Prison Tales: Al Capone and Alcatraz

Today’s column from the Kankakee Daily Journal and The (Ottawa, Ill.) Times

Prison Tales: Al Capone and Alcatraz


Oct. 30, 2010

Throughout Chicagoland this weekend, plenty of people are no doubt dressing up as Rod Blagojevich. But I’m wondering what Blago himself is going as for Halloween.

Perhaps, come tomorrow, Rod will step out the front door of his Chicago home decked out in prison stripes – a little cap perched atop his coiffure – and take his daughters trick-or-treating along the streets of their neighborhood.

Or, maybe Rod will scrap that idea and just keep on pretending he’s Elvis until his federal corruption retrial, which last week was postponed until April 20.

Although, it seems April 1 would have been more fitting.

Or, even better: April 15.

Somewhat ironically, it was the 15th of April – or, at least, what it represents – that brought down the most notorious federal target in Chicago history, when legendary gangster Al Capone was found guilty of tax evasion in 1931.

Capone’s conviction sent him on a seven-year odyssey through the U.S. federal prison system, including a four-year stint at a place that’s worthy of the spookiest ghost tales:


Last month, I toured Alcatraz Island and learned about Capone’s time on “The Rock,” as well as his descent into madness there. And, in honor of Halloween, I thought I’d share a few details.

On Aug. 22, 1934, Alphonse Capone arrived at Alcatraz, the new maximum-security prison in San Francisco Bay reserved for troublesome federal prisoners. The 35-year-old Capone already had spent two years incarcerated in Atlanta, and hadn’t been particularly troublesome. His reputation, however, had been.

In Atlanta, rumors swirled that Capone had a phone in his cell and was allowed perks such as silk underwear and custom-made shoes. Such allegations were never proved, but prison officials still transferred Capone, likely to make it look as though they were cracking down on his supposed antics.

In his receiving document at Alcatraz, Capone’s criminal specialty was listed simply as “Hoodlum,” and among the items he was allowed were music writing sheets, a World’s Almanac and family photos.

From the prison library, Capone would check out books such as, “Common Errors in English Corrected,” “Practical Flower Gardening,” and “Life Begins at 40.” Meanwhile, one person tried to send Capone a picture of his dog. Another wanted him to contribute to a book of funny sayings for tombstones. And one woman even sent him a cryptic letter along with a check for sixteen octillion dollars ($16,000,000,000,000,000,000,000,000,000.00), signed “Holy Moses.”

Prison officials feared the correspondence might be some type of code, and asked the Bureau of Internal Revenue to investigate. It determined, however, that letter and check were nothing more than “the products of a person lacking proper mental balance.”

By 1938, Capone had begun losing his own mental balance. Years earlier, he had been diagnosed with syphilis, a then-incurable sexually transmitted disease. On Feb. 5, he began having convulsions that doctors diagnosed as “paresis,” mental deterioration brought on by syphilis affecting the brain. From then on, Capone would never be the same, and news that he was “going crazy” circulated fast outside the prison.

Until his transfer from Alcatraz in January 1939, Capone remained in the prison hospital. But, with the development of penicillin still years away, doctors could do little to help him.

As his condition continued to deteriorate, Capone began getting into fights, throwing fits and one day even compulsively making and unmaking his bed over and over again.

It was years before that Capone had made his bed. But it sounds as if after being forced to lie in it at Alcatraz, he desperately wanted, in his madness, to make it again.

How’s that for a scary thought?

Happy Halloween, everyone

Scarface at The Rock
Scarface at The Rock