The Chicago Outfit: Still Chugging Along in 2016

The Chicago Outfit is most famous for Al Capone, who was only boss for about seven years. The FBI used to called it the Capone Mob.  They thought it died when he went to prison and when they found out it was still active, they called the unit tasked with looking into the Chicago Outfit “the reactivation of the Capone Mob.”

The fact is the Outfit ran smoothly under the watchful eye of Tony Accardo aka Joe Batters for decades without the press of Capone.

Today the Outfit continues to move along just below the surface of respectable business.  The days of controling the city are over, but they still have power and influence.  People hear about some cartel or some gangbangers and they talk about the mafia losing control.  The mafia was never in the same low level businesses as the fly-by-night crime groups.  The mafia is about making money.  Unions, Trucking, Carting, Gambling and Shylock are what they specialize in handling.

Ideal Motors Dealership was what R.J. Serpico and his father called the used car business they opened in Melrose Park, Illinois. The business was started with a 300k loan from Michael "Mickey" Davis.  Mickey Davis was a longtime associate of Outfit Bosses Peter and John DiFronzo so the Serpico’s knew this was no ordinary business loan. They agreed to payback the principle in 3 years and pay 300 dollars a car they sold as interest for the loan.

The problem with the whole car lot was the senior Serpico was a bad gambler.  He owed Outfit Bookies thousands of dollars and he dipped into the car lot money to finance his losing streak.

Micky finally had enough, so he went to speak to R.J. Serpico and he showed him how much his father owed the bookies.  He then asked him to pay the loan back because it was not the deal he lent them the money for when the asked.  

R.J. Serpico fired his father and made Mickey his partner after the meeting.  

R.J. Serpico came up with 60k in cash and a car that he gave Mickey but that was not enough.

One day R.J. Serpico could not take it and he just walked away from the car lot, giving it to Mickey.  Mickey still wanted his cash because that was the deal.

Mickey reached out for some leg breakers and another associate recommended Paul Carparelli who wanted to move up in the Outfit ranks.

The only problem in this whole deal was George Brown, a 300lbs MMA fighter and Union bodyguard who had flipped and was wearing a wire against Paul Carparelli.

The FBI knew when Carparelli met with Mickey.  They had him on tape planning to have George Brown stage a fender bender with R.J. Serpico so he could break his legs.

The FBI stopped the whole thing before they could finish the job.

Paul Carparelli would get 3 ½ years.  Mickey would get 4 ½ years and George Brown the informant that started the investigation got just under 2 years last week.

These were all associates but Mickey Davis was a heavily connected guy.  The Outfit is still alive.

Inside The Outfit: Frank Calabrese Jr part 1

The mafia in Chicago was once known as the Capone Organization by Law Enforcement because they had no idea how the mafia worked. Known as the Outfit by those on the street it was a highly successful Criminal Empire. The man who led the Outfit into the new age was Anthony Arcardo also known as Joe Batters. He ruled with an iron fist, yet he never spent one night in jail.  He may also have been responsible for the decline of the Outfit. So what was it like in an Outfit Crew? Read on...

Family Life in the Chicago Outfit.

Recently Frank Calabrese Jr and I were talking about the life and he said one thing that rang true for me also.  He said at one point in his life he bought into the life fully, he was a true believer. That is how I felt and also so many of my friends who have since left the life.

Frank Jr.’s story starts when he was in 3rd grade and his family moved to Elmwood Park into what was known as the Compound. It was a three story home and the family lived on the top two stories.  The basement was a family room that they referred to as the Garden Department because it was just below ground level.  A couple of years later they would add a huge addition to the house with more rooms and a professional gym and sauna.

Frank's father was Frank Calabrese Sr AKA “Frankie The Breeze” a Capo in the Chicago Outfit.  He had worked his way up from associate to made guy under Angelo J. "The Hook" LaPietra the boss of the Outfit’s Chinatown crew.  Frankie would later lead this crew and he knew how to make cash.

Frank Jr and his brothers were raised to be tight lipped about his family.  One day he came home from school and he asked his father what he should say that he did for a living.  Frank Sr told him to say he was an Operating Engineer.  What his father really did was make Juice Loans.  These were loans that required no credit checks and no collateral except yourself.  He was a Shylocks’ Shylock and he would make everything from a knockdown loan (Principle and Interest) to an interest only loan at 2.5 percent a week.  I personally think people are better off with a juice loan than a payday loan or a title loan because these local lenders would work with you if you fell behind.

Frank Sr also ran a huge sportsbook and during the Arcardo years Chicago Bookmakers were organized into one huge book.  This was highly effective because they had a lock on the lines and the players.  Frank Sr schooled Frank Jr on how to basically rate a player’s credit.  They would look at the player, what they did for work and then decide how much they could play a week.  The main reason was so nobody got in over their head because it could turn out real bad if a wife got scared and ran to the FBI.  If a player did not pay there were no threats, they would just cut him off and there was no place he could bet.  He had his name out there and no Outfit book would deal with him. Frank Sr would eventually drop the bookmaking and just collect a fee of 1000 dollars a week from every bookmaker.  This was a lot less work and he didn't have to deal with politics or numbers of the liars and cheats that ran the books.  It was a flat fee and it got rid of the drama and bullshit.

The Outfit was not the type of Family that encouraged the sons of made guys to join.  Most of the guys in the Outfit made sure their sons went on to bigger and better things.  This was not what Frank Sr had in mind for Frank Jr. Frank Sr started to see some of himself in Frank Jr so he started off having him do little things and showing him what the life was about.  He learned how to make the loans and how the interest rate worked.  He would do the books for the juice loans and Sports Books.

Then Frank Sr got his hooks into a porn guy who owned 8 adult bookstores with booths to watch a loop.  These were huge money makers, bringing in all quarters.  The skim on these booths are huge. Frank Jr would go and collect the quarters from the machines.  This would average about 4,000 a week and he would set aside 1800.00 for the Outfit. Frank Sr did not want to put a dime back into the business and he was so hard on the guy who owned them that the guy fled in terror.  He probably could have had a bunch of stores if he just was a little nice, but nice was not in Frank Sr’s makeup.  Frank Jr would order more loops for the booths and his father would get pissed that he wasted any money “investing”. He would also get pissed when the stores were down and not hitting the numbers he expected.

This is when Frank Jr stepped up and threw himself into the life full force.

Frank Sr’s crew was one of the two crews that did all the hits for the Chicago family.  They had even killed the Spilatro brothers in a scene made famous in the movie Casino.  Another series of killings they took part in, was killing some of the burglers that hit Anthony Arcardo’s house.  These burglars were tortured and their faces were blowtorched.  They had been warned to give everything back and refused to listen, and that was their punishment.  This was the crew that Frank Jr was about to join.  Now that you know a bit of the background, next week stay tuned for more on Frank Jr’s experience growing up gangster.

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