I believe I never posted this old project on this place before, which I created with some help from other researchers and also some might be on this forum also. The project is mainly about all ethnic, including Italian/Sicilian gangs that started around the city of Chicago and created the base for all future organized crime.

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As the headline goes, this particular project is about Chicago’s crime syndicates and gangs from the pre-Prohibition era, or from 1900 until 1920, and we managed to collect at least 11 most prominent groups that even in those days played a major role in the creation of what we call today, the Chicago Outfit. The main reason for this was the close business relationship between these particular groups which in turn belonged to different ethnicities, but it seems that the main “ingredients” for the so-called collaboration were money and political connections.

Many researchers believe that the whole bloody chaos that was going on in the second largest city during the days of Prohibition was something that lasted since the beginning of the 20th century, until Al Capone organized every single gang in Chicago. That’s completely false because things were already different and stable to extent decades before that, meaning the Irish, Italians, Jews, Germans, African-Americans etc., all worked together in different areas of illegal business, all donated cash to the same politicians, all were protected by those same politicians and they all made a lot of money.

So the whole point of this project is to show you that Prohibition was only a “bump on the road” for organized crime in Chicago and possibly the U.S. in general, obviously because of the huge amounts of easy money something which in fact tripled the number of killings and created disharmony and greed that lasted for over a decade. You will notice that many of the old syndicates, such as the Irish and Jews, often bombed their opponents’ homes or business establishments but murder was their last resort. Also, many of the most prominent Italian clans often had internal conflicts and vendettas but they rarely went against other high level syndicates from different ethnicities, unless they had the right backing or if the scheme was huge.

You will notice that during those two decades, the Italian crime syndicates, especially the Sicilians and Mainlanders constantly brought so-called recruits from their homelands to different cities around the U.S. thus forming their own criminal networks and national organizations. You’ll see that both Chicago’s Sicilian Mafia and Camorra most of the time were in alliance, although there were few conflicts which mainly arose from financial or personal problems.

You will also notice many infamous names who survived the days before and after Prohibition, which in fact is a proof that some of those same various ethnic criminals already witnessed the “glory days” before all the chaos erupted, but they needed someone to bring back the “good old days” and to get organized again, and obviously later that guy was Capone. This is also another proof that it was inevitable for Chicago’s leading Italian organization to include other racketeers from different ethnicities in their own inner workings, mainly because at the beginning they were the ones who gave the Mafia or the Camorra a big push to rise in the upper levels of organized crime and politics.

During the first decade of the 20th century, most of the various ethnic and larger syndicates coexisted between each other, meaning some of them even created their own underworld “commissions” or “combines” and controlled all illegal operations and politics within the Chicago area. So years later, Capone possibly copied on what was going on before Prohibition and created his own “commission” but with him at the top. Capone obviously didn’t organize them for the second time in a peaceful way but by the end of the day, he also managed to place them under one umbrella which in fact was a huge score for the Sicilian Mafia in Chicago mainly because Capone and his men were accepted as members of their brotherhood.


SOUTH SIDE 1900 - 1920

First Ward, Loop and South Halsted St, Chinatown, South Side and Near West Side

Michael Cassius McDonald (First Ward political crime boss who operated from a four story building located next to City Hall) (member of the Trust/gambling commission) (died on August 8, 1907)

- George Murray (assistant for McDonald and the Trust)

- Hall Varnell (McDonald’s second in command)

- James O’Leary (South Side rackets boss with headquarters at 4183 South Halsted and also at 6300 S Cottage Grove) (member of the Trust/gambling commission)

- John Ryan (top enforcer for McDonald and O’Leary)

- Dickie Dean (top enforcer for McDonald and O’Leary)

- John Condon (owner of Harlem racetrack)

- Tom McGinnis (Kennas’s gambling operator)

- Patsy King (policy operator on the South Side)

- Charles Smith

- Harry Perry

- Bud White

- Patrick O’Malley (W Clark and Polk streets, Loop)

- Maurice Enright (union racketeer and enforcer for O’Malley) (killed February 1920)

- Thomas Enright

- Sonny Dunn

- Patrick Paddy Ryan (leader of the group known as the Valley gang and Enright’s lieutenant) (killed in June 1920)

-Danny Vallo (precinct captain for the 19th Ward and Ryan's second in command)

- Cornelius Con’Shea

- Walter Quinlan

- Mickey Norris (saloon owner and agent for Lime and Cement Teamsters Union)

- George Vogel

- John Nolan

- Pete Kusanski

- James Linden

- Harry Bartlett

- William McPadden

- Hughey McGovern

- Raymond Cassidy

- Frank Carpenter

- Frankie Pope

- Frankie Lake

- Terry Druggan

- Danny Stanton

This particular syndicate was Chicago’s oldest organized crime group that mostly included criminals from Irish heritage, followed by few Jewish, German and Italian racketeers, and this was Chicago’s original Irish Mob, not the latter one during Prohibition which was wrongfully labeled by the newspapermen at the time. In fact, these were Chicago’s first racketeers and political corruptors who formed the base for all future organized crime.

Michael Cassius McDonald was an Irishman born in 1839 in Niagara Falls, between Canada and the United States and lived together with his good mannered father Ed McDonald and mother Mary, two brothers and one sister. In 1854 McDonald moved to Chicago where he worked as a candy vendor on railroad cars and trains, while selling half-filled boxes of candy and fake jewelry to unsuspecting passengers. At the time guys like McDonald were known as “train butchers” and it is believed that McDonald was the inventor of the “prize package” swindle.

By 1863 McDonald was already a very wealthy guy and he was only 24 years old. He bought a residence in Bridgeport, in an Irish neighborhood. In those days Bridgeport was named as the “Terror District” which in fact was the place where McDonald received his nickname “King Mike”. In 1885, McDonald formed a bookmaking syndicate which controlled gambling at the Chicago and Indiana race tracks and some reports say that in just one season his syndicate alone profited to the extent of $900,000 which was a lot of money in those days.

During this time, that in an effort to overcome many reform activities, McDonald contributed lots of cash to many political figures and so he sort of “created” the first real corrupted political machine of Chicago which became known as "Mike McDonald’s Democrats". He built a four-story building which was placed next to Chicago’s City Hall, which in fact was a big gambling parlor at Clark and Monroe known as The Store and was reportedly the largest brothel and gambling house in Chicago.

Back in those days every big shot criminal had a desire to win respect also as a legitimate businessman and so one day McDonald purchased the Chicago Globe newspaper and also took over as manager of Chicago`s first elevated rail system, the Lake Street Line, which became known in gambling circles as “Mike`s Upstairs Railroad”.

By the early 1900’s, McDonald had an army of younger and more powerful notorious thieves, forgers, gambling operators, smugglers, corrupt aldermen and other associates of every nature. The most prominent of those was one big time gambler known as James “Big Jim” O’Leary, and two very powerful political crime bosses Michael Kenna and John Coughlin. They became his legacy and also became Chicago’s most high profile organized crime faces at the beginning of the 20th century.

James O'Leary was an Irishman born in 1869 in Chicago and his childhood was filled with shame because of the blame that his family carried over the Great Chicago Fire. O’Leary grew up among the South Sides slaughterhouses and later worked at the Union Stock Yards, where he acquired the nickname "Big Jim." He also began working for many gambling and saloon operators and made many connections which caught the eye of one of McDonald’s associates "Prince" Hal Varnell. During the mid 1880’s because of the threat of reforms, McDonald decided to expand his gambling operations around northwest Indiana and so he instructed Varnell to send O’Leary to act as their scout.

By the early 1900’s the big cash started falling into O’Leary’s pockets when he made a connection with the Santa Fe Railway which ran three “Gamblers Special” trains out to O’Leary’s gambling joint while the Western Union provided the wire services and with the protection of police officials like Nicholas Hunt, O’Leary became the rising star of illegal gambling in Chicago.

During that time O’Leary became the most prominent gambling boss in Chicago and so he opened another joint which became Chicago’s most prominent two-story gambling local at 4183 S. Halsted, which included a billiards room, several bowling alleys, a saloon, a barbershop, and a sauna. The name "O'Leary" was written in giant electric letters on the front door as a sign of his pride and the joint also had false partitions, tunnels, hidden passageways and reinforced doors. He also opened a branch of suburban shopping malls in Du Page County with the help of new contacts from different syndicates such as Mike Heitler and Jim Colosimo.

Michael Kenna and John Coughlin were born in the same shack at Polk and Sholto Sts. at the western edge of Connelly’s Patch. Kenna was born in 1858 and Coughlin was born in 1860 and both grew up in the same Irish Slum District .They went to the first Jones School at Harrison and Plymouth Court and to get to school they would have passed the Custom House Place Levee in the " Cheyenne " District every day, in those times perhaps the wickedest place in America.

Coughlin at the age of 15 left school and began working in a Turkish bathhouse at Clark St, rubbing down politicians and underworld figures. It was here he made some of the connections that would later propel him upward in First Ward Politics. The bathhouse was often visited by Varnell and McDonald and they became his mentors. Later Coughlin opened a bathhouse himself, where he gained the nickname “Bathhouse John”.

As a teenager, Kenna was a very quiet boy but very aggressive in the business sense, thus making connections with many madams, prostitutes and anyone who might come in handy. In his late teens Kenna also owned his own newsstand but later decided to leave Chicago and went to Colorado. Over there he worked as a circulation manager at Lake County Reville in Leadville. After few years Kenna came back to Chicago and opened his own saloon, which was visited by many politicians and with that Kenna got mixed in the world of politics. The hooking up with Coughlin made them the most infamous duo in Chicago’s politics.

The duo hung around at a saloon at 120 East Van Buren which was called the "Workingman’s Exchange" and it was a sort of a “home” to many Chicago racketeers, followed by a well disciplined army of voters on every Election Day. They even had a so-called defense fund that was headed by two lawyers who were always placed on retainer to immediately appear in court anytime if some of Kenna’s and Coughlin’s associates were arrested.

At first their territory, the Levee, occupied the blocks between Harrison and Polk, from Dearborn to Clark St, but later their operations were relocated between 19th and 22nd Streets. During the early 1900’s the Levee was now in the Second Ward and this troubled the two crooked aldermen and in order to regain control of the Levee, Kenna and Coughlin with the help of their supporters and the resistance from the unsatisfied residents, they proposed a redistricting ordinance that would return the Levee to the First Ward. The "New Levee," as it was called, now consisted over two hundred brothels with Kenna’s and Coughlin’s headquarters being the Frieberg’s Dance Hall which was a big prostitution house.

In 1903, McDonald gathered all leading political crime bosses, racketeers and gamblers and formed Chicago’s first underworld commission which became known as “The Trust”. This was in fact a so-called gambling combine, which included gambling bosses from all four sides of the city, meaning North, West South and all southern suburbs. For example, McDonald and Jim O’Leary controlled the First Ward, Loop, South Side and all southern suburbs, followed by Mont Tennes on the North/ West and the Gazzolo family together with Mike Heitler on the West Side. O’Leary was represented by McDonald’s successors and First Ward political bosses Kenna and Coughlin, while the Gazzolos and Heitler were represented by 19th Ward Alderman John Powers.

Kenna and Coughlin were also often seen in the company of Alderman Johnny Powers who in turn was also very important regarding the Italian voters. These guys were the main representatives at the time who were followed by numerous street bosses, such as Jim Colosimo, the Benvenutti bros, Patsy King and Sam Young.

Patsy King was a former Mississippi riverboat gambling operator who arrived in Chicago sometime during the late 19th century and became closely associated with McDonald’s syndicate on the South Side. Even though the policy game was a black man’s racket, legend goes that King was allegedly the one that devised the game and became closely associated with many African-American and Italian racketeers from the South Side. In 1903, King together with another one of Kenna’s underlings, Tom McGinnis, controlled the policy wheel companies called the ''The Union and the Phoenix'', which were headquartered at The Emporium.

By 1906, the so-called “Trust” broke apart and all hell broke loose, with dozens of bombs being unleashed around the city of Chicago. In 1907, Mike McDonald died of natural causes and later his “throne” was shared by McDonald’s protégés Kenna, Coughlin and O’Leary, the leading figures from the former “Trust”. In July 1907, John Condon’s residence on S Michigan Av was completely destroyed by a bomb, followed in August 1907, O'Leary's resort on S. Halsted was also bombed and later in 1908 his gambling place was bombed twice and each time he rebuilt. This situation became known as the infamous “Gambling Wars” that lasted until 1911.

One source stated that some of the bombings that occurred at the time were in fact thrown or planted by the owners themselves, so later they were able to collect the insurance. Frauds and schemes like these were very often used by many criminal ethnicities, and this was only “the tip if the iceberg”. For example that same year, the Empire Voting Machine won a $1,000,000 contract from the election commissioners but a scandal occurred after some of the investigators found out that McDonald’s associate John Condon and some of his associates were the largest stockholders in the company through some of their front men. This was probably one of the biggest schemes ever executed by the old Irish Mob.

Patrick O’Malley was another Irish racketeer and close associate of both Condon and O’Leary, who owned a saloon in the Loop area at corner of W Polk and S Clark streets. Few of O’Malley’s close associates were the Enright brothers, Maurice and Thomas, and also Simon O’Donnell and Sonny Dunn. Now these guys were probably few of the most ruthless enforcers in Chicago at the time, who completely opened the doors to the field of labor racketeering. This was a result from the gambling conflicts and government pressure over the gambling racket in Chicago at the time.

During the waning years of the Harrison administration 1913-14, the massive gambling operations and conflicts stabilized because Mont Tennes from the Northwest Side consolidated his holdings at the expense of his rivals and allies. Condon passed away in 1915 and O’Leary kept his old gambling parlor but also turned to other more legit businesses, which was a sign that this particular faction slowly began to lose its influence and power within Chicago’s underworld. This was the same time period when the Italian and Jewish syndicates from the South Side somehow “inherited” a large criminal empire.

In 1920 Robert E. Crowe was elected as state’s attorney and declared war on the gambling business and the bosses and so a “big haul” was made and O’Leary’s ancient stronghold and was closed for good. So Crowe’s campaign at the time shook the foundations of the Irish handbook empire in Chicago and spread panic through Chicago’s underworld, so some of the old bosses like O’Leary used the illegal schemes of the recently arrived law of Prohibition.

Story goes that O’Leary allegedly joined Torrio’s gang in the bootlegging ventures. That same year O'Leary, who had been delivering whiskey to Colosimo's Cafe under arrangement with Torrio, was also a suspect of being involved in the murder of Jim Colosimo. Despite his connection, there were no charges brought against him. But few weeks after Prohibition went into effect, federal agents discovered a large supply of liquor in O’Leary’s basement, although he produced a pharmacist`s license that he claimed allowed him to sell whiskey. But one not-too-sympathetic judge revoked that license and ordered the saloon shut down as a public nuisance.

Other younger remnants from the old Irish Mob, such as Enright and his gang of followers, continued to bring illegal income from the unions which they extorted, and so this particular crew was “formed” sometime during the mid 1910’s. For example the leader Patrick “Paddy” Ryan was a strong Irish lad who used to be involved in planting bombs during the infamous gambling wars and later became a protégé of Enright . But besides being a product of the South Side syndicates, still by the late 1910’s most of Ryan's taverns were located around the Near West Side in an area which back then was called the "Valley” and was known as Irish enclave, though surrounded also by Jewish and Italian population.

Ryan owned a saloon at 1403 S Halsted St and was also part owner together with his associate and brother-in-law Mickey Norris in another saloon at 1916 Halsted St. Norris was a business agent for the Lime and Cement Teamsters Union, and so Ryan and his gang were often used as labor sluggers and also slowly wedged their way into labor politics, like for example one of Ryan’s prime enforcers and partner in the labor field was Cornelius Con’Shea.

Another close and most valuable associate of Ryan was Danny Vallo who in turn was a prime connection to various gangs, including the Mafia from the Northwest Side. Vallo’s blood ties were possibly from Potenza, Basilicata and he worked as a precinct captain for the 19th Ward but he didn’t live in that area, which gives the impression that he probably had strong Mafia and Camorra contacts in that same ward. In 1919, Vallo managed to escape from the state’s attorney’s office while being under arrest on robbery charges, while that same year their associate George Vogel shot to death a police detective in one of Ryan’s saloons during a quarrel between members of the gang.

At beginning of the year 1920 and with the start of Prohibition, the gang managed to steal $162,000 worth of booze during a holdup in one wholesale liquor house but the problem was that they started bothering other bosses and began making trouble in different areas around the city. For example, it seems that Ryan’s boss Moss Enright was different than some of his mentors and predecessors, meaning he possibly despised the Italian faction from the South Side and created many problems for them and also the Irish racketeers that were closely associated with the Italians.

For example, Enright and his gang harassed Johnny Patton from the Burnham area who in turn was close associate of Jim Colosimo and the South Side Italian faction, followed by Mike Heitler who was also connected to the Italians through the prostitution business. In February 1920, Enright was eliminated by those same Italian racketeers who he despised the most and also tried to extort. Reports say that Enright received a lavish funeral that blocked the main streets of the city, and Ryan together with few of his gang members were honorary pallbearers.

So Ryan was the next one to go and just like in their own style, the Italians or the Colosimo syndicate possibly picked one of Ryan’s close associates John Nolan to finish the job. In June 1920, Ryan was murdered by his own gang and his “throne” was instantly taken by Vallo, who in time slowly managed to transfer most of the gang members on the Northwest Side, while some remained on the South. In fact, as they entered the new era of Prohibition, this gang also gave the “birth” to future bootleggers and racketeers such as Frankie Pope, Frankie Lake, Terry Druggan and Danny Stanton.


Loop and Levee, South Wabash and 22nd St, S Clark St, S State St and W Harrison St

James Colosimo (Loop and Levee rackets boss with headquarters on South Wabash Ave) (member of the Trust/gambling commission until 1906 and later associated with the Sicilian Mafia)(killed in May 1920)

- Rocco DeStefano (member of the 19th Ward and Colosimo’s lawyer)

-Robert Vanella (Colosimo’s top lieutenant)

-John Torrio (Colosimo’s top lieutenant)

-Victoria Moresco

- Joseph D’Andrea (labor boss associated with both Colosimo and the Mafia) (killed in 1914)

-Joseph Moresco

-John Moresco

- Maurice Van Bever

- Mike Potson

- Mike Carrozzo (president of the Street Sweeper’s union and connection to other South Side gangs)

- Jerry Riggi

- Joe Bovo

- Thomas Colosimo (cousin of Colosimo)

- Ed Weiss

- Alphonse Capone

- Sylvester Agoglia

- Vincenzo Cosmano (South Side crew boss on Wentworth Av and associated with Mike Carrozzo and Jim Colosimo)

- Tim Murphy (union racketeer with connections to other South Side gangs)

- James Murphy

-James Vinci

- Sam Vinci

- Mike Vinci

- Bruno Roti

- Sam Roti

- Vito Roti (cousin of the Roti brothers)

- Vito Bertucci (killed in 1908)

- Bruno Perrino

- Frank Romano

- Nick Romano

- Tommy Fusco

- Tony Cifaldo

- Ralph Buglio

- Paul Bolanti

- Edward Geirun

- John Patton (Mayor, brothel owner and Colosimo’s associate in Burnham Ill and northwest Indiana)

- Joe Hogarty (killed November 1916)

- Charles Costantio

- Julius Rosenthal

- Jerry Orlando


We believe that this was the prime group that either presented the Italian Camorra organization or gave “birth” in the Chicago area to that same old organization, meaning many Italian Mainlanders arrived in already formed groups or crews that were also in alliance with other syndicates such as the Irish, Jews, and the Sicilian Mafia.

Vincenzo Colosimo was born in 1875 in Cosenza, Calabria, Italy and he left his homeland in 1895 at the age of 20 and sailed towards the US. When he arrived in Chicago, Colosimo first started working as a street cleaner, shoe shiner, newspaper boy and also as a water carrier at the railroads. In fact he grew up around Chicago's Loop and he also became a good fist fighter and was involved in many street fights, thus earning the nickname ‘Big Jim”. Legend goes that Colosimo made friends in Chicago’s underworld and became very popular among his fellow Italians, and began to rise as one of the representatives for the Italian population on Chicago’s South Side at the time.

By 1901, Colosimo worked as a precinct captain and also as personal bagman for First Ward political crime bosses Mike Kenna and John Coughlin. In 1902, Colosimo met Victoria Moresco, a middle-aged Madam who operated four second-rate brothels around Armour Square. Colosimo quickly took over the management of one of his wife's brothels renaming it The New Brighton, and he also took over operations in another brothel named “The Victoria” and by 1903, began making contact stations in New York, St. Louis and Milwaukee. This is a proof that during this time period Colosimo began making national connections and raises the question on whether his new bride and her family already belonged to some criminal network.

In 1903, Colosimo joined forces with another prominent “pimp” known as Maurice Van Bever who in turn took the white slavery business on a higher level. Van Bever drove around the Levee in a red carriage which was driven by top hatted coachmen and together with his wife Julia, ran two huge brothels and with Colosimos help, they made contact stations around the country. Over the next few years, they allegedly imported more than 600 young women for sale into the Levee and other fleshpots across the country.

When the gambling combine known as the Trust was formed, the year after that or in 1904 Colosimo opened the so-called Colosimo Billiard and Pool Room. With the help of the old Irish Mob, Colosimo also made connections with North Side gambling boss Mont Tennes by connecting his parlor with a telephone wire, a sure sign in those days that a horse racing handbook was operating within, as race information needed to be distributed quickly to bookmakers. In addition, Colosimo hired two of his brothers-in-law, Joseph and John Moresco, to work at the gambling joint.

Colosimo was also connected to some Jewish syndicate from the around the Lawndale and Ogden Av areas, such as the Guzik crew which was headed by the head of the family Max Guzik. Both Guzik and Colosimo thrived in the prostitution racket and both of them once worked as precinct captains for Kenna and Coughlin around the First Ward and Levee. In fact it was allegedly Kenna, Coughlin and Colosimo that brought the Guzik family on the South Side.

By the mid 1900’s Colosimo became a big shot in Chicago’s underworld and acquired another nickname, which was "Diamond Jim". He got the nickname because he frequently dressed in a white suit and wore diamond pins, rings, and other jewelry, usually at his headquarters that was known as Colosimo’s Café at 2126 South Wabash Av. This was a proof regarding Colosimo’s lucrative connection to the Irish racketeers and after the breakup of the “Trust” in 1906, Colosimo kept his close contacts within the First Ward through Kenna and Coughlin, but he also began forming his own crew and alliances allegedly for his own protection against numerous extortionists like the ones from the Black Hand gangs and other groups.

One source from that period stated that Colosimo allegedly called upon some “leaders of the Camorra” with the help of one of his bodyguards but the source didn’t state any names. Story goes that a meeting occurred which also included some three Italian guys who tried to extort Colosimo and later or that same night, those same three fellas were allegedly shot to death between Clark and LaSalle streets. Two died instantly but the third one was taken to a hospital and before his death, he allegedly shouted in Italian “Colosimo is a traitor”. This also might answer our question regarding the alleged connections that the Morescos had to their associates back in New York or even to their homeland in southern Italy.

We don’t know if Colosimo was preparing to protect his wealth from any potential extortionists but we are quite certain that he began creating his own “army” in Chicago by bringing more than few enforcers from the New York and the east coast. Most of the info shows that Colosimo had humble beginnings, meaning he started climbing the ladder from the bottom and he allegedly wasn’t born in a family that was connected to Italian organized crime but when he connected to the Morescos and the gambling syndicates, his connections suddenly spread to other cities from around the Midwest and East Coast, and maybe even Italy. In 1907, one alleged Camorra boss Antonio DeLucia was arrested in Naples with $20,000 allegedly received from recruits that were previously sent to New York, so maybe some of that cash was also from Colosimo’s organization in Chicago.

During that period or by the late 1900’s two of Colosimo’s most prominent enforcers who arrived from the New York area, were John Torrio and Robert Vanella. We are not able to confirm if Torrio or Vanella had any blood connections to the Colosimos or Morescos, but we are sure that they probably belonged to some of those “contingents” of reinforces sent from New York to Chicago, similar to the DeLucia situation.

It seems that the first time Torrio’s name reached the newspapers was in 1909, when he was accused of being one of Colosimo’s managers in his establishments but also as one of his prime lieutenants in the prostitution racket who was connected to a criminal network between Chicago, St Louis and New York. We don’t know if Torrio arrived that same year in Chicago but it is possible that he arrived the year before that according to one sporting event. You see, by 1911 Torrio was known for sponsoring many wrestling tournaments and it seems that he favored the same wrestler since 1908.

In 1912, one lounge that was controlled by Colosimo, Torrio and the Guzik family, was raided by investigators and they found one staggering information, that the establishment alone was making more than $3,000,000 a year or 80 million dollars in today’s money. In 1913, Torrio began managing another saloon located at 2001 Archer Av and from that point on the group opened up few additional establishments like the ones at 2031 and 2014, 2016, 2017 Federal St, and also at 2015 S Clark St, 45 West 20th St and 108 W 20th St. Some sources say that all of these establishments were overseen by Colosimo’s associates Van Bever and also Greek racketeer known as Mike Potson.

Back in October 1907, Torrio’s associate Robert Vanella killed one Italian in Billings, Montana and the next year was sentenced to 50 years in prison but in 1914, he was paroled and was located in Chicago. This also might be another proof that some of Chicago’s Mainlanders already devised a criminal network around the country thus sending their enforcers to eliminate any obstacles in certain areas. Vanella received interests in a brothel at 2119 Federal St and sources say that he was also the head of the largest combination of owners of “concessions” in the Levee.

That same year, Vanella together with one of his lieutenants Mack Fitzpatrick got into a gunfight with government detectives with one of them being killed during the shootout, and sources say that Vanella fired the first shot. Vanella was wounded in the leg and reports say that he was carried away to hospital by John Torrio with his car. But it seems that like any other Mob case from that time period, the whole thing was swallowed up by other events and became completely forgotten.

During this period Colosimo allegedly hosted a banquet on which many politicians, government detectives, mobsters and racketeers were present, including Colosimo’s right-hand man John Torrio, one of the Mafia’s leaders Mike Merlo, Joseph D’Andrea and Joseph Esposito aka Diamond Joe. Joe D’Andrea was a Mainlander who arrived in Chicago sometime around the early 1900’s and started from the bottom by working as sewer digger. We don’t know the exact reason on why D’Andrea and Colosimo became close associates but we believe that Colosimo’s contacts to some of the Irish racketeers in the labor field, gave additional push for some of the Camorra and Mafia factions to receive a cut from it.

As the years passed by, D’Andrea slowly became the president of the Tunnel Miners’ and Sewer Diggers’ union and lived at 913 South Halsted St. His Mafia connections came through the boss Tony D'Andrea (no relation) and so we are not quite sure if Joe D’Andrea belonged to the Colosimo group, although many sources say that he was both close friend and associate of Colosimos and so we’ve decided to include D’Anrdea in this particular list. In 1914, Joe D’Anrdea was killed on the orders by the recently appointed Mafia boss Tony D’Andrea.

Colosimo also set his sight at Burnham and northwest Indiana and key individual who brought him in those areas was again one Irish hoodlum known as Johnny Patton. Born in 1883, Patton became one of the most extraordinary individuals who largely contributed to this so-called menace to society. Story goes that Patton since young age, to be precise at the age of 14, worked at a local bar in Burnham, which was visited by many interesting figures such as politicians, business men and of course big time gangsters and hoodlums.

During the elections for village president in 1908, Patton was elected as village president or the so-called position as “Mayor” of Burnham. He came by the nickname “the boy Mayor of Burnham” because he had taken office somewhere around the age of 23 and when first elected, Patton became the youngest Mayor in Illinois at the time.

By the early 1910’s, Patton’s second in command was one Joe Hogarty and they also controlled a burglary crew which operated in the Calumet City, Burnham, Gary, and Hammond areas and had a good score like at least three robberies a week. Patton’s right hand man and leader of the crew was Italian gangster and saloon owner Charles Costantio and their street guy or man on the field was one Julius Rosenthal. Other prominent gang members were the Dominick brothers, Jerry Orlando, Ben Chaken, Frank Lemar, Charles Dwartz, Martin Duffell, Frank Quinn and Jerry Raffles.

Sometime by the end of the Civil War, Patton met Jim Colosimo and together they bought a brothel known as the Arrowhead Inn, which of course was located in Burnham at Entre and Chippewa Streets. Previously the joint was owned by one Chicago big shot Ike Bloom but now it was operated by people who were instructed personally by Patton himself. After the gambling wars and all of the problems that began to surface around the Levee, Burnham became the new place for fun because it was the era of the automobile and the town was just 15 miles south of the Levee, which was a very short distance by car.

The club became a real “cash cow” for Colosimo and the rest of the gang and so the Italian boss became one of the most prominent guests at the place, and story goes that with Colosimo’s help, many old Jazz headliners provided musical entertainment to the Arrowhead crowd.

Not all of Patton’s associates in the old Irish Mob were happy because of his new connections and so he began receiving some pressure. For example, Maurice Enright and his band of followers began making problems when one day Enright’s brother Tommy entered Patton’s joint with Sonny Dunn and few other men, who were accompanied by few nice looking girls and they were greeted by Joe Hogarty himself, who was also accompanied by two girls. In the end, 18 bullets were pumped into Hogarty’s body and after that Enright’s party left the joint and quickly took a train which was headed for Chicago.

Since Colosimo’s empire was slowly growing, he needed additional enforces to defend his illegal income and so again with the help of his associates, during the late 1910’s other recruits began arriving from the New York area such as Alphonse Capone and Sylvester Agoglia. Some sources say that Capone was involved in a murder in New York and so he fled the city and went to Chicago, supposedly with the help of Torrio and one Gaetano Ricci.

This is another proof that the so-called Mainlanders were still re-enforcing their contacts and factions all around the country in alliance with the Sicilian clans, and for the second time this raises the question on whether the Camorra and the Mafia worked together in Chicago since “day one” and slowly began forming some type of mixed or “hybrid” criminal organization. We don’t know if the whole evolution process began in the U.S., because there are quite few chances that the “alliance” was already established back in Italy.

As we previously sated, the gambling business in Chicago was under huge pressure and so many criminals began to look for other illegal income such as labor racketeering. The Irish racketeers began to infiltrate the unions and so they were simply followed by their associates in the Italian community. Mike Carrozzo’s blood ties came from Avellino Campania, and he allegedly was also one of Colosimo’s prime enforcers, both on the streets and the union business, and reports say that Carrozzo also made alliances with other South side gangs such as the ones headed by Jim Cosmano, Tim Murphy, the Vinci, Roti and Bertucci families.

Both the Vinci and Roti families came from Simbario, Calabria and they were all “stationed” around Chinatown and Near South Side. For example Bruno Roti was born in 1880 and by the early 1900’s he posed a young meat dealer on Ohio and Sangamon streets but in 1903, he together with three of his family members were involved in all kinds of burglary activities and often acted as fencers and in fact that same year, the Rot clan was arrested on charges for receiving a stolen property. In addition, one of Roti’s associates was John Nolan who in turn was connected to the old Irish clans from the South Side.

The Rotis married with the Bertucci clan since during the mid 1900’s Bruno Roti married Marianna Bertucci who in turn was the sister of Vito, Joseph and Michael (or James) Bertucci. It is possible that Roti married the Bertucci sister before the 1909 murder of her brother Vito, in which the Rotis and Vincis were allegedly involved. It seems that some family quarrels occurred in which besides Vito being dead, Mike Vinci was also wounded and later died. One report says that the whole problem started when Joseph Bertucci killed their uncle Vito Umbrillo, and because of that Bertucci was sent to prison. It seems that the conflicts between the Roti, Vinci and Bertucci families never really ceased even during the following decades and many of them fell as victims under the judgment of “vendetta”.

Vincenzo Cosmano was involved in all kinds of rackets including extortion, burglaries and racketeering, and according to some investigators from that time period, this crew extorted around $15,000 on monthly basis from South Side Italians. In 1912, Cosmano survived an assassination attempt and in the hospital, he allegedly asked for help from Tim Murphy who in turn walked into the hospital, knocked down the cops and took Cosmano out of state. Later Cosmano survived another assassination attempt and this time he was stabbed almost 20 times but survived. In April 1915, investigators suspected that Cosmano was behind the bombing of one Joseph Coco’s home but the family was very lucky because they weren’t in the house during the huge explosion.

Tim Murphy and his brother James were also “products” from the former “Trust” or in plane words they were hired as enforcers by old time gambling bosses such as O’Leary and Tennes. By the late 1910’s Murphy became business agent for the Garbage Handler’s with the help of union racketeer Maurice Enright. It is possible that Carrozzo “received his badge” when he together with one of Colosimo’s right-hand men John Torrio allegedly orchestrated the murder of Enright.

Some sources at the time reported that Torrio asked for help from their “relatives” far on the east coast or in the Buffalo area. So the problem was solved when their guys on the east coast sent one of their best hitman only known as “Tommy the Wop”, who in February 1920 pumped hundreds of shotgun pellets into Moss Enright’s body. Later information came up that two weeks before the slaying of Enright, the imported Italian hitman was first seen with Carrozzo and later with Torrio at Patton’s joint the Burnham Inn. Carrozzo, Cosmano and Murphy were arrested regarding the murder.

In fact, two young hitmen arrived for the job such as Tommy or Tony Fusco and Tony Cifaldo who together with the rest of the crew were also arrested by investigators for the murder. It is interesting to note that one assistant state’s attorney and Sicilian leader of 17th Ward Steve Malato quickly became involved in the case and wanted to question both witness alone.

We will talk more about Malato in the following text regarding North/West faction, but after his investigation all of the guys were later freed after posting their bonds and according to reports, both Fusco and Cifaldo were ordered to appear as witnesses against the rest of the gang, including Carrozzo and Vinci. Later both Fusco and Cifaldo simply disappeared from the face of the earth and whole case went nowhere.

This was also a sign that the old Anglo-Saxon Mob was slowly fading away, while other criminal ethnicities began to take over what they already built. Some newspapers at the time even reported that the Camorra organization was behind Enright’s murder, and that Colosimo, Torrio, Carrozzo, Cosmano and Roti belonged to that same group. In fact the same statement was used by investigators when later they also executed the murder of Enright’s right-hand man Patrick “Paddy” Ryan. The connection comes with Ryan’s alleged slayer, John Nolan who in turn was closely connected to the Roti clan since the early 1900’s.

In May 1920, Colosimo walked out to the half darkened lobby of his restaurant where his killer or killers were allegedly hiding in the telephone booth. Two shots were fired with the first one hitting Colosimo in the head or behind the right ear, and the second missed and hit the wall. Colosimo hit the tile floor face first. The killers rushed out from they’re hiding place, ripped open Colosimo’s shirtfront, withdrew his long leather wallet and fled. The killer left a message on the check “So long vampire, so long lefty.”

Almost all of the reports say that Colosimo’s demise was simply orchestrated by Torrio and the rest of the gang and maybe the theory is true, but we believe there were also some other complications. You see, Colosimo divorced his old wife Victoria and married to a much younger girl, so few reports at the stated that Colosimo’s demise might’ve included some love problems.

As we already stated at the beginning, Colosimo allegedly started from the bottom and there’s no evidence regarding he being connected to some Italian organization at the start, but instead he possibly got his push from the old Irish syndicate and was later recognized by some of his Italian associates, allegedly when he married Victoria Moresco.

So if the Moresco family was connected or belonged to the Camorra, it is possible that when Colosimo dumped Victoria, he signed his own death warrant. Colosimo’s and Victoria’s marriage was obviously a business relationship at the start, meaning the wife owned all of those numerous brothels while the husband took care of the political protection with his connections to the Irish. Please don’t take this theory for granted because there are at least a dozen of other theories on who orchestrated Colosimo’s demise and why.

Colosimo’s end was also one of the signs regarding the end of an era and the old world of crime in general, and the beginning of a new era which was followed by the law of Prohibition. As already most of us know, Torrio became Colosimo’s successor but it seems that the new leader didn’t change a thing, meaning he was still connected to remnants from the old Irish faction like Jim O’Leary and representatives of the First Ward, followed by his connections to the Sicilian Mafia under Tony D’Andrea and later Mike Merlo, and Torrio also kept the connections South Side Jewish Mob, now under the Guzik family.