Forget the wine and flowers, the real story of Valentine’s Day is guns and blood.
In the late 1920s, the ban on booze, ushered in by the passage of the 18th Amendment in 1920, opened up opportunities for those willing to buck the establishment. The rise of bootlegging (the illegal manufacture and sale of alcohol) and speakeasies (illicit drinking establishments), as well as gambling and prostitution, proved lucrative for mobsters. And the biggest mobster of them all was Alphonse Gabriel Capone.
Born in Brooklyn, New York in 1899, Al Capone quickly became acquainted with street gangs. A middle school dropout, Capone worked odd jobs to make ends meet. When he turned 18, Capone’s boyhood friend, Johnny Torrio, introduced Capone to Frankie Yale. Six years older than Capone, Yale gave Capone a job as a bouncer and bartender at one of the brothels he owned. While at work, Capone got into a fight with a patron (reportedly over a pretty girl) and was slashed across the face three times with a knife, earning him the nickname “Scarface.”
Despite his wild beginnings, Capone got married a short time later and moved his family to Baltimore with intentions of making an honest living. But the call of the underworld was strong: when Torrio asked Capone to move to Chicago and help him run his burgeoning mob empire, it was an offer Capone couldn’t refuse.
The move proved to be lucrative – reportedly the pair took in nearly $100 million annually – but also dangerous. In 1925, after barely escaping an assassination attempt, Torrio decided to leave Chicago. But first, there was the small detail of who would take over. Torrio passed the torch to Capone, saying, “It’s all yours, Al. Me? I’m quitting. It’s Europe for me.”
But Capone wasn’t the only mob boss in town. George “Bugs” Moran controlled the North Side. Capone controlled the South Side. And neither was terribly content to stay put.
By 1929, the blood was flowing nearly as freely as the booze. And it was about to get worse. Capone allegedly put out a hit on Moran. On February 14, 1929, while Capone was at his Florida home, a plan was set in motion. The North Side Gang was lured to a garage with the promise of stolen whiskey. The gang arrived without Moran who was running late that day.
Witnesses saw four men enter the garage: two of the men were dressed as police officers. The “officers” ordered Moran’s gang to line up against the wall where they were hit with a spray of machine-gun and shotgun bullets: 70 rounds of ammo were fired. All seven men inside died – most of them immediately. One of the victims, Frank Gusenberg, survived long enough to allegedly tell police, “No one shot me.”
Moran escaped the slaughter. When he heard about it, he remarked, “Only Capone kills like that.” Capone retorted, “The only man who kills like that is Bugs Moran.”
No one was ever charged with the murders. After the shootings, the FBI dubbed Capone “Public Enemy Number One,” a label Capone reportedly hated.
Capone would serve two short jail sentences beginning later that year – not for murder but on lesser charges of carrying a concealed weapon and contempt. Capone was both smart and resourceful: he was able to charm and bribe his way out of more serious charges.
That changed in the 1930s. Despite his lavish lifestyle, Capone never filed an income tax return, claiming that he had no taxable income. Under the Tax Code, income is reportable even if the source is illegal activities: that’s still true today. Using forensic accounting, Special Agent Frank Wilson and Internal Revenue Service “T-Men” (as they were called) put together a case against Capone for failing to report millions of dollars in income.
On June 5, 1931, Capone was indicted on 22 counts of federal income tax evasion. On October 17, 1931, Al Capone was sentenced to prison. Despite Capone’s reputation, he wasn’t put away for murder or gambling or bootlegging but for tax evasion.