Feature Articles

April 2001

The Valley Gang

By John William Tuohy

     The Valley. The toughest place in Chicago. It's gone now, and for the most part, only a handful of obscure historians even know that it ever existed.

     The Valley was one of the first enormous Irish ghettos in North America. It was separated from the Levee, Chicago's earliest red-light district and birthplace of the Chicago mob, by the south branch of the Chicago River. It was a low level stretch of land, partial to flooding in the winter months and insufferably humid in the summer. It was bordered by Chicago's once famous water canals and Halstead Street to the west, Fourteenth and Fifteenth Streets to the north and south, boundaries to a dreary land of warehouses and shacks, weather-beaten shanties, overcrowded tenements, empty stores and packed saloons.

     One resident recalled the "drab hideousness of a slum. All of the basements were damp and wet and the area was considered to be unsanitary in general. The better people were always leaving the place for the better neighborhoods. It was enmeshed in a network of railroad tracks, canals and docks that were new back then, factories and lumberyards, breweries and warehouses. There was nothing fresh or clean to greet the eye, everywhere is unpainted. Ramshackle buildings, blackened and besmirched with smoke of industry."

     In 1850, the Valley became the center for Irish immigration into Chicago with most of its Celtic inhabitants hailing from the barren western coast of Ireland.

     But, by 1871, just after the great fire destroyed most of the neighborhood, the Irish began to leave the valley, quickly being replaced by the Jews and Italians. But all of the Irish didn't leave immediately and for a while there was an imaginary line between the Irish and Italian sides of neighborhoods with sidewalk brawls between the two being a daily occurrence.

     However, the Valley gang's membership was still made up mostly of the sons of policemen and lower level politicos whose city hall connections kept their sons out of any serious troubles with the law.

     Using that clout, the gang was able to transform itself from a ragtag group of street urchins who stole fruit off vendors' wagons into a working criminal/political organization.

     With time, the gang moved from its basement headquarters on 15th street to its first official first headquarters, a popular saloon on the corner of 14th and Mulberry Streets. From here, the Valley gang organized itself even more and moved into armed robbery and big dollar larceny.

     But the gang was still a small time, local operation in most respects. Then, in about 1880, the Germans began to move into the Valley, followed by the Jews, the gang terrorized both groups, beating them into submission and extorting their shop owners for cash and extortion became the new moneymaker. The gang continued to rule supreme over the Valley until the turn of the century when the great mass of Irish, Germans and Jews moved out and were replaced by tens of thousands of southern Italians. Numerically superior and just as tough as the Irish they replaced, the Southern Italians were less prone to intimidation than were the Germans and Jews. And the Italians had their street gangs as well, some of them numbering in the hundreds.

     Inevitably, enormous street wars between the Irish and the Italians broke out and as a result the Maxwell Street police station had the highest number of assault and attempted murder cases of any court in the country, outside of the Superior Court in Brooklyn.

     Again, what kept most of the Valley gang members out of jail were their enormous political contacts, made even stronger by the gang's willingness to rent itself out as polling booth enforcers.

     However, unlike the smaller street gangs from the Valley, the Beamers, the Plugs and the Buckets of Blood, who also rented out their services, the Valley boys were known for their penchant to switch sides in the middle of the battle if the other side was paying more or it appeared that they might win the election.

     By 1910 the gang still ruled supreme in the Valley by having enough sense to allow in a limited number of Jews and Germans into its ranks; the Valley gang remained the largest and deadliest gang in the area and a whole new generation of Irish-American boys in Chicago grew to admire the Valley gang and its leaders "in much the same way" one sociologist wrote "that other boys looked up to, in a fanciful way, Robin Hood or Jesse James."

     By 1919, the Valley gang and the Irish lost majority status in the Valley but managed to retain political control over the area, just as the Irish did throughout most of the rest of Chicago as well. By that time, the gang transformed itself, in times of peace anyway, into a social and athletic club, which stood solidly behind, in both votes and money, the career of several dozen important politicos whose careers were launched out of the gang.

     In its earliest days, the gang was ruled over by its first important leaders, Heinie Miller and Jimmy Farley, both expert pickpockets and burglars who flourished in the 1900's.

     Miller and Farley, and their lieutenants, "Tootsie" Bill Hughes and Cooney the Fox, were described by the police as "four of the smoothest thieves that ever worked the Maxwell Street district."

     Smooth or not, they all went to jail in 1905 for extended stays and the gang's leadership fell to Red Bolton.

     Bolton's reign was made short by his own stupidity. He robbed a store in the middle of the Valley, in the middle of the day, killing a cop in the process.

     No amount of political connections could help and Bolton was sent away to prison where he died a few years in the prison infirmary of pneumonia.

     After Bolton left, the gang started to weaken, compared to what it was, although it had a brief resurgence during the First World War when the city was under a temporary prohibition and the gang went into the rum running business.

     Rum running brought the gang big time money. For the first time the Valley boys drove Rolls Royce cars, wore silk shirts and bought their way out of murder charges with the best lawyers money could buy including the talents of the legendary Clarence Darrow.

     In the mid 1890's, when the gang was under the leadership of Paddy the Bear Ryan, the Valley boys were transformed into labor slugger goons for hire, with Paddy the Bear, acting as the salesman, boasting that his boys were the best bomb throwers and acid tossers in the business.

     The Valley gang solidified that reputation during the building trades strike of 1900, which put some 60,000 laborers out of work for twenty-six weeks.

     Operating under the street command of Walter "Runty" Quinlan, who would eventually lead the gang, the Valley boys terrorized strike breakers with unmerciful beatings and earned a reputation as pro-labor thugs in an age when the bosses paid better.

     Paddy the Bear ruled the Valley for years and it was the Bear who taught Tommy, Johnny, Joe and Eddie Touhy, the finer points of the criminal's life.

     In 1919, Terry Druggan and Frankie Lake took over the Valley gang. Druggan was a dwarf-like little man with a hair trigger temper and a lisp who took over the valley after Paddy the Bear was killed.

     Druggan was ambitious and found the Valley territory to restrictive for his high ambitions and soon extended his criminal reach far beyond its borders.

     Over the years, Terry Druggan has gained a reputation as a fool and a clown but Druggan was, although comical, a highly effective leader, a smooth operator and highly intelligent hood who made himself and most of his gang members rich beyond their wildest dreams by the third year of prohibitions.

     By 1924, Terry Druggan could truthfully boast that even the lowest member of his gang wore silk shirts and had chauffeurs for their new Rolls Royce.

     Druggan was smart enough to enter into several lucrative business agreements with Johnny Torrio and was wise enough to pull the valley gang off the streets and remodel them after Johnny Torrio's restructured version of Big Jim Colosimo's outfit.

     With his booze millions, Druggan bought a magnificent home on Lake Zurich and a winter estate in Florida. He surrounded himself with yes-men and flunkies and parked 12 new cars in his garage.

     He had a swimming pool but he couldn't swim, a tennis court but he didn't play the game, dairy cattle, which he admitted scared him, sheep and swine in his pastures. He owned a thoroughbred racing stable and raced his horses at Chicago's tracks, the horses draped in his family's ancient Celtic color scheme.

     One time, when he was ruled off the turf at one track for fixing the race, Druggan pulled his gun on the officials and promised to kill them all then and there, if they didn't change their ruling. They changed their ruling.

     Frankie Lake grew up with Druggan in the Valley and was Druggan's business partner in everything and inseparable companion as well. They even went to jail together.

     In 1924, during the height of prohibition both Druggan and Lake were sentenced to one year in the Cook County jail by judge James Wilkerson for contempt of court for refusing to answer questions regarding their business dealing.

     Lake appealed to the President of the United States for help, however, the President refused to interfere and the pair went to jail...sort of.

     For a $20,000 cash bribe to Sheriff Peter Hoffman, "for the usual considerations and conveniences" as Druggan put it, he and Lake were allowed to turn their cells into working offices and came and went as they saw fit. They were seen in several caf�s late at night being driven in their new limousines along Lake Shore Drive where they lived, Druggan owning a 15-room apartment with a tremendous view of the Great Lakes.

     On those rare days when they actually stayed in the jail, arising late and having breakfast brought into bed for them, their wives were regular visitors. In fact, on several occasions Druggan had his dentist brought in to do some fill-in work.

     Later, when the story broke and a reporter asked Druggan to explain his absence from jail, the gangster said: "Well you know, it's awfully crowded in there."

     He was right too. In 1924, the Cook County jail, which had been built to house no more then 500 inmates was home to over 1,500 men.

     The same thing happened again in 1933 when Druggan was supposed to be in Leavenworth federal prison for two and a half years on a tax evasion charge.

     Once again, he had bought his way out of the jail and was living in the tiny town just outside the prison, in a three-bedroom apartment with his girlfriend Bernice Van De Hauten, a buxom blonde who moved down from Chicago to keep Terry company, much to his wife's surprise.

     The story broke and Druggan was moved from Leavenworth to Atlanta, without his girlfriend this time.

     With the end of prohibition, the Druggan and Lake gang, as the Valley gang was then called, was completely saturated into the Chicago syndicate's operations and for all given purposes, ceased to exist.

Mr. Tuohy can be reached at

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