her infamous relative.

And, of course, you can thumb through Capone's official IRS tax records.

The consolidated lesson from all these publications is that everyone, regardless of how much or how little they make and how the money is obtained, needs to pay their due taxes on the income. 

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TAX-SAVVY WAYS 
TO WRAP UP 2026

It’s over! With October’s extended filing deadline behind us, it is now time to focus on year-end moves to reduce your 2026 tax bill. 

You’ll find ways to do just that on the Tax Tips page (see the More Tax Posts drop-down menu at the top of the blog), as well as the separate tax tip pages for each month, notably October through December. If you’re on the Tax Tips page, you’ll find a monthly list at the end of this column. If you’re on another blog page, you can head straight to the October tips; at the bottom of that tips page you’ll find links to all the other 11 months’ collections of tax advice.

Not to spoil what you’ll find in that tax advice, but it does cover such things as tax deductions for charitable donations, investment moves that could reduce tax due, and ways to max out your tax-favored retirement savings. 

Finally, as the year winds down, things get hectic. There are lots of other things to occupy our time, like the much more fun upcoming holidays. But don’t lose sight of taxes, since timing is key. To be of use, most tax moves must be made by the end of the tax year. That’s Thursday, Dec. 31, which also is the last business day of the year. 

So that you don’t miss that final tax year deadline, also keep an eye on the countdown clock below. It will keep you on top of just how much time is left to make important, tax-saving moves. (Note: I’m in the Central Time Zone, so adjust accordingly for where you live.)

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