Valley Gang: The Valley, which is gone now, was a warehouse district inside Chicago’s loop and, in the late 19th century, was home to the city’s burgeoning, but poverty stricken Irish immigrant population. In its earliest days, the Valley 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 various charges and the gang's leadership fell to a criminal named Red Bolton whose 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 policeman 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, 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 enormous 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 enforcers for hire, with Ryan, 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 trade’s 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.
In 1919, Terry Druggan and Frankie Lake took over the Valley gang after Ryan was murdered. Druggan was a dwarf-like man with a hair trigger temper and a lisp. Druggan was also 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, four years into the national prohibition, 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 Jim Colosimo's Outfit.
With his 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. His home in Chicago had a swimming pool but he couldn't swim, a tennis court but he didn't play the game. He owned a farm with dairy cattle, which he admitted scared him, and herds of 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. During one race when he was ruled off the turf at a track for fixing the race, Druggan pulled his gun on the officials and promised to kill them all, on the spot, if they didn't change their ruling. They changed their ruling.
Frankie Lake, Druggan’s partner, grew up with Druggan in the Valley and was his 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 from the jail as they saw fit. They were seen in several cafés 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 him company, much to his wife's surprise.
The story broke and Druggan was moved from Leavenworth to Atlanta, this time without his girlfriend. With the end of prohibition, the Druggan and Lake gang, as the Valley gang was then called, was completely incorporated into the Chicago syndicate's operations and for all given purposes, ceased to exist.
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 various charges and the gang's leadership fell to a criminal named Red Bolton whose 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 policeman 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, 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 enormous 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 enforcers for hire, with Ryan, 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 trade’s 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.
In 1919, Terry Druggan and Frankie Lake took over the Valley gang after Ryan was murdered. Druggan was a dwarf-like man with a hair trigger temper and a lisp. Druggan was also 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, four years into the national prohibition, 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 Jim Colosimo's Outfit.
With his 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. His home in Chicago had a swimming pool but he couldn't swim, a tennis court but he didn't play the game. He owned a farm with dairy cattle, which he admitted scared him, and herds of 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. During one race when he was ruled off the turf at a track for fixing the race, Druggan pulled his gun on the officials and promised to kill them all, on the spot, if they didn't change their ruling. They changed their ruling.
Frankie Lake, Druggan’s partner, grew up with Druggan in the Valley and was his 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 from the jail as they saw fit. They were seen in several cafés 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 him company, much to his wife's surprise.
The story broke and Druggan was moved from Leavenworth to Atlanta, this time without his girlfriend. With the end of prohibition, the Druggan and Lake gang, as the Valley gang was then called, was completely incorporated into the Chicago syndicate's operations and for all given purposes, ceased to exist.