During the 50's and early 60's,James "Jimmy The Monk" Allegretti was one of the Outfit's biggest earners on the North Side of Chicago under boss Ross Prio.I mean really,this dude owned or had shares in half of Chicago's joints.Dude was a real power house during his life period.I gathered this info mostly from FBI reports from that period.

In 1936 Jimmy Allegretti lived with his wife Florence Ramsey at 19 East Ohio Street in an small apartment.In 1940,Allegreti moved to a bigger apartmetn on 822 South Bell Street.In 1947 he stole and sold sugar stamps coupons and worked with punch boards and made a lot of cash.After this he moved to Darborn Plaza Hotel 1031 North Dearborn Street and lived as a big shot.Later he took profits from gambling operations,extortion and mostly prostitution.He held many clubs,restaurants,taverns and also held an army of bookies,prostitutes and hitmen under his rule.He ran prostitution and gambling rackets mostly at 35 and 36 districts of Chicago to whole North Avenue.With this he made millions of dollars a year.In 1952 Allegretti gave his occupation as a restaurant owner.HIs wife Florence Ramsey was usually the front for most of his locals and maybe sometimes Nate Zuckerman or Mike Glitta would do the front.In 1956 Allegretti was the Outfits representative on the North Side and almost every hotel,tavern,bar or club on North Side paid protection money or held at least 20 of Allegretti's prostitutes night and day.Mostly the price for his hookers went from 20$ to 500$.Main rule was that Allegretti took 10% of every joint on the North Side of Chicago.Every one paid street tax and Allegretti made over 15.000 a month from extortion.He was also involved in fur burglaries.The biz generated from 500 to 700.000 a year and they sold from 200$ to 1000$ dollars for one fur coat.It was a big business.He even was involved in horse betting and wire services wich generated almost half a mil per year.He also had shares in several casinos in Hot Springs,Arkansas and was involved in the bartenders and waitress unions.Allegretti also was connected to a car theft ring and shipped cars to Guatemala,wich generated 10.000$ a week and also held a lot of meat markets and stores.In 1957 he lived in a nice house at 21 East Cedar Street,Chicago but Allegretti had only one big problem aside the feds...he suffered from diabetes.Allegretti was imprisoned in July 1965 and served a 7 year sentence.In prison he,suffered from blindness and other defects from the disease.


Here's just a part of Jimmy's criminal empire...


Taverns,Clubs and Retaurant's

Chez Paree Night Club,610 North Fairbanks Street,Chicago -Big time Chicago Outfit hangout and Allegretti held over 30 prostitutes at the place.The prices went from 500$ for a "date" and 20$ drinks.Every sunday night at the Chez Paree was called a "hoodlum night".Sam Giancana was a frequent guest star.

The Playboy Club,182 East Walton Street,Chicago-Very expensive night club with a large prositution ring.Also Sam Giancana was a frequent guest star.

Ciros Restaurant and Bar 800 North Wabash,Chicago-Allegretti was the actual power at this place and it was a front for prostitution.Over 20 prostitutes worked at the place day and night.Generated over 10,000$ a week.

Mardi Gras 939 North Rush Street,Chicago-owned by Allegretti in 1959 and it was a front for a big prostitution ring.

Valentinos Restaurant at Berkshire Hotel 15 East Ohio Street,Chicago-In 1957 Allegretti was the owner and the place operated as horsebook parlor.He made 120.000 $ per year.

Radio Club 433 North Wells,Chicago-In 1957 Allegretti was the silent owner and in 1958 the club was destroyed by a fire.

The Spa 917 North Rush Street,Chicago.Allegretti was a part owner and took 10% out of this place.It was a front for prostitution.

The Windup Club 669 North State Street,Chicago-Very profitable place for Allegretti during his ownership in 1956.He took 1000$ a day.

Trade Winds Clubs at 35th District,Chicago-A big gambling joint.In February 1958 there was a mob meeting at the Winds.Present were Marshall Caifano Felix Alderissio,Leonard Patrick and James Allegretti,in the company of many girls.

Silver Frolics Night Club 400 North Wabash Avenue,Chicago-In 1951 Allegretti was a part owner and held a massive gambling and prostitution rings.Frequent guest was Paul Labriola.

Marble Stairway 624 South Michigan Avenue,Chicago-In 1957 the place operated as horse race book and was a place for bookies.

Caucho Club 10027 Skokie Road,Chicago-Allegretti was a part owner and held a small prostitution ring.

Toy Tap Tavern,Clark Street Chicago-Big gambling joint owned by Allegretti in 1958 and also the joint paid 1000$ a month protection money.

The Diamond Lounge 660 North Clark Street,Chicago-Allegretti made over 10.000$ a month out of this joint.

The Walton Club,Walton And State Streets,Chicago-Operated as big gambling joint

The Peek A Boo Inn 666 North Clark Street,Chicago-Operated as a front for prostitution and Allegretti took 1000$ a month protection money

Larve 32 Rush Street Chicago-In 1958 Allegretti was a part owner and was a front for prostitution rackets.

Front Page Lounge and Headline Room 530 North Rush Street,Chicago -operated as a boomaking parlor.

La Rue 32 Club North Rush Street,Chicago-The club paid protection money and purchased most of the products that the Sterile Glass Company offered,wich was owned by Allegretti.

Cafe Continental 44 East Walton Corporation -In 1959 an expensive cocktail bar owned by Allegretti and Joseph DiVarco.Later they sold the place for 150.000$


Other restaurants,clubs and bars owned(or just paid protection money)by Allegretti from 1956 untill 1960:

Torch Club 900 North State Street,Chicago
Dream Bar 1312 South Cicero Avenue,Chicago
Talk Of The Town Club 1159 North Clark Street,Chicago
Club 19,19 East Chestnut Street,Chicago
Backstage 935 West Wilson Avenue,Chicago
KItten Lounge 424 South State Street,Chicago
Eddie Foy's 754 South Wabash Avenue,Chicago
Cabana Club 517 South Wabash Avenue,Chicago
Crossroads Restaurant and Cocktail Lounge 400 South State,Chicago
Playhouse 550 North Clark Street,Chicao
Normandy 108 North Clark Street,Chicago
The Ship 1801 West Madison Street,Chicago
L & L Cafe 1316 West Madison Street,Chicago
Warren Inn 5713 West Roosvelt Road Cicero Illionis
The Vine Gardens 616 West North Avenue,Chicago
The Prow Tavern Rush Street,Chicago
Club Continental Rush Street,Chicago
The Cadillac Lounge 33 East North Avenue,Chicago
Sands Bar Rush Street,Chicago
Shore Club 528 North Clark Street,Chicago
Black Orchid, North Rush Street,Chicago

Other Local's:The Lemon Twist,The Peper Doll,Carousel,The Glass Pub,1149 Snow Lounge,Lock and Key club,The Parady Club,Gold Coast,The Casaba-All of these cubs were owned by Allegretti and were fronts for many gambling and prostitution rackets.

James Allegretti also owned clubs and restaurants in Calumet City,Illinois:Rip Tide Club,The Shay Club,Brass Rail,Show Club,21 Club,The Playhouse,The Rainbow Club,The Star Club.

Also he had shares in the Tropics Night Club,Midtown Ohio-the biggest and most expensive night club in Dayton with a massive prostitution ring.


Companies

The Midwest News Service Company(Horse racing)343 South Dearborn Street Chicago-It was a wire service to many bookmakers and in 1947 it was taken over by the Chicago Outfit and James Allegretti.

Sterile Glass Company 35 East Wacker Drive,Chicago-In 1958 owned by Joseph DiVarco and Allegretti.THey sold glass and glass cleaning devices all around Chicagos North Side to many bars,taverns and restaurants.No one resisted.

C & C Meat Company 1136 West Randolph Street,Chicago-In 1958 operated by Allegretti and DiVarco.They sold meat to every tavern,restaurant,club or hotel around the area and they had only 5 employees.For example to the CLub Continental sometimes they sold over 10.000$ merchandise.They made over 500.000$ per year.

Cupid Enterprises 105 East Ontario,Chicago-In 1958 owned by Allegretti and DiVarco together with Frank Cupido.A big time company that generated over 10.000$ a month.Cupid Ent. was a very,very serious business for Allegretti.

Pocius Enterprises Inc. 3600 S.Halsted,Chicago-Construction company in which Allegretti had shares in it.


Hotels

Ambassador East Hotel,1301North State,Chicago-Allegretti held a big prostitution ring.

Devonshire Hotel East State Penthouse,North Side Chicago-In 1958 owned by Allgretti.He controlled a massive gambling and prostitution rings out of this place.

Berkshire Hotel 15 East Ohio Street,Chicago-Expensive hotel and Allegretti was a part owner in 1957.It was a front for prostitution and gambling operations.The whole hotel generated over 200.000$ per year.

Lincoln Hotel North Park Street,Chicago-In 1957 Allegretti was a part owner and held mostly gambling operations.

Lansing Hotel 1036 North Dearborn,Chicago-Allegretti's wife was a frontman in this place.It was also a front for Jimmy's prostitution racket.

Also in 1956,James Allegretti had connections to the Key Motel,Royal and Plaza Motel at 221 East First Street,Dayton,Ohio.

Saxony Hotel,Miami Beach,Florida-Allegretti also had some shares in hotels in Florida for example.At the Saxony Hotel,Allegretti operated the punch boards and some of the prostitution rackets.Joe Epstein was Allegretti's connection in Miami.


Secret Gambling Joints

Various basements at 808 North Wabash Street Chicago-Since the 1950's untill the early 60's many of the basements were owned by Allegretti and Joseph DiVarco.


Racing Tracks

In 1958 Allegretti also had shares in the Oaklawn Race Track in Hot Springs,Arkansas

incredible ..how much business he was doing. thanks

No problem.Yeah Jimmy had a hell of a empire under his rule.You can also add his profits from the hookers,that were placed in 90% of the locals(the hookers paid 200$ a month street tax) ,his bookie and other gambling operations(he made 200.000$ per year from the wire service) and ofcourse union profits and loansharking...but the thing is...his reign as a big earner was short.He was a diabetic at the time and had a lot of problems with the feds because when he became big time on the North Side in 1956,thats the same time when Giancana was placed as front boss and made a lot of noise and it wasnt good for business.So when the big earners like Jimmy went to jail,the other bosses decided that its time for Sam to take a vacation.

Jimmy was allied with the old Capone gang and during the 40's he worked as a frontman for the Outfit.He became big time with the night clubs becase he was in debt to some other dangerous people.Story goes that somewhere around the late 40's,Jimmy lost more than 100.000$ on horse betting and he had to work his debt out and was given the job to locate night clubs and later to muscle in and take over.

Later he was also known as the pay off guy(he had good connection on several police districts)and political fixer.The prominent people around Jimmy were Dominic Hunk Galiano(big time Rush Crew member,also club operator,loanshark and was murdered during a card game)John Capone,Joe DiVarco and Dominic Nuccio(one of the "Three Doms" who was also a partner and did the dirty work for Jimmy).