Capone tried a different tactic; he would push Touhy to see how far he could get before a shooting war broke out. Starting in the early summer of 1927, he tried to work his way into Touhy's territory by opening several whorehouses just inside Des Plains. That same day, Roger and Tommy Touhy, backed by several truckloads of their men and a squad of Cook County police, raided the bordellos, broke them up and chased the women back to Chicago. All the while, Capone kept sending his beer salesmen into Touhy's territory where they achieved a fair amount of success by drastically undercutting Touhy's prices, but the ever shrewd Kolb recognized Capone's ploy and refused to be prodded into a price war that they couldn't win. Instead, the Touhys responded by sending a simple message to any saloon keeper who sold Capone's beer inside their territory. If the bar owner sold Capone's brew, they would wreck the place. If he continued, they would burn his place to the ground.
To the newspapers, the public, the police and the politicians, Roger's Des Plains operation looked exactly the way he and Kolb wanted it to look;
To the newspapers, the public, the police and the politicians, Roger's Des Plains operation looked exactly the way he and Kolb wanted it to look; like a hick, two-bit operation that grossed a few hundred thousand dollars a year. "And Touhy, " Ray Brennan said, "was careful to foster that illusion. He lived well, but not lavishly in Des Plaines as it was a quiet town where he was considered a leading citizen. He was a contributor to charities and a member of fraternal organizations and golf clubs. Touhy and Kolb had a million-dollar-a-year business going plus a neat income from slot machines and a few road houses but they were wary enough not to brag about it. They were smart enough to pay income taxes on it."
Roger, who was now the father of two boys, made his final move to the suburbs in the spring of 1926 and purchased a large, comfortable home, just north of the center of Des Plains. His neighbors considered the bootlegger and his family respectable, hardworking people. "Nice," recalled one neighbor. "Not what you would think for a bootlegger. They were quiet people...refined."
'There was no stigma to selling beer." Touhy wrote. "I bought a place that some of the newspapers later called a 'mansion' or a 'gang fortress.' It was a six-room bungalow and later I put a sixty-foot swimming pool in the back. The only gang I ever had around there was a guard with a shotgun after the Capone mob tried to kidnap my kids....I lived quietly with my family during those big money years. I put a workshop, office and bar in my basement. There was a playhouse for the kids in my backyard. My wife got along well with our neighbors."
Even when Tommy and Roger were being hounded by the police during the John Factor kidnapping, their neighbors supported them. Des Plains historian Mark Henkes wrote, "Touhy gave his money freely to people and families in a pinch. He left baskets of food on the doorsteps of homes with a $20 bill attached to the basket handle. The recipients sometimes never knew where the food came from. He paid medical bills for some families. He made good money selling beer and he gave some of it away." Even though Roger did his best to fit in, there were occasional setbacks like the incident when the Chicago Tribune and other groups were planning a historical pageant for Des Plains in which citizens would dress as early settlers and travel down the Des Plains river in wooden canoes. Meanwhile, Touhy wanted to get rid of some mash, the fermentation of beer, by pumping it into the river. He hired a crew to dig a trench and lay a sewer line from his plant to the river.
He poured hundreds, perhaps thousands of gallons of the mash into the river. The problem was that Des Plains was going through a dry season and the river was low and barely moving. The stench from the mash was unbearable. Father Patrick O'Connor, head of St. Mary's Training School in Des Plains and a member of the parade committee, got a whiff of the foul smell in the river and immediately knew what happened. O'Connor knew Roger and called him about the problem he had created. 'What in the hell were you thinking, Rog? Half of Chicago will be here in a day and you turn the river into a flood of bootleg booze! Do something before the pageant starts."
Roger apologized and hired more then twenty boys from Maine High School in Des Plains to dump thousands of gallons of perfume into the river, "and the pageant was a sweet-smelling success."
So, while the public, the press and the police may have been fooled by Roger's small time image, A1 Capone knew exactly how much money Touhy and Kolb were earning out on the dusty back roads of Cook County. He wanted a piece of it, a large piece of it. As he always did, Capone first tried to talk his way into a partnership explaining the benefits of working within his operation. They met a total of six times that year, in Florida, during the winter months on fishing trips, and Capone offered to let Roger use his yacht.
Touhy said, "He offered to let me use his yacht or stay in his big house, surrounded by a wall about as thick as Statesville's (prison) on Palm Island in Biscayne Bay between Miami and Miami Beach. I didn't accept. "
Roger wrote that he had two business deals with Capone in 1927 because Capone had trouble getting beer for his joints. Capone called Touhy and asked him to sell him 500 barrels and since Touhy had a surplus he agreed and told Capone to send 500 empties to the cooperage. He would send 500 barrels back for the price of $37.50 per barrel, a discount because of the large order.
Capone called back and asked for another 300 barrels. Touhy agreed and told Capone when he expected to be paid. The day before the money was due, Capone called and said that 50 of the barrels were leakers and that he wouldn't pay.
'I'll pay you for seven hundred and fifty, ok?" 'You owe me for eight hundred and I expect to be paid for eight hundred."
"Well the boys told me there were some leakers, but I'll check on it."
Capone paid the $30,000 in cash and called a week later and asked for more. Touhy refused, saying his regular customers were taking all of his output. Knowing that it may have been Capone testing his ability to draw him in or to see what he could produce by taking him to be his biggest customer, 'What was the use of needling him by saying I didn't do business with weasels."
In late 1927, Capone told Willie Heeney, Roger's former business partner, to go out to Des Plains to see Roger and encourage him to come around to Capone's way of thinking. By now, Heeney was working full time in the outfit's enormous prostitution racket where he would stay until the depression set in and he switched over to labor racketeering and narcotics. He soon became his own best customer and became hooked on heroin.
Roger agreed to meet Heeney at the Arch, one of his road houses in Schiller Park, managed by his brother Eddie. Arriving with Heeney at the meeting was Frankie Rio, Capone's favorite bodyguard and enforcer whose presence was no doubt meant to impress Touhy. Heeney was the spokesman, telling them that Capone wanted to open the county for brothels, taxi dance halls and punch board rackets. He was willing to split the proceeds evenly with Kolb and Touhy to which Rio added, "A1 says this is virgin territory for whorehouses."
Roger told Henney that he didn't want or need Capone as a partner, and that although the locals might tolerate speakeasies and gambling dens, whorehouses and taxi dance halls were something else. However, there was at least one brothel in operation in Des Plains at 304 Center Street, apartment 38, above Matt Kolb's brother's laundry store/handbook operation. There were at least three women working on the property and photos of the nude women were later taken from Willie Sharkey when he was arrested in Wisconsin. The FBI later noted that "there were many noisy parties in this apartment and numerous men visited them." A neighbor noted that "six men at a time would enter or leave the apartment together. The next group would enter the apartment only after the first group had left."
FBI agents later tracked down two of the women and described them in their reports as "nice looking women" and "very attractive women. "
Among those identified as regulars to the apartment were "Chicken" McFadden, Basil Banghart and George Wilke. Willie Sharkey, Touhy's enforcer, rented an apartment in the building under the name T.J. Burns and used the Park Ridge Chief of Police as his reference.
He (Roger) left Chicago for St. Paul, but he was unable to find work. Touhy describes his plight, "[I was] dead broke. I bummed my way out of the city aboard a freight train."
Eventually, Roger found work as a telegraph operator for various railroads and commercial houses as he made his way out west. During his travels he worked as an operator for the Union Pacific Railroad, then as a telegraph operator and later as a brakeman on the Northwestern Railroad. Finally he accepted a position as a telegrapher for $185 a month on the Denver & Rio and Grand Railroad and was sent out west by the company, often to Colorado, with most of his time spent in Eagle County.
It was here in Eagle where he befriended Clyde Nottingham, who was said to be the meanest cowboy in the region if not in the state. A giant of a man with a short temper, Nottingham grew up in the rough and tumble world of mining camps. He was a man beset with endless personal problems, and he acted as the local bully. 'When he wanted something," a relative noted, 'he just took it."
In 1899, Clyde married Tillie Samuelson. They had three children, a daughter Lola and twin sons, Harold and Clyde Jr. Harold, who was said to have been a bright child, died at age two, after a week's illness, and Clyde Jr. died in infancy.
Clyde had moved to the area from Iowa at the age of seven. Like his father, teamster William Henry Nottingham, he was known to be mean to the bone. Both men were known to threaten with death anyone that dared cross them.
In 1904, Clyde Nottingham beat and threatened to kill a depot agent named H.G. Comstock and then ordered him out of town. A few days later the clerk spotted Nottingham walking toward him, pulled out a revolver and fired three shots. Comstock failed to kill him but did manage to cut a hole through his pants and give him flesh wounds in two other places. A trial was held, but the jury, knowing Nottingham's reputation, acquitted the depot agent, who left town that same day. A while later Nottingham was arrested for beating up another depot agent-the one Roger Touhy replaced.
Several days after arriving in town Roger Touhy-the five-foot four-inch, ninety-eight-pound kid from Chicago's Valley who never backed down- met Nottingham, the giant rancher with the quick fists.
Roger remembered Nottingham: "I got my first warning of western bad-man danger when a local merchant told me, 'You won't be here long, sonny, we got a rancher, Clyde Nottingham, who runs depot agents out of town. He carries a gun. Guess he don't like you depot agent dudes.'"
He continues, "It was cold that first night in Eagle and I had the stove red hot as I jiggled the telegraph key, handling the freight car, stock car and personnel messages. The waiting room door opened and in came a big man in cowboy clothes and a sheepskin coat. He spat on the potbellied stove.
"I walked to the ticket window, looked out and saw the caller was carrying a .45. He didn't look pleasant, but damned if he was going to run me out of town. 'Mr.,' I asked. He nodded and I said 'Mr. Nottingham anytime you want to spit on the stove go right ahead. But come back the next day after the stove cools and polish it. I ain't going to do it.'"
Remarkably an agreement was reached. Touhy agreed to put Nottingham's letters on the late train and in turn, Nottingham agreed to stop spitting in Touhy's fire. This was the beginning of what Touhy would deem "a fine friendship." Touhy was invited to spend time at Nottingham's ranch with his family. Touhy admits this gave him a "sense of belonging," which he appreciated.
Spending his free time at Nottingham's three- hundred-acre ranch, complete with stream, lake and seven bedroom house, Roger learned big game hunting and horseback riding. He became a better-than- average marksman and acquired his life-long obsession with fishing.
Roger left Eagle after a two-year stay and in 1918 enlisted in the Navy and was eventually stationed at Harvard University where he worked as a wireless operator and taught officers the Morse code.
'The Navy," as Roger liked to point out, "gave grounds for me, a boy from the eighth grade to say honestly to cops, bootleggers, convicts, prison guards and interviewers, 'I've been to Harvard.'"
Opting for an early out with the Navy Reserve, Roger was back in Chicago by 1919, living with his father in suburban Franklin Park and dating Clara Morgan, having kept in touch with her through long letters from Colorado and later from Boston. There was talk of marriage, but Roger set off for the west again, landing in Drummund, Oklahoma where the oil business was in full boom and fortunes were being made overnight.
"I didn't know any more about the oil business then a mink knows about sex hygiene, but I could learn....The Sinclair Oil people, in a moment of laxity hired me as a scout. The experience I had in that line was confined to watching silent western movies in which army scouts killed Indians,"says Tuohy.
Actually the position he filled was as a driver to the world famous geologist Dick Raymond who had been brought in to determine which wildcat wells were producing the most oil and from that, decide which land was worth leasing. "There was nothing," he wrote "against my buying leases that Raymond recommended."
Learning everything he could about the oil business from Raymond, Roger took $1,000 out of his savings and purchased a 150-acre site that Drummond recommended. Within a month, he resold the lease for a 200 percent profit. He repeated the process twenty times in one year. Of that time Touhy said, "[I] never lost on any of them...the money was good, but I was a guy who liked the city. And my mind was on the girl at the telegraph key in the Blackstone Hotel."
He returned to Chicago with $25,000, a respectable fortune in 1920, "and,"he liked to point out, "it had taken me less than a year to earn it."
As dyed-in-the-wool members of the old Valley Gang, the older Touhy boys learned the dark arts of burglary, daylight holdups and labor extortion, at which they excelled. There is a story that became underworld legend, how one stormy night in 1909, Patrolman James Touhy was walking his beat when he confronted his eldest son, Jimmy leaving Paddy the Bear's saloon with a burglar's bag over his shoulder. The normally quick-tempered Touhy remained uncharacteristically calm.
"Open the bag," his father said.
When the young man did as he was told, out rolled burglary tools and a bottle of nitroglycerin- an explosive used on difficult safes around the turn of the century. The elder Touhy cuffed his son and then called a paddy wagon to have the boy taken to the station to be booked.
"You book him,"he told the cop behind the desk. "It's bad enough to arrest my own son without going to court to testify against him."
Nothing good came from the Touhy boys. In 1917 Jimmy Touhy was killed in a botched robbery attempt. His brother, Joe Touhy was killed in a freak shooting ten years later. Brother John tracked down Joe's killer and murdered him, only to die of consumption in the state prison several years later. Tommy Touhy, the second eldest and most fearless and feared of the lot, grew to be a ruthless outlaw who well deserved his nickname 'Terrible Touhy." By 1919, Tommy was one of Chicago's leading hoods.
With poverty and crime on the rise in the Valley, James Touhy gave up on his elder sons, and, early in the summer of 1908, he moved his daughters, Eleanor and Eileen, and ten-year old son Roger to the tiny village of Downer's Grove. The village had been created only seventy-five years earlier, taking its name from a New Englander, Pierce Downer, who settled on what had been the crossing of two ancient Indian trails.
In Downer's Grove, Roger became a better-than- average baseball player and an above-average student. In general it was a pleasant time in his life. "It was a good enough boyhood," he remembered. "I played baseball and raised the usual amount of the devil and got teased because my hair was curley. [sic] If I had anything to gripe about, I didn't realize it, because the other boys didn't have any more than I did, generally speaking."
He took up ham operations as a hobby and built his own set at home and learned the international code. He attended St. Joseph's Roman Catholic church and school while the parish was still being run out of a hall over the top of the Des Plains hardware shop.
Since the family was strapped for cash, Roger worked around the parish as a handyman and assistant to the parish priest and its first pastor, Father Eneas Goodwin. Roger's duties included serving mass as an altar boy and accompanying the priest as his driver in a rented horse buggy on his twice weekly rounds. "At whatever house we stopped there would be refreshments-apple pies, lemonade, thick sandwiches, salads, pickles, ice cream. Father waved the food away, but I ate fit to bust a gut....In the church there was a big oil painting of the Last Supper. Father Goodwin explained it to me, saying that a man called Judas had betrayed Jesus Christ for thirty pieces of silver. A thing like that can have a remarkable influence on a kid. I began thinking of Judas as a stool pigeon, a word I knew as did all youngsters. While sweeping up the church and dusting the pews I would stop and look for a long time at the painting. I picked out the face of a man I figured was Judas, and I would stand there hating him."
Roger Touhy," wrote the Chicago Tribune, "is one of those rare cases in which the man measured up to the legend."
He 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 tenements, 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 policeman. 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, graduated 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 headquarters, 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 owners 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 number 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 middle 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 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 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 majority status in the Valley but managed to retain political 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 lieutenants, "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 reputation 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 pictures 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 blindfolded."
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 enormous 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 everything 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 unrelated 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 pistols 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 murder 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 reputation as a fool and a clown. Despite this reputation 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 magnificent 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 cattle (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 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. He and Druggan were inseparable companions, 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 contempt 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 spacious 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 evasion 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 girlfriend 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 operations and for all practical purposes ceased to exist.
Epilogue: The Pardon
In 1962, just two days before he was to be deported from the United States to a jail cell in England, John Factor was granted a Presidential Pardon by John F. Kennedy.
• • •
Shortly after Roger Touhy was out of the way, the Chicago mob saw fit to push Factor out of the Stardust casino and place the operation into the steady hands of Moe Dalitz. But when the facts behind the transaction hit the media-that John Factor had sold one of the largest and most profitable casinos in the world for the paltry sum of $15 milllion-Attorney General Robert Kennedy ordered an investigation into the sale. The United States Internal Revenue Service along with the State of Nevada Gaming Commission started a joint investigation into the Stardust sale.
The joint force intended to call Factor in for questioning. However they were beaten to the punch when the Los Angeles Office of the Immigration and Naturalization Service (INS) suddenly ordered him in to show due cause why he shouldn't be deported to England where he was still a wanted felon. The INS had now decided, based on Jake's arrest and conviction in 1942 for fraud, that he was an undesirable alien. At seventy years of age, John Factor, who had lived in America since at least 1919, was being ordered out of the country.
The problem was that the INS had never closed its record on Factor since he entered the country through Mexico after the British stock swindle. It was a minor, white lie that kept the record open. Jake had told the INS at the border that he had been born in England while their records said he was born in Poland and the INS could prove it. Unable to show due cause why he shouldn't be deported, Factor was ordered to surrender to the INS on December 25, 1962, at which point he would be arrested and deported to Poland.
At the time, Poland was a backward, war-torn country, crushed under the iron-fisted rule of the Russian Communist Party. The conditions in Poland caused Factor to fight hard to prove to the government that he was, in fact, a British citizen. The problem with sending Jake to Britain was that his conviction for stock fraud remained in force. The second he landed at Heathrow, he'd be jailed. Adding to Factor's woes was the ongoing IRS investigation into payment of his back taxes for the years 1935 through 1939. The government wanted Factor to explain where he received $479,093.27 in income, and Factor couldn't remember. If he was deported, the Government would impound his holdings, which Factor estimated to be $13 million, until the matter was settled, which meant that he would leave the country the way he came in, penniless.16
The only thing that could save Factor from deportation was death or a miracle. The miracle came straight from the White House in the form of a pardon.
Presidential pardons, the last imperial power of the Executive Office, have long been the golden parachute for the mob's monied elite looking to avoid deportation, obtain a position in the casino business or a labor union, or to help muscle their way into a legitimate enterprise.
Abusing the pardon privilege has had a torrid and often astounding history, even on a state level. In the early 1920s, Illinois' incredibly corrupt Governor, Len Small, sold an estimated 500 pardons before he was indicted and chased from office. Small's broker on the pardon deals was a union extortionist named "Umbrella Mike" Boyle, a bigwig in the Electrical Workers Union. Among Boyle's clients was Spike O'Donnell, who started the great Chicago beer wars of 1926 upon his release.
In the 1970s, when federal prosecutors tried to deport southwestern Pennsylvania mob boss, John S. LaRocca, Governor John Fine pardoned the alleged godfather of corruption along with his capo, Frank Rosa. Later, Governor George Earle pardoned Mafia bosses Joe Luciano, Luigi Quaranta and alleged Caporegime Nicholas Piccolo. He also pardoned Frank "Binkie" Palermo, allegedly a made member of the Mafia; Felix Bocchiccio, a fight fixer; Leo Kamminski and Louie Barish, suspected mob members.
One of the most outrageous pardons on record belongs to Harry Truman who pardoned "Ice Pick" Danny Motto, a labor thug in the Gambino family. He had been convicted of wartime racketeering and as a result, Danny the Ice Pick wasn't allowed to hold an "elective" office in New York's Bakers Union local 350, a 900-member local which he terrorized from 1939 until his death in the 1980s. Motto's 1947 federal racketeering charge, plus a previous one for murder, gave the Justice Department due cause to deport him.
However, at the last moment, after deportation had been ordered, Truman granted a pardon and the deportation was canceled. The man who worked behind the scenes on Motto's behalf was his lawyer, Herb Itkin. Itkin was a shadowy figure with unspecified connections to Naval Intelligence and later to the CIA. It was Itkin who introduced New York's mayoral administration (under John Lindsay) to labor mobster and loan shark Anthony "Tony Ducks" Corralo, who was also Danny Motto's boss. That meeting would eventually lead to the James Marcus scandal of 1966.
Truman also pardoned many felons from the Boss Pendergast political machine. More than half of those pardoned were convicted of interfering with a citizen's right to vote, or, in other words, were members of Owney Madden's goon squads.
And now it was John F. Kennedy's turn. During his brief presidency, Kennedy issued 472 pardons, more than any chief executive before or since. About half of these appear to be questionable, at best.
On November 26, 1962, Attorney General Robert Kennedy did something unusual: he changed the laws that govern presidential pardons. It was unusual because the fourteen sets of rules, all advisory in nature that govern presidential pardons, have seldom been tampered with, since they were written in 1893.
The change that Kennedy made in the rules,17 only sixteen days before John Factor was pardoned, allowed all pardon requests to go directly to the White House and then to the Justice Department, and not the other way around.
A few days after Kennedy changed the rules for pardons, an alcoholic Chicago hood named Chuckie English, a former 42 Gang member and bodyguard to Sam Giancana, strolled out of the Amory Lounge and leaned up against the FBI observation car parked just across the street from the tavern. The agents reported, "English is bemoaning the fact that the federal government is closing in on the organization and nothing can be done about it. He made several bad remarks about the Kennedy administration and pointed out that the Attorney General raising money for the Cuba invaders makes Chicago's syndicate look like amateurs."
Business executives and CEOs across the country were whispering the same thing. Many of the executives were amazed to find themselves talking on the phone with the Attorney General of the United States and were even more amazed at what they heard. Kennedy operated shamelessly. He told businesses he wanted money for the Bay of Pigs program, and reminded them that they had either pending contracts before the government or criminal cases before the Justice Department. Before they could respond, Kennedy again mentioned the fund to free the Cubans, and hung up.
John Factor also knew about the fund to free the Cubans. In fact he threw $25,000 into the project and later explained to a curious press corp that James Roosevelt, the problem child of the clan, had approached him about the donation.18
Factor had already given Kennedy $25,000 to help retire his campaign debt and his wife gave several thousand more. Despite the endless rumors to the contrary, Factor denied that he had given $1,000,000 to the Joseph P. Kennedy Foundation19 as well.
Miraculously, on December 24, 1962, after Factor's contribution to the Bay of Pigs fund, President John F. Kennedy signed a presidential pardon for Factor for the mail fraud conviction. As a result the deportation proceeding against him was dismissed. For mob watchers and law enforcement employees, who had put so much faith in Robert Kennedy's war on crime, Jake the Barber's presidential pardon fell from the skies like a bolt of lightning.
It was never made clear if Kennedy's actions also killed the investigation of Factor's dealing in the Stardust but one way or the other, that investigation was closed.
Factor always denied that the mob used pressure with the White House to win him his pardon but in mid-1963, while Jake was trying to gain control of the National Life Insurance Company of America and was buying up the company's shares at $125 each; he sold 400 shares to Murray Humpreys at $20 each. Factor's loss was $105 per share. Humpreys then sold the shares back to Factor for $125 a share, making him $42,000 richer in one day.
As far as the Hump's unusual and creative stock transaction with Jake20 the Barber was concerned, the government decided that it was a taxable exchange "for services rendered" and sent capital gains tax bills to both of them.
A presidential pardon was good but just to be sure, on July 16, 1963, in Los Angeles, John Factor, the poor kid from the ghettos of Chicago, raised a slightly shaking hand and along with a dozen other more recent arrivals took the oath of citizenship of the United States of America. "I'm the luckiest man alive, “he said and he was probably right.
• • •
John Factor died after a long illness at the age of ninety-one in 1984. More than 400 mourners, including California's Governor Pat Brown and Los Angeles Mayor Tom Bradley attended his wake.
During the last half of his long life Factor contributed millions to charitable causes and made serious efforts to change his life and his reputation, but nothing ever changed.
Once, after giving an enormous donation to a charity in the mid-sixties, the newspapers that covered the event wrote about Factor's shady past. The report brought on a rare display of public anger when Factor called the reporter on the story and demanded to know "What, my dear, must one do...how much does a man have to do...to bury his past?"
It was proof that despite his incredibly agile mind, John Factor either never really understood or refused to recognize the harm he had inflicted on others during his long life.
His stock swindle in England had fleeced thousands of people out of their life savings. His self managed kidnapping had sent five innocent men to jail for a total of 125 years. The skim from the Stardust he helped to shelter produced an estimated $2,000,000 a year, net income, for each of the Chicago bosses who held points in the resort casino.
A better question would have been, "How much should a man pay before he is allowed to bury his past?"
• • •
In the end there were no winners, only losers. All that was left was the tragic tale of two men who willfully lived outside the law and then refused to accept the consequences of their actions. Up to their dying day, neither Roger Touhy nor John Factor would ever fully admit to wrongdoings in their lives or to the suffering they had created for others, including those who loved them.
16. If his wife, Rella, went with him, he would have been more fortunate; the INS estimated her wealth to be, in 1960, $40 million.
17. The rules that govern federal pardons are just those...rules...not laws. They can be made, broken or ignored by the President. All of these rules are simply procedural in nature. Pardons are the last imperial power of the presidency, and aside from the few pardons that have outraged Americans, such as Jimmy Hoffa's highly questionable pardon, the practice goes on, unregulated.
18. James Roosevelt, then a member of Congress, strongly supported Factor's bid for a Presidential Pardon as well.
19. The Foundation refused this writer access to their records and refused to deny or confirm that Factor donated money to its treasury. The reader should note that the Foundation is a privately held trust; it does not have to account for its spending or explain salaries given to its executives, many of whom are, and have been members of the Kennedy family.
20. In 1960 an FBI informant, believed to be Jimmy "The Turk" recorded Humpreys and Joey Glimco discussing Roger Touhy's murder, a month after it happened. Humpreys said, "But this Factor, he's a dirty cocksucker...here's a guy I've always gone along with. We go ahead, and we do it, originally, and I wouldn't...so he says, ok...200,000." It’s not clear from the transcripts if Humpreys was referring to a payment from Factor to him of $200,000 to murder Touhy. Humpreys added, "I had to give the cocksucker ten thousand dollars."
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