Speakeasies represent the classic image of The Roaring Twenties and Prohibition – people having fun breaking the law. Some were dives, located in run down cellars and providing “rot-gut” to customers, while others had genuine liquor, good entertainment and excellent food. It was estimated that there were 100,000 speakeasies in New York City alone. (TFC, 160) So many speakeasies flowed with bootleg booze that New York was known as the “City on a Still.”
The most famous of the New York “Speaks” were The Twenty-One Club and The Stork Club, where Walter Winchell, the leading society columnist of the day, hung out and wrote about “café society”. (Id.) At Small’s Paradise in Harlem, waiters danced the Charleston, carrying trays loaded down with cocktails. Popular stars like Fred and Adele Astaire entertained at The Trocadero. And at the Cotton Club, Duke Ellington led the house band as tap dancer Bojangles Robinson and jazz singer Ethel Waters packed the house.
Speakeasies survived by paying graft to federal, state and local law enforcement authorities. Local cops, who were on the take, would warn the speakeasy owners when the feds were going to do a raid, and the owners moved all the booze to another location. (Jennings, p. 122)
Prohibition gave rise to the criminal underworld that supplied illegal booze and ran the speakeasies where it was drunk. Gangsters such as Jack (Legs) Diamond, Bugsy Siegel and Dutch Schultz ran the show in New York. Al Capone, the quintessential hood, who had a 700-man army backing him up, was the Chicago kingpin. There were some 500 gangland killings in Chicago during the decade of the 1920s, including the infamous St. Valentine’s Day Massacre. (Cantor, 112) (See a fuller discussion of Gangsterism in the section about the 1930s.)
Al Capone’s gang manufactured, sold and transported illegal liquor products, stole goods manufactured by other gangs, controlled border access points to manage the flow of “merchandise”, ran speakeasies and “protected” those operations they did not own. It is reported that Capone’s operation controlled 10,000 speakeasies in Chicago. The gross income in 1927 from beer and liquor was estimated to be $60 million, $25 million from gambling, $10 million from prostitution, and $10 million from the “protection” schemes. (Allen, IX, 6)
Capone’s operation faced competition from rival gangs – the O’Banions, the Gennas, and the Aiellos. This competition led to killings and wars. The gang murder rate in Chicago rose from 16 in 1924 to 46 in 1925 and to 76 in 1926. (Moore, P. 36) Capone’s Gang murdered Dion O’Banion, leader of the North Chicago gang and Capone’s archrival. In retaliation, George “Bugs” Moran, O’Banion’s successor, put a $50,000 bounty on Capone’s head. O’Banion gangsters drove six cars past a hotel in Cicero, Illinois, where Capone and his associates were having lunch and showered the building with more than 1,000 bullets. (Id.) Capone survived.
The most notorious of the gangland killings of the era was the St. Valentine’s Day Massacre in 1929. Moran and his henchmen had avenged the Capone Gang’s earlier murder of O’Banion by killing several Capone cohorts. Capone ordered retaliation. On February 14, 1929, seven Moran cronies were waiting for a delivery of illegal booze in a Northside warehouse. Moran was expected to be there, but he was late. Capone’s men, dressed as police, walked in. Moran’s men thought it was a legitimate raid and assumed they would be bailed out later. However, the fake cops pulled out machine guns and murdered the seven. Moran arrived as the fake police officers were entering the warehouse. Moran waited outside, thinking that his gunmen inside were being arrested in a raid. When the shooting started, he hid. The assassins were never caught.
The St. Valentine’s Day Massacre proved to be the last confrontation for both Capone and Moran. Capone was jailed in 1931, and Moran lost so many important men that he could no longer control his territory. On the seventh anniversary of the massacre, Jack McGurn, one of the Valentine’s Day hit men, was killed in a crowded bowling alley with a burst of machine-gun fire. McGurn’s killer remains unidentified, but was likely Moran, though he was never charged with the murder. Moran was relegated to small-time robberies until he was sent to jail in 1946. He died in Leavenworth Federal Prison in 1957 of lung cancer. Capone died in prison in 1947, serving time for federal tax charges.
“St. Valentine’s Day Massacre”, Mark Foggo’s Skasters https://youtube/ujcqvhtW7MI
It was 10:20 AM, February the 14th, 1929
Me and the boys were surrounded by the guns of Capone and the South side…It was a cold windy morning, I had a shipment to meet
On 2122 North Clark Street
We checked the coast and the coast looked clear
So in It went the boys, the time was nearIt was bootleg liquor (3x)…
I waited a while just to look outside
Well, you don’t take Bugs Moran for a ride
A car drew up with four men inside
With long overcoats their pockets hung wideThey lined my friends up against the wall
And said “Let ’em have it”, and that was all
He killed my boys, yeah, he took their lives
With a hundred rounds of .45’sOnly Capone kills like that…Only Capone kills like that…
Only Capone, a murdering ratThis all took place on St. Valentine’s Day
Capone was pissed that I got away
I have a very special place in my heart
For that two-faced bad taste debased murderous fartThis is the story of Bugs Moran…
This is the story of Bugs Moran…
This is the story of a very lucky man
“The Saint Valentine’s Day Massacre”, parody of song “The Night Chicago Died”, originally performed by Paper Lace, parody written by Mikey F, https://youtu.be/vtJ27y_9LOg
They paid off the cops
on the South side of Chicago
Back in the USA back in the bad old daysIn the cold of a winter’s night
in the land of the dollar bill
when the men of Chicago died
and they talk about it still
When a man named Al Capone
tried to make that town his own
and he called his gang to war
as the forces of the lawI heard that mobsters died
I heard they were killed when the men of Chicago died, brother what a night it really was, brother what a fight it really was, Glory Be!
I heard that mobsters died
I heard they were killed when the men of Chicago died, wonder what made all the people ran,
wonder why they tried to take Bugs Moran, Yes Indeed!and the sound of the battle rang, through the streets by the old North side, till the last of the hoodlum gang,
had been gunned down with pride, there was shouting in the store, and the sound of a barking dog, and I asked someone who said, bout a dozen men are dead,I heard that mobsters died
I heard they were killed when the men of Chicago died, brother what a night it really was, brother what a fight it really was, Glory Be!
I heard that mobsters died
I heard they were killed when the men of Chicago died, wonder what made all the people ran,
wonder why they tried to take Bugs Moran, Yes Indeed!then there was no sound at all, but the stakeout across the hall, and the door opened wide, two cops with guns held at their side, and the mob got in their place, and they blew the men away
The night the mobsters died
na na na na na na na na na na na the men of Chicago died, brother what a night it really was, brother what a fight it really was, Glory Be!The night the mobsters died
na na na na na na na na na na na the men of Chicago died, brother what a night it really was, brother what a fight it really was, Glory Be!The night the mobsters died
na na na na na na na na na na
the men of Chicago died, wonder what made all the people ran,
wonder why they tried to take Bugs Moran, Yes Indeed