Frankie Lake and Terry Druggan were leaders of The Valley Gang from Chicago, the were one of the most successful bootleggers of their time, amassing a fortune from bootlegging and rum-running. Its said they were making so much money that even the lowest gang member drove around in a Rolls Royce.

The Valley, which is long since gone, was described as one of the toughest places, an Irish ghetto in Chicago. It was separated from the Levee, Chicago’s red-light district, by the Chicago River. It was a low stretch of land, which flooded in the winter and was insufferably humid in the summer. It was bordered by Halstead Street to the west, Fourteenth and Fifteenth Streets to the north and south, a dreary place of warehouses and shacks, shanties, overcrowded tenements, empty stores and packed saloons.

The Valley gang were originally formed in the 1800’s in the Bloody Maxwell section of 15th Street, they started with low level crime, pick-pocketing and progressed to armed robbery. By the 1900’s they were one the leading gangs in Chicago and rivals of another Irish gang, Ragens Colts. By the 1910’s Paddy Ryan also known as Paddy the Bear was the leader of the Valley Gang, who was running the gang from his saloon on South Halstead Street, Ryan hired out the gang for illegal activities ranging from labor slugging to murder for hire. Paddy the Bear, however was killed by a rival, Walter “Runt” Quinlan. But soon enough the same fate came for Walter Quinlan, Paddy the Bear’s son killed Quinlan. And the leadership of the gang was passed to Frankie Lake & Terry Druggan, just as the Prohibition Era was beginning.

The two leaders of the Valley gang Druggan and Lake took the gang onto greater heights during the Prohibition Era. Druggan is described as a dwarf-like man with a hair trigger temper and a lisp. Druggan had gained a reputation as a fool and a clown but a highly effective leader, a smooth operator and highly intelligent. He was ambitious and soon found that the Valley was to restrictive for his high ambitions and extended his criminal enterprise far beyond its borders. Frankie Lake grew up with Druggan in the Valley and was Druggan’s partner in everything, the two were inseparable. They even went to jail together.

Frankie Lake (left) & Terry Druggan (right)

By the third year of Prohibition, 1923, the gang were raking in millions in un-taxed cash from bootlegging alcohol. By 1924, Terry Druggan & Frankie Lake could truthfully boast that even the lowest member of the gang wore silk shirts and had chauffeurs for their new Rolls Royce. Lake and Druggan made a series of deals with John Torrio and restructure the gang, they pulled all their men off the streets and focused on alcohol distribution and breweries.

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 dealings. Frankie Lake appealed to the President of the United States for help, however, the President refused to interfere and the pair went to jail. But it wasnt really jail, according to reporters, Lake and Druggan turned jail into paradise of sorts, where they could come and go as they please. For a bribe of $20,000 or as Terry Druggan said “for the usual considerations and conveniences” to the sheriff and warden of the jail, the pair were allowed to turn their cells into work offices.

Terry Druggan in court at the Federal building

The two, having being accustomed to the finer things in life soon turned jail into a vision of their own, Druggan & Lake would spend the day walking around in silk pajamas and expensive bathrobes, until it was dinner time and then they would change into their finest evening suits, waiting to be picked up by their chauffeurs at the back door of the jail. Sometimes they would come back at midnight, sometimes they would stay out all night partying. Druggan would sometimes dine at his own home, while Frankie Lake would be seen at nice restaurants with a beautiful woman called Carrie. If they didnt feel like going out, their food would be brought in from their favorite restaurant, if they didnt want to go to their offices, they could use the private phones in their cells and have their secretaries come to them. They lived like kings.

But that would soon come under investigation, a reporter, looking into the murder of a bootlegger and thought Lake and Druggan might have something to say, visited Druggan in prison, Druggan it seems wasnt up to talking that day and hit the reporter, bloodying his nose. The reporter then exposed the goings on inside the jail and wrote a story about it. But to make things worse, a Grand Jury also visited the jail in connection with the same murder but at the time of their visit, the Lake & Druggan were “out”.

Some time later a missing log book was found, it was discovered the pair were out of jail just as much as they were in it, and every time they were out of jail, they were at the dentist. The Chicago American newspaper detailed every visit to the “dentist” the pair took, sometimes they were accompanied by the Assistant Warden and a lot of the time with a prison guard. The newspaper were also able to interview one of Druggans visitors to the jail, on one of the days he was actually there, he said, “he lay luxuriously in the bed with his purple silk pajamas, a reading lamp above his pillow and half a dozen books on a lacquered table beside the bed. Morocco slippers and several pairs of patent leather pumps hung on trees under the bed”

For their part Sheriff Hoffman was fined $2,500 and got 30 days in jail, and Warden Westbrook got four months.

With his millions, Druggan bought a magnificent home on Lake Zurich and a winter estate in Florida 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.

Star Tribune (Minneapolis, Minnesota) · 20 Dec 1925, Sun · Page 75

Owen Forsyth

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