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Jimmy Allegretti Was No Monk: Debaucherous Mobster Ran Chicago's Red Light District

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:

FBI Documents: Special Agents Asked Chicago Mobster Jimmy Allegretti About Jack Ruby A Week After The Kennedy Assassination

Gay Racket Was Very Good To Chicago Outfit

Windy City Watchdog Robert Wiedrich Dies

Robert Wiedrich, "one of the original watchdog reporters who went after Chicago's corrupt politicians and mobsters," died at the age of 85 last Saturday as reported by Erin Meyer for the Chicago Tribune.

Wiedrich was born to investigate wise guys and dirty cops.

The veteran reporter from The Chicago Tribune recently published his memoir Windy City Watchdog, and his nose for news was evident even as a boy growing up during the depression on the Near North Side when Al Capone still ruled the town.

He recounts as a kid watching a steady parade of men using a back staircase to an office over a neighborhood restaurant, and no longer able to contain his curiosity one day endeavored to get to the bottom of the mystery:

[A] couple of us kids snuck up the stairs and heard a man's voice calling out names and numbers over a loud speaker.  We peeked into the large room, which covered the entire second floor, and saw a lot of men milling around exchanging green backs with other men who appeared to be clerks.

The juvie snoops dutifully told the neighborhood beat cop of their discovery -- an operation Wiedrich understood only years later as a book-making parlor -- who snapped back "mind your own business, you little bastards."

The reporter-in-the-making had his Chicagoland baptism, and the relationship between organized crime and public corruption would become a regular theme in his stories for the Tribune.

Wiedrich dropped out of high school when just a junior to join the military with a forged birth certicate during World War II, and after the war with no degree in hand got his start in the newspaper business as a copy boy.

By the late 1950s Wiedrich was covering the Outfit's rackets, and in 1959 investigated its infiltration of the restaurant industry through control over Local 450 of the Hotel and Restaurant Employees and Bartenders Union. In pursuing the story Wiedrich and his colleague George Bliss talked with "several hundred waitresses, bartenders, cooks, and porters, plus owners of plush restaurants and of small greasy spoon hamburger joints," and he learned the sad truth about "how strong gangster influence can be and how difficult it is to uproot it."  Indeed, Wiedrich writes "in the decades that separate the time of that series and the present day, the union has been continually investigated by federal authorities, has been placed under federal trusteeship, and is still being investigated for hoodlum influence."

The six-article restaurant series established Wiedrich as the Tribune's "resident expert on mob activities," and during the 1960s he "was in the paper about four or five times a week with stories on the vast enterprises that the mob had involving sports betting, loan sharking, and the infiltration of legitimate businesses."

Hits were a dime a dozen in Chicagoland, and Wiedrich covered a number of them.  Among those was William "Action" Jackson who was whacked in 1961.  The naked body of the 350-pound West Side enforcer was discovered in the trunk of a car, and Wiedrich uses the hit to illustrate the moral depravity of the mobsters and the violent world in which they lived:

Jackson was noted as a sadist who when he hired prostitutes would bite off their nipples.  So the death that he met, however horrible, probably was appropriate.  From evidence found at the scene, the police were able to determine that Jackson had been physically hung on a meat hook in a fat rendering plant on South Wentworth Avenue, which was owned by a hoodlum associate.  Then an electric cattle prod had been repeatedly applied to his testicles and his body had been punctured by thirty ice pick hits.  He had not died quickly or easily.

Other hits covered by Wiedrich included the 1973 murder of dirty cop and made man Richard Cain who got two shotgun blasts to the face. Wiedrich writes that "only a town like Chicago could spawn a creep like Richard Cain," and he does not hide his disdain for the "bum":  "if you ever watched him in action, plying his sleazy trade, the warning bells sounded and just enough of the stench that was the real Richard Cain escaped for you never to forget it."

Wiedrich had good reason to despise Cain.  Ten years earlier Cain, then the chief investigator for the Cook County Sheriff's Office, arranged a midnight meeting with Wiedrich at a cocktail lounge under the pretext that he had a tip for the reporter, but upon arrival Wiedrich and his associate quickly discovered Cain was attempting to lure them into a honey trap:

He tried to middle us with the loveliest looking creature in his stable, an incredibly constructed blonde who dangled lazily from a velvet swing over the heads of the assorted playboys, professional thieves, and crime syndicate thugs who frequented the joint.

Fortunately, we had the good sense to flee that saloon before Cain could keeo his whispered promise of a private showing of the swinging lady's charms in some plush Near North pad, undoubtedly equipped with a zoom lens movie camera and stereo recording gear.

That well could have proved the most expensive picture show in town for us, with the price our personal integrity at a time when we specialized in exposing gangsters, including Salvatore (Momo) Giancana, the mob's operating boss whom Cain would later join in exile in Cuernava, Mexico.

Although not discussed in Wiedrich's memoir, in 1959 Cain murdered Harry Figel who used underage teenage boys to shake down chicken hawks in the Greyhound Bus terminal.  Cain claimed he shot Figel in self-defense in an attempt to arrest him pursuant to an undercover investigation into the sextortion racket.  However, Figel's murder likely was the resullt of a failure to pay street tax to the Outfit.  Indeed, a witness alleged that a week earlier Cain and another detective beat up Figel for not making payments, and after Figel's murder dirty cops and mob thugs took over the so-called chicken-and-bulls extortion racket until the feds busted it in 1966.  Cain was forced to resign from the Chicago police force in 1962 once several of his crimes came to light, and very few shed a tear with his murder a decade later.

Wiedrich regrettably had to write about more than a few dirty cops, and during the 1970s reported on pervasive corruption within the police force.  Dozens of cops in multiple districts were indicted by the feds for not only taking bribes to protect mob interests but further shaking down legitmate businesses including taverns and restaurants on the Far West Side and nightclubs on the Near North Side.  When Wiedrich reported about proprietors complaining they had been threatened by police officers not to cooperate with the federal investigation, he even got a visit from a district commander asking for their names.  Of course, Wiedrich refused the request:  "It was obvious that if I had done so, the informants would have suffered dire consequences."  Unfortunately, the 1970s were a time when many cops were not your friends.

Wiedrich long had reported on the dirty role that mobsters and cops played in the nightlife industry.  For example, in the mid-1960s Wiedrich exposed the role of the Chicago Outfit in the gay bars on the Near North Side.  Johnny Gattuso, a Cook County sheriff's deputy and nephew of Rush Street crew boss James "the Monk" Allegretti, had convinced dozens of tavern owners to convert their strip tease joints and B-girl dives into gay watering holes, and "he would receive 50 percent of the profits" in cash and half of the tavern's corporate stock was "placed in the name of a mob front man" as Wiedrich reported in a May 15, 1966 Tribune article:

In the last year, mobsters have been using force or the lure of high profits to convert at least 14 financially foundering taverns into lucrative hangouts for homosexuals.  Investigators estimate that these places are putting at least one million dollars a year into crime syndicate coffers.

Moreover, the cops were involved with the Outfit's gay bars as Wiedrich reported nearly a decade later in a September 30, 1973 Tribune article:

In a certain North Side police district, crime syndicate operators of a network of homosexual bars have been cavorting with vice detectives and some of their bosses for almost a decade.  * * *  If anyone doubts such illicit liaisons, listen to what has occurred in the lives of two former vice dicks bounced for shakedowns:  Both are now employed as managers of crime-syndicate-owned gay bars.  One is suspected of sharing a hidden interest in a joint with the mob's New Town vice merchant.

Following the death of Allegretti in 1969, Joseph "Joey Caesar" DiVarco became the Rush Street crew boss to whom Gattuso reported, and Wiedrich expressed outrage over the suspected relationship between the gangster and the police in allegedly trafficking drugs, skimming profits and blackmailing homosexuals out of the gay bars.  In an October 4, 1973 Tribune article Wiedrich reported the following:

Scholars seeking a textbook example of the unholy alliance between crooked police, politicians, and mobsters need look no further than Chicago's North Side.  For there, in a network of 20 nightclubs and bars catering to the specialized recreational needs of homosexuals, the mutually avaricious interests of these groups are interwoven in a tragic tapestry of corruption.  In short, thieving lawmen and politicians have joined forces with crime syndicate gangsters to prey upon some of society's most vulnerable—the gay people.  * * *  From the Chicago River to the northern city limits, the Justice Department men have spent two years probing a cesspool of extortions and blackmail, not only of tavern owners, but successful and prosperous homosexuals fearful their secret will be exposed to business associates.  Also involved in the inquiry is an estimated multi-million dollar rip off of state, local, and federal taxes thru the illicit "skimming" of profits from certain gay bar operations in which gangsters are known to have a hidden interest, plus a flourishing traffic in narcotics.  * * *  Probably the most tragic victims of the widespread shakedowns, investigators report, are the well to do homosexual businessmen who have submitted to continuing blackmail under threat of arrest on real or trumped up charges.

Investigating the mob back in the day involved a lot of old-fashioned gumshoe-style detective work.  Wiedrich recounts pounding the streets of Gary, Indiana in 1959 to uncover the Outfit's prostitution and and gambling dens which operated behind pizzeria fronts, and trailing the Outfit's floating crap game in the mid-1980s to take "licene plate numbers in an effort to identify some of the participants."

Bob Wiedrich viewed his mission to expose wise guys and dirty cops as a public service, and in Windy City Watchdog he makes no bones about taking sides in his coverage:  he was on the side of the good hardworking people of Chicago.

Further reading that may be of interest:

Gay Barkeep Jim Flint Beat The Chicago Outfit

Gay Racket Was Very Good To Chicago Outfit

Chuck Renslow Biography Documents Chicago Outfit Role In Gay Bars

Gay Barkeep Jim Flint Beat The Chicago Outfit

Long before Stevie Nicks first sang "Leather and Lace" Jim Flint was running leather bar Redoubt and drag club Baton in Chicago, IL.

The gay club owner is the subject of the new biography The Boy From Peoria by Tracy Baim and Owen Keehnen.  Like their earlier book Leatherman in which Baim and Keehnen delved into the life of barkeep and bathhouse operator Chuck Renslow, the authors once again tell a page-turning story of a gay businessman in the Windy City against a backdrop of the Mafia underworld.

The Boy From Peoria dramatically underscores with exhaustive research how the gay experience for decades was defined by wise guys, and in the fight for liberation the community had to eliminate the Mafia from its bars.  Flint began his nightlife career as a bartender during the 1960s in suspected mobbed-up joints, later opened his own venues during the 1970s under the mob's extortionate thumb, and then testified for the feds at a 1984 mob trial.  In the end Jim Flint came out on top.

The first gay clubs at which Flint worked in the mid-1960s were drag revue joints The Chesterfield and The Annex which were owned by Nick Dallesandro, and Baim and Keehnen write:

The Chesterfield and the Annex were both managed by Nick's nephews. Skip Dallesandro ran the Annex, and Bobby Dallesandro ran The Chesterfield. It was widely suspected at the time they were on the fringe of the Mafia, but nothing was certain. "I know one time they said the payments weren't in, and they [the Outfit boys] came behind the [Chesterfield] bar at 2:30 in the morning and cleaned all of our registers out and left us a dime, a nickel and a quarter in each register to work with," Flint said.

Jim Henritze, a manager of The Chesterfield, recounts that in 1962 Rush Street crew boss Jimmy "the Monk" Allegretti showed up with money on his mind:

"I remember two weeks after I started at The Chesterfield, this black Cadillac pulled up and Benny Allegretti got out with four bodyguards and walked in and took Nick to the back office. After a couple minutes they came out and cleared all the money out of the two front registers and the two back registers and then went back out to the car and pulled away."

Whether Nick Dallesandro was a mob front or an extortion target one thing was certain:  he cared more for gay money than gay rights, and one early activist says that Dallesandro would not allow the Mattachine newsletter to be openly distributed at his bars.

Flint parted ways with Dallesandro after police raids on The Chesterfield and The Annex.  Flint suspects that Dallesandro set him up as the fall guy in a bid to save the liquor licenses, and in The Boy From Peoria expounds as follows:

Flint said he would go to court and everybody else would be found not guilty. "However, they wouldn't find me not guilty. They kept filing it and reinstating it. I think they [the Dallesandros] were trying to say that I was really soliciting for prostitution. They were using me, trying to bargain me through the court system as a way to find me guilty so I'd be gone. Then they could say, 'Hey, the bartender who was a bad element is gone, we didn't know what was going on.' In that way they could reopen. "They were trying to use me as the scapegoat to get the bar license back after the raids."

Flint moved on to the popular cruise bar Sam's which was owned by brothers Walter (Wally) and Julius (Jerry) Fleischmann.  The pair also reportedly owned the Man's World bathhouse.  One bar patron from those days says the Fleischmann brothers "were considered part of the Mafia by most people." The two brothers testified about police payoffs at a 1973 federal trial which brought down nearly two dozen vice cops from the 18th District who targeted gay venues in a shakedown scheme, and police corruption is discussed extensively in The Boy From Peoria.

Wise guys and gay men may seem like strange bedfellows but it was inevitable that from time to time they would cross swords given the pervasive role of the Mafia in the bars, and Flint recounts a roll in the hay with one supposed button man:

"I remember this one guy who used to come into Sam's. He'd been after me for six or seven weeks. He'd wait for me every night after work, but I was scared of him so I'd never go with him. He was beautiful and persistent, so one night I took him back home to the Tuscany Hotel, and that was the first night I realized there were those Outfit guys who liked gay guys. He started undressing and the first thing he did was take off his gun. I had no idea. I thought I was going to get killed."

Of course, not everyone was getting into bed with the mob.  Well before the 1969 riots against the Mafia owners of the infamous Stonewall Inn in New York City some gay activists in the Windy City were refusing to play ball with the syndicate boys.  Attorney Ralla Klepak represented Flint after his arrests at The Chesterfield and The Annex, and when approached by the Fleischman brothers she told them to take a hike based on mob rumors surrounding the pair:

In a 1995 interview with Jack Rinella, attorney Ralla Klepak explained: "Sam's was owned by the Fleischmann brothers …. One day one of the Fleischmann brothers came to me and said, 'We'd like you to represent us, and we’d like to put you on retainer.' I said, 'No, thank you.' They said, 'You know, name your price, you want $1,000 a month, just to be on call in case we call you?' And I said, 'No, thanks.'

"When they asked why, I said, 'Because word has it that you're a Syndicate bar, and I don't represent the Syndicate—I represent the patrons.' He said, 'Sure we can't change your mind?' I said, 'That's right, I don't want anything from you, and you can't have anything from me.'"

After Sam's closed up shop the Fleischmann brothers launched The Normandy Inn at which Flint briefly worked.  However, eager to spread his wings and seeking greater riches, Flint opened up his first club The Baton in 1969 and then Redoubt in 1976.  The Mafia had its extortionate hand out according to Flint:

In a 2008 interview for WTTW, the Public Broadcasting Service affiliate in Chicago, Flint told filmmakers Alexandra Silets and Dan Andries that in the early 1970s, the payoff rate was about $1,800 per month to police and $1,800 to the Mafia. "How that shifted from person to person, I don't know, but that's what I know that I handed them in two envelopes," Flint said. "I had to do that before I even had to pay my rent. Because I couldn't afford an apartment, I had to live in the basement here [the Baton]. Those were hard years back then."

Flint one day would have his revenge against the mob. 

In December 1983 the feds indicted five defendants, including reputed Rush Street crew bosses Joseph "Little Caesar" DiVarco and Joseph "Big Joe" Arnold, for their alleged roles in shaking down gay bars in the Old Town and Near North Side neighborhoods.  Charges were dismissed against DiVarco after his defense lawyers produced records showing that a bar from which he allegedly extorted payoffs in 1979 had gone out of business three years earlier, and three out of the other four defendants, including Arnold, were later acquitted at trial.

Taking a page from a homophobic playbook the defense strategy in part was that the gay barkeeps were not extortion targets but nervous nellies, and one lawyer told the press:

"How does anyone become a criminal because of what’s on some fag's mind?  Some fruit who only in his own mind is afraid has become the subject of a federal case. A federal case should be a federal case, not a fruit parade."

Flint claims that before the trial some thug came into his bar threatening that the "bar owners they better be quiet or somebody's going to get hurt."   Undeterred, Flint testified that he had stopped paying off the mob, and in 1979 received visits and calls from supposed mobsters including Joe Arnold during which they requested "safety money":

"I said no, I was not going to pay it, I was not getting involved in that. * * * Yes, I said I wasn't going to get involved because the FBI was there, and I went through this before, and I was not going to do it again."

In an FBI tape recording of a telephone call played to the jury Arnold told co-defendant Frank DeMonte "that motherfucker, he's got balls, that Jimmy Flint."

Other gay bar owners who testified at the trial included Glory Hole owner Robert Hugel, and afterwards he reportedly went into the witness protection program.  Flint stayed in town notwithstanding a supposed contract on his life.

Nobody messes with Jimmy Flint, and by taking on the Chicago Outfit in the mean streets he did more for the gay community than any political activist ever did on Capitol Hill.

Further reading that may be of interest:

Gay Racket Was Very Good To Chicago Outfit

Veteran Chicago Tribune Reporter Bob Wiedrich Releases Memoir Windy City Watchdog

Chuck Renslow Biography Documents Chicago Outfit Role In Gay Bars

Gay Racket Was Very Good To Chicago Outfit

For decades the Outfit had a nice piece of gay nightlife in Chicago, IL, and during the 1960s and 1970s its operations were overseen by John Gattuso according to recently released FBI files on the mobster.  The FBI noted in June 1973 that under Gattuso's watch "business operations among homosexuals has become highly lucrative source of income for Chicago LCN Family."

The FBI commenced its investigation into Gattuso in late 1971 after confidential informants advised that he had undisclosed interests in numerous gay bars on Chicago's near north side and was paying off dirty cops in the 18th, 19th and 20th police districts to avoid raids against them.  The investigation continued for three years, and the reports generated by the G-men read like a cross between a gay guide and pulp fiction involving tales of iconic establishments and mob ownership, vendor placements and profit skimming, political corruption and police payoffs, and beatdowns and other bullying tactics for control over the lucrative industry.  One confidential informant told the FBI in 1974 that "one had to be connected with the outfit or at best have the outfit permission to open and operate a homosexual tavern."

In 1955 at the age of twenty Gattuso married the niece of Rush Street crew boss Jimmy "the Monk" Allegretti, and by the early 1960s was managing the Monk's interests in strip clubs, B-girl joints and gay bars.   The Monk was a degenerate who was charged in 1959 with paying $30 for oral sex from an underage girl -- although the case inexplicably was dismissed a month later -- and he was a natural to run the vice rackets for near north side boss Ross Prio.

Gattuso first came to the attention of the FBI when busted in January 1962 "in connection with a vice investigation at the French Doll Lounge" of which he was the nominal licensee, and his brother Dominick "was also arrested for running a gay bar about the same time."  In June 1964 a confidential informant advised the FBI "that Gattuso has operated the Playhouse and the French Casino for Allegretti" which "were former strip shows and now are operating without strippers but now have B-girls," and in July 1965 another confidential informant told that FBI that "Gattuso controls gay taverns on the near north side for Jimmy Allegretti."  A confidential informant advised that "Allegretti considered Gattuso to be like his son and very trusted," and Gattuso ultimately was sponsored by Allegretti for membership into the Outfit.

Gattuso's star continued to rise within the Outfit even after the death of Allegretti in 1969. The gay bar operations were raking in a lot of money for the Outfit, and Gattuso had developed a strong relationship with Ross Prio.  Gattuso bought Prio's suburban Glenview home in 1964 for $65,000, and the FBI noted in 1972 that "on Sunday afternoon, Gattuso will frequently entertain members of the Ross Prio family of the LCN, when weather permits a backyard barbecue will be held."  Gattuso further was close to Joseph "Little Caesar" DiVarco and Joseph "Big Joe" Arnold who took over the Rush Street crew after Allegretti's death, and he frequently was seen at the shirt shop the pair operated on North State Street.  Gattuso and Arnold would "both go on fishing trips together in Minnesota and Canada."

A 1973 FBI assessment on Gattuso describes more of a hustling businessman rather than an Outfit mobster, and states:

Gattuso appears to be a high-strung individual who moves about rapidly, and is always in motion.  Gattuso dressed in a business-like manner with a slight modish touch and seems to favor double knit suits.  He also indicated that he likes to play a little golf.  He also gives the impression of being always occupied in his business ventures, working 12 hours or more a day.

During the FBI investigation Gattuso allegedly arranged in November 1972 for someone to carry $3 million in cash out of the country for deposit into a Swiss bank, and afterwards "allegedly said that he was no longer worried about the 'G' because they could no longer touch his money."

In light of Gattuso's history with his operation of the French Doll Lounge he was precluded from obtaining a liquor license, and he necessarily relied upon a series of clean names or front men to operate the establishments on his behalf pursuant to a profit split where he and his Outfit bosses took 50 percent and the frontmen took the other 50 percent.

Among the more notorious gay bars in which Gattuso allegedly had an interest according to multiple people was New Jamie's on North Clark Street which supposedly served as a meat market for rent boys and their admirers.  One confidential informant stated that "New Jamie's is well known as a place to pick up male prostitutes."  Another source advised the FBI in early 1972 that Gattuso intended to buy the building out of which the bar operated, and "remodel the rest of the building and make rooms which he will rent to patrons of the bar for what the source considered to be obvious activities."  In August 1973 a confidential informant told the FBI:

The hotel above New Jamie's is known as the Crystal Hotel and is now open.  The charges are $14 a night for the room.  It is daily pay for the room and there are 32 rooms in the hotel.  Source advised that there is no organized prostitution taking place at the Crystal Hotel till this time.

In May 1975 a confidential informant to the FBI "advised that the young homosexuals who live in the Crystal Hotel above New Jamie's Tavern . . . have credit to drink in New Jamie's," and that "most of the young men in the hotel are male prostitutes."

Gattuso also was accused by multiple people of having undisclosed interests in gay bars operated by Chuck Renslow who opened the leather bar Gold Coast in 1959, and went on to build a gay nightlife empire.  The FBI interviewed Gattuso on November 20, 1973, and told the mobster "that his [alleged] involvement in taverns such as Sparrow's, The Gold Coast, and The Club Bath at 609 North La Salle Street, was of interest to the Federal Bureau of Investigation."  All three establishments were Renslow operations, and Gattuso told the G-men that "he has nothing to do with the ownership of the taverns that [redacted] is connected with."  However, he admitted that "he [Gattuso] does have connections with Chicago Police Officers and has asked police officers in the past to not harass [redacted] and [redacted] friends."

With respect to Renslow's Club Bath franchise in Chicago one source stated the following to the FBI:

When the Club Baths first opened in Chicago at 609 North La Salle Street it was at the instigation of [redacted] and [redacted] both of Cleveland, Ohio.  When they got to Chicago and tried to establish themselves in the homosexual scene, they were placed in contact with [redacted] told [redacted] in front of her that Johnny Gattuso was his man.  She stated [redacted] told her that Gattuso receives one third of all the gross from the Club Bath.

Multiple people told the FBI that the Club Bath was paying off cops to avoid raids.  For example, one "source has advised that [redacted] makes $2,000 per month payments to the Chicago Police Department to allow that homosexual bath house to operate," and allegedly the payments got results:

[Redacted] would let them know what was happening at the Police Department in regard to the bath and source stated that on one occasion, approximately two years ago, [redacted] advised the club would be raided by the Police Department in the near future.  The bath was called the day before the raid was to take place and advised to close for the day, that they were to be hit on that day, and when the Police came no customers were present.

A former Chicago Police officer advised the FBI on August 21, 1973 "that Club Baths at 609 North La Salle Street, was off limits to police officers in 1971 and 1972," and he "stated that it was his belief that the Club Bath was receiving protection from the downtown police headquarters."

Renslow further opened up a Club Bath franchise in Kansas City, MO, and a June 8, 1973 teletype from the FBI's Chicago field office to its Kansas City field office alleged the following: 

Investigation in Chicago has also revealed that Chicago LCN figure John Gattuso operates numerous homosexual bars and an extremely lucrative homosexual bath house in Chicago.  [Redacted] is frontman for Gattuso's homosexual operations and investigation indicates the bath house operation has been extended to Kansas City, Missouri.  Officers of corporation operating bath house Kansas City known associates of [redacted].

The FBI was concerned whether Renslow's new Club Bath franchise "may be collusion between Gattuso and [Kansas City mob boss Nick] Civella."  A relative of Civella was Louis S. "Red" Chiavola who not only worked in Chicago's 19th District Station until his 1973 death but further allegedly had undisclosed interests in three unidentified Windy City gay bars.  The Chicago G-men advised their Kansas City colleagues that they "should note involvement of deceased Chiavola in homosexual operations and relationship to Kansas City LCN leadership."

In 1976 and 1977 there were a series of confirmed and suspected cases of arson involving gay bathhouses along the west coast including the Folsom Street Barracks at 8 Hallam Street, San Francisco; Club Bath at 328-330 Ritch Street, San Francisco; Steve's Bath House in Sacramento, California; and Club Bath in Portland, Oregon.  The FBI launched an investigation to determine whether "organized crime groups, using extortion, threats, and arson" were attempting "'take overs' of homosexual bath houses in the San Francisco, California area."  The FBI was concerned whether the Mafia had infiltrated the west coast gay bathhouses because it suspected "[o]ther homosexual bath house chains have been determined as being financed by organized crime," and more specifically claimed the following:

Chicago investigation entitled [redacted] ANTI-RACKETEERING (Chicago File 92-3518) indicates organized crime influence in Club Bath Chain.  * * *  Investigation at Chicago has indicated LCN associates as having been involved with some Club Bath Chain Bath-houses in the Chicago area approximately five years ago.

The FBI closed out the San Francisco case after investigation "failed to show any organized crime influence in captioned case and has established that insurance fraud was not possible as a motive in this case," and said that "remaining explanations of local competition in the homosexual bathhouse trade or random pyromania remove the case from FBI jurisdiction."

Renslow is the subject of the recently published biography Leatherman by Tracy Baim and Owen Keehnen in which the barkeep and bathhouse operator is quoted extensively concerning the historic pervasiveness of the Outfit in the industry.  In Leatherman Renslow insists that he was not a mob front; however, he admits that he otherwise had to play ball with the syndicate boys which included monthly protection payments to them and the use of their vending services. 

Although many people alleged to the FBI that Gattuso had interests in Renslow's bars and bathhouses, some accounts by confidential informants generated during the investigation corroborate Renslow's position.  For example, one source claimed in August 1971 that when Gattuso learned Sparrow's was not serving beer from his distributorship "John Gattuso came around and there was a confrontation" which remedied the situation.  Moreover, others told the FBI on more than one occasion that Gattuso was complaining that he was not getting enough in payments.  For example, in March 1973 a confidential informant told the FBI that "Gattuso is complaining that [redacted] is not giving him much money from the bath house operation and he cannot understand why."  There's a big difference between an extortion target who went with the flow and a clean name who fronted for the mob, and on balance the evidence suggests Renslow more likely was the former rather than the latter.

Neither Gattuso nor Renslow were ever charged by the FBI, and by memo dated February 20, 1976 the Bureau placed "[t]his case . . .  in a closed status inasmuch as no information has been developed concerning violations of criminal status."

In the end it wasn’t the FBI who brought down Johnny Gattuso but the Outfit.

On February 10, 1983 Gattuso and Jasper Campise botched an Outfit-ordered hit on Ken Eto who ran the numbers racket, and two days later the FBI's Chicago Field Office sent a priority teletype to the Bureau Director in Washington, D.C. that "throughout the law enforcement community in Chicago it is believed that the LCN would attempt to kill both Campise and Gattuso for the 'sloppy job' they did on Eto."

Gattuso knew it was coming.  In the biography Leatherman Renslow recounts how Gattuso visited him after the Eto mess to confess that he feared for his life.  Sure enough, a few months later in July 1983 the decomposing bodies of Gattuso and Campise were discovered in a car trunk.

Download John Gattuso FBI Files Part 1

Download John Gattuso FBI Files Part 2

Download John Gattuso FBI Files Part 3

Download John Gattuso FBI Files Part 4

Download John Gattuso FBI Files Part 5

Download John Gattuso FBI Files Part 6

Download John Gattuso FBI Files Part 7

Download John Gattuso FBI Files Part 8

Further reading that may be of interest:

Chuck Renslow Biography Documents Chicago Outfit Role In Gay Bars

Veteran Chicago Tribune Reporter Bob Wiedrich Releases Memoir Windy City Watchdog

Chuck Renslow Biography Documents Chicago Outfit Role In Gay Bars

The old men behind the gay bars and bathhouses of yesteryear are like Grizabella the Glamour Cat singing Memory.

And they're also singing like canaries.

In recent years memoirs have come out by Steve Ostrow who owned the Continental Baths and Charles Scaglione Sr. who owned the hustler bar Rounds in which the historic role of the mob in New York City's gay venues is discussed.

And now Chuck Renslow, the 82-year-old businessman who has been a dominant fixture in gay nightlife in Chicago, IL since 1959 with the opening of Gold Coast, is the subject of the biography Leatherman by Tracy Baim and Owen Keehnen in which the barkeep and bathhouse operator is quoted extensively concerning the historic pervasiveness of the Outfit in the industry.

Renslow believes that at the time he opened Gold Coast it was the only gay bar "not Mafia controlled," and claims he remained one of the few operators well into the late 1970s and early 1980s -- a period during which he owned dozens of gay establishments -- who was not a mob front.  However, he readily admits that he otherwise had to play ball with the syndicate boys which included a monthly cash payment of $200 and the use of their vending services.  Renslow states:

That was the reality of having a bar in Chicago at that time.  I got lucky.  I had some protection early on.  In all fairness, they didn't want to own you -- they just wanted a little bit, they just wanted their cut.  It was maybe a couple hundred a month.  Like clockwork on the first of the month or whatever, two bagmen in silk suits would come around asking for money.  Then there were other things, like we had to use the Outfit's jukebox company. * * * We also had to use their towel distributors, glass distributors and bar goods companies -- things like that.

Although $200 a month in 1959 was no small sum, Renslow says the Mafia "made more money" by requiring the use of its suppliers.

The principal contact with whom Renslow dealt was Johnny Gattuso who was a Cook County sheriff's deputy and the nephew of Rush Street crew boss James "Jimmy the Monk" Allegretti .  The Monk, a degenerate who was charged in 1959 with paying $30 for oral sex from an underage girl although the case inexplicably was dismissed a month later, controlled many gay bars for the Outfit on the Near North Side.

When someone attempted to muscle in on one of Renslow's bars in 1971 he went to Gattuso who promptly took care of the problem by "beat[ing] the crap" out of the interloper.  In 1972 the FBI opened an investigation after an informant alleged that Renslow was a front for Gattuso; however, Renslow always denied that he was a mob front, and no charges were ever brought.

Frankly, Gattuso let Renslow off cheap.  By the mid-1960s Gattuso had convinced dozens of tavern owners to convert their strip tease joints and B-girl dives into gay watering holes, and "he would receive 50 percent of the profits" in cash and half of the tavern's corporate stock was "placed in the name of a mob front man" as reported by Robert Wiedrich in a May 15, 1966 article from the Chicago Tribune:

In the last year, mobsters have been using force or the lure of high profits to convert at least 14 financially foundering taverns into lucrative hangouts for homosexuals.  Investigators estimate that these places are putting at least one million dollars a year into crime syndicate coffers.

Although Renslow may not have been a front for Gattuso, he certainly jumped when Gattuso said jump.

In May 1973 Renslow purchased the landmark three-story limestone Dewes Mansion for $240,000.  However, after accusations surfaced at the end of the decade that Renslow was holding the property for the Outfit, Gattuso and "the clothing store mobster who had a men's store on State Street" together allegedly told him to swap it at a significant loss with a local politico for a more humble dwelling.  The "clothing store mobster" to whom Renslow refers presumably was haberdasher Joseph "Little Caesar" DiVarco who took over as the Rush Street crew boss after the death of Allegretti in 1969.  That certainly would have been one high-powered visit for a mere barkeep to receive.

DiVarco was a focus of an intense FBI investigation in the early 1970s -- perhaps the same investigation which encompassed Renslow -- for his suspected role in trafficking drugs, skimming profits and blackmailing homosexuals out of the gay bars.  An October 4, 1973 article ("Cops, pols, mob in gay bar payoffs") by Bob Wiedrich from the Chicago Tribune states:

Scholars seeking a textbook example of the unholy alliance between crooked police, politicians, and mobsters need look no further than Chicago's North Side.  For there, in a network of 20 nightclubs and bars catering to the specialized recreational needs of homosexuals, the mutually avaricious interests of these groups are interwoven in a tragic tapestry of corruption.  In short, thieving lawmen and politicians have joined forces with crime syndicate gangsters to prey upon some of society's most vulnerable—the gay people.  * * *  From the Chicago River to the northern city limits, the Justice Department men have spent two years probing a cesspool of extortions and blackmail, not only of tavern owners, but successful and prosperous homosexuals fearful their secret will be exposed to business associates.  Also involved in the inquiry is an estimated multi-million dollar rip off of state, local, and federal taxes thru the illicit "skimming" of profits from certain gay bar operations in which gangsters are known to have a hidden interest, plus a flourishing traffic in narcotics.  * * *  Probably the most tragic victims of the widespread shakedowns, investigators report, are the well to do homosexual businessmen who have submitted to continuing blackmail under threat of arrest on real or trumped up charges.

Gattuso's last visit with Renslow was in early 1983 when the mobster confessed to the barkeep that he had botched the February hit on Ken Eto who controlled the numbers racket, and now feared that his own number was up.  Eto incredibly survived 3 bullets to the head to become a government informant.  A few months later the decomposing bodies of Gattuso and his accomplice Jasper Campise were discovered in a car trunk.  DiVarco fared much better.  Investigators suspected he merely was demoted, and that Joseph "Big Joe" Arnold -- DiVarco's partner in the haberdashery -- took over the Rush Street crew.

As a result of Eto's cooperation in December 1983 the feds indicted five defendants, including reputed Rush Street crew bosses DiVarco and Arnold, for their alleged roles in shaking down gay bars in the Old Town and Near North Side neighborhoods.  However, charges were dismissed against DiVarco after his defense lawyers produced records showing that a bar from which he allegedly extorted payoffs in 1979 had gone out of business three years earlier, and three out of the other four defendants, including Arnold, were later acquitted at trial.

The Outfit allegedly continued to shake down some gay bars at least well into the 1980s.  During the so-called Family Secrets trial against the Outfit in 2007 government witness Red Wemette testified that from 1974 through 1988 during which he operated his smut shop "all the adult bookstores and gay bars in the neighborhood a mile north of downtown were paying street tax to mob extortionists" from the Grand Avenue crew headed by Joseph "Joey the Clown" Lombardo.

Who knew running gay bars and baths could involve such mob drama?