Yet amazingly, just as Touhy proved a thorn to the FBI, he was equally regarded as a true terror by Al Capone, who regarded Touhy as one of the stumbling blocks to his plans to organize all crime in Chicago.
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Roger "Terrible" Touhy was pretty much a creation of sharp public relations, his own. As far as the entire underworld had it figured, the Terrible TouhysRoger, the boss, and his five brotherscontrolled all booze operations in the Chicago suburban area of Des Plaines and had their empire backed with such firepower that they were impregnable.
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Press coverage indicated the Touhy Gang to be about the most vicious in the Midwest. Yet Touhy was a middle-class bootlegger, one who employed no more muscle than necessary to convince all the speakeasies and saloons in his area to handle Touhy beer and booze exclusively. Indeed, firepower was less a reason for Touhy's success than his ability to handle the fix as well as any figure in the underworld. Not only was Touhy the master of the fix, but he knew how to supplement cash payoffs with fringe benefits that meant so much. He rewarded the local politicians and police brass with bottled beer brewed especially for them and often bearing their own personal labels.
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Perhaps Touhy's reputation as a ferocious gangster was sealed by his lookskinky-haired, beady-eyed, with a hawklike face, clearly a man to be feared. And Touhy knew how to act the part, forcing even Al Capone to back down to him. Touhy had once sold the Capone boys 800 barrels of his superior beer for $37.50 a barrel (his cost of production was $5.50 at most), and Capone then tried to short Touhy with $1,900 in the payoff, claiming that some of the barrels had leaks. (Capone always pressured people that way.) Touhy came back with his regular routine. He assumed his famed hard stare, and said softly, "Don't chisel me, Al." Capone paid the $1,900.
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Roger and his five brothers had not started out as criminals. They grew up in respectable circumstances, the sons of a policeman. In the early 1920s, the Touhys went into the trucking business, "strictly legit," at least by Touhys word. Business, however, did not boom until they started filling the trucks with beer. The Terrible Touhys raked in a fortune.
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Roger Touhy took control of the Des Plaines area in the northwest section of Cook County. In those days a bootlegger was hardly an unpopular figure, and Touhy found ways to increase the esteem in which he was held. He kept out lowlife criminals and especially clamped down on brothels. Whenever a group of mobsters tried to open a roadside whorehouse, Touhy would relieve the local police of the need to take action. He sent in his own enforcers to wreck the joint. Even when Capone personally noted that Des Plaines was, as he charmingly put it, "virgin territory for whorehouses," Touhy's response was his hard-eyed stare, which convinced Capone to drop his plans.
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Whenever rivals made noise about wanting to move in, Touhy would invite them to his headquarters for a visit, where they were greeted by what appeared to be an armed camp, the walls lined with submachine guns. What the visiting hoods didn't know was that the weapons had been made available by cooperative local cops just for a good show. While the gangsters were conferring with Touhy, underlings would come rushing in for weapons, mumbling something about having a great chance to rub out some party. Touhy would nod his head slightly in assent and return to the dialogue as though the matter was of minor importance. When Touhy's visitors left, they were fully convinced they would be the loser in any war with the Terrible Touhys. At various times such Capone gunners as Murray "the Camel" Humphreys and Frank Nitti were so shaken that they reported back that Capone would be facing a terrible bloodletting if he tried to move in.
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Still the Capone gang tried to get Touhyeven after Big Al went to prison. Deciding violence was out, they resolved to use another method, helping the law get something on him. Suddenly Touhy found himself in big trouble with the FBI. It is unclear if the Chicago Outfit had anything to do with the first incident, but it is not beyond the realm of possibility. Touhy and several of his henchmen were arrested for the kidnapping of William Hamm Jr. The FBI announced it had a strong case against Touhy, but a jury thought differently, finding him not guilty. Later, the FBI switched the charge to the real culprits, the Barker-Karpis gang. By coincidence Alvin "Creepy" Karpis had long been close to the Capone Gang.
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Next the FBI arrested Touhy for the alleged 1933 kidnapping of Jake "the Barber" Factor, an international confidence man with ties to the Capones. This was despite underworld grapevine information that indicated the abduction was a fake masterminded by Factor and the Capones. Special agent Melvin Purvis announced that his arrest of Touhy in the Factor snatch was a landmark in the art of detection. "This case," he said, ''holds a particular interest for me because it represents a triumph of deductive detective work. We assumed from the start, with no material evidence, that the Touhy gang was responsible for the crime."
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Touhy's first trial ended in a hung jury. He was convicted the second time around and was sentenced to 99 years. Touhy went to prison screaming frame-up while the Capones swarmed into Des Plaines.
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In 1942, Touhy escaped from prison but was recaptured soon and saddled with an additional sentence of
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