Frank “The Enforcer” Nitti – One time Outfit Boss

Frank “The Enforcer” Nitti started off in the Outfit in Chicago at the bottom. After coming to Chicago at the age of 24, leaving his family behind in Brooklyn, Nitti arrives in Chicago sometime in 1913. It is unclear if he goes somewhere else after leaving New York City. He is also a boyhood friend of one Al Capone who grows up in the same neighborhood as him boys. They would soon form a gang to protect each other from the Irish kids who lived nearby. They called themselves the “Navy Street Boys” It is possible this is the youth division for the “Navy Street Gang” which operated in Brooklyn as well. Al Capone is known to have been in more than one youth gang including the 40 thieves and the Navy Street Gang.

Frank “The Enforcer” Nitti (1886-1943) - Find a Grave MemorialFrank Nitti soon takes up the role of barber and is cutting hair in an exclusive area of Chicago where many rich and powerful people lived. He soon made the acquaintance of one of his customers named Louis Greenberg, a thief who needed a fence for his stolen goods. He soon convinced Nitti to become his fence and Nitti leads a double life of barber and fence for stolen items at night. The business is lucrative.

However, Nitti had higher aspirations and wants to get closer to the most powerful man in Chicago at that time which was Johnny Torrio. Later Al Capone’s arrival might have signaled Nitti’s chance to get an introduction. Nitti would soon join the outfit just as Prohibition had gotten underway. He soon shows his skill at organization and accounting and becomes a valuable asset to Johnny Torrio. He is used to bringing whisky and distilled spirits in from Canada and supervising the shipments of alcohol to distributors and clients. During Prohibition, the price of a shot of Whiskey went from 15 cents to 75 cents, a major mark up and the money began to pour in.

Frank NittoNitti however did not get his start this way in the Outfit. he started like many as a debt collector or Muscle for the outfit and was very good at it. He wasn’t known to be violent, instead, cool, calculated, and calm which unnerved many who associated with him. He was known to be secretive in his movements and dealings and shunned publicity in any form. He was completely opposite of his friend Al Capone who enjoyed the notoriety that came with his later role as head of the Outfit upon Torrio’s retirement after surviving an attempt on his life. A dispute had broken out earlier in the spring of 1924 when Dion O’Banion the leader of the Northside Gang offered to sell Johnny Torrio his Brewery. In fact, the whole deal was a setup and the Brewery was busted just as Torrio took possession of it. He received 9 months in Jail. While Torrio was in Jail, Al Capone took command and along with Nitti proceeded to go to war with the Northside gang. This war would rage off and on over the following five years. With many casualties on either side.

On November 10th, 1924, 3 men kill Dion O’Banion in his flower store, when Torrio is released from prison Bugs Moran and Hymie Weiss try to kill him personally and fail, only wounding him in the neck and stomach. After Torrio’s recovery, he would retire leaving the whole operation to Capone with Nitti as his second in command. Al Capone at the age of 26 is the leader of one of the biggest organized crime families in the country, Chicago’s “Outfit”.

Frank Nitti became an integral part of the Outfit’s operation. He made sure shipments of alcohol were on time and payments were made. He handled logistics and kept detailed records of transactions, as well as bribes given to police and other elected officials. These files would almost be his undoing. In 1925 Frank Nitti moved to an office at 2146 South Michigan Avenue under the name Dr. Frank Ryan. This office would be where most of the documents pertaining to the Outfit would be centralized.

On April 6th, 1925 authorities received a tip from an informant about the office and promptly raided it. Inside they found a treasure trove of documents outlining a massive criminal conspiracy and network. It also showed authorities the size and scope of the Outfit as well as payments made, shipments delivered, names of illegal speakeasies, etc. This arrest and bust made front page news.

Al Capone wasn’t worried about the bust as much as the authorities turned the files over to the government. Before this could happen Capone’s lawyers used their clout and Capone’s political connections to get the case in front of a friendly judge who promptly returned the files to Capone’s lawyers citing some legal precedent. Everyone however knew that this judge was probably bribed and Capone and Nitti were off the hook once more.

In 1926 the war with the South Side Gang began to escalate, and murders in Chicago had tripled since 1920 due to the violent wars that broke out for control. Chicago was different than other major cities in that it had many gangs all vying for control at one time. As many as nine different gangs existed in and outside of the Chicago area during the earlier years of prohibition.

In 1927 the Outfit made 100 Million Dollars,1 Billion dollars in today’s money. In addition to their alcohol empire, Capone also had a dog racing track, brothels, illegal gambling, and other rackets. By far alcohol was the biggest racket of all to have and Capone controlled the majority of it for a time.

Frank Nitto was discovered dead alongside a railway fence after three shots were fired at his head. There was only one fatal shot. Photo via Bill Helmer

In 1929, the war with the Northside gang still raged. With Bugs Moran at the helm after the killing of both Obanion and Weiss in the same year, Moran took up the struggle against Capone and started to target the upper strata of his leadership, including several attempts on Capone’s and Machine Gun Jack Mcgurn’s life as well. Capone, tiring of the drawn-out war, entrusted the details of the murder of Bugs Moran to his second in Command Frank Nitti, who along with Machine Gun Jack Mcgurn planned what would later come to be known as “The Valentines Day Massacre”.

On February 14th,1929 seven of Moran’s gang were ushered into a warehouse where a meeting was supposedly going to take place to buy some stolen alcohol which someone had contacted Moran’s people saying was for sale. This was a set up of course and what these men didn’t know is that there were two Capone men hiding in the warehouse wearing fake police uniforms. Moran had arrived late to the meeting and was spared the fate of his men who were gunned down after being disarmed. This violent killing would change the way many viewed organized crime. It was also a huge blow to Moran’s organization. Both Nitti and Capone would skip town to avoid the heat.

Capone was arrested two days later in Philadelphia Pennsylvania when he was found carrying a handgun, he received one year in jail. This event left Nitti in charge of the Outfit at a critical juncture. The “Untouchables” squad is now investigating Capone and actively trying to disrupt his operations by raiding his breweries and doing anything else they can do to harass or slow down his operations. In an earlier raid, documents had been found outlining what was going on and the scope of some of Capone’s operations.

These documents also showed that Capone was obviously underreporting how much he made on his taxes. Authorities decided to use a new tool to try and get Capone, they decided to charge him with Tax Evasion which they were successful in doing in 1931, sentencing Capone to 11 years in prison. Nitti who had also skipped town with his girlfriend Anna Ronga.

In March of 1930 authorities attempted to Arrest Frank Nitti for Tax Evasion charges, he had fled the city of Chicago but was only 8 miles away. After authorities got a tip that Anna Ronga his wife had rented an apartment outside the city they staked out the address but were unsure what apartment Nitti was in or if he was there at all. After trying to watch the house from a church across the street, it became too cold for the men watching the house. An apartment was rented across the street. Realizing Nitti’s wife’s car was parked out front, they pushed the car closer to a fire hydrant and called the fire department to report a fire. When the firetrucks arrived and were blocked by the car, Nitti’s wife came out to see what was going on, after a brief conversation it was ascertained it was her car, and her address and apartment number were confirmed. With the apartment, number authorities could now get a warrant to search the premises for Nitti.

On October 31st, 1930 Frank Nitti was found inside the apartment when it was raided by police and arrested. On January 1st, 1931, after taking a plea deal offered him, Frank Nitti was sent to Leavenworth prison. Capone who had been released after his year in prison would not be out of jail long. In 1931 he was also indicted on tax evasion charges and sentenced to 11 years in prison. He would never run the outfit again and due to his having syphilis was released early from prison and was never the same man again.

In 1932 Frank Nitti was paroled from prison and went back to Chicago at the age of 42 to run the Outfit again. Times were changing and prohibition would soon end. Nitti being ever resourceful steered the outfit into the business of labor unions. Especially the unions representing bartenders and waitresses, whom he forced to only sell organized crime alcohol to customers. He also had control over some of the unions servicing the movie industry, such as the Stage Employees Union which he took over in April 1934 getting George Brown elected. Nitti and the outfit slowly began to squeeze the movie studios for more and more money, allegedly setting up a deal in which the 4 major studios paid the outfit 50,000 dollars a year each so everything ran smoothly and no strikes were called. Nitti also sometimes would have labor leaders kidnapped and held for ransom, which many times was paid. After someone at Columbia Pictures complained to authorities about the extortion, an investigation was launched.

On May 23rd, 1940 George Brown, the mob plant in the Union was indicted on two counts of racketeering and one count of conspiracy. Brown began to cooperate with authorities telling them all about Nitti’s involvement. Nitti also had to worry about a new Mayor named Anton Cermak. Cermak had allied himself with a man named Ted Newberry, a known former associate of Bugs Moran and the Northside Gang. While Newberry had told most he was retiring, he actually had no intention of doing so. Instead, he had opened up gambling houses and was trying to actively overthrow the outfit and was also funneling money to Cermak’s campaign. He and Mayor Cermak both had plans to rule the city and remove Capone and the Outfit from power. Cermak soon appointed Detective Harry Lang to a special detail whose mission was to apprehend Frank Nitti by any means necessary.

On December 19th, 1932 a raid on Nitti’s headquarters was ordered. During the raid, Detective Lang entered the back office after other officers apprehended Nitti’s other men. 3 shots were heard to ring out and Detective Lang exited the office claiming to have been shot in the arm by Nitti and having shot Nitti twice. Nitti although critically wounded in this incident survived and was charged with the attempted murder of Detective Lang. Lang was awarded a special commendation and extra pay for his role in the shooting. on April 3rd, 1933 frank Nitti’s trial for the attempted murder of Detective Lang began. When one officer Callahan was called to testify in defense of Lang’s story, instead, he said he had not seen Frank Nitti fire a gun at Detective Lang, instead, he saw Lang shoot Nitti twice and then shoot himself in the arm. This contradiction of Lang’s version of the story was enough to cause a mistrial and Nitti was released. The district attorney at first was so upset that he later charged Lang with attempted murder but later dropped the charges. Lang was forced to resign letting Nitti escape yet again from prosecution.

On February 15th, 1933 Anton Cermak was shot and killed while approaching President Roosevelt at a speech he was giving. The shots were intended for the President but hit Cermak instead killing him instantly.

On November 17th,1940 Frank Nitti’s wife, Anna Ronga, died of Acute Ulcerative Colitis, a disease which at the time there was no treatment for. Nitti was now alone, sick himself with ulcers and a bad heart, and trying to raise his six-year-old adopted son.

Although Nitti had escaped several prosecutions in his day, he could not escape the investigation into the allegations made by Columbia Pictures about extortion. On March 17th, 1943 Frank Nitti was indicted on charges of racketeering, mail fraud, and conspiracy. Facing up to 15 years in prison for his crimes and told by others inside the Outfit that he had to take the fall for this crime or face elimination, on March 19th, 1943 Frank Nitti killed himself with a shot to the head in a train yard in Chicago. The first two shots apparently missed and went through the top of his hat, due to Nitti being slightly drunk. The third shot hit its mark and took his life. He was later found after two train conductors who had seen him wandering on the tracks heard the gunshots and called the police.

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