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"Jake the Barber" The Story of a Successful Conman

With apologies to Joseph "the Yellow Kid" Weil, John Jacob Factor ranks as one of the most successful swindlers of all time. In his heyday, which spanned the era of the Roaring Twenties through the 1960s, Factor engineered frauds on both sides of the Atlantic, consorted with the Chicago mob, and charmed President John F. Kennedy and his "Rat Pack" pals during the golden age of JFK's self-styled "Camelot" regime.
He was a rabbi's son, born Lakow Factrowitz, the youngest of ten children. Jake, as he preferred to be called, was born in England but was taken to Lodz, Poland before his first birthday where he lived until he was 11 years old.
At the turn of the last century, the family emigrated to St. Louis, Missouri and then on to Chicago. Although not illiterate, Factor could barely read or write. "I have," he said, "a hazy recollection of several months of schooling in Poland."
The family was desperately poor and it was Factor's mother who supported the family in hard times through various menial jobs, mostly as a street peddler.
Jake's half brother, Max Factor, eventually made his way out to California and settled in West Los Angeles where he found work as a makeup artist with the major studios. Max Factor helped invent pancake make-up.
Jake Factor took the low road to success. While still a teenager in the early years of the century, he went to work as a barber in his brother's West Side shop, using the money he earned to support his parents. Then later, he took at job at Chicago's elegant Morrison Hotel, trimming the sideburns of the rich and well born while making important contacts that would prove useful to him later in life.
From these humble beginnings, Factor acquired a nickname that would haunt him for the rest of his life, a name he hated so much he sometimes paid reporters not to call him "Jake the Barber" Jake abandoned the shop in order to peddle securities in the stock market but he was indicted under a federal warrant for stock fraud in 1919. The case was closed after he agreed to return the funds, but Factor was indicted again in Florida in 1922 and 1923, this time for land fraud.
In the next few years there were additional indictments for mail fraud and larceny. He participated in a gold mine stock swindle in Canada and another in Rhodesia, but the government was never able to seal a conviction in these cases. Jake the Barber returned to Chicago, rich enough to live in a 14 room Gold Coast apartment, but still he wanted more.
In late 1923, Factor convinced New York's master criminal, Arnold "the Brain" Rothstein (the gambling boss who fixed the 1919 World Series), to put up an initial cash investment of $50,000 that Factor needed to pull off the largest stock swindle in European history.
Handsome, relaxed and a pleasant sort of man, Factor arrived in London, England in early 1924 and began selling worthless penny stocks to gullible British investors with great success. He advertised his operation in a publishing venture known as the Broad Street Press, which were edited and distributed by Factor's henchmen.
In any successful scam, greed is always the hook. Factor assured the investors a guaranteed return of between seven and 12 percent on their initial investments, an enormous sum of money in those days compared to the one and two percent normally paid out by banks and brokerage houses.
Factor was careful to pay each dividend on demand, but only because he knew his trusting investors would generate additional business by spreading the news among their friends.
Factor accumulated $1.5 million and skipped town secure in the certain knowledge that the bilked victims would not dare file a formal complaint. To do so would reveal their stupidity and avarice. Not a single charge was filed against Factor.
Bankrolled by Rothstein, Factor returned to England in early 1925, to pull a second deadly scam. At the heart of the swindle was the Tyler Wilson and Company stock brokerage firm Factor had invented. After presenting his client list a legitimate stock offering called Triplex which sold at $4.00 a share, Factor offered to buy the stock back at $6.00 a share, thus earning his victims a quick 50% profit. A month later, Factor, operating through Tyler Wilson, offered another stock called Edison-Bell at $3 a share. He quickly bought it back at $6 a share, always careful never to actually deliver the stocks certificates to the buyers, because he knew it was a worthless paper transaction. If the transactions had been real, Factor stood to lose $750,000.
Established in a luxury suite of rooms in Grosvenor Square, London, Factor sent his investors information about two worthless stock certificates, Vulcan Mines and Rhodesian Border Minerals, reputed to be lucrative South African gold mining companies, which Factor hinted, were on the verge of a big hit.
The Barber sold shares in the companies for as low as 25 cents each, allowing thousands of new investors to enter the scam. He then pumped up the earnings up to $2.50 a share.
Tens of thousands of money hungry buyers flooded in, and Jake made sure that each one received an unspecified plot of land in Africa, making fraud difficult to detect and prove.
In 1930, English newspapers took note of Factor and his "Ponzi" schemes. There were persistent rumors that members of the royal family had invested hundreds of thousands of dollars in his phony stocks.
Then, without warning, Jake the Barber closed Tyler Wilson & Co and fled England with an estimated 1,619,726 pounds, or about $8,000,000 U.S. dollars, an incredible sum of money in the Depression. Jake made one big mistake that would come back to haunt him in later years. He returned to the United States by way of Mexico through El Paso, Texas, in December of 1930. Factor was admitted back into the United States as a visiting immigrant. He swore out a statement that he was born in Hull, England on October 8, 1892.
The United States Immigration Department already had papers on Jake, sworn out by his parents upon their arrival to the States in 1905, that Jake the Barber was a Russian national, born in Lodz, Poland on January 10, 1889.
Immigration officials opened a "Factor file," which they later used to deport him from the country. Meanwhile, the notorious New York beer runner and gangster Jack "Legs" Diamond followed Factor's adventures in England with interest, and decided he wanted every penny the scam had earned for his narcotics business.
Arnold Rothstein taught Legs Diamond everything there was to know about the narcotics racket, molding him into an expert heroin importer.
The drug money made Rothstein careless and lazy, and that was a dangerous position to be in, in the volatile world of narcotics smuggling.
Soon others began following the dope trail that Rothstein had blazed. They started to hedge in on his territory. What Rothstein refused to surrender to rivals, they took by force. One of those takers was Legs Diamond, alleged to have participated in the murder of Rothstein at a New York card game in 1928.
With Rothstein disposed, the remnants of his once vast criminal empire were up for grabs. Legs Diamond laid claim to Rothstein's European drug smuggling operation, import routes and contacts. But laying claim to the routes and controlling them were two different issues. Control of the U.S. side of the narcotics market hinged on the money-earning European hoods that needed to export their dope into the lucrative and insatiable American markets.
They wanted to do business with someone who had the cash flow to saturate the states with low cost, high quality dope on a continuous basis.
Legs Diamond had the money, in theory, at least. Prohibition had made him rich, but all of his cash was tied up in a street war for control of the Manhattan bootleg beer outlets. He tried to raise the seed money to enter the narcotics market from different sources, including the Mafia. The underworld also knew and understood that Diamond lacked real organizational ability and that he drank to excess, and was violent and mentally unstable to effectively deal in the sedate and shadowy world of international narcotics trafficking.
With no where else to turn, Diamond sent word to John Factor over in England that he was assuming control of all of Rothstein's rackets and demanded his share of the take from the stock swindles. Factor never responded, assuming that once Arnold Rothstein, his original financier in the scheme was dead and buried, that the proceeds from the swindle were his and his alone. Diamond disagreed, and took a luxury liner to England to meet with the Barber, but Factor avoided his own execution by simply returning to the United States and hiding out in Chicago, enjoying the hospitality of Murray "the Camel" Humphreys whom he cut in for a percentage of the take. Factor knew that a killer like Legs Diamond didn't give up that easily, especially when millions were at stake. Never a violent man, Jake the Barber had enough sense to partner with those who had no aversion to violence.
Legs Diamond gave up the chase to attend to his own trial in New York State for attempted murder of a competitor. The jury found him not guilty, and that night Diamond went out with friends to celebrate. Returning to his room in an Albany, New York boarding house in the early morning hours of December 17, 1931, Legs fell into a drunken stupor. A half an hour later, two well-dressed men entered Diamond's room and pumped three .38 slugs into his head at point-blank range, instantly killing him.
Murray Humphreys was suspected of engineering the murder, if not committing it himself, on behalf of his new business partner, Jake Factor, but the suspicions were never proven, nor was there an investigation into the murder. No one seemed to care.
With Diamond out of the way, Jake the Barber emerged from hiding, only to be arrested in Chicago on demand of the English government for receiving property known to be fraudulently obtained. Factor was freed on a $50,000 bond.
On December 28 1931, the United States Commissioner in Chicago ruled that Factor should be extradited to England, where he had already been tried, convicted, and sentenced to eight years at hard labor (in absentia).
Factor's lawyers argued unconvincingly that each of his victims had received a small plot of land in South Africa, or at least the deed to one, and therefore, no one was swindled.
A federal judge agreed with Factor and over-ruled the Commissioner. The Justice Department appealed and the case was on its way for review to the Supreme Court in Washington.
It was generally agreed in legal circles that Factor had a weak case and would be extradited before the spring. Armed with several million in cash and the best lawyers money could buy, the Barber managed to delay his hearing until April of 1933.
Two days before Factor was due to appear before the Supreme Court Jake the Barber's son Jerome, was kidnapped in Chicago. A ransom note arrived asking for $50,000. Murray Humphreys, the syndicate labor plunderer and Jake the Barber's close friend, led the negotiations with the kidnappers from a suite adjoining Factor's room.
Humphreys' role in the kidnapping would have gone unnoticed but the messenger who delivered the ransom note was hauled into detective headquarters for questioning and was grilled for 45 minutes. When he was released, the young man was swarmed by news reporters "I can't talk to you guys," he said "Murray Humphreys told me to keep my mouth shut"
Chicago police raided a suite at the Congress Hotel, which the press dubbed "the Hoodlum detective agency," and arrested the heirs to the Capone syndicate; Murray Humphreys, "Machine Gun" Jack McGurn, Sam "Golf Bag" Hunt, Tony Accardo, Frankie Rio, Phil D'Andrea, Rocco Di Grazio and a half dozen other mob hangers-on, all of whom told the police the same thing: they were there because they had been brought in by Murray Humphreys to secure Jerome Factor's safe returned.
The cops locked them up on vagrancy charges, but within an hour Factor posted their bail and all were released. While Police were in the apartment they found a ransom note from Jerome's kidnappers. When questioned, Factor claimed that he had written the note "to confuse the kidnappers" After eight days in captivity, Jerome Factor was released on a Chicago street unharmed. Many people in Chicago simply assumed that Jerome, the good son, had agreed to a kidnapping rigged by his father and Murray Humphreys to delay the Supreme Court hearing.
With Jerome Factor returned home safely, Jake's appointment to appear before the United States Supreme Court was put back on the docket.
Factor was an exceptionally smart and practical man, he knew no matter how many shrewd lawyers he could buy, he was going to lose his case before the court and would soon be deported.
While discussing his limited options with the attorneys, Factor mentioned the delay in the hearing brought about by Jerome's kidnapping.
They reasoned that if Jake were to be kidnapped, and then returned safely to his custody, following capture of the kidnappers, then the ensuing trial would be delayed long enough for the statute of limitations against him to run out. It wasn't a sure thing, but Jake's deportation to a jail cell in England appeared certain.
Factor presented the idea to Murray Humphreys. Frank Nitti signed off on the plan to help out his pal, Jake. Humphreys and Nitti, and Paul "the Waiter" Ricca, Nitti's lead counsel in the mob, may have already had information that Jerome's kidnapping had been pulled off by independents who were employed by Roger "the Terrible" Touhy, a bootlegger who was operating out in the Northwest suburbs of Cook County. The Touhy gang was small but persistent, and had waged a sporadic war of attrition against the Outfit since 1927.

The shrewd and calculating Ricca decided to blame Roger for the kidnapping. After all, the mob wasn't having any luck shooting Touhy to death, or blowing him up, which they had tried to do on several occasions in the past year. But framing Roger for a kidnapping might work, so Nitti gave his approval with the understanding that none of the syndicate people were to be involved. Kidnapping without a long-term goal wasn't what the Chicago outfit specialized in. They were racketeers by trade. Kidnapping was a dirty business, and a high profile crime sure to invite the headline-loving FBI.
In the latter part of August 1942, Roger Touhy, once an important Chicago bootlegger, was serving a life sentence for a crime he never committed. Touhy was framed by the Capone mob with the apparent connivance of a corrupt Cook County State's Attorney named Thomas Courtney, who made political hay out of this page-one conviction. At the end of his rope and out of aces, Touhy was desperate to take matters into his own hands.
In 1933, when the international con-man Jake "the Barber" Factor was on the verge of extradition back to Great Britain for a raft of stock swindles foisted on overseas investors in the 1920s, it was decided to arrange a bogus kidnapping with the help of Frank Nitti, boss of the Chicago mob, and heir to Al Capone's empire. Factor was "abducted" outside the Dells Roadhouse in suburban Morton Grove, taken to a safe house until a phony "ransom" was paid and his release assured.
With the connivance of the Nitti gang, Factor had "fingered" Touhy as his abductor. Factor was held by the government as a material witness, just long enough to ensure that he would be released under a writ of habeas corpus. U.S. laws required that a person who is not extradited within sixty days, be released. Factor's lawyers of course, played the percentages and were able to spring their client, who fled to Los Angeles where he invested his ill-gotten fortune in real estate.
Virtually every motion Touhy filed to have his case reopened was denied without a hearing, despite mounting evidence that proved his innocence.
"I stayed awake until dawn in my cell, thinking," Touhy wrote. "I was without hope. I was buried alive in prison and I would die there. I couldn't see a light ahead anywhere. Nothing but darkness, loneliness, and desperation. The world had forgotten me after eight years. I was a nothing. Well, there was one way I could focus public attention on my misery. I could escape. I would be caught of course but the break would show my terrible situation. What cockeyed thinking that was, my mental attitude was a mess, I later came to realize."
The convict who convinced Touhy to escape was Gene O'Connor, a.k.a "James O'Connor," which was another name he used in long criminal career. Actually, his real name was Eugene Lathorn, and he was serving a one to life sentence for a May 1932 robbery-slaying of a Chicago policeman. For O'Connor, prison escape was a way of life. By October of 1942 he had already scaled the walls twice.
Touhy and Banghart were released from prison in 1959 and 1960 respectively. Roger Touhy was murdered by vengeful mob assassins on the front porch of his sister's house in Chicago's Austin community just twenty-five days after walking through the prison gates. Jake Factor was in Chicago at the time, wining and dining his entourage on Rush Street when he heard the news. Factor expressed false sympathy when questioned by reporters.
Basil Banghart retired to Washington where he lived out the remainder of his life in relative comfort, after inheriting a small fortune from a widowed aunt.
As to the man most responsible for Roger Touhy's collective misfortunes, American justice finally played its hand in 1943, though it was probably a moot point to Touhy by this time. Jake "the Barber" Factor was sentenced to six years in prison for mail fraud. He served his time and was released in 1948. He returned to the West Coast where he made a fortune in questionable real estate deals.
In the 1950s, Chicago mob moss Tony Accardo installed Factor as Chicago's "front man" at the Stardust Hotel in Las Vegas, a "low roller" casino that was the place to go for sports betting. It was an ideal marriage. Factor hustled the celebrities and made his bones with the movers and shakers of the nation who passed through Las Vegas.
In 1960 Factor donated a considerable sum to John F. Kennedy's political war chest, which earned him a full presidential pardon in 1962 from the grateful Kennedys. Factor continued to curry the favor of national political leaders like Hubert Humphrey and Richard Nixon up until the moment of his death in 1984. He is buried in Hollywood not far from the show business celebrities he had entertained in real life.
wikipedia
John "Jake the Barber" Factor was a Prohibition-era gangster. He was the brother of prominent businessman Max Factor, Sr., the founder of Max Factor, a makeup company.


Early years

Born Iakov Factorowitz or Faktorowicz, the son of a rabbi, he and his family left England, returning to Lodz, Poland, not long after his birth. He claimed he was born in Hull, Yorkshire, when he later faced prosecution in the United States. According the LA Times of the day, he produced an affidavit in court said to be from the rabbi who circumcised him to confirm his birth place. He could not produce a birth certificate. The family immigrated to the United States in 1904, settling in St. Louis, Missouri. Even though he was poorly educated, Factor had a sharp mind and by the early 1920s was becoming known as a successful confidence man. In 1923, after moving into stock fraud and selling worthless real estate during Florida's "land boom" during the early 1920s, he was loaned $50,000 by mobster Arnold Rothstein to pull off what was then considered the largest stock swindle in European history.
Jake Factor's "kidnapping"
In 1933, Factor was on the run from England, where he had been sentenced to a total of twenty-four years. Factor worked a deal with Al Capone to fake a kidnapping and blame it on Roger "Terrible" Touhy. Touhy was convicted on false evidence and sentenced to 99 years in prison. The kidnapping had been set up to eliminate Touhy from competition in Chicago.

Touhy, Factor's wrongly accused kidnapper, escaped from prison in 1942, but was soon recaptured. He was finally found innocent of all charges and released on November 25, 1959. Touhy was shot to death while visiting his sister on December 17. He was probably murdered on the orders of Murray "The Camel" Humphreys, whom he had humiliated many years earlier, and who was acting on behalf of Jake Factor. Touhy had written a book about his false imprisonment, The Stolen Years.
Later years
At the time of Roger Touhy's death, Factor, now well involved with mob interests in California and Las Vegas, was in Chicago, enjoying a steak at The Singapore, a Mob-controlled restaurant on Rush Street. He later became the front man for Chicago at The Stardust Casino, after its creator, Los Angeles gambler and crime figure Tony Cornero, died in 1955, shortly before the casino was finished being constructed. On December 3, 1962, when Factor was finally about to be deported back to England, he was given a Presidential pardon by John F. Kennedy. In exchange, Jake gave Kennedy $25,000 in cash to help fund the Bay of Pigs fiasco. He sold the Stardust Casino for $14 million and then claimed bankruptcy.
The IRS looked into Factor's financial records and found that Jake had not paid taxes from 1935 to 1939. He was also found to have the lump sum of $479,093.27 in his name. When the government asked Jake how he got the money, he claimed he could not remember. Later, Jake tried to bail out Teamsters Union boss Jimmy Hoffa of his financial Florida real estate problems. He was also involved in a questionable stock transaction with Murray Humphreys.
Jake spent the last twenty years of his life as a benefactor to California's black ghettos. He spent millions of dollars building churches, gyms, parks and low-cost housing in poverty stricken black ghettos. When Jake Factor died, three U.S. senators, the mayor of Los Angeles and several hundred African-Americans attended his funeral.

Baby Face Nelson and the Touhy gang




Lester Gillis was born on December 6, 1908 and grew up in Chicago but he became known as Baby Face because he had a very youthful appearance. His habit of stealing other people’s cars meant that his teenage years were spent in and out of reform schools. Although he married his sixteen year old girlfriend in October 1928 after she became pregnant, the birth of a son did not motivate him to stay out of trouble. Instead, he joined a gang that stole tires before graduating to driving trucks with bootleg whiskey. Two years later, the need to feed a wife and two children led him to form a gang that specialized in armed robbery, including jewelry stores, banks and the homes of rich people. Despite assuming the alias of George Nelson, the frequent number of jobs meant that he would eventually be recognized, although mugging the wife of William “Big Bill” Thompson, the mayor of Chicago, did not help. He and most of his gang were arrested in February 1931, but he used a smuggled gun to escape while being transferred to prison in February 1932.
Contacts with Roger Touhy’s gang got Nelson a job guarding liquor shipments in San Francisco where he came to know Johnny Chase and Joseph “Fatso” Negri. After six months, he felt there was too much chance of being caught so he went to Reno, where he met Alvin Karpis, who was on vacation. He wanted to work with the Barkers but Karpis felt he was too rash, so arrangements were made for Nelson to learn from Ed Bentz, a veteran bank robber. Bentz selected a target, prepared a getaway map and even suggested that Homer Van Meter and John Dillinger take part in the first job but Nelson refused to work with strangers. Against his better judgment, Bentz found himself agreeing to lead the actual raid at Grand Haven, Michigan on August 18, 1933. The robbery was almost a disaster, since the two men left outside proved unable to stop the owner of a nearby furniture store from scaring off the getaway car. Bentz was able to grab another car but the getaway map had been in the getaway car. Worse, a member of the gang was captured by the bank manager and the car quickly ran out of gas, while a second commandeered car developed two flat tires. It took all night to make it back to their meeting place and when it turned out that each person’s share was $600 Bentz said good-bye to Nelson and his band of incompetents.
Nelson’s brief career as bank robber nearly came to an abrupt end a few weeks later when Frank Nitti, Al Capone’s successor, ordered a hit against him because of his ties to rival gangster Roger Touhy. Warned by Karpis, Nelson avoided Nitti’s hitmen and shifted operations to St. Paul, where he recruited Homer Van Meter and Tommy Carroll. They robbed the First National Bank in Brainerd, two hours north of St. Paul, on October 23. After forcing the janitor to let them into the bank before it opened, they then took the employees prisoner when they arrived for work and walked out with $32,000. 
 

The FBI's Public Statement on Touhy

Roger "The Terrible" Touhy's Gang

In the latter part of 1933 and the early part of 1934, the Chicago gang of Roger "The Terrible" Touhy was smashed.
Singly and in groups, the Touhy mobsters were accounted for. James Tribble was murdered on September 8, 1933 in Chicago. William Sharkey committed suicide at St. Paul on December 1, 1933. Touhy himself and two of his henchmen were convicted in state court at Chicago on February 23, 1934, and sentenced to serve 99 years in prison for kidnapping John "Jake the Barber" Factor and holding him for ransom. The FBI had investigated the Factor kidnapping, but had stepped out at the conclusion of the investigation and turned over all evidence to state authorities. The federal courts had no jurisdiction because the kidnappers had not taken their victim across a state line.
Charles C. Connors was murdered at Willow Springs, Illinois, on March 13, 1934. On the same date, Basil "The Owl" Banghart, machine gunner and aviator for the mob, was convicted in state court in Chicago and sentenced to serve 99 years for participating in the Factor kidnapping. Two months later, Banghart was also tried in federal court at Asheville, North Carolina, and sentenced to serve 36 years in prison on a charge of robbing United States mail.
Two remaining members of the Touhy gang, Isaac A. Costner and Ludwig Schmidt, were also convicted on the mail robbery charge.
Thus, by the end of May, 1934, three members of the mob were dead, and 11 were in prison serving long terms.
 
For half a decade, the northwest section of Cook County, Illinois, had been known as Touhy Territory and the infamous mob had made bizarre history throughout the Midwest and along the Atlantic seaboard under the leadership of Roger Touhy, one of six notorious sons of James Touhy, deceased, a former patrolman in the Chicago Police Department.

Touhy "The Terrible" was quickly forgotten after he was received in Stateville Penitentiary at Joliet in 1934. Banghart started serving his long term in the Illinois State Prison at Menard. After a break from Menard in 1935, however, he was transferred to Joliet, where he renewed acquaintance with Touhy.
For seven years, Touhy and Banghart remained in prison, keeping in touch with their old outside contacts through the fantastic medium of the underworld grapevine, watching for any possible chance of escape.
They took no one into their confidence. Banghart already had four previous escapes on his record, and when he went to Joliet, he boasted that no prison in the world could keep him. He observed the activities of prison guards and assimilated every item of information that might be important in a planned escape. He learned the exact location of all prison facilities; the height of the walls; the position of the prison towers and the distance between them; and the number of guards and the kind of weapons they carried. He even claimed to know that the guards carried rifles sighted in at 100 yards, although they manned towers which were 300 yards apart.
Ultimately, a plan of escape matured, a plan which necessitated assistance both inside and out.
First of all, Touhy and Banghart needed guns; so they took Big Ed Darlak into their confidence. Edward Darlak was a 32-year old lifer, received at Joliet on October 14, 1935, under a 199 year sentence for murder. Darlak sent word to a young brother, Casimir, on the outside. Casimir got two .45 caliber revolvers, together with ammunition, and one night in August, 1942, tossed them into bushes near the prison. The guns were smuggled into the prison by a trusty who had the duty of lowering the prison flag each evening. He carried the guns in, wrapped in the flag.
With this accomplished, Banghart started negotiations for outside assistance. He needed a getaway car and a hide-out. Tentative arrangements were made but the plans were never consummated. The shabby characters willing to provide such services for a fee were not punctual or reliable. Again, it was "The Owl" who overcame the difficulties. He observed that a prison guard who manned tower number three drove his own car to work and left it parked near the tower gate, outside the prison wall. Banghart felt he could shift for a hide-out once he reached that car, because the entire Chicago area was familiar territory.
Touhy, Banghart, and Darlak passed word to four other Joliet long-termers willing to risk a break:
-William Stewart, 43 years old, under two 20-year sentences as a habitual criminal, parole violator and highway robber;
-Eugene Lanthorn, 36 years old, under a sentence of one year to life for assault to commit murder and for two previous escapes from Joliet;
-St. Clair McInerney, 31 years old, under sentence of one year to life for robbery, burglary, and violation of parole; and,
-Martilick Nelson, 40 years old, under sentence of one year to life as a robber, habitual criminal and parole violator.
Shortly before 1:00 p.m., on October 9, 1942, Touhy began the break from Joliet. He assaulted the driver of a prison garbage truck, obtained the truck and drove to the mechanical shop where Lanthorn was working, arriving there simultaneously with Banghart, McInerney, Darlak, Stewart, and Nelson. Working together, the seven convicts overpowered guards on duty in the shop, cut telephone wires, ripped some ladders out of locked racks, piled into the truck and headed for the northwest corner of the prison yard, holding two guards as hostages. Touhy and Banghart were brandishing .45 revolvers. Lanthorn was armed with a "Molotov Cocktail"—a crude incendiary bomb which he had fashioned in the prison shop and which he intended to use to start a panic if necessary. He did not need to use his bomb, however.
When the truck pulled up at the foot of tower number three, one of the convicts fired at the guard in the tower, bringing him under control. Others threw ladders up against the wall. Touhy led five of the men up into the tower where they disarmed the guard and seized the keys to the tower gate and the keys to the guard's car. Banghart stayed below to cover them and the guards who had been brought from the shop as hostages. Nelson went down the outside wall by rope, opened the tower door with the guard's keys, and the gang ran out. They fled in the guard's automobile taking the cinder road that would bring them out on the highway to Chicago. The convicts were well armed. From tower number three, they had taken two high-powered rifles and a .45 caliber handgun.
At eight o'clock that evening, the getaway car, traveling at furious speed, broke through a police blockade at Elmhurst. At 11:00 p.m., the car was abandoned at Villa Park, in the middle of town where it could not be missed; the gang's way of notifying the FBI that they had not taken a stolen car across a state line.
From Villa Park, they fled into the Cook County Forest Reserve on foot and hid out in a shack for four days. Banghart foraged for food at night. On the evening of October 13, he returned to the shack with a stolen automobile and moved the gang to a 13th street apartment on the West Side.
Posing as long-distance truck-drivers, they all lived in his apartment for almost two months. Banghart was trying to hold them together long enough to plan and execute some big-time hold-ups which would bring in the fabulous sums of money needed in their schemes. They wanted to buy a farm near Chicago for a hide-out; they wanted legitimately purchased automobiles to obviate the danger of traveling in "hot" cars; and they wanted plastic surgery work done to change their appearances and destroy their fingerprints. Touhy was said to have the contacts for the plastic surgery, but the cost was $100,000.
Holding such a collection of desperate men together and keeping them in safe hiding was no easy job. Banghart ruled them with an iron hand. He allowed no drinking, except for an occasional bottle brought into the apartment, and permitted no promiscuous associations with outsiders. Every day when a man went out for food and supplies, Banghart, armed with a sawed-off shotgun wrapped in a newspaper, followed to convoy. The convicts changed clothes with each other frequently, made every effort to disguise themselves and, when on the streets, always walked facing oncoming traffic so that police or FBI cars could not slip up on them from behind.
About December, 1, 1942, the gang, feeling that neighbors had begun to notice them, moved to a nearby apartment, but bedbugs drove them out in two days. Their next residence was in the Doversun Apartments on Sunnyside Avenue.
They had been at Doversun only a few days when the first serious rift occurred; Stewart and Nelson went out alone one night and returned to the apartment drunk. Banghart disarmed them and pistol whipped them both, beating them until they were unconscious. Leaving the two battered and apparently dying, the other five convicts immediately abandoned the apartment and lived for a few days in a garage where they had their stolen car hidden. Banghart, Darlak, Touhy, McInerney, and Lanthorn ultimately moved into the Norwood Apartments at 1256 Leland Avenue. Stewart and Nelson somehow recovered, got out of the Doversun Apartments before they were discovered, and separated—Nelson to go to Minneapolis and Stewart to seek refuge with a former girlfriend in Chicago.
Although this crowd escaped from Joliet on October 9, 1942, the FBI did not enter the search for them until October 16, 1942. They were state prisoners, and in escaping they violated no federal law. But after a week had passed and they had failed to present themselves for registration under the Selective Service Law they became draft delinquents. The FBI formally filed on them for failure to register and obtained federal warrants of arrest.
Realizing that this gang of desperadoes constituted a grave threat to the public safety, Director J. Edgar Hoover personally took charge of the Touhy investigation at its inception. From his Washington Headquarters he directed a continent-wide man hunt that had no equal since the days of Dillinger.
Agents at FBI Headquarters dug into the old voluminous files on the Factor kidnapping for every fragment of information about Touhy and Banghart's past associates, hide-outs, habits, friends and relatives. Agents were sent into Joliet to review prison records for the names of all relatives, visitors, and correspondents of all seven escapees. They interviewed prison guards and convicts who were known to have associated in any way with any of the seven subjects. Convicts who had formerly associated with them but who had already been discharged from prison were located. Old prison records in other institutions where the subjects had served time were examined. Every known relative, every former friend or character witness, every attorney who was known to have represented the men - every possible contact of all seven subjects was located. Those who were cooperative were interviewed for their assistance, while others were watched night and day. Photographs, descriptions, and brief criminal histories of all the escapees were sent to every law enforcement agency in America, to all leading newspapers and to agencies in Canada and Mexico. Stops were placed along the borders and all patrol stations were given photographs of the convicts.
Every lead, no matter how shadowy, was cautiously and thoroughly run out.
In the initial stages, the investigation was primarily an exhaustive preparation of a nation-wide network of ambushes. Sooner or later a break would come—one of the fugitives would attempt a contact that was covered.
Mere waiting, however, was not enough. To conserve manpower and expenses and to bring these desperadoes into custody at the earliest possible moment, it was necessary to make deductions on which to predicate offensive action.
Director Hoover and his staff deduced that Banghart would try to hold the gang together; that they would hide out in Chicago; and that, by means of pocket picking and petty stick-ups, they would obtain identification papers such as Selective Service cards to avoid an accidental arrest for vagrancy or the like.
Agents carefully reviewed the Chicago police files on unsolved petty stick-up cases in which the victim had lost a wallet containing draft cards and other identification.
The first break came on December 15, 1942, when Nelson attempted to contact a relative in north Minneapolis. Knowing, therefore, that Nelson was in the area and that he was not staying with relatives, agents assumed that he was stopping at some cheap hotel using an alias. A logical alias would be the name of some Chicago citizen who had lost his wallet in a recent stickup.
An FBI agent and an officer of the Minneapolis Police Department checked these possibilities. The next day, December 16, 1942, they found Nelson in a hotel, in bed with a loaded gun under his pillow and his door barricaded with a chair. He was registered under the name of Harold Seeger. Harold Seeger, it should be noted, was a Chicago grocerman who was held up by a masked bandit on December 11, 1942, and robbed of his wallet, identification papers and pocket money.
Nelson would not talk, but the half-healed, grievous wounds on his head were a significant indication that the gang had had trouble. On the same day that Nelson was arrested, agents located Stewart.
Several days before, Stewart had made a telephone call to Milwaukee. The call was traced to a pay station telephone in a drug store on North Broadway in Chicago. Within an hour after this call was made, agents were combing that area of Chicago. Contacts were developed in hotels, barrooms, night spots, rooming houses, and restaurants. Many reliable persons, when shown Stewart's photograph, believed that they had seen the man recently.
Finally on December 16, 1942, agents observed a known acquaintance of Stewart's standing near a bank at the intersection of Oak Park and Harrison Streets. He was carrying a newspaper high under his left arm, rather awkwardly. To the trained observer, he had the air of a man waiting to be met by someone he did not know. The newspaper could very well be the tag by which he was to be recognized.
The agents waited. Their assumption was correct. The man did have a rendezvous but agents did not recognize the individual who came to meet him. They followed the unknown man and found that he lived in a hotel on West Harrison Street. A surveillance at the hotel soon located Stewart. He was known at the hotel as James Shea, this being the name of a man robbed of his wallet and identification papers in Chicago on November 22, 1942. He was also known as "The Deacon," because he dressed in black and wore his clothing like a minister in an effort to disguise himself. When in public, he always carried a Bible, which he frequently opened and read.
Agents did not arrest Stewart immediately. They hoped he would lead them to Touhy and his gang. For four days there were no significant developments.
Then, on December 20, 1942, Stewart had a rendezvous with two men unknown to surveilling agents. The agents surmised that Stewart was not in direct contact with the gang and that these two men were couriers between him and Banghart. Agents quietly took Stewart into custody and followed the two couriers.
The next day, December 21, 1942, agents following one of the couriers recognized Banghart and Darlak whom the courier met in a crowded, downtown area. Agents instinctively realized what was wrapped inside the newspaper that Banghart was carrying. They also realized that it was not time to take Banghart and Darlak. They knew that Banghart, if approached on the street, would start shooting wildly and that the lives of bystanders would be imperiled. They also knew that if they took Banghart and Darlak, the search for the remaining fugitives would become even more difficult. The thing to do was to follow Banghart and Darlak until they led to the hide-out so that all five fugitives could be taken at once without endangering the lives of innocent citizens.
The surveillance on Banghart for the next seven days was most difficult. He carried his shotgun at all times and he knew all of the tricks of shaking off or detecting surveilling officers. The hazardous surveillance, however, paid off. Banghart never realized that he was being followed.
Within five days, agents had learned that the entire gang had been living in apartment number 31 at 1256 Leland Avenue, but that they were splitting into two groups. McInerney and Lanthorn were remaining in apartment number 31; Darlak, Touhy, and Banghart were moving into an apartment at 5116 Kenmore Avenue.
Only one thing remained to be done before arrangements could be made for the arrests. The agents, who had never before seen McInerney and Lanthorn, had to be absolutely certain that these were the right men before attempting the arrest, because they knew there would be gunplay. On Sunday afternoon, December 27, 1942, the two men believed to be McInerney and Lanthorn both left their apartment for a few minutes. While agents were following them on the streets, two other agents slipped into their apartment and obtained some discarded bottles which could be processed for fingerprints. In the Chicago office they developed on these bottles fingerprints identical with those of the two fugitives.
Director Hoover hurried to Chicago to make final plans for the raid. In both apartment houses, unsuspecting neighbors who might be in the line of fire had to be secretly evacuated. Arrangements had to be made with the police department to block off the streets. Every conceivable means of an exit had to be covered, and the agents deployed so that they would not be caught in their own cross fire.
On Monday evening, December 28, 1942, McInerney and Lanthorn again left their apartment and went to visit the other fugitives. Two agents slipped into their room to await their return. other agents filtered into the building to cover all possible means of escape. At 11:20 p.m. the two fugitives returned. They approached the door of their apartment with their guns drawn. After a tense, listening pause before the door, Lanthorn inserted a key and threw the door open.
One of the agents in the room called for their surrender: "We are federal officers. Put your hands up."
Both convicts fired in the direction of the voice. The agents opened fire. Both men lurched from the room, stumbled over the banister and fell dead on the second-floor landing. On the bodies of both men were found large sums of money. In McInerney's pockets were two strange items: (1) the address of an undertaker, and (2) a fragment of verse:
I wish I now were old enough
To give some sound advice
To make each person weigh his thoughts
And turn over twice.
I wish my eyes had seen enough
So I could make him see
The way impressions in this life
Can fool us easily.
I wish my heart had held enough
So it could not impart
The worthiest philosophy To every human heart.

McInerney, 31, was the youngest of this group of convicts.
Director Hoover next took his men to 5116 Kenmore Avenue where they surrounded the building and took up their assigned posts in adjoining apartments. They waited until just before dawn.
At 5:00 a.m., on December 29, 1942, powerful searchlights were turned on to illuminate the apartment building and to play on the windows of the fugitives' first-floor apartment. As the lights went on, one of Director Hoover's assistants began speaking into a microphone connected with a loudspeaker outside the apartment door.
"Touhy, Banghart, Darlak, we are the FBI. Surrender and come out with your hands up. There is no hope of escape. You are surrounded. You have ten minutes to decide. We will then start shooting."
These words were repeated several times, then: "Banghart, you come out first. Come out backwards with your hands in the air. Touhy, you come out next and Darlak, you come last. Come out one at a time. Come out backwards with your hands in the air." The agents could hear excited and muffled voices in the apartment:
"Let's fight."
"No! They've got us covered on all sides."
"What do you say - let's give up. I know how these guys operate!"
"Listen to that voice. It sure gives me the creeps!"
A few seconds later, Banghart backed out of the apartment, hands held high in the air, talking fast:
"Don't do anything. Don't do anything. Don't worry—I won't do anything!"
He had no chance to do anything. Director Hoover seized him and he was handcuffed.
Next came Touhy, the very ghost of the once feared "Black Roger." His curly, black hair had been peroxided to a reddish-blond and was the texture of straw. Clad in flaming red satin pajamas, he was trembling and silent as he backed out of the apartment holding his hands over his head. He stared morosely at the floor while he was being handcuffed. Darlak, as instructed, backed out last.
Banghart was the first to regain his composure. His owl-like eyes had been darting about, taking in everything that happened. He was the first to speak after all the convicts had been taken into custody.
"You're Mr. Hoover, aren't you? I pegged you from your picture in the paper. It's not everybody that has the honor of having the big Chief get him." Touhy was glum and one of the agents asked him what he was thinking. Banghart chirped a reply: "Well, Boss, he's thinking as Molly said to Fibber the other night—it ain't funny anymore." On the way to the FBI office, Banghart chattered endlessly:
"We picked the wrong time for this break. A fellow has to have a Selective Service card, a Social Security card, and is hindered by too many wartime restrictions."
After wistfully thinking it over, Banghart added:
"If I had broken out two years ago, I could have gotten out of the country, maybe gone to South America and gotten a job flying."
He even grew expansive and paid the FBI a compliment:
"Mr. Hoover," he said, "you've got a good outfit. That sound chilled us. It was coming through the window, through the front door, through the back door—from all over. At first, I thought some of our enemies were out to get us."
In connection with this investigation and the searches incidental to the arrests, FBI agents recovered a total of $13,605.84 which the gang had taken in the robbery of an armored car in north Chicago on December 18, 1942. Also recovered were stolen automobiles, guns, expensive clothing and draft and Social Security cards of persons who had been robbed.
 
The Selective Service complaints which agents had filed in October were all dismissed. Nelson, Stewart, Darlak, and Touhy were returned to state custody. Banghart was sent to Alcatraz.

All the way through, Banghart had been the undisputed leader of this mob.
He was born in 1900 at Berville, Michigan. He finished high school and had one year at college before he turned definitely to a career of crime.
The record indicates that he stole over one hundred automobiles in and around Detroit before his first arrest and conviction in 1926.
On January 4, 1926, he was arrested in Cincinnati and returned to Detroit to stand trial for car theft. He pleaded guilty and threw himself on the mercy of the court. The judge placed him on probation for one year.
Two months later in April 1926, he was again arrested, this time in Dayton, Ohio and was charged with a violation of the National Motor Vehicle Theft Act.
He was convicted and sentenced to serve two years in the United States Penitentiary at Atlanta, Georgia, where he deliberately made the acquaintance of long-termers, making what was the equivalent of a post-graduate study in crime.
Assigned to the window washing detail, Banghart had good opportunity to saw the steel bars enclosing a window. At dusk on January 25, 1927, together with other convicts, he made his escape through the window, jumped twenty feet to the ground and made a headlong dash across an open field. Outrunning the bloodhounds, he plunged through swamps and marshes to freedom.
He made his way to Montana where he cooled off for a period before going back east to organize a business of stealing automobiles. He established a ring of car thieves which operated in and around New Jersey. Some of the stolen cars were driven south; others were sold in the same city where they had been stolen after Banghart had changed the motor and serial number.
In October 1928, he was arrested in Pennsylvania and turned over to a United States Marshal at Pittsburgh for arraignment on a National Motor Vehicle Theft Act charge. While in the custody of the marshal in the federal building at Pittsburgh, Banghart asked permission to go to the lavatory. Walking down the corridor, he suddenly shoved the Marshal off balance and dashed out of the building, pointing in front of him and shouting, "Get the police." Stop that man!" The ruse worked and Banghart made good his escape. Two weeks later, however, he was arrested in Philadelphia. In that two weeks he had dyed his hair, shaved his moustache, and put on glasses.
He was returned to Atlanta and served out his sentence, which expired on February 14, 1930. When he left, however, he did not go free. He was taken into custody on a detainer and removed to Knoxville where he was confined in the Knox County Jail to await prosecution in federal court. He made an unsuccessful attempt to escape from this jail. When he was tried he pleaded guilty and asked for probation, saying that he had never had a chance to go straight. The judge, however, sentenced him to two more years in the penitentiary at Atlanta.
Banghart served this sentence, but in January, 1932, less than two months after his release, he was arrested in Detroit as a robbery suspect. He was released to local authorities at South Bend, Indiana, for prosecution on an armed robbery that had occurred in that city in 1927. On his way to South Bend, Banghart boasted that he had belonged to the Purple Gang in Detroit and that the South Bend Jail could not keep him long. He was right. On March 27, 1932, he blinded a turnkey with pepper, took his jail keys, seized a machine gun, and shot his way out of jail.
It was at this point that he fled to Chicago and became a machine gunner and top leader of the Touhy mob, at that time engaged in an underworld war with the Capone interests.
It was Banghart who planned and led the kidnapping of John Factor by the Touhy mob in 1933. In the final stages of this case he narrowly escaped capture after a running gun battle with police. Accompanied by his paramour and two of the Touhy gangsters, he left Chicago and hid out for a while in Tennessee, ultimately moving to Charlotte, North Carolina.
In November, 1933, Banghart and his two henchmen robbed a United States mail truck at Charlotte, obtaining $120,000. He was next arrested in a fashionable apartment in Baltimore, Maryland, on February 10, 1934.
After standing trial in Chicago for participating in the Factor kidnapping and standing trial at Asheville, North Carolina, for participating in the mail robbery, he was returned to Illinois and incarcerated in the state prison at Menard to serve the 99 years for the sentence which he had drawn for the Factor kidnapping.
On October 2, 1935, he and other inmates at Menard assaulted prison guards and, in a commandeered truck, crashed through the prison gates. Banghart was soon recaptured and, as previously pointed out, was sent to Joliet to complete his sentence.

The Teamsters Building Raid

On May 5, 1932, the day Al Capone was taken from Chicago to begin his sentence in federal prison for tax evasion, gangster Roger Touhy, who was at war with the Syndicate, walked into a meeting at the Teamsters headquarters armed with a machine gun and held a hundred people hostage.
     With Touhy was his top enforcer, the unbalanced Willie Sharky and two other men who were unidentified. Each of them carried a machine gun and a pistol.
     The Touhy's had been paid, and paid well, by Chicago's union bosses to rid their locals of the Syndicate's growing influence. Once that was done, the bosses had said, they would not only pay the Touhy's an additional $75,000 in cash, a staggering amount of money in depression racked America, they would also give them control over any local they wanted...forever.
     The raid on the Teamsters Chicago headquarters was the Touhy's first public foray into the mob's most profitable territory. The gangsters herded up the twelve union officials they found in the building and lined them up against the wall. As more members entered the building for a special emergency meeting, over the next three hours, Touhy and company put a gun in their face and pressed them into the hall until they had over one hundred members held hostage.
     After two hours Roger stood before the crowd and said, "Listen up you mugs, we've come here today to clean the dago syndicate out of the Teamsters union."
     Touhy looked over the faces in the union hall and spotted Murray Humpreys' enforcers; John Orms, Tommy Keegan, Al Sogerstorm, John Cassidy, Harry Conway, Mike Burns, George Willows, and Artie Barrett whom Touhy had known from the Valley.
     "We thought you were a right guy. What are you doing hanging around these rats for?" Roger asked.
     "Well I gotta eat Rog," Barrett said.
     Touhy looked through the crowd and pulled out two union leaders named Goldberg and Sass. Goldberg's father-in-law, Jacob Kohn, worked as an aide to Cook County treasurer McDonough and his brother Frank Goldberg, worked as secretary to the city prosecutor Michael Rosina. Touhy pulled them into an office and told them to call Murray Humpreys, a Capone labor goon, over to the building. When they said they couldn't remember the number Touhy said, "Well get together and think it up or we'll give it to you right outside the door."
     Then Touhy walked back into the room where the membership was being held and said, "None of you other mugs have to be afraid. We're after Klondike, Hump Humprey and Jack White and we won't hurt anybody else."
     There was another roar of approval.
     Out of ignorance or fear, Goldberg and Sass wouldn't or couldn't place the call. After a while Touhy became certain that word had slipped out and that Humpreys wouldn't arrive. He rounded up his men and left the building 11:30 in the morning, three full hours after they had arrived taking Goldberg and Sass with him. His last words to the membership were: "These two are going to get theirs," and the membership exploded in cheers.
     Sass and Goldberg were released two days later and said they were not harmed or abused. "Actually," said Goldberg, "they treated us fairly well. The food was excellent. The conversation was good."
     Touhy's brazen daylight raid on the heart of the Syndicate's union operation was a slap in face for Red Barker and Murray Humpreys.
     The Syndicate, less than several hundred in number, were able to rule over these unions with their vast memberships by fear and the threat of violence. Touhy's raid had temporarily taken that edge away from them. They needed to get it back.
     The mob retaliated by pulling off a daylight drive-by shooting at Wall's, a Bar-B-Que and rib joint on Harlem and North Avenue, a place known to be frequented by Roger Touhy and his gang. Roger had developed a well known friendship with the waitress, Peggy Carey and so he was there regularly. All Nitti's gunners had to do was wait.
     On June 16, 1932, the Touhy's struck the Dells, an enormous speakeasy and casino operating just inside Touhy's territory, but the raid backfired. The Touhy's had come to the Dells looking for a Nitti hood named Fred Pacelli, 35, who was spotted by one of Touhy's people as Pacelli entered the club earlier in the evening. Pacelli was the younger brother of soon-to-be congressman Bill Pacelli.
     To kill him, Touhy sent his three best men, Willie Sharky, Roy Marshalk and George Wilke who was also Touhy's business manager.
     The three hoods arrived at the Dells driving Roger Touhy's new Chrysler Sedan. They knew exactly what to do. They quickly strolled into the bar, Roy Marshalk stepped up to Pacelli and fired off a round into his face, put another one into the small of his back and then fired one into Maryanne Bruce, Pacelli's girlfriend after she tried to wrestle the pistol out of Marshalk's hand. Sharky smacked another guest across the face with the barrel of his gun and then told the other hoods to follow him out of the club.
     However, in the parking lot, unknown to them, the Cook County police were waiting. Sgt. Joseph Cantello of the Cook County Sheriff's department took the call about the robbery at the Dells and arrived to the casino's parking lot just as Touhy's men were leaving the building. Cantello stepped out of his patrol car, gun drawn and yelled, "Put down those guns!"
     Sharky fired off six rounds at Cantello who returned fire and put a slug through Roy Marshalk's hand and another through his arm.
     At that point Cook County Highway police Lt. James Meyering arrived with his brother Sheriff Wilbur Meyering and policeman Sam Lucas and a full fledged gun battle was in place. Wilke managed to fire a round into Lucas's right ankle before Officer Cantello, who had reloaded his weapon, fired off two more rounds that caught Wilke in the arm and Sharky in the left leg. The hoods shot their way to safety.
     Wilke and Sharky were wounded at the Dells shoot-out. Wilke was shot in the arm and was unable to climb a nearby fence, however Sharky pulled him over the fence and several times over the next few weeks Sharky would remind him that he had saved his life because the cops were out to kill that night.
     Touhy had them sent to a Minneapolis, Minnesota Hospital to recover and then recuperate at the Sheridan Hotel in June 1932. Sharkey was limping from a bullet in the leg.
     The two year street war between Roger Touhy and the Chicago mob was on.


Hare Sam:

Hare Sam: Died April 1946. Lived at
415 Aldine Avenue
. Manager of the Victoria, A Colosimo brothel where girls were brought in from St. Louis and broken in. He later managed the Dells, a massive casino in Morton Grove in partnership with Lou Silversmith.(2797 North Pine Grove). Silversmith was the owner of the high powered rifle that killed Red Barker in 1932. The Touhy gang was said to have taken over the Dells in 1931 and took credit for killing Barker. The Dells (Named for a waiter named Dell Jones) was robbed several times and fire bombed twice, the last bombing coming on October 8, 1934. Another of Hare’s clubs, the Moulin Rouge on
511 Diversey Highway
had mysteriously caught fire earlier in the year. Hare held a $25,000 policy on the property. In 1931, the Touhy gang tracked Capone killer Fred Pacelli to the Dells and killed him. That same year, while at least 300 people watch, Touhy gunmen marched into the Dells and shot and killed Fred DiGiovanni, a suspected Barker spy within the Touhy organization. Hare was rumored to paid reporter Jake Lingle as much as $20,000 in bribes to keep him from writing stories on his gambling dens/night spots.  

The Valley Gang: The origins of the Touhy Outfit

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.

Gilbert, Daniel




Tubbo Gilbert crawled out of a Chicago slum called the Valley and grew to be one of the most politically powerful, and wealthiest lawmen in American history. A neglected child, Gilbert went to work as a wagon boy at age 11 at the busy train depot that once dominated the valley’s center. An ambitious young man, in 1913 Gilbert ran for, and won, a position as the Secretary of the Baggage and Parcel delivery union, local 725. It was an easy win. His opponent withdrew in the middle of the election, on Christmas night, after somebody shot him in the rear end.


He ruled over the local with brute force, fear and intimidation. During one wildcat strike, called by the membership without his authority Gilbert beat the striker’s leader so badly that he was indicted for assault with intent to kill. The indictment, of course, was later suspended with leave to reinstate. However, the records later disappeared from the criminal courts building. Gilbert served on the governing council of the very mobbed up Chicago Teamsters Union until 1917, when he was appointed, through political clout, to the Chicago Police force on April 6, the day the United States entered the First World War. While on the force, Gilbert pursued a separate career in union politics, keeping his position as the secretary treasurer of local 725. On the force, Tubbo earned a reputation as a brutal, thick necked cop, who was smart enough to surround himself with more capable and brighter underlings. He also engaged openly in city politics, and, before long, Gilbert was a political power in Cook County. As a result, his rise in the police department was unprecedented. After serving less then five years as a patrolman, he was promoted to the rank of sergeant and a year later he became a lieutenant. By 1926 he was a captain, and, from 1931 until December 5, 1932, he held the rank of supervising captain, when he was promoted to the States Attorney, or the District Attorney’s, chief investigator, a position he held for eighteen years. Most people in Chicago thought that it was only a matter of time before he was appointed chief of police. As the states attorney’s office, chief investigator, Gilbert was the head of his own private police force, which would eventually number over one hundred seasoned investigators, and, as he did in the unions, Tubbo ruled over his department with an iron fist. Once, during a city wide election, Tubbo learned that one of his investigators was a spy for Mayor Edward J. Kelly’s camp. Tubbo took the cop into his office, locked the door, and beat the man senseless with his fists. Charges were filed, but again they were dropped, and all records concerning the charge, disappeared. Around 1930, Tubbo needed money to finance his political ambitions and, as a result, he called a press conference and announced that the States Attorney would “look into the internal workings of the city’s unions and clean that business up.” Critics quickly noted that he never said he would close it down.
In November of 1936, Tubbo was questioned about his role in helping the Chicago Teamsters, still under the mobs control at that point, fix milk retail prices in Chicago.
The scandal also involved Dr. Herman Bundesen of the Chicago Board of Health, and officials of local 753 of the milk driver union. All of them, the indictment read, conspired to fix the amount of milk delivered in the city to squeeze out the smaller guys.
States Attorney Thomas Courtney, who had high political ambitions of his own, refused to allow Tubbo to resign over the scandal, or even to request his resignation, telling the press: “If many people feel that politics has entered into this,” Courtney said, “then I won’t disagree with that conclusion.” Of course, Gilbert and Courtney were close.
Once, in 1935, they were both accused of using the States Attorney’s Office to selectively harass a political leader named Harry Perry, who was also a city Alderman.
Perry had stated publicly that he feared for his life, and, on March 24, 1935, after Perry had filed a formal complaint against Courtney and Gilbert, he was driving home from a political rally on the South side under the protection of two Chicago police detectives. Suddenly, a dark sedan pulled up alongside Perry’s car and a pistol fired from the back seat let off eight rounds into Perry’s car, which swerved out of control and crashed.
Remarkably, no one was hurt but Perry withdrew his complaint against Gilbert and Courtney the next morning. In April of 1935, the mob almost had its own police chief, when Gilbert temporarily left his job in the States Attorney’s Office to take another job in the department, as commander of the uniformed patrol. This position placed him one step behind the chief of police. Interestingly enough, this job also placed Gilbert over the vice and gambling units. Nevertheless, in July of 1935, Gilbert stepped down from the uniform position and returned to the chief investigator’s post after disbanding the gambling squad. The fact that Gilbert was a mob flunky was reaffirmed in May of 1939, when Gilbert was seen, over a three-day weekend, at the Arlington Hotel in Hot Springs, Arkansas, with Frank Nitti. They were spotted in the hotel’s bar, and on the links, where Gilbert used gold-plated golf clubs that Nitti had given him as a present.
During all this time, Gilbert remained in the union business. By the fall of 1938, Gilbert controlled at least seven unions. He dictated who would, or would not, hold office, and, obtaining Gilbert’s approval was essential before union leaders began organizing drives.      
    When labor leaders conducted business without him, Gilbert never hesitated to have them arrested. Before the 1948 election, both candidates for the states attorney position were asked if they would keep Gilbert on if they won, and both said they would fire him.
But, the contest winner, John Boyle, reneged, and said that he would only fire Gilbert on Mayor Kennelly’s directive. That directive, of course, never came.
By 1950, most Chicago crime reporters considered William “Tubbo” Gilbert, now a Captain, not only to be the political boss of the Chicago Police Department, but also a full-fledged member of the Chicago crime syndicate, answering directly to Murray Humphreys. However, Gilbert’s career took a turn for the worse after he was nominated to be Cook County Sheriff, and was widely considered a shoo-in for the post.
The major issue in Gilbert’s campaign was gambling, and Gilbert swore, that if elected, he would close down all of the illegal gambling in Cook County within six months.
The Chicago Tribune, which had opposed Gilbert’s nomination from the start, published papers it had stored away since 1941, papers which Jake Guzak, the mob’s money man, had accidentally left in an oven when he moved out of an apartment.
Those records summarized the profits and loss of the gambling for the mob for one month and they said that under the monthly payoffs “Tub ... $4,000.” Gilbert denied the charges by explaining that his friends called him “Tubbo” and not Tub, so, by his logic, it couldn’t have been him. The newspapers, television and radio covered Gilbert’s ties to organized crime, but the voters didn’t seem to be listening. Tubbo Gilbert would win the election, hands down. Then Gilbert’s name came up during the Chicago hearings of the Kefauver Committee, and Tubbo was requested to testify before the committee. Ray Brennan, a renowned Chicago crime reporter said: “What Happened to make Dan Gilbert testify before the Kefauver committee was that Rudy Halley, Chief counsel and some other senate committee people were at the Morrison hotel the night before the Chicago hearings opened. Halley telephoned Gilbert at home after talking in private with Kefauver. Kefauver, a politically ambitious democrat, was aghast at the peril of annoying the all powerful Chicago democratic organization. Halley told Gilbert by phone, in effect ‘you are invited to testify at tomorrow’s hearings. You are not under a subpoena. You may accept this invitation, or you may decline.’ Of course Gilbert declined.
“I listened in on the conversation on an extension phone without Halley’s knowledge. As a result we carried a page one story and banner headlines saying Gilbert was afraid to testify. Dan couldn’t stand the heat from the Sun Times. He made a deal with the committee.” Dan Gilbert testified, for two hours, but his testimony was behind locked doors, a most unusual thing and the transcript was impounded.
Since it was just before the election and Kefauver was a good democrat, he agreed to the terms that Tubbo Gilbert had set up. They questioned Gilbert for two hours behind closed doors. When it was over, Estes Kefauver gave a briefing that left “more questions then answers.” Brennan tried everything he could to find out what had happened behind those closed doors, but was unsuccessful. He had more or less given up, and had retired to Nick’s Bar for a drink “when inspiration struck.” Brennan flew to Washington, learned the location of the committee stenographic service, and then, posing as a Senate staff member, he dropped by the service “to pick up a copy of some guy’s testimony.”
Remarkably, he was handed a complete copy of Gilbert’s testimony. Reading the testimony over in a Senate bathroom, Brennan found out that Gilbert acknowledged the charges of assault, with intent with intent to kill, against him in the 1940 election, leveled by Judge Oscar F. Nelson, who was running for the states attorney’s office against Courtney. The indictment was suspended and later disappeared from the police and court records. Gilbert said that it was true that his records from the police department were missing, and that he found that “suspect” and that he was a frequent guest of gangster Owney Madden in Hot springs. Gilbert also admitted that, while he was in office, justice in the states attorney office was on a “cash and carry basis.” Gilbert, whose wealth was estimated to be in the millions by the newspapers, told the committee the right figure was around $300,000. He said most of the money came from trading on the speculation market where he was once listed as the biggest trader on the Chicago grain market.
He admitted owning hundreds of thousands of bushels of wheat, which would eventually lead to his being hauled in for questioning, the federal government looking into manipulation of the grain on the Chicago Board of Trade. Gilbert also admitted that he owned 18,000 shares of Royal Crown Cola, extensive utility holdings, and to being “a gambler at heart” who gambled illegally while enforcing the law. The testimony also included Gilbert’s income tax records, which showed that he earned $7,310 in 1948 by wagering on football, baseball and prize fights and elections. When questioned about that, Gilbert bragged that the 1933 elections alone he made a $12,000 bet on Roosevelt and he boasted to the committee that he had bet on and won every election since 1921.
When asked where he placed his bets Gilbert named a gambling joint owned by John Mcdonald at
215 North LaSalle Street
. “That is not legal, betting, is it Captain Gilbert?” a committee member asked. “Well, no, it is not legal, no,” Gilbert lied to the panel of lawyers. He also admitted that he had gambled in mob locations and that he gambled on everything and anything, baseball, football and even elections. The Kefauver committee secretly concluded that Tubbo Gilbert’s administration as Chicago’s top cop “was neglect of official duty and shocking indifference to violations of the law.”
The Sun Times printed the testimony, which both fascinated and appalled Cook County voters, who turned out in record numbers to vote against Gilbert. To add insult to injury, Brennan dubbed Gilbert “The World’s richest cop” the day before the elections and the name stuck. Gilbert’s defeat brought down most of the democratic ticket and handed the sheriff office to John “Two Gun” Babb, a Second World War hero who beat Gilbert by 400,000 votes. A few days later, Gilbert retired from the force and announced that he would take a position as chief of police at the Arlington & Washington race tracks, where his brother, Maurice, was a lieutenant. That was another mistake. Ray Brennan discovered that Maurice Gilbert had been out on sick leave from the Chicago police department since 1948, and had been drawing a steady paycheck from the department and the race track at the same time. Gilbert never held a grudge against Brennan for bringing him down, in fact, in one of Tubbo Gilbert’s last tirades against the Chicago press he jabbed his finger into a reporter’s chest and barked: “All of you’s are a pack of rat ... the only one of you’s who has any class at all, is Ray Brennan ... and he’s a rat too.”
Brennan understood the back-handed compliment. President Harry Truman was less forgiving. He threw a fit over the Democrats’ beating in Illinois, and Brennan was indicted for posing as a federal official to get Gilbert’s testimony, a charge that carried a six-year term. The case against him dragged on for three years before the Justice department ruled that he “no criminal intent as we generally understand it.”
After that, Gilbert packed up his millions and moved to California, where he said he planned to open a detective agency in Los Angles, however, a few years later, he suffered a massive heart attack and went into a comfortable semi retirement. He returned to Chicago in the early 1970s, confined to a wheelchair, his legacy forgotten. He died there in 1977.