Mobsters and their groupies insist that the Mafia is a society of honorable men with family values who respect women and children.
Apparently Jimmy "the Monk" Allegretti never got the memo.
The FBI recently released its files on the Chicago mobster, and he not only ran the prostitution racket on the Near North Side from the mid-1940s to the mid-1960s but was a frequent customer of the fleshy treats with a particular fondness for underage girls.
The prostitutes were pimped out of hotel lounges and dive bars including several establishments allegedly under the direct control of Allegretti such as Ciro's (later Eros) in the 800 block of North Wabash where his brother Benny Policheri supposedly was the so-called majordomo. There were about two dozen girls working out of Ciro's, and apparently by Benny's own admission the operation generated $7,000 a week. One informant advised the FBI that "the prostitutes often worked for $100 per trick and made many of their dates with wealthy guests of the Ambassador East Hotel."
Allegretti enjoyed personally screening many of the working girls who operated out of his meat markets. One informant "stated that Allegretti liked to be surrounded by good looking girls and that is one of his weaknesses," and the mobster directly admitted to FBI agents in a 1958 interview "that he likes girls, is in the company of them frequently, and has sexual relations with prostitutes quite often." Of course, the short fat thing -- he was 5'7" and 200 pounds -- no doubt was unable to attract anyone but a whore. An informant "said that Allegretti always wears a business suit, but being fat he seldom looks well dressed."
Even the underage girls were fair pickings for Allegretti. He paid $30 to one 16-year-old girl, and after she ratted to police the mobster sicked his goons on her. Nothing like a beat down and death threat to silence a complaining witness -- particularly a young child -- and the charges were dropped against Allegretti. Of course, the control freak understood the enforcement value of a good beating, and more than a few of his working girls felt the pimp's hand. One of Allegretti's former prostitutes told the FBI "that in the latter part of June, 1957, she attempted to break off business relations with Allegretti, following which she was visited by four men at her Division Street apartment, and they beat her up and broke the furniture in the apartment." She "continued working for Allegretti until the first part of November, 1957, at which time she told Allegretti that she was going to get married," and "his reply was that he had better never see her around Chicago again."
Allegretti and his first wife, Harriet Everly, divorcd in 1936, and the breakup was initiated by Harriet who no longer could stomach his decadent lifestyle. Allegretti's second wife, Florence Risner, told a friend that the mobster "'took her off the streets' when she was about 14 years of age" although he didn't marry her until 1939 when she was 22-years-old. According to Florence she quickly became too old for Allegretti, and the degenerate found himself another underage teen to bring into the home. However, rather than divorcing Allegretti, Florence was content to remain married while taking his money. The couple lived in the same buildings -- first at 20 East Cedar Street and then at the more upscale 1300 North Lake Shore Drive -- but in adjoining apartments. Indeed, Allegretti told the FBI that "his wife does not care how many prostitutes he has relations with as he lives his life and she lives hers."
Among Allegretti's fun spots was the cabaret-style Chez Paree at 610 North Fairbanks Street. According to one informant during the post war years "the Chez Paree was regarded by the hoodlum element as a second home," and "every Sunday night the first table at ringside is reserved in the name of Jimmy Allegretti for the second show which commences at 12:15 A.M." The Allegretti entourage varied from between six and sixteen hoodlums and their girlfriends. Allegretti was "occasionally accompanied by Sam 'Mooney' Giancana," and Allegretti "is unquestionably subservient to Mooney."
The afterhours party often was held on the penthouse floor of the United Coin Exchange building according to one woman who escorted Allegretti:
[O]n several occasions following the closing of the Chez Paree in the evening, she, accompanied by Allegretti, would go to a very plush penthouse located on the top of the building known to [informat] as the United Coin Exchange, located on the Northwest side of Chicago. [Informant] advised that it was her understanding that the United Coin Exchange manufactured pinball machines and juke boxes, and was a syndicate operation.
[Informant] advised that frequently the top entertainers from Chez Paree would be brought to this Penthouse for afterhours entertainment. She advised that this apartment was very elaborate in decorations and included some four or five bedrooms and steam baths. She advised that many of the individuals frequenting these parties wore shoulder holsters.
Apparently Allegretti and Giancana were members of the Playboy Club at 182 East Walton Street according to records shown by an employee to the FBI. A November 2, 1961 article by Jack Willner from the Chicago Daily News claimed that additional mobsters seen at the Playboy Club were Joey DeVarco and Marshall Caifano, and "Giancana and Caifano also have been seen after hours with some of the 'Bunny' waitresses from the club."
Although Allegretti was diagnosed in 1951 as a diabetic and required insulin he didn't let his illness get in the way of partying. The hedonist told the FBI "that he drinks quite heavily in spite of his having diabetes although he knows that it is extremely bad for him and may eventually kill him" but "he would rather die sooner and have fun while he is living."
Of course, being a mobster isn't all fun and games, and the vice rackets were a serious business. Allegretti often "was in the company of two or three bodyguards all of whom wore shoulder holsters and did his bidding without question." Allegretti was the Rush Street crew boss for Outfit underboss Ross Prio, and oversaw most if not all the whore houses, strip clubs, gay bars and gambling dens on the vice strip.
There were many ways in which Allegretti exercised control over and profited from the seedy establishments in the red light district.
First, at any given time he indirectly owned a dozen or two of them. In the early 1940s his second wife Florence often was the name on the building leases and liquor licenses, including the Windup Lounge at 669 North State which was "notorious as a Lesbian and 'queer' hangout," but as his empire grew over the years Allegretti allegedly used an increasing number of suspected fronts including Nate Zuckerman and Mike Glitta. Glitta allegedly fronted the plush Shore Club at 528 North Clark Street among other places, and he purportedly quipped "you can’t make money in Chicago with a legitimate place," and "you've got to have a gaff such as B-drinking or prostitution." A bar with B-drinking made money because the bar girls conned lonely men on holiday into running up high-priced liquor tabs, and a bar with prostitution made money because the working girls typically handed over a 25% cut from their earnings.
And for those joints he didn't own Allegretti extracted protection money which typically ranged between a couple to several hundred dollars a month. The cash payments weren't simply protection from mob violence -- although more than a few vice purveyors got a beat down for opening up without Allegretti's okay -- but protection against cop raids.
A healthy chunk of the extorted cash went to pay off the dirty cops in the 35th Police District which covered the Near North Side, and one informant recounted to the FBI that in December 1957 he saw Allegretti in his office with about $20,000 in a "roll of bills," and the mobster said "today is payoff day." For the record, Captain Thomas Harrison who ran the 35th Police District told some visiting FBI agents on March 25, 1958 that "he ran his district on a very strict manner and did not allow crime which included gambling and prostitution to operate in his district with his knowledge." Occasionally, the cops did raid an Allegretti whore house but they were staged events, and only a couple of token girls who were paid to take the fall would get arrested.
Allegretti teamed up with Joseph "Joey Caesar" DiVarco -- a fellow mobster who served overlord Ross Prio on the Near North Side -- to operate so-called legitimate companies which provided foodstuffs and supplies to the area's nightspots. The eateries bought their meat from C & B Meat Provision Company, and the taverns purchased automatic glassware washers from Sterile Glass Company. The boys acquired hidden interests in more than one nightclub after its owner's accounts became past due.
When one barkeep indignantly told the FBI that he had no dealings with the mob a street smart special agent queried him on who were his vendors:
On June 19, 1958, [name redacted] of the Black Orchid, North Rush Street, Chicago, advised [FBI agents] that he knew JAMES ALLEGRETTI and other Chicago hoodlums by sight as customers, but had no dealings with them. [Name redacted] stated that he had never been muscled by anyone concerning his business and had no hoodlum partners and made no payoffs to any hoodlums. [Name redacted] advised that he is operating a legitimate business and as such does not have to knuckle down to the syndicate members. When asked how he washed glasses at his bar, he stated that he had a new glass washing device, which upon inspection appeared to be similar to the glass washing device sold by [DiVarco salesman]. When asked about his meat purchases, [name redacted] stated that a portion of his meat was purchased from the C&B Meat Company, in which the subject [Jimmy Allegretti] has an interest.
A September 9, 1958 article ("Hoodlums Progress") from the Chicago Tribune states:
A few days ago we noticed that Joseph DiVarco, hoodlum, has invested the pennies he saved from horse betting and dice in a glass washer machine business. Di Varco seems to be a comer. His salesmanship is so good that it is only after his customers, the Near North Side bars and clubs, have bought the glass washers that they discover they have no use for them. Advertising men may have noticed that Di Varco's sales theme is of the personal endorsement type like the sports star who lends his name to the promotion of equipment ; Di Varco's salesmen extol the product and then close with this line: "Joey wants you to buy this machine." No one can resist.
If you were running a nightspot on the Near North Side there was little chance of escaping the mob's grip.
Allegretti worked out of his restaurant Valentino's -- referred to in the underworld as Allegretti's Restaurant -- which was located in the Berkshire Hotel on 15 East Ohio Street where he also maintained two permanent rooms on the 8th Floor. The lease on Valentino's was signed by Allegretti's wife Florence, and the hotel's manager told the FBI in 1957 that "as long as Allegretti continues to serve good food at a reasonable price and does not cause any disturbance in the hotel restaurant, he has no reason to break the lease of Valentinos Restaurant." He typically would leave home each day about 2 pm, and return home about 8 the next morning. During the 1950s Allegretti often could be seen at Valentino's collecting receipts from the nightclub owners at 4 or 5 in the morning, and then towards the mid-1960s these early morning meetings were "at Musket and Henderson Drug Store and Restaurant on Oak Street near Michigan." Allegretti regularly met with Ross Prio, Joey DiVarco, Rocco Fischetti, Felix Alderisio and other Outfit mobsters for lunch or dinner in the upstairs dining room of Augustino's restaurant or at a secluded table in the Water Tower Inn where they sometimes were seen dividing up piles of cash.
The law and bad living finally caught up with Allegretti.
The feds indicted him in June 1960 for his role in a conspiracy to hijack 875 cases of whiskey, and the mobster launched a protracted legal battle to stave off prison. Allegretti attended an affair of the Regular Democratic Organization of the 25th Ward of Chicago in the Grand Ballroom of the Sherman House on March 31, 1962, and sat at the same table with Illinois Governor Otto Kerner Jr. A 25th Ward alderman "warmly greeted Allegretti and extended his sympathy to him for the trials and tribulations he is experiencing in connection with the [federal] government case against him." The feds ultimately won its case, and Allegretti was imprisoned in July 1965 to begin serving a seven-year sentence.
Due to the mobster's deteriorating health the Bureau of Prisons assigned him to the Medical Center for Federal Prisoners in Springfield, MO where he literally rotted away from diabetic ulcers and vascular disease. Poor eyesight -- he was nearly blind in the left eye -- kept him from reading and watching tv, and he spent much of his time staring off into space in apparent daydreams. Allegretti was viewed by the other prisoners as nothing more than "an old man," and he did not "get any special treatment from [corrections] officers." His wife Florence occasionally would visit, and inmates observed that she appeared "always doped or hopped up."
It was no secret that Mrs. Allegretti was a hardcore alcoholic and pill popper -- speed for the day and sedatives to sleep -- who had become a liability to the Chicago Outfit. By January 1966 she told a friend that she feared for her life, and had drafted a document which would expose the rackets if anything happened to her. Indeed, she certainly was aware of what the mob was capable. In March 1944 Ross Prio associate James De Angelo, her partner in gay bar The Windup, was found stuffed into a car trunk after he was tortured and slain during a turf dispute among rival mobsters for control over the cheese market. Allegretti and other mobsters commonly referred to the car trunk disposal method as "Route 66." Florence may have been of the fairer sex but she certainly was no babe in the woods. Throughout the 1940s she regularly collected receipts and payoffs from nightclub owners, and clearly relished the supposed respect she received as Mrs. Allegretti.
Several weeks after she first told a friend that her life may be in jeopardy, Florence Allegretti died in a fire at her North Lake Shore Drive apartment on March 6, 1966. Apparently the poor thing fell asleep while smoking in bed. The prison doctor said that "Allegretti was emotionally upset over the death of his wife but not overly so," and "he is of the opinion that Allegretti has taken this loss probably better than most people who may have suffered the death of a close relative." Indeed, the doctor opined that Allegretti's attitude "is good considering everything that has happened." If his wife in fact had written an expose on the rackets it apparently never was found (at least not by the right people).
During Allegretti's court case the mobster told FBI agents "he has already lived three lifetimes, and has enjoyed every minute of it" but was obsessively afraid of dying in prison. An Allegretti employee earlier told FBI agents in December 1962 that Rush Street "was Allegretti's street and JIMMIE said on several occasions that he would prefer to live and die on this street and would not consider changing his way of life."
Allegretti got his wish not to die in prison. Sort of. He was released on medical parole on December 15, 1969 at 11 am. But he never made it back alive to Rush Street. The 64–year-old died of a heart attack later that day on a commercial flight en route from Springfield to Chicago.
Meanwhile, the rackets must go on, and Allegretti's nephew John Gattuso took over the Rush Street vice strip until he was whacked on Outfit orders and got the Route 66 disposal in July 1983.
Download James Allegretti FBI Files Part I
Download James Allegretti FBI Files Part II
Download James Allegretti FBI Files Part III
Download James Allegretti FBI Files Part IV
Further reading that may be of interest:
