All I’m saying Compared to other Families and Crews when it comes to the Irish they were the Least to be Talked about for Many Reasons and feel like They were All the same from Whitey Bulger to Danny Green Dean O Banion to Mickey Featherstone they Give up their Own People on the Drop of a Hat and over the Slightest bullshit reason to Betray one another even Jimmy Connan seating Mickey Featherstone up despite him doing Life

As @Gia and I previously said, guys like Owney Madden were national and were associated with many families from around the country, meaning Madden and possibly Chicagos William O'Donnell were the prime examples of racketeers who in turn had Italian mobsters literally learning the scheme from them and also listened to them like they were their commanders.

Probably Owney Maiden and Howie Winter are probably the only 2 Stand up Irishman I know about and Jimmy Burke from the Lucchese and Eddie Boyle from the Gambinos but other then those Handful of Irishman there’s nobody Really

What about Michael Cassius McDonald? I believe he "invented" the term "organized" and later connected it to "crime", and also formed probably the first crime "commission" which included Irish, German, Italian, African-American and Jewish representatives. I believe McDonald is THE underrated crime boss when it comes down to racketeering, corruption, gambling and white slavery aka prostitution, and also played a major role in dividing the city of Chicago on different areas controlled by different crime groups, a blueprint which was later also used by the rising Italian crime families, especially by Al Capone and his Outfit.

There are so many small Irish Crews in Chicago and New York During the 1800s and 1900s and they Disappeared so Frequently cause that’s one thing about the Irish Historically Here Today gone Tomorrow and I understand the Irish were here before the Italians

"King Mike" controlled a very large crew which mainly included some of the "pioneers" in labor racketeering, gambling and prostitution. Heres one list of Mike's "original" Irish crew which I made some time ago, including an explanation regarding the project...

SOUTH SIDE 1900 - 1920

First Ward, Loop, the Levee and South Halsted, Near South Side and 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)

- Mike Kenna (political crime boss)

- John Coughlin (political crime boss)

- 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 (Kenna’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.

Good stuff TD.

Don't forget Mae Coughlin, Capone's wife, was a tough Irish girl. (April 11, 1897 – April 16, 1986)
Despite the rivalry between Italian-American and Irish-American groups at the time, there is no evidence that Capone's parents opposed their marriage.It is speculated that Al's parents were probably in favor of the union, because an Irish partner was seen as higher status than an Italian at the time.
From Al's imprisonment up until his death, Mae, along with Al's brothers and sisters, was in charge of his affairs: possessions, titles, and belongings.

"Black Jack" McGinty
From the Old Angle to the Desert Inn

Like world champ Johnny Kilbane, Thomas McGinty saw boxing as a way out of the poverty that was endemic among Irish immigrants in early twentieth century Cleveland.

https://clevelandhistorical.org/items/show/326

99 Percent of the People Never heard of These Chicago Irishman

Both Bathouse John and Mae Capone were Coughlin the family name, rich with Irish historical significance, symbolizes a legacy of strength, resilience, and cultural depth.

I agree the Irish had some very bad apples, the guys you mention are good examples and became notorious, but there were also plenty of good Irish guys.

What do mean by Good ?

Guys who weren't murderous and although they were criminals they took care of their guys.

Can you name Any ?

Owney Madden is a great example, he was used to brutal violence in the Gopher Gang , but since his Cotton Club he was never involved in murders.

I think that is Ridiculous thst Owney Madden was not a killer here’s proof he was

He rose to lead the area's most violent gang, the Gophers. In 1911, Madden married and briefly lived with Dorothy Rogers, with whom he had a daughter named Margaret, his only known child. A professional killer and gunman, he was wounded many times

When he was younger ys, but after he left NYC for Hot Springs the last 30 years of his life (1935-1965), I haven't seen anything indicating he was still killing people.

My point is also there were plenty of 'powerful' guys who didn't make the newpapers like Greene, Featherstone, Bulger etc..

Cause they were Nobody’s and Weren’t Important Enough