The city of Chicago was too rich in racket revenue for the mob to simply give up after Capone's conviction on tax evasion. He had left a sizable territory for gambling, vice, corruption, and murder. The Chicago Outfit's empire extended across Illinois into Wisconsin and Indiana, not to mention the pull they exerted over Milwaukee, St. Louis, Kansas City, and Rockford.
After he died in 1947, the Chicago mob, or the Outfit, was already becoming a more streamlined, efficient moneymaking machine, one that would rule Chicago through to the 21st century.
Capone's right-hand man Frank Nitti was the obvious successor. With his underboss Paul “the Waiter” Ricca and a cohort of Italian, Irish, Polish, and even Welsh gangsters under his command, Nitti expanded the Outfit's lucrative rackets all the way out to Hollywood, where the Chicago boys were shaking down movie studios and infiltrating the labor unions.
Nitti ran into some trouble with the cops, and he was not well respected by his underlings. When the movie studio extortion ring was indicted, Nitti decided to make a grand exit. He shot himself on the railroad tracks; he was one of the few bosses to take his own life.
The Big Tuna
Tony “Big Tuna”/“Joe Batters” Accardo was a Capone henchman whose uncanny intellect and cagey ability to evade law enforcement put him in a good position to lead the Outfit in the post-Capone era.
While Paul Ricca took over after Nitti's death, Accardo became boss, and though he only officially served for a few years, he was considered by many to be the actual boss behind the scenes, putting figurehead bosses (most notably Sam Giancana) out front to take the heat from the feds.
The Big Tuna retired to Palm Springs in his later years. When he died in 1992 at the ripe old age of 86, he outlasted most of his mob cohorts, and spent little time in jail.
Mob hit man Frank Calabrese obviously had some serious family issues. When he went to trial in 2007 for racketeering and murder, his own brother and son both testified against the aging South Side crime figure. Calabrese kept a big smile on his face throughout the testimony. But in the end his brother and son got the last laugh when Frank was found guilty.
The Outfit expanded its hold not only over the Chicagoland area, but down into Indiana, west to Rockford, north into Wisconsin, and way out west to San Diego. They skimmed cash from casinos in Vegas and stole millions from union pension funds. And although the Tommy-gun happy days of the 1920s were over, the Outfit still used murder as a way to keep the troops in line.
In 2005 the feds announced the biggest indictment ever against the Outfit's bigwigs. Dubbed Operation Family Secrets, the parade of senior citizen mobsters was the culmination of decades of law enforcement activities. They were charged with a host of murders and criminal acts dating back over 30 years. Some of the names like Joey “The Clown” Lombardo were familiar to mob watchers. Then there were guys like Frank Calabrese. Frank grew up on the South Side of Chicago, along with many of the Outfit's other soldiers. Calabrese became known as a hit man, loanshark, and all around tough guy.
In the end, Calabrese, Lombardo, and the current reputed head of the Chicago Outfit, Jimmy Marcello, were all found guilty. But despite the outcome of the Family Secrets trial there are plenty of Windy City mobsters waiting in the wings to continue Scarface Al Capone's legacy.