Memorial Day -- Chicago Style

by Libby Hellmann


The Chicago Tribune ran a story a couple of weeks ago on “colorful” Chicago characters, most of them elected officials. Included in their “Colorful Servant Hall of Fame” were


Big Bill Thompson, maybe the most corrupt mayor the city has ever known



John D’Arco, a convicted felon, state senator, and self-proclaimed poet

“Bathhouse” John Coughlin, a 1st Ward alderman and another poet .
(come to think of it, what that says about politicians with literary pretensions is probably best left to posterity) who, along his partner/alderman “Hinky Dink” Kenna, were the kings of graft and protection money at the turn of the last century



Betty Lauren-Maltese, Cicero’s town president who eventually went to jail for fraud. Betty, the wife of mob bookie Frank Maltese (for whom she named the town’s police and fire stations), was quoted (among other outrageous things) as saying the US Constitution didn’t apply to the gangs she wanted to kick out of Cicero.


So, on this Memorial Day, I thought it might be fun to remember a few other characters who didn’t make it into the article but have swaggered their way into Chicago history by their cavalier actions, personalities, and sheer chutzpah. Not all of them were elected officials, but all of them are part of the tradition of “bad boys and girls.”


Ed Vrdolyak: Has Fast Eddie finally had his comeuppance? The once powerful
Alderman (known as “Fast Eddie” because of his speed at rushing through legislation) and one-time head of the Chicago City Council was generally a major thorn in the side of the city’s first black mayor, Harold Washington. But he is also known as a mob lawyer, and is known to be the power behind the throne in Cicero (see Betty above). The one time head of the Cook County Democrats made a fast switch into the Republican Party so he could run – unsuccessfully -- against Mayor Daley. Unfortunately, just a few weeks ago, Fast Eddie was indicted for fraud and bribery related to a kickback scheme involving Gold Coast real estate. Shocking.

Jane Byrne: The first female Mayor of Chicago served only one term: from 1979 to 1983.
I like to call her the “Snow Queen” – her election came after a series of bizzards that paralyzed Chicago and made the current mayor, Michael Bilandic, seem incompetent. She was the one who installed Fast Eddie as the head of the Cook County Democrats (he repaid the favor by becoming a Republican), but, in the long run, she wasn’t able to muster the necessary political clout to survive. After Harold Washington won the Democratic primary, she played the spoiler, waging a write-in campaign, which split the white vote (Richie Daley was the other candidate), and made Washington’s election inevitable.

Richard Bailey: He probably couldn’t be elected dog-catcher, but he’s a creepy guy who’s now in jail for his role in the murder of candy heiress Helen Brach. Bailey, a con-artist who specialized in fleecing wealthy older women out of their savings, was connected to the horsey set. Racing, that is. "His favorite prey were women who were wealthy due to having been widowed, women whose thinking was not as straight as it should be because perhaps they were dying, very sick or acutely lonely," said one investigator. He’d con them out of their money by proposing they invest in horses, then skim most of the money for himself. As it happens, I have a personal note about Bailey. My former babysitter, a very attractive young woman, took a job with him and his girlfriend for three weeks and moved into their North side home. She became convinced she was being drugged, and we had to help her get away from him.

OK -- this post is getting a little long, so it’s time to quit. But don’t forget Commander Jon Burge, the former police commander who, for 20 years, tortured suspects to make them confess.

Or George Ryan, the Republican governor who, despite ending the death penalty in Illinois, was convicted of corruption and racketeering last year.

Or – going back in history – .
the famous and enterprising Everleigh sisters, whose Chicago bordello on South Dearborn at the turn of the century was possibly the most luxurious of its time and counted as their patrons politicians, writers, actors, and even royalty.


Clearly, I’ve just skimmed the surface. Who are some of the other Chicago “characters” you remember? And why do Chicago’s scoundrels and criminals seem so much larger than life than other cities? Although that just might be a subject for another blog.