Chicago Gangster Tour -- June 3, 2009

On June 3, 25 OLLI members had yet another unique learning experience: The Chicago Gangster Tour, a trip back in time to experience Chicago during the Roaring Twenties.

Upon arrival in the Windy City, “Shakespeare,” a loud, wisecracking step-on tour guide nattily dressed in a pinstriped suit, suspenders, and fedora, delighted OLLI members with fascinating anecdotes about Chicago’s windiest politicians, rollicking red-light districts, and notorious mobsters as the bus cruised in search of old hoodlum haunts, brothels, gambling dens, and sites of infamous gangland shootouts.

Shakespeare led a two-hour, fact-filled tour of the city, driving past well-known landmarks such as Holy Name Cathedral, which still has a bullet hole in the limestone façade from the assassination of Hymie Weiss; the former Lexington Hotel (otherwise known as “Capone’s Castle”), which Al Capone used as his headquarters; and through Levy District (formerly known as The Devil’s Mile), where vice and corruption once led to a crime rate higher than the rest of the country combined.

The tour took OLLI through Chinatown, Little Sicily, and the neighborhood of Pilsen, home to a building that once housed the famous Schoenhofen Brewery. The building itself is full of lore: Capone used it to brew legal “near beer” then spiked it with rot-gun whiskey; Frank Lloyd Wright once called the structure the perfect example of prairie architecture in America; and it was used during the filming of the orphanage scenes in The Blues Brothers movie.

Seemingly mundane neighborhoods were revealed as the sites of notorious assassinations during the 14 years of Prohibition. An innocuous parking lot on Clark Street was pointed out as the site of the city’s worst mafia murder: the St. Valentine’s Day Massacre, Al Capone’s elaborate 1929 scheme to kill enemy Bugs Moran. The site has been a parking lot since 1969, when former Mayor Daley tore down the garage to improve the city’s image.

Shakespeare had plenty of anecdotes about the gangsters, too. For instance, the term “bootlegging” was coined by Deanie O’Bannion, a gangster who would hide samples of liquor in 5 oz. flasks in his boots and share them during mass at Holy Name Cathedral. Immigrants from Sicily were employed by Angelo Genna and his five brothers as “alky cookers,” earning $15 a day mixing ingredients for rot-gut whiskey in 5-gallon copper stills. Workers kept $14 of their earnings; the other dollar went to the “flower fund,” used to purchase funeral flowers for employees who were killed during frequent explosions during the cooking process.

It was the anecdotes about the Al Capone, however, that intrigued OLLI members the most. They learned that Capone once sent $10,000 and flowers to a woman injured during an attempt on his life; kidnapped a pianist, forced him to play at his speakeasy for three days, then let him leave after shoving $20,000 in his pocket; and bought a belt that spelled out “Thanks From Al” in diamonds for a newspaper reporter who tipped him about upcoming government raids.

After the tour, the OLLI group headed to Tommy Gun's Garage, Chicago’s only speakeasy dinner theater, for lunch and a musical comedy revue that featured gangsters, flappers, and a raid by the cops. One lucky member of the group, John Maher, was taken on stage for an interactive "sobriety test" and radio show.