The Valley

Roger Touhy was born in a lawless neighborhood called “the Valley.” It is gone and largely forgotten now, except by a scant few descendants of the tens of thousands of Irish immigrants who huddled there for a time, making that brutal slum the largest Irish ghetto west of New York.

Located in the heart of Chicago, the Valley was a flat stretch of land partial to winter floods that would fill the water with human waste from the nearby canals. In the summer it was insufferably humid. It was always a dreary place, full of ancient wooden warehouses, overcrowded with stinking ten-ements, stores with near-empty shelves, and saloons packed with men who had long since given up their dreams of a better life.

Roger Touhy was born there in 1898. He was the last of seven children in one of the thousands of working families jammed into the Valley. While he was still an infant, Roger’s mother was burned to death when the kitchen stove exploded. It was a remarkably common occurrence at the time, leaving his father, James, an Irish immigrant and a lowly but otherwise honest beat cop, to raise the family.

“My father,"Roger wrote, “was a Chicago police-man. An honest one. Otherwise, he would have had a hell of a lot less trouble getting the grocery and rent money.”

James Touhy eventually lost his four eldest sons to a local thug named Paddy “the Bear” Ryan. An enormous hulk of a man, Ryan led the notorious Valley Gang, which was organized in the middle 1860s. It inducted members as young as twelve years of age, and, at least in the beginning, gradu-ated them to the big leagues of crime at around age nineteen or twenty.

In 1870, its membership was mostly made up of the sons of policemen and lower level politicos whose city hall connections kept their sons out of serious trouble with the law. Using that clout, the gang was able to transform itself from a rag-tag 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 head-quarters, a popular saloon on the corner of 14th and Mulberry Streets. From there, the Valley Gang moved into armed robbery and big dollar larceny. But the gang remained 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 coercing cash from their shop own-ers when extortion became the new money maker.

The gang continued to rule supremely over the Valley until the turn of the century when great masses 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. The Italians had their street gangs as well, some with membership in the hundreds.

Inevitably, street wars between the Irish and the Italians broke out frequently. As a result, the Maxwell Street police station had the highest num-ber of assault and attempted murder cases of any police precinct in the country, outside of Brooklyn. Again, what kept most of the Valley Gang members out of jail were their powerful 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 mid-dle of a battle if the opposite side was paying more or if it appeared that they might win the election.

By 1910, the gang continued to grow in power in the Valley by having enough sense to allow a limit¬ed 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 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 Irish had surrendered their majori¬ty status in the Valley but managed to retain politi¬cal control, just as they did throughout most of Chicago as well. By that time, the gang transformed itself into a social and athletic club which, in both votes and money, stood solidly behind several dozen important politicos whose careers had been launched by the gang. 

The first important leaders of the Valley Gang were Heinie Miller and Jimmy Farley. Both expert pickpockets and burglars who flourished in the 1900s. Miller and Farley, along with their lieu-tenants, “Tootsie” Bill Hughes and Bill Cooney (aka “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 leadership of the gang fell to “Red” Bolton. Bolton’s reign was cut 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 influence could help. Bolton was sent away to prison where he died of pneumonia in a few years.

With Bolton gone, the gang started to weaken compared to it’s previous power, although it had a brief resurgence during the first World War when Chicago was under a temporary alcohol prohibition and the gang went into the rum-running business.

Rum-running brought the gang a lot of money. For the first time, the Valley Boys drove Rolls Royces, wore silk shirts and managed to get out of murder charges by affording the most talented lawyers, including the legendary Clarence Darrow.

In the mid 1890s, when the gang was under the leadership of Paddy the Bear Ryan, the Valley Boys were transformed into labor goons for hire, with 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 their reputa¬tion as pro-labor thugs in an age when the bosses and factory owners 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 life. Weighing in at least 450 pounds, the Bear waddled when he walked. But he was a solid figure full of fighting vigor and brutal vitality. He was also an ignorant man, blatant and profane, utterly fearless when given to one of his choking rages.

The Bear’s place was a dingy saloon at 14th Street and South Halstead. There was a sawdust floor “to soak up the blood” as Jack Lait said. A dirty, bent bar filled an entire wall. The rest of the room was packed with rickety tables and grimy wooden benches. On the drab smoke-stained walls hung pic¬tures of John L. Sullivan, Jake Kilrain and dozens of other Irish fighters whom the Bear admired.

The Bear, whose specialty was making police records disappear, worked seven days a week. With a dirty apron tied around his enormous waist he held court, ruling over his kingdom with an iron fist like an absolute dictator. The Bear was feared by the killers that surrounded him, so much so that throughout his long career none dared to question him or usurp his authority.

During the Bear’s leadership, no gang in all of Chicago was tougher or bolder. Every criminal in the Valley had to swear allegiance to Paddy the Bear or they didn’t work in the Valley.

It came to be that the Bear’s friend, Red Kruger, was sent to Joliet Penitentiary on a variety of charges. Soon afterward Runty Quinlan, the Bear’s second in command, started sleeping with Kruger’s wife.

This sordid romance threw the Bear into one of his rages. One day when the Runt stopped by Paddy’s saloon for a beer, the Bear came from around the bar and called him every name in the book. He punched the Runt to the floor, picked him up and punched him to the floor again and again and again. It was a terrible beating, even by Valley standards. When it was over, the Bear told the Runt that he would beat him senseless every time he saw him.

Runty Quinlan swore his revenge.

Several days after the beating, Paddy the Bear was summoned to the Des Plains police station to answer a charge for receiving stolen property. “He could have,” noted one cop, “found his way blind-folded.”

It was morning when the Bear started out for the police station. He waddled along Blue Island Avenue and stopped by Eddie Tancel’s place. Eddie was another Valley Gang graduate who operated a bar in the area. Once a professional fighter, Tancel—who was called “the Bulldog of Cicero”—had won almost all of his fights with his famous knockout punch. He retired to his Blue Island bar after he accidentally killed an up-and-coming fighter named Young Greenberg with his gloved fist. The police would eventually close down Tancel’s Blue Island saloon after it became the scene of one too many shooting murders.

After leaving Tancel’s place, the Bear crossed an alley just a half block from his saloon when Runty Quinlan sprang up from behind some trash cans and shot Paddy the Bear several times in his enor-mous belly. Paddy reeled out into the middle of the street, slumping down on the cobblestone and fell to the ground. Quinlan stood over the Bear and fired four more bullets into him.

Paddy the Bear was rushed to a hospital where a cop asked if he knew who had shot him. To which Paddy replied, “Of course I know who shot me, you idiot.” Then he paused and said, more to himself than to anyone present, “But I didn’t think that the little runt would have the nerve to do it.”

Then he died.

For the cops, the Bear’s last words were every-thing but a confession. Runty Quinlan was dragged in for questioning but was released due to lack of evidence.

Shortly after killing the Bear, Runty Quinlan went down state to Joliet State Prison on an unre-lated charge. He was released several years later during Prohibition and opened a saloon on 17th and Lommis Streets at the border of the Valley. The place soon became a favorite hang-out for the Klondike and Myles O’Donnell boys. Once, when police raided the joint, they found ten bulletproof vests, two machine guns and a dozen automatic pis-tols hidden behind the bar. “The Runt’s saloon,”said Jack Lait “was that kind of joint.”

Paddy the Bear had one son, known as “Paddy the Cub.” Paddy the Cub idolized his father who, for all his wicked ways, was an indulgent and doting parent. Young Paddy never forgot his father’s mur-der and for years nursed his hatred of Runty Quinlan. As a teenager he would see the Runt on his way to school, leaning against the doorway of his saloon, uneasily smiling down at him.

One day the Runt was lounging in a booth in his saloon with three Valley Gang graduates: Fur Sammons, Klondike and Myles O’Donnell. The group had been drinking for several hours and were mildly drunk when Paddy the Cub slipped up to the Runt, jammed a revolver in his left temple and whispered ‘This is for my father, you son-of-a-bitch.”

He shot the Runt through the back of the head. After the Runt fell to the floor, Paddy the Cub fired several more shots into the body and then slowly and calmly walked out the front door of the saloon.

• • •

In 1919, after the Bear was killed, 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. He was ambitious and found the Valley territory too restrictive for his high ambition. He soon extended his criminal reach far beyond its borders.

Over the years, Terry Druggan had gained a rep-utation as a fool and a clown. Despite this reputa¬tion Druggan proved to be a highly effective leader. He was a smooth operator and a highly intelligent hood, and by the third year of Prohibition he had made himself and most of his gang members rich beyond their wildest dreams. By 1924, Terry Druggan could truthfully boast that even the lowest member of his gang wore silk shirts and had a chauffeur for his new Rolls-Royce.

Druggan was smart enough to enter into several lucrative business agreements with Johnny Torrio. He 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 alcohol millions, Druggan bought a mag-nificent home on Lake Zurich and a winter estate in Florida. He surrounded himself with yes-men and flunkies and parked twelve new cars in his garage. He had a swimming pool although he couldn’t swim, a tennis court although he didn’t play, and dairy cat-tle (which he admitted scared him), sheep and swine in his pastures. He owned a thoroughbred racing stable and raced his horses, draped in his family’s ancient Celtic color scheme, at Chicago’s tracks.

Once, when he was ruled off the turf at one track for fixing a race, Druggan pulled his gun on the offi-cials 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. He and Druggan were inseparable compan-ions, as well as business partners in everything. They even went to jail together.

In 1924, during the height of Prohibition, both Druggan and Lake were sentenced to a year in the Cook County jail by Judge James Wilkerson for con-tempt of court for refusing to answer questions regarding their business dealings. Lake appealed to the President of the United States for help. The President refused to intervene and the pair went to jail—sort of. After 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. They came and went from the jail as they saw fit and were often seen in cafes late at night, retiring to their spa-cious apartments on ritzy Lake Shore Drive.

On those rare days when they actually stayed in the jail—waking up late and having breakfast in bed—their wives were regular visitors. In fact, on several occasions Druggan had his dentist brought in to fill a cavity. Later, when the story broke, a reporter asked Druggan to explain his absence from jail. The gangster explained, “Well you know, it’s awfully crowded in there.”He was right. In 1924 the Cook County jail, which had been built to house no more than 500 inmates, was home to over 1,500 men.

The same thing happened in 1933 when Druggan was supposed to be in Leavenworth Federal Prison for two and a half years on a tax eva¬sion charge. Once again he 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 girl¬friend Bernice Van De Hauten. She was 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 absorbed by the Chicago syndicate oper-ations and for all practical purposes ceased to exist.

Sometime around 1915 “Terrible Tommy” O’Connor brought Tommy Touhy, and his brothers, Johnny, Eddie and Joe into the fold of organized crime.