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Milwaukee’s Third Ward was a kind of land lost to the law for the first decades of the 1900s. Around the turn of the century, the neighborhood had become the primary residential area for Italian immigrants (who replaced the largely Irish-American community that had been there since the 1850s), and a small but powerful criminal element emerged that dealt in various nefarious activities, including extortion and counterfeiting. (For more on this, check out the upcoming book, The Milwaukee Mafia: Mobsters in the Heartland by Gavin Schmitt). Investigations into these crimes proved exceedingly difficult, as the Italians of the area were seldom inclined to talk to police for fear of retaliation. By 1913, Milwaukee’s district attorney had publicly stated that the Third Ward was home to “secret murder and blackmail organizations” that the city’s police department could do little to combat.
Perhaps it was fitting, then, that when prohibition came to Milwaukee in 1920, the Third Ward became a center for both the illegal production and sale of “intoxicating liquors.” Indeed, it was the area’s stills and speakeasies that introduced most Milwaukeeans—non-Irish or Italian Milwaukeeans, anyway—to the Ward. According to a 1927 Milwaukee Journal report on the neighborhood, the early years of prohibition in the city were a cautious time. Late night parties with live music and dancing were not to be found. Liquor pickings were slim and prices were high. At this time, there were few saloons in the Third Ward, but thanks to the closed-off nature of the area, they operated mostly the same as they had prior to prohibition, serving beer and home-brew wine to a familiar customer base.
The Third Ward might have been a neighborhood where secrets were kept, but just as today, Milwaukeeans of the era seemed to have a preternatural ability to sniff out cheap booze. Soon, neighborhood wine makers could not keep up with demand. Grape wine, the pre-influx favorite, was replaced with raisin wine, which could be made more quickly and cheaply. By 1922, jazz bands kept the beat at a dozen or more hot spots of late-night activity. Buildings that might have appeared to be near condemnation from the outside were home to lavishly-dressed night clubs. From all across the county, well-heeled citizens in tuxedos and glitzy dresses would “do the Ward.”
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While many Third Warders were able to cash in on this trend, it was likely the old criminal element that profited most handsomely. Peter and Angelo Guardalabene, sons of Vito Guardalabene, allegedly the first boss of what would become the Milwaukee mafia, ran the Monte Carlo at 171 Detroit Street (now East St. Paul), “Milwaukee’s best-known late night rendezvous,” per the Milwaukee Sentinel. Dozens of smaller establishments were run by locals also thought to be affiliated with Guardalabene organization.
The Unassuming exterior of the Monte Carlo in the Third Ward. (Milwaukee Sentinel, October 16, 1926)
The party in the Third Ward, however, was rather short-lived. It did not take long for W. Frank Cunningham, the local federal prohibition agent, and his team of a dozen “G-men” to crack down. By the mid-1920s, raids on both speakeasies and stills were common in the ward. Dozens of raids hit the neighborhood through 1926 and ’27, prompting both the Journal and the Sentinel to proclaim the death of the city’s “cabaret district.” While the various saloons, rum-holes, and wine cafes were padlocked, feds took axes to wildcat breweries and hidden distilleries. One raid on a home on East Clybourn uncovered a 200 gallon still and an 11,000 gallon underground mash tank.
A Prohibition Agent takes a sledgehammer to a Third Ward still. (Milwaukee Sentinel, February 17, 1927)
Cunningham took such a significant bite out of the action in the ward that by New Year’s Eve, 1929, the Milwaukee Sentinel openly worried if there was enough booze left in the city to ring in 1930. Headlines like “DRY FORCE TO STEM HOLIDAY CHEER” and “RAIDS IMPERIL SUPPLY,” greeted anxious readers. The paper went on to warn that Cunningham’s men would be posing as out-of-town “playboys” looking for a tip on a good party and that private citizens toting hips flasks or discrete bottles while walking down city streets could be arrested for transporting intoxicants.
Of course, by 1933, prohibition had ended and the spirits once again flowed without restraint in the Third Ward. Sadly, almost none of the buildings in which all this illicit revelry went on survive today. The heart of the Third Ward Cabaret district is now beneath Interstate 794 and the rest of the old neighborhood was bulldozed for the various developments that sit between N. Milwaukee Street and the Festival Grounds.
The 400 block of North Jackson Street, in the heart of what once was the Third Ward’s ‘Cabaret District.’ 1936 and present-day. (Library of Congress/Google Street View)
