January 2011

In 1933 Capone was in prison, his appeals exhausted. The nation had reached economic rock bottom. In March machinegun emplacements guarded Roosevelt’s inauguration as the Depression seemed to threaten the very foundation of government. In April John Dillinger walked out of an Indiana prison with five dollars and a new suit. A year later he would be known around the world.

Dillinger represented a breed that differed in fundamental respects from the gangsters who ruled Chicago. The history of the outlaw goes back at least to Jesse and Frank James, who robbed banks and trains on behalf of the Confederacy. The line runs through Butch Cassidy down to Charles Arthur (“Pretty Boy”) Floyd, the Barker gang, and other Depression-era bandits.

Night life is one of the most ephemeral aspects of any time. Fashions change, performers pass, clubs and dance halls fade into memory. Two spots offer the Chicago visitor a chance to turn back the clock.

Tommy Gun’s Garage is a dinner theater in a warehouse at 1237 South State Street. The police department once used the place as a target range, but the guns here now shoot only blanks, and a waggish atmosphere is enforced. You need to know the password in order to gain admittance at the back-alley entrance. Waiters and waitresses all dress in period costumes and speak a contagious Damon Runyon patois. They later join in the song and dance onstage, which includes some competent torch singing and brisk comedy routines. A real 1928 Model A Ford sits in one corner, a prop for souvenir photographs.

The massacre represented the high-water mark of Capone’s power. The Depression hit Chicago hard. Big Bill (“The Builder”) Thompson had plunged the city into debt and would soon be turned out of office a second time. A sobered citizenry was less inclined to tolerate high-living gangsters and their political cronies. Capone was booed when he showed up to watch a Northwestern football game in the northern suburb of Evanston.

American Heritage celebrated its fortieth anniversary last December, and to mark the occasion the editors asked a variety of people what they thought was the most significant change to have overtaken the nation in the past four decades. The breadth of the response is suggested by these replies to the same question, all of which came in since the issue appeared.

Back when the Franks and the Goths were trying to muscle in on the Roman Empire, a pagan priest named Valentine offered succor to persecuted Christians. Eventually he converted to the new religion and was clubbed to death for his trouble. St. Valentine’s feast day absorbed the trappings of a Roman fertility cult. It’s been linked to hearts and flowers ever since, but in Chicago it brings other associations to mind.

After the death of Hymie Weiss, the North Side mantle fell to George Moran, a thug of Polish extraction. His temper tantrums earned him the nickname Bugs.

Capone meanwhile quietly shifted his headquarters back to Chicago, settling eventually in the Lexington Hotel. The Lexington still occupies the corner of South Michigan Avenue and Cermak Road. The handsome edifice was built for the 1893 World’s Fair—President Cleveland addressed a crowd here—but its fortunes have gone downhill since the 1950s. Today it stands alone on a lonely block, its ornate terra-cotta trim surrounding gaping windows.

Once Capone’s entourage occupied most of two floors. Al’s office looked out from the turreted southwest corner of the building’s fourth floor. His bathroom featured gold-plated fittings. His initials were inlaid in the parquet floor. His high-back swivel chair was armored, and a bodyguard slept on a cot outside his bedroom door.

On the night of April 27, the Big Guy himself went out to spread fear. He tailed a Lincoln carrying Klondike’s brother Myles and some of his henchmen. On the way to the Pony Inn O’Donnell had picked up twenty-five-year-old Bill McSwiggin. Bill lived at home with his parents. His father was a Chicago cop, and he himself was an assistant state’s attorney, a sharp young prosecutor who had won seven of the eleven first-degree murder convictions in the city the previous year. He’d once unsuccessfully prosecuted Myles O’Donnell for murder.

As the O’Donnell group alighted in front of the tavern, Capone’s car approached from the east. A burst of machine-gun fire ripped into three of the men. Myles and his driver escaped unharmed. They wrestled the bloody bodies of two of their companions, including McSwiggin, into the car and dumped them in another suburb.

The towns that ring Chicago’s city limits are referred to as suburbs. In fact they have long been as built up as the adjacent city neighborhoods. What distinguished the town of Cicero in the mid-1920s, when Capone made it his headquarters, was the pliancy of its government. It was a pliancy Capone himself engineered. In 1924 he descended on the town with a band of hoods and stole the election for his candidates. Frantic officials called out a squad of Chicago police officers and deputized them as special agents, but Capone men pistol-whipped and intimidated enough voters to decide the results. It was during this campaign that Al’s brother Frank was shot dead by police. It has gone down as one of the dirtiest elections in American history.

The Capone gang ran Cicero along the lines of a feudal dukedom. When the president of the village board, Joseph Z. Klenha, balked at one of his orders, Al personally slapped him around and shoved him down the steps of the town hall. A police officer looked on but dared not interfere.

During the mid-1920s the six Genna brothers dominated Chicago’s Little Italy, the region around Taylor Street west of the river. They amassed considerable power and wealth by organizing residents into freelance alky cookers. The still tenders mixed up a mash with yeast and sugar; the rats that inevitably fell in became part of the recipe. After the yeast did its work, the mixture was slowly heated, alcohol wrung from its vapor. For this, urban peasants were paid the tantalizing remuneration of fifteen dollars a day. The Gennas were a violent lot with a background in the strong-arm extortion methods known as the Black Hand. Their gunmen subscribed to the old-world superstition that a smear of garlic made bullets more lethal. As the Genna power grew, they came into conflict with both the North Side forces under Weiss and with their nominal ally Capone. The inevitable clashes resulted. Three of the brothers were killed during a six-week period in 1925.

It’s a short drive from South Prairie Avenue to another important site. On the evening of September 25, 1925, Spike O’Donnell, the leader of a South Side gang, was walking in front of a drugstore on the northwest corner of Sixty-third Street and Western Avenue. From a car a voice greeted him: “Hello, Spike.” O’Donnell, who’d been left out of one of the early territorial partitions, had always bridled under the ascendancy of Torrio and Capone. “I can whip this bird Capone with my bare fists,” he bragged. He also risked incursions into territory controlled by the rival gang leader Frank McErlane.

The Illinois Association for Criminal Justice labeled McErlane “the most brutal gunman who ever pulled a trigger in Chicago.” The previous year, drinking in an Indiana saloon, Frank’s pals were chiding him about his marksmanship. McErlane drew his pistol, picked out a stranger at the end of the bar, and dropped him with a bullet through the temple.