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10 facts about the Chicago Outfit





The Chicago Outfit is a crime syndicate that has a strong hold in the City of Chicago.  Al Capone was its most famous leader.  Through the 20th century the Outfit had a stronghold on illegal activities in Chicago.  The Outfit manage to destroy all the other organized crime families in Chicago during the 1920s.  Since that time, they took over the City of Chicago and its surrounding suburbs, and rule the underworld by using street crews.  The Outfit has been romanticized in Hollywood, it has ruled Las Vegas by fear, and almost destroyed by the Family Secrets trial. 



1.       The film Casino

The film starred Robert Deniro, Joe Pesci, and Sharon Stone, and they portrayed real life people.  The film was loosely based on events that happened in Las Vegas, but in typical Hollywood fashion they had to create a story to put on the silver screen.   Joe Pesci portrayed the real-life hitman for the Chicago Outfit Anthony “The Ant” Spilotro.  Spilotro along with his brother Michael were brutally murdered years later in the basement of a home located in Bensenville, Illinois.  The bodies were found in a farm near the border of the State of Illinois and Indiana on June 26, 1986.  In the film, Casino Joe Pesci’s character is permitted to say a prayer just before he is killed.  Frank Cullota a known associate of Spilotro stated that he believed that asking god for forgiveness was his ticket into heaven.  Spilotro was sent out to Vegas to keep an eye on illegal activities, to include the skim.  The murder of Spilotro brothers went unsolved until the family secrets trial in June of 2007., where prosecutors revealed how they were killed.  Nick Calabrese testified that he was one of the six that killed the Spilotro brothers.  They were killed in a home that belonged to Outfit member Louis Eboli on the afternoon of June 14, 1986. 



2.       The Skim

The Skim was originated by the Kansas City, Milwaukee, and Cleveland families, who had control of Las Vegas from the minute that the foundations were poured.  There was a beef between the families and the Chicago Outfit was called in to solve the issue, they resolved it and added themselves as part of the skim that ran from 1974-1983.  The Outfit controlled the Stardust Casino using Teamster union funds.  The Outfit had strategically placed made-members to work in the casino in various roles.  Las Vegas was considered opened in regards to La Cosa Nostra, meaning any mafia family could operate freely.  The mafia families were from Chicago, Kansas City, Cleveland, and Milwaukee, the skimming netted these families from $40,000 to $65,000 per month, and sometimes $100,000.  Members of the teamster union were also in on the skim. 

Gamblers would place bets at the tables, and the slots.  Once the money was removed it was taken to a secure room in the casino, hotel employees would count the money and a portion of it was given to made members of the each of the families.   Once the mob received their cut the rest of the proceeds were officially entered as revenue. 

The Chicago Outfit officially controlled the Stardust, Marina, Fremont, and Hacienda casinos. At the end of it all, mob families lost control of the Casinos because the City of Las Vegas cracked down on how Casinos conducted business, and if you were a known associate of any mob family your name was placed in the Black Book.  This would officially ban you from entering any Casino in Vegas.  In the end the mob lost and the Government won.  


      3.       The 1st ward-Chicago

The 1st ward was controlled by Fred Roti, a man that had a short stature.  His father Bruno Roti was a member of the black hand crew that ran out of Chinatown.  The crew belonged to the Chicago Outfit, and Al Capone would visit Bruno on many occasions. 

From 1968 to 1990, Fred Roti served as the Alderman of Chicago’s 1st ward.  During his tenure, Roti fixed murder cases, appointed Judges.  Fred Roti was a member of the Chicago outfit with strong political ties.  Roti fixed murder cases, bribe judges, and change zoning laws to accommodate illegal activities. He was ultimately convicted on Racketeering charges and served his time in prison in 1999 he passed away from lung cancer.


      4.       Operation Greylord

Fred Roti was the Alderman of the 1st ward in Chicago.  A judge in Cook County could not be assigned to the courts without approval from Roti.  The Chicago outfit controlled appointments to the Cook County justice system.  If a judge wanted to be appointed, he needed to bribe Roti and eventually he or she would receive the appointment.  By paying the bribe the Judge would be under to control of the Chicago Outfit.  Outfit attorneys could get many of its members exonerated because of crooked judges. 

Operation Greylord resulted in the arrest and conviction of many officials, Judges, law enforcement, attorneys, and court employees. The FBI ran the sting and it netted 92 indictments.  After Greylord, Cook County judges had to be appointed.  Fred Roti and the 1st ward survived Operation Greylord, in fact they were left untouched.


    5.       Sam Giancana

Sam Giancana was a mobster in the Chicago Outfit, who rose through the ranks and eventually became boss of the family.  In the 1920s Giancana was a young kid who got involved with a local street gang in Chicago known as “The 42s”.  They were running low level street operations for Al Capone’s Outfit.  In the 1940s after a sting in Prison Giancana took over an illegal lottery racket in Chicago’s west side.  Murders, extortion, loan sharking followed for the next several years.  Giancana took over the family when Accardo decided to step down from his role as boss of the Outfit.  Giancana had a lot of information on the current members of the Outfit, and it is believed that the bosses were afraid of what he would say.  In the 1960s Giancana was constantly in the newspapers, this bothered the high-ranking leadership of the outfit.  Giancana was exiled to Mexico for the next several years. In 1974 Mexican Officials sent Giancana back to the United States.  It is believed that Giancana was exiled by former boss Tony Accardo who did not approve of how he conducted business.

On June 19, 1975, Giancana was at home making sausage and peppers in his basement kitchen.  The same room where he would be killed.  Police revealed that there were no signs of breaking and entering his home, it is alleged that he knew his killer.  Giancana was set to speak with a Senate committee a few days later in Washington, it is believed to be one of the reasons for his rub-out. Anyone that could be a suspect in ordering his death has since been killed or passed away.  Giancana’s daughter believes that the CIA killed her father.  JFK assassination files released in 2017 confirmed that the Cia recruited Giancana in a plot to kill Fidel Castro, the ruthless leader of the Cuban people.


6.       Operation Family secrets

Frank Calabrese Jr. was serving his time in the same prison with his dangerous father Frank Calabrese Sr.  Junior wanted to serve his time, and be done with the mafia life.  He wanted Sr. to also serve his time and leave his mafia ways after prison.  Eventually Junior realized that his dad would not leave his mob ways.  In 1998 while in prison he wrote the FBI and soon after became a cooperating witness against his father.  Junior says if his father would have released the control he had over him, the letter to the FBI would have never been set.  Junior wore a wire for the FBI and secretly recorded his father as he incriminated himself.  Calabrese Sr. operated a crew with his brother Nick Calabrese, and both committed many of their crimes together.  Nick had been serving time in a different prison.

The trial for Operation Family secrets began in 2007 and lasted for 3 months. In all the leadership of the Outfit at the time, was convicted and sent to prison.  The five defendants were, James Marcello; consigliere Joseph Lombardo; South Side crew leader Frank Calabrese Sr.; and the crime family’s West Coast representative, Paul Schiro, stationed in Arizona since the 1970s, the last defendant was a corrupt Chicago Cop Anthony Doyle.  The Governments star witness Nick Calabrese testified against his fellow Outfit criminals.  The testimony from Nick Calabrese and Frank Jr. was enough to convict all 5 defendants.  The murders of the Spilotro brothers were solved, Nick Calabrese was one of the participants. 



7.       St. Valentine’s Day Massacre

The incident occurred on February 14, 1929.  Al Capone the current boss of the outfit at the time wanted to rub-out Bugs Moran, the leader of the North side gang.  The plan was set for Valentine’s day when Capone would be out of town in Florida, thereby establishing a legit alibi. The name on the warehouse was SMC Cartage Co. and it was located on 2122 N. Clark street in Chicago.  The warehouse was leased to Bugs Moran.  The Northside gang used this warehouse to run illegal booze.

Across the street in a 3rd story apartment, Capone had placed two lookouts. For several days, they searched for Moran.  The only problem was that neither of the lookouts new exactly what Moran looked like, they just had a physical description.  Once the lookouts saw the man they believed to be Moran they gave the signal to the crews standing nearby the warehouse.  They had outfitted a sedan with sirens to make it seem like they were police.  Four men entered the warehouse, two dressed as cops and two in regular street clothes.  They forced the seven men inside the warehouse against the wall and began to spray, killing all of them.  The two assailants dressed as officers made it appear as they arrested the other two.  The only problem was the Bugs Moran was not one of the men killed that day, he had overslept.  Effectively, the massacre ended Bugs control of the North side illegal booze.  This is one massacre that will never be solved because all parties involved have since passed away, or have been killed. 


8.       Al Capone’s conviction

Al Capone was born and raised in New York City.  Al Capone became involved with the mafia at a very young age.  Capone grew up with Lucky Luciano, and met Johnny Torrio in New York.  Torrio would later be the boss of the Chicago Outfit, and he requested Al Capone to come to Chicago and work for him.  Capone rose to the top rank of the Chicago Outfit in the mid-1920s.  In 1929 after the St. Valentine’s Day massacre Capone and the outfit finally became the powerhouse of organized crime in Chicago.  Capone ruled Chicago with fear and it was very difficult to convict him in court.  The federal government’s treasury department was secretly developing a case against Capone for tax evasion.  In 1931 Capone pled guilty after striking a deal with prosecutors.  The trial judge was not pleased and denied the deal.  Capone went on trial and in October of 1931 was convicted and later sentenced to 11 years in prison.  In 1939 Capone was released from prison because he was sick.  Capone spend the last few years of his life in Florida, he died in 1947 from complications of syphilis.    


9.       Tony Accardo-Capone era lieutenant

Tony Accardo was the boss of the Chicago Outfit from the 40s into the 50s.  Accardo is believed to have been one of the gunmen in the 1929 St. Valentine’s day massacre that occurred on Chicago’s north side.   Accardo was involved with the outfit from the 1920s until his death in 1992.  Accardo was the last member of the outfit to die that had ties to Al Capone.  Accardo had two nicknames that he was known for, “Big Tuna” because of a 4oo pound fish he once caught, and “Joe Batters” because of his preferred weapon of choice at the height of his career in the outfit.  He had been arrested many times dating back to the 1920s, he spent one night in jail because he was arrested on a holiday weekend and the courts were closed.  Accardo was succeeded in boss of the outfit by Sam Giancana.


10.   Chicago different from New York

The Chicago outfit is different than New York City.  Since the late 1920s Chicago’s organized crime has been controlled by one family.  New York City is currently ruled by five families.  The outfit has stayed away from drugs, they have made their money the more traditional way.  The family secrets trial destroyed the Chicago Outfit.  I believe that because of the 14 individuals that were convicted and sentenced to life in prison, the outfit has learned to stop killing people.  They rather take control of businesses because missing bodies bring heat from law enforcement.   The outfit today does not wield the power it once had, but it still exists and they still make money through illegal activities. 


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