The Truth About The St. Valentine's Day Massacre

The United States Prohibition era created quite a mess for the 1920s and early '30s. The bootlegging trade provided alcohol to the thirsty masses while putting money in the hands of the wrong people. The only positives were giving moonshiners a reason to perfect their craft and providing story fuel for innumerable films, then and for decades to come. Sure, speakeasies and jazz are pretty cool, but criminal penalties for raising a Manhattan to good health certainly balanced all that out.

Along with the music and expertly hidden watering holes, the Prohibition Era also gave birth to mobsters. Modern western culture has a thing for romanticizing these crime bosses. They've become staples of popular culture, and no crime boss was more famous than Al Capone — "Scarface" (a nickname he hated, by the way).

Capone has been immortalized thanks to a couple of noteworthy films, but the real deal would've made latter-day fans think twice before throwing their praise. As charming as Capone was in front of the camera and to reporters, he's believed to have killed enough people to make anyone sick, and he did it all for power and cash. Being on Capone's bad side wasn't somewhere you wanted to be, and the St. Valentine's Day Massacre is generally believed to be the most prime example of this. The execution-style killings were an attempt by Capone (or so it's believed) to "take care of" his long-term rival, Bugs Moran. Here's how it all shook out.

Capone had a history of making his rivals disappear

Al Capone wasn't exactly known for taking it easy on the opposition. According to History, the Capone gang's kill count reached as high as 64 murders in a single year. If Capone had eased off, there's a good chance he wouldn't have been worth roughly $100 million (and that's in 1920s money). Messing up Capone's business and running booze in the same area as Capone's gang — pretty much all of Chicago — was asking to be killed. Oddly enough, Capone's "snuff out the competition" attitude is exactly what put his rival crime boss, George "Bugs" Moran, in power in the first place.

Moran, as Britannica explains, was the right-hand man to one Dion O'Bannion, a notorious gangster and previous rival to Al Capone. Long story short: Al Capone didn't like O'Bannion's hold on the Northside liquor trade in Chicago, so he sent a few of his goons to O'Bannion's flower shop (sweet cover for a mob boss, right?), and the aforesaid goons whacked him, says Britannica. This slingshot Moran to the top of the O'Bannion gang, and he picked up right where his late friend and employer left off. Capone didn't like that, either.

A little trickery goes a long, bloody way

As far as mass murders go, the St. Valentine's Day Massacre is one of the trickiest, best-crafted slaughters of the 1920s. The year was 1929; the day was Valentine's Day, and all was quiet in Bugs Moran's place of operation, the SMC Cartage Co. garage, located at 2122 North Clark Street in Chicago. Moran's men were hard at work, presumably putting together an order of illegal liquor for a paying customer, when a car rolled up and four men, two of them dressed as police officers, popped out.

Moran, according to Britannica, was heading to the garage when he saw the police car arrive. Being the astute crime boss he was, Moran decided to get out of there so he wasn't caught in what he believed to be a raid. Moran's boys also must have thought it a raid, seeing as the four faux police officers had no trouble rounding up the seven armed gangsters and convincing them to line up against the wall. According to Chicago Mag, not a single one of Moran's men reached for a weapon. That was it. They were all in place. The four invaders, believed to be Capone's men, opened fire.

Witnesses on the street could hear the rapid clack of two Thompson submachine guns and a shotgun as they tore Moran's crew apart. Though Moran himself escaped the massacre, the incident put an end to his mob boss career.

A back and forth game

You'd think a mass murder as straightforward and deadly as the St. Valentine's Day Massacre would've led to Al Capone's arrest, but the elusive crime boss had an iron-clad alibi. At the time of the shooting, according to Chicago Mag, Capone was hanging out in the courthouse of Dade County, Florida. He was on a vacation of sorts, having traveled down the East Coast to meet with a prosecutor who was investigating the murder of a different crime boss in New York.

Moran knew exactly who had slaughtered his men in the failed attempt to get rid of him once and for all. In an interview, the now crewless mob boss had a few choice words for reporters. "Only Capone kills like that!" he yelled, according to History. When Capone was interviewed about the massacre shortly after, he responded with a smug smile on his face, saying, "The only man who kills like that is Bugs Moran." The comment was an obvious taunt at his defunct business rival.

It would seem that Moran got a modicum of revenge for the slaughter when he (possibly) murdered one of Capone's men — more specifically, one of the men who had fired on his crew. But Moran was never proven to have been behind that killing. On the brighter side (if there is a brighter side), the guy outlived Capone by a decade, so that's something, right?

The stick that broke the mob boss's back

Al Capone was never convicted of the crime, even with, as Chicago Mag explains, the mob boss's cocky side running unchecked. Capone bragged left and right about his airtight alibi. After all, he was sitting down with a prosecutor, which is pretty much the epitome of a verifiable alibi. Whether or not Capone committed the crime wouldn't matter to the country. The St. Valentine's Day Massacre was crossing the line, and law enforcement began to double down. The heyday of organized crime was over.

President Herbert Hoover (pictured above) took office less than a month after the massacre, and one of the first things he did was warn the country about the growing threat of organized crime. He needed to make an example out of a powerful gangster to get the country back on track, and he set his sights on Capone. Hoover urged the authorities to find the evidence that would link Capone to the slaughter, but nothing solid turned up. Instead of charging the crime boss as an accessory, since it wouldn't stick anyway, Hoover had to find a different route. Capone would finally be put away in 1931 for tax evasion and was never officially linked to the massacre. There are several theories on who may have killed Moran's men that day, and only one involved Capone. Maybe he really was innocent. Not that it mattered. Moran's men were still dead.