The Greyhound Bus Station – located at either 64 and 74 W. Randolph Street – was a well known gay cruising and hustling zone populated with drug addicted and/or teenage hustlers nearly since its opening in 1953, and was a favorite hunting ground for serial killer John Wayne Gacy in the 1970s. Among those who worked the station in the 1950s was a gang of young hustlers under the command of Harry Figel who – much like Ed “the Skull” Murphy in New York City – used the boys as tools for extorting gay men. Harry Figel was murdered by Chicago cops Richard Cain and Gerald Shallow on March 22, 1959 under the pretense of self-defense pursuant to an effort to arrest him after an undercover investigation into the extortion racket. However, Figel’s murder appears to have been the result of a failure to pay street tax to the Outfit. Richard Cain in fact was a made member of the Outfit and was a bagman and enforcer for its vice operations. Indeed, Richard Cain, whom the FBI identified as “possibly the most corrupt police official in the history of Chicago,” subsequently was forced to resign from the Chicago police force once several of his crimes came to light. After a brief prison term Richard Cain divided his time between Chicago and Mexico conducting business for mob boss Sam Giancana. Mob hitmen killed Richard Cain in 1973 by blowing away his face with a couple of close-range shotgun blasts.
A June 9, 1949 article (“2 Ex-Convicts Get Year; Used Youngster in Shakedown Scheme”) from the Chicago Tribune states:
Earl Cunningham, 21, of 6126 S. Tripp Av., and Harry Figel, 28, of 2448 47th St., ex-convicts, were sentenced yesterday to a year in the Bridewell . . . after they pleaded guilty to contributing to the delinquency of a minor. The two were arrested Tuesday at Adams and State Sts. By Lt. John Murphy of the confidence game detail, who accompanied Wesley E. Olsen, 35, of 3511 S. Washtenaw Av., there after Cunningham and Figel had taken $30 from him and demanded $500 to be delivered at that corner. Olsen told police he picked up Frank Whitefield, 15, of 5019 S. Racine Av., as a hitchhiker and was asked to drive him to Loomis and 53d Sts., where Cunningham and Figel stepped up, accused him of an act of perversion, extorted $30 and ordered him to deliver the $500 later. Whitefield, a former inmate of the state training school for boys near St. Charles, has been returned there.
A March 23, 1959 article (“Kill Ex-Convict in Loop Gun Fight”) from the Chicago Tribune states:
A Loop gun battle with police brought death Sunday morning to Harry Figel, 37, of 2531 46th St., an ex-convict with a long record as an extortionist and robber. Detectives Gerald Shallow and Richard Cain fired five shots into Figel after he had fired at Cain in an alley south of Lake Street between Clark and Dearborn Streets. Figel, police said, had been suspected of being the leader of a gang of young men who posed as perverts to make dates with actual perverts. Figel’s role was to appear suddenly and pretend to be the uncle of his young accomplice, then extort money from the victim. Sgt. Thomas Mulvey, head of the sex bureau, to which Cain and Shallow are assigned, said he learned of the Figel gang’s activities about a month ago and assigned Cain and Shallow to work on the case. The detectives found one member of the gang who promised to cooperate in capturing Figel, known to the gang as “Uncle Harry.” With Cain masquerading as a pervert, the young informer told Figel he had set up a meeting for 5:15 a. m. in the rear of the Greyhound bus depot. The detectives went to the scene. Shallow hid in a doorway across Lake street while Cain and the young man waited for Figel to show up. When he did, Figel told Cain he was the informer’s uncle and pulled him into the alley, where Cain pretended to plead for mercy. Figel offered to let Cain go for $100. Cain agreed, and handed over the money in marked bills. While Figel was counting the bills, Cain pulled out his badge and arrested Figel. By this time Shallow was running down the alley to help. Figel drew a .25 caliber automatic pistol and fired one shot at Cain and one at Shallow, but missed. Bullets fired by both detectives killed the ex-convict. Police did not reveal the identity of the informer.
A March 31, 1959 article (“Inquest Hears Cops Accused of Shakedown”) from the Chicago Tribune states:
A charge that Harry Figel, 37, ex-convict and suspected extortion ring leader slain by sex bureau detectives March 22, was a victim of a police shakedown was made Monday by Atty. Edward L. Kelly, representing the Figel family, at a coroner’s inquest. Kelly said he had a witness who saw two detectives beat Figel at 63d Street and Ashland Avenue a week before Figel was shot to death in a gun battle in an alley south of Lake Street, between Clark and Dearborn Streets.
A March 22, 1963 article (“Nab 5 in Bus Depot Shakedown”) from the Chicago Tribune states:
Four men and a 16-year-old youth were arrested yesterday as police broke up a ring which allegedly extorted money from homosexuals who frequented the Greyhound Bus terminal at 74 W. Randolph St. Charged with bribery were Virgil Lamb, 38, of 1606 E. 50th Pl., terminal manager; Herman Westerhoff, 36, of 10155 Lafayette Av., a captain for the Inter-state Detective Agency. 407 S. Dearborn St.; Henry Meyer, 46, of 2518 Haddon Av., an Inter-state patrolman; and Ronald Monaco, 30, of 9 W. Harrison St., whom police described as a pander. * * * Breakup of the ring came after two Central district detectives picked up the juvenile, Warren Todd, 16, of Lake Geneva, Wis., in the bus terminal early yesterday. Police said Todd admitted he took money from homosexuals and said Lamb, Westerhoff, Meyer, and Monaco made him “steer” homosexuals to them for a “shakedown.” * * * Todd was turned over to juvenile authorities, police said. He admitted “working” the terminal for three months, sleeping in various places on the near north side, they said.
A December 21, 1973 article (“Ex-cop Cain Shot to Death”) by Michael Sneed and Thomas Powers from the Chicago Tribune states:
Richard Cain, the hoodlum who once was chief investigator for the Cook County sheriff’s office, was shot to death yesterday in gangland style. Cain, 49, was killed by two gunmen wearing ski masks as he stood against a wall in a sandwich shop at 1117 W. Grand Av. Witnesses said that only 15 minutes earlier Cain had been seen conferring with four other men in the restaurant. Investigators speculated that Cain may have been lured to his death in the sandwich shop. When the masked gunmen arrived, the four men with whom Cain had been talking had left. Tho the gunmen ordered Cain and others in the sandwich shop against the wall, only Cain was hit by two shotgun blasts fired from close range. The blasts tore away his face. Frightened witnesses said no words were exchanged between the killers and Cain. * * * The shotgun blast struck Cain in the lower jaw and so disfigured his face that it was several hours before he was identified. * * * In recent years, Cain had been a driver and lackey for Sam Giancana, a former Chicago crime syndicate leader. * * * Cain was taken to the county morgue from the sandwich shop, Rose’s Poor Boy Sandwiches, as an unidentified murder victim. * * * Cain was a former Chicago policeman in 1962 when Richard Ogilvie was elected sheriff as a reform candidate. Ogilvie named him chief investigator. During two years as chief investigator, Cain forced suspected mob informers to take lie tests at the public’s expense to determine if they were giving away underworld secrets. Cain’s efforts to work both sides of the street, serving as both a policeman and a mobster, came to an end in 1964 when Ogilvie forced his resignation. Cain had been implicated in a $240,000 burglary of the Louis Zahn Drug Co., warehouse in Melrose Park and later was convicted with other mobsters for his part in a 1963 Franklin Park bank robbery. Cain served three years in prison for the bank job and for lying to a grand jury about the warehouse burglary. After his parole in 1971, Cain fled to Mexico and joined Giancana.
Four days after the Figel shooting detectives Cain and Shallow were recommended for the Mayor’s Youth Award – which they subsequently received – by the following letter from their supervisor:
During the course of numerous investigations over a long period of time in which homosexuals were involved from conversation with these people it became apparent that they themselves were being victimized. The name of the individual involved was Harry Figel who was the ringleader of a group of young men who plied on the weakness and immoral characteristics of homosexuals by extorting money from them.
Detectives Richard Cain and Gerald Shallow were assigned to direct their activities towards Figel and his gang. After a week of background investigations, the investigating officers had determined that Harry Figel had an extensive criminal record for robbery, con-game, extortion and contributing to the delinquency. He had served two sentences to Joliet penitentiary, House of corrections and the New York penitentiary. He was known among his associates as a ruthless sadist, who enjoyed inflicting pain upon both his victims and his young hustlers. He was alleged to have from 15 to 20 fruit hustlers working for him in the Loop area, Wilson-Broadway area and South Side areas. His method of operation was for one of his gang to make contact with a homosexual and Figel was notified as to where the gang-member and the homosexual would be at a given time. Figel would then appear and claim to be either a police officer or the uncle of the young gang-member. He would then extort money or jewlry from the homosexual or assault and rob him and then later split the proceeds with the gang member or “hustler.”
An immediate canvass of establishments suspected to be frequented by Figel and his associates was begun by the investigators. At the Greyhound Bus Station, 64 W. Randolph Street, one of the young “hustlers” was located and kept under surveillance for a period of four days and then the officers identified themselves to him and after assuring him that his identity would be kept confidential because of the expressed fear the young man had of Figel, his cooperation was obtained to establish a contact with Figel.
Detective Cain was to pose as a homosexual and by pre-arrangement with the young gang-member at 2:00 A.M. on March 22, ’59 Detective Cain was waiting at a public phone booth in the Greyhound Bus depot. The informant was to contact Figel and then call Detective Cain who was supposed to be a homosexual “roped” in by the informant. If at the time of the phone call, Figel was with the informant he would cue Detective Cain by calling him “Baby.” At about 2:05 A.M. the phone rang and when Cain answered the informant on the other end of the line said, “Is that you, BABY?” Detective Cain answered in the affirmative and an appointment was made to meet at the Lake Street entrance to the Bus station at 5:15 A.M. supposedly for Detective Cain and the “hustler” to meet to go to a hotel together. By the use of the word “baby,” Cain of course knew that Harry Figel would be there, supposedly unexpected by Cain.
At 5:15 A.M. Detective Cain was standing in the pre-arranged spot while his partner, Detective Shallow, maintained surveillance from an advantageous position across the street. At about 5:20 A.M. Harry Figel came up to Detective Cain, poked a finger into Cain’s chest and said,, “you’re the son of a bitch that’s been fooling around with my nephew John, I want to talk to you!” With that he took Detective Cain by the arm and walked him around the corner, through a parking lot and into the alley in the rear of 64 W. Randolph St. Detective Shallow moved from his vantage point and followed. In the alley, Figel then said, “Now I’m going to take care of you” and drew back his arm in a striking position. Detective Cain protested and asked if this whole thing couldn’t be “straightened out.” Figel then answered, “well, we can straighten it out right now for one hundred dollars.” Detective Cain then counted out $100 in marked money and held it out towards Figel. As Figel reached for the money, Cain also displayed his star, announcing his office and proclaiming Figel under arrest. Figel then looked and saw Detective Shallow hurrying towards them and with that he quickly stepped back, drew a pistol from his pocket and fired twice at both Cain and Shallow. After this overt display of viciousness, the Detectives then withdrew their pistols from their holsters and returned the fire. Figel bolted and ran down the alley while the officers continued firing, Figel then turned around raised his pistol again, pointed at the officers and fell to the ground fatally wounded. The gun used by Figel was .25 cal Colt automatic. He was pronounced dead on arrival at St. Luke’s hospital.
The actions of the two investigators truly displays exemplary action and bravery. Through their actions and complete thoroughness they brought to a conclusion the sadistic career of a malicious felon who victimized people whose morals were not normal and used this condition to threaten and force them to pay him money. A “racket” that he had been successfully conducting for quite some time. In view of these facts, it is therefore respectfully requested, if the Commissioner of Police so approves, that the actions of Detective Richard Cain and Gerald Shallow, be brought to the attention of the Committee for consideration of an award from the Mayor’s Youth Foundation and as a department gesture in recognition of praiseworthy duty they be given a creditable mention.
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