Capone’s audacious “Valentine’s Day Massacre” became an instant legend in the history of Prohibition-era gangland violence even though it failed in its primary objective. Bugs Moran, it turned out, was running late that morning and thus escaped certain death.
George “Bugs” Moran was born to an Irish father and Polish mother in rural Minnesota in 1893. They moved to the North Side of Chicago when George was 6 and despite his loyal service as an altar boy at Holy Name Cathedral, he soon fell in with a rough crowd. By the time he turned 21, he’d been arrested countless times and spent three short stints in prison. Along the way he earned his nickname “Bugs” (as in crazy) for his hair trigger temper and penchant for violence.
By his mid-20s Moran had earned a place in the North Side Irish Gang of Chicago’s soon-to-be-infamous Dion O’Banion. They started out as small timers, content to make off with minor hauls taken from local shops but soon moved up to more grand heists, seizing whole truckloads of top-shelf clothes bound for downtown retailers and cracking safes. When business was slow, they hired themselves out as debt-collectors, arsonists, and enforcers at both civic and union elections. The latter work earned them friends in Chicago’s high places of power, among people who appreciated the value of controlling polling sites. Before long O’Banion, Moran, and crew found the police looking the other way and judges quite willing to let them walk.
The ratification of the Eighteenth Amendment banning the manufacture, sale, or transportation of alcoholic beverages in 1919 was greeted by many Americans with dismay. But to organized crime, Prohibition ushered in a 14-year gold rush. Americans in those days were a law-abiding people, but they also liked their whiskey, wine, and beer and were willing to pay black market prices for it.
Enter the bootleggers who set up networks for the distribution of illegally made liquor or booze smuggled in from Canada. Chicago’s top gangster at the outset of Prohibition was Johnny Torrio, whose right-hand man was Al Capone. To prevent costly gang wars that might undercut profits and draw unwanted public scrutiny, he called a summit of regional gang leaders in 1921 to divide the city into territories.
O’Banion was present at the meeting and received official approval to control the city’s North Side. The deal lasted three years later O’Banion died in a hail of gunfire ordered by Torrio and Capone.
The assassination devastated Moran who idolized O’Banion as his mentor. Yet it also moved him up the ranks in the North Side Irish Gang to the No. 2 leadership position. One of Moran’s first decisions, in keeping with his hot-headed reputation, was to knock off Capone and Torrio. Capone narrowly escaped a drive-by shooting in January 1925. A few weeks later Moran actually managed to corner Torrio only to have his gun jam. Torrio escaped but decided to “retire” and handed operations over to Capone. Moran detested Capone even more than Torrio and mocked
him whenever the chance arose, especially when reporters were near, calling him “Scarface,” “The Beast,” and “The Behemoth.” Both men soon became obsessed with doing the other in. On Sept. 20, 1926, for example, Moran led an assault on Capone’s headquarters, pouring over 1,000 rounds into the building in a spectacular drive-by. Capone
escaped and three weeks later knocked off Hymie Weiss, the leader of the North Side Irish Gang, leaving Moran as the new number one.
The two rivals kept at it for the next two years, attempting assassinations and knocking off associates. Eventually Capone devised an ingenious trap. He had a man pose a liquor hijacker eager to sell a load of whiskey to Moran at a cut-rate price. Moran bought it all, made a huge profit, and a few weeks later agreed to accept a second delivery.
It would arrive at the S-M-C Cartage Company Garage on the morning of Feb. 14, 1929. Moran and his men agreed to meet there at 10:30 a.m. to unload the liquor and begin distribution.
A few minutes after 11 a.m. they heard the front door open and assumed it was Moran. Instead, in walked several of Capone’s hit men dressed as policemen. They ordered the seven men to face the wall for frisking and then opened fire, killing them instantly. Moran was only a few blocks away when he noticed scores of policemen around the garage. Thinking his men had been arrested in a Prohibition raid, he ducked into a nearby coffee shop and made plans to get them bailed out. It didn’t take long for word to arrive that his men had been set up and massacred.
Moran had enough luck on his side to save
his life, but his gangster days were now over. He was, in the words of historian John H. Lyle, a “mobster without a mob.” Capone had won the
war and was now the undisputed king of Chicago’s underworld. His reign was short-lived, however, as federal authorities sent him to prison in 1932 for tax evasion.
Moran hung around and managed to avoid Capone’s hit men for the next few years, but all his attempts at a comeback failed. In the mid-1930s he left the city and worked with several Midwest gangs in
Wisconsin, Minnesota, and Ohio, robbing banks and gas stations.
Arrested in 1946, he spent the rest of his life in federal prison and died of lung cancer in 1957.
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