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
