Alphonse Capone or just Al Capone instantly recognizable as one of the most notorious and well-known figures of the Twentieth Century. He had many other aliases, Snorky, Scarface, Scarface Al, and Al Brown, used furniture salesman. Capone was both an ally and enemy to many Irish mobsters throughout Chicago during the Prohibition Era. 

A lot has been written about Capone over the last hundred years, but in this story, we will just focus on the interactions with Irish and Irish-American gangsters.

Although Al Capone is associated with Chicago, Illinois, Capone was born in Brooklyn, New York. Capone’s parents emigrated from Italy and settled in Brooklyn in 1893. His parents, Gabrielle and Teresa had nine children in total. Al and his two brothers Salvatore or Frank and Raffaele or Ralph “Bottles” were associated with crime and prohibition.

Al Capone with his father and uncle

Al Capone with his father and uncle

Interestingly, Al Capone’s elder brother Vincenzo ran away and disassociated from the entire family when he was a teenager and began a new life, he changed his name to Richard James “Two Gun” Hart.

He became a successful Prohibition Agent in Nebraska and later an agent for the Bureau of Indian Affairs, he was also known for his cowboy style. Much later in life, Richard made efforts to reunite with his family, meeting with his mother and brothers, including Al.

Richard James "Two Gun" Hart / Vincenzo "Jimmy" Capone

Vincenzo Cappone / Richard James “Two Gun” Hart Photograph – Jeff McArthur.

When Al Capone was a teenager he came in contact with a local Brooklyn mobster, Francesco Ioele or Frankie Uale better known as Frankie Yale, who ran a bar called the Harvard Inn, the location where Al Capone insulted a woman, in turn, led to her brother, Frank Gallucio “defending his sisters honor” and slashed Al, leaving him with the famous scars. In an added twist, years later, Capone employed Frank Gallucio, as a sign of no hard feelings.

Al Capone was self-conscious about the scars and hated the nickname “Scarface”, some accounts say he was ashamed of how he got the scars and would sometimes powder his face in an effort to hide them. He would often make attempts to hide them in photo’s, always trying to have his photo taken from the opposite side or with the camera at an angle so that the scars couldnt be seen.

Through his association with Frankie Yale, Capone met another man who would influence his rise to become one of the most recognizable names in history, John Torrio also known as “The Fox” or “Papa John”. John Torrio was a gangster from the Navy Yard area of Brooklyn who went to Chicago to his cousin “Big” Jim Colisimo, one of the biggest gangsters in Chicago, a move that would change the course of history.

The Navy Yard area of Brooklyn ran along the boundary of Irishtown, the part of Brooklyn where earlier Irish immigrants had settled. Al Capone fell in love with an Irish woman.

Mary Josephine Coughlin was born and lived in the Carol Gardens section of Brooklyn in 1897. Her parents Michael Coughlin & Bridget Gorman were immigrants from Ireland, though their county of origin is not known.

Known as Mae she would marry Al Capone and stay married to him right up till he died in 1947. They had one son, Albert Francis “Sonny” Capone.

Mae and Sonny Capone

Mae & Frances “Sonny” Capone

No doubt Capone would have had interactions with Irish gangsters during his life around Brooklyn, one story goes that Capone was on a death list compiled by his rivals in the White Hand Gang, a notorious Irish gang from the Irishtown area of Brooklyn. Irishtown was a relatively small section of Brooklyn along the waterfront west of the Navy Yard, and east of where the Manhattan Bridge now stands. The Irish communities at that time, stretched to and included, Red Hook, Carrol Gardens and Bay Ridge, among other parts of Brooklyn.


A code of silence was observed in Irishtown, more faithfully than Omerta is observed by the mafia. Nobody ever talked in Irishtown 

Willie Sutton 

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The White Hand Gang

Murder on the Brooklyn Docks - The White Hand Gang - Owen Forsyth
The prevailing story, until recently, was that the Irish White Hand Gang, so named as a play on the Black Hand name the Italian gangs used, were at war over control of the Brooklyn docks and Capone, the rising star, was on a list of targets, marked for death, so he went to Chicago to lay low for a while. 

While a mob war between the Italian’s and Frankie Yale’s gang in particular and the White Hand Gang does sound exciting, the truth is there isn’t much evidence that this mob war happened, all the evidence points to an internal feud within the White Hand Gang itself, which was also known as the Bill Lovett gang, in a battle for the leadership, with multiple murders and successive leaders, “Dinny” Meehan, “Wild Bill” Lovett and Richard “Peg Leg” Lonergan being killed.


Dennis “Dinny” Meehan

William “Wild Bill” Lovett

Richard “Peg Leg” Lonergan

In my research, I have found that in almost every murder attributed to the White Hand Gang, Irish mobsters were arrested, questioned, or otherwise involved, in almost every case no Italian gunmen were involved, and the same stands for the Italian gang murders, Irish names were rarely attributed to a murder. The Brooklyn Police arrested the same men in several linked murders and seemed confident that it was an internal dispute. However, in one case, the death of Richard “Peg Leg” Lonergan, Italians were involved.

Please watch the four part documentary including my research on the White Hand Gang here…

The murder of Richard “Peg Leg” Lonergan, was a high-profile murder for several reasons, it occurred in Italian territory, which led to speculation that Lonergan and his men were ambushed in a plan hatched by Frankie Yale and Al Capone. 

One theory suggests that a disgruntled White Hand gangster named Eddie Lynch set up Lonergan, but Lynch was in prison at the time. Eddie Lynch was also found dead later in the 1920’s, believed to be in relation to the ongoing murders within the White Hand Gang.


Another story goes that Al Capone arrived at the Adonis Social Club with some of his men and some women who appeared to be Irish, a drunken and enraged “Peg Leg” Lonergan chased the women out of the club while shouting racial slurs and ranting about “White Slavery”, a term used for prostitution and pimping.

Prostitution and pimping seemed to be a contentious issue between the Italian and Irish gangsters, for example, Dean O’Banion in Chicago also found this a contentious issue between himself and John Torrio. And other gangsters would also look down on pimping.

The Adonis Social Club

The Adonis Social Club

Al Capone was in Brooklyn at the time of the murders on Christmas Night in 1926 but it’s not clear if he was present at the time of the shootings, the witnesses never mentioned Capone being there. Upon further research, there is no mention of the incident involving Lonergan and any women in any newspapers at the time. 

Lonergan’s group were sitting at a table, at a table across from them were four other men, presumably Al Capone and his group. Needles Ferry was summoned to the table with the four Italians, words were exchanged between the groups. And then the lights went out and the shooting started. By the time the shooting stopped, Aaron Harms and Peg Leg Lonergan were dead on the floor, while Needles Ferry was dead outside. All the other occupants had vanished, the two eyewitnesses left, hailed a taxi, and went home. 

Patrolman Richard Morano, who was on patrol in the area, found the body of Needles Ferry outside with a trail of blood going back into the building, it’s believed that Ferry was shot in the face and stomach and was left outside by his friends. Patrolman Morano went inside to investigate where he found the bodies of Peg Leg Lonergan and Aaron Harms lying side by side they were shot in the head and chest. A gun was found near Peg Legs’ body, while another was found near Aaron Harms and two more behind the bar. 

James Hart was found wounded further away from the Adonis Social Club, he had been shot in the leg, ear, and hand. Hart was brought to the hospital and claimed that he was shot by someone in a passing car, however, he was identified by the two eyewitnesses. Patrick Maloney and Joseph Howard were also identified by the eyewitnesses, they were arrested later. 

Police then started rounding up the other suspects, the following day Anthony Desso, Furi Agoglia, and the barman John Stible were taken into custody. Later, Ralph D’Amato, George Carrozza, Frank Piazza, and Al Capone were taken into custody and held. Al Capone was visiting from Chicago at the time. All were released without charge due to lack of evidence. 


Al Capone, George Carrozza, Frank Piazza, Joe Howard, Andrew Desso, John Maloney, Sylvester Aggolia, Ralph D'Amato, and John Stabile.

Al Capone, George Carrozza, Frank Piazza, Joe Howard, Andrew Desso, John Maloney, Sylvester Aggolia, Ralph D’Amato, and John Stabile.

Its most likely that if Capone & his group and Lonergan’s group were in the same place at the same time, it was a chance encounter rather than a planned ambush.

Other murders were attributed to Frankie Yale and Willie “Two-Knife” Altieri too that seem to be wrongly attributed, or not enough evidence to conclude they were involved. 

In one story, for example, the murder of “Dinny” Meehan, it appears that “Wild Bill” Lovett was responsible for Meehan’s murder, Dinny Meehan’s wife, Sadie, identified Lovett years after his death.

“Wild Bill” Lovett Murder Scene

Again, in the case of “Wild Bill” Lovett, it’s said that Yale was responsible for Lovett’s murder, gangsters from Cleveland were brought in specially to do the job, however, all suspects with Irish surnames were brought in for questioning, Frank Byrnes and Matty Martin were two main suspects in Lovett’s murder. Matty Martin married Lovett’s wife Anna Lonergan, who was Peg Leg Lonergan’s sister. Frank Byrnes went to prison for seven years after Lovett’s murder, he too was murdered after his release from prison, found floating in the river with his hands tied behind his back and a sack cloth over his head.

One theory about Lovett’s death suggests that his murder was revenge for “Machine Gun” Jack McGurn’s father, Tommasso Gibaldi. The only Italian, that “Wild Bill” Lovett was in a restaurant, Lovett and a man named “Red” Donnelly were brought in for that.

However, the truth is that it’s more than likely that John Torrio asked Capone to come to Chicago after Capone’s father had a heart attack. Torrio saw a lot of potential in Capone. Al Capone headed out to Chicago in 1919. In 1920 “Big” Jim Colisimo was murdered, possibly on the orders of John Torrio. This meant John Torrio was now the boss of the outfit and Capone was his protégé. 

Frankie Yale was identified as the shooter in Colisimo’s murder, a porter had identified Yale by a mugshot, but he changed his mind as the trial drew near.

Frankie Yale was killed in a car chase, by unkown gunmen in 1928., allegedly on the orders of Al Capone. The relationship between Yale and Capone had become strained.

Big Jim Colosimo murder scene

“Big” Jim Colosimo Murder Scene

Some believed the hit squad to be  Capone gunmen Tony “Joe Batters” Accardo, Fred “Killer” Burke, Gus Winkler, George “Shotgun” Ziegler, and Louis “Little New York” Campagna. Some of these were suspects in the St. Valentine’s Day Massacre, which would occur seven months after this.

The decision to whack Colosimo was accepted without many repercussions, Colosimo was seen as reluctant to get into the bootlegging trade, crooked local politicians such as “Hinky Dink” Kenna & “Bathhouse” John Coughlin, bosses of Chicago’s red light district, stated that all previous arrangements would continue to be honored.

John Torrio was initially based in the notorious Four Deuces establishment on Wabash Street. The Four Deuces had a saloon on the ground floor, the second and third floors were gambling and casinos, and the fourth floor was used as a brothel. Capone began working in the Four Deuces, as a bouncer and as someone who would stand outside and bring in clientele to the brothel. He then later became part owner and manager. 

Capone then opened a “front business” near the Four Deuces, a used furniture store, he would also start using the alias, Al Brown.

The Four Deuces

The Four Deuces as it stood in the 1930’s

"Ragtime" Joe Howard

On the evening of 8th May 1923 “Ragtime,” Joe Howard was sitting in Hymie Jacobs saloon with three other men. Joe Howard was a small-time crook, who was around the beer-running business and known as a dynamiter, someone who would throw bombs into speakeasies or businesses if they refused to pay up or if they were selling rival bootleggers alcohol.

That evening, two men entered the saloon and began to talk with Howard. Witnesses say one man was described as short while the other was big and stocky. They asked Howard to go outside but Howard refused, it was then the big stocky man grabbed Howard by the collar put a gun to his cheek, and fired six shots quickly, Howard took four in the face and two in the shoulder

Ragtime Joe Howard - Killed by Al Brown - The Murder of Dean O Banion - Owen Forsyth

“Ragtime” Joe Howard

Ragtime Joe Howard murder scene

“Ragtime” Joe Howard Murder Scene

On the evening of 8th May 1923 “Ragtime,” Joe Howard was sitting in Hymie Jacobs saloon with three other men. Joe Howard was a small-time crook, who was around the beer-running business and known as a dynamiter, someone who would throw bombs into speakeasies or businesses if they refused to pay up or if they were selling rival bootleggers alcohol.

That evening, two men entered the saloon and began to talk with Howard. Witnesses say one man was described as short while the other was big and stocky. They asked Howard to go outside but Howard refused, it was then the big stocky man grabbed Howard by the collar put a gun to his cheek, and fired six shots quickly, Howard took four in the face and two in the shoulder.

Within a couple of hours, the police were looking for a man named Al Brown, who ran a speakeasy called the Four Deuces. What the police did not know, at that time was, that Al Brown was a name that Al Capone used as cover.

There were many witnesses at the saloon where the shooting took place but they had all suddenly forgotten what happened, a case of “Chicago Amnesia”. The saloon owner also just happened to be looking in his safe at the time it happened too. The three men who had been with Howard at the time all vanished.

Sometime after Howard’s murder, Al Capone turned himself in at a police station, the police in turn handed him to prosecutor William McSwiggin for questioning and later released. William McSwiggin was later gunned down by Capone’s men, mistakenly, when he was caught in the crossfire of a mob shooting.

“Greasy Thumb” Jake Guzik

The motive as to why Ragtime Joe Howard was killed was believed to be a couple of nights previously, Ragtime Joe Howard stuck up “Greasy Thumb” Jake Guzik outside a 22nd Street gambling joint for $1500. “Greasy Thumb” Jake Guzik was John Torrio’s and Capone’s financial and legal advisor. Guzik was probably the only man that Al Capone really trusted.

Guzik tried to talk Howard out of the robbery by offering him a job. Ragtime Joe sneered he’d never work for a pimp like Capone.

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The Westside O'Donnell's

Wikkiam "Klondike" O'Donnell from the Westside O'Donnell's

William “Klondike” O’Donnell

Myles O'Donnell from the Westside O'Donnell's

Myles O’Donnell

Klondike O’Donnell and his brother Myles were notorious mobsters throughout the Prohibition Era. Joining up with Al Capone throughout the later years of Chicago Beer Wars and in the union rackets. It’s worth noting that the Westside O’Donnell’s were not related to the Southside O’Donnell’s, they were separate gangs.

Myles O’Donnell was arrested and stood trial for the murder of Eddie Tancl in what became a running dispute between Tancl and the O’Donnell’s because of selling beer in Cicero, Illinois, which was also considered Westside O’Donnell territory.

Eddie Tancl

Eddie Tancl

Cicero had also become Torrio and Capone territory since they had to move out of the Four Deuces, due to pressure from local officials. 

In November 1924 Myles O’Donnell and James Doherty paid a visit to the Hawthorne Park Inn to see Eddie Tancl. It is worth pointing out that this Hawthorne Park Inn is different from Al Capone’s Hawthorne Hotel. An argument broke out in the bar between them which turned into a gunfight. Doherty and O’Donnell turned the guns on Tancl, Tancl then pulled his gun but the other two fired at him, Tancl also fired but his gun jammed.

O’Donnell and Doherty ran out of the bar and split up, Tancl followed O’Donnell, both firing their guns at each other, hitting each other and both fell on the ground. A barman from Tancl’s bar had followed them and just reached both Tancl and O’Donnell in time to take Tancl’s gun from him. Tancl’s last words to the barman were “Kill him, he got me.” The barman jumped on O’Donnell until the police arrived.

William McSwiggin The Hanging Prosecutor

William McSwiggin

The Assistant State Attorney William McSwiggin prosecuted both Doherty and Myles O’Donnell for the Eddie Tancl murder but it was unsuccessful and the men were freed. William McSwiggin was gunned down two years later along with some O’Donnell gangsters. 

On April 27, 1926, McSwiggin joined Jim Doherty, Klondike, Myles O’Donnell, and Thomas “Red” Duffy, a childhood friend of McSwiggin for a night out in Cicero. All of them went to Harry Madigan’s bar, The Pony Inn, where they were joined by another man named Edward Hanley. As they left the Pony Inn a car pulled up alongside them and the passengers opened fire on the group, the O’Donnell brothers and Edward Hanley dropped to the ground, avoiding being hit but McSwiggin, Doherty, and Duffy were all riddled with bullets.

In the aftermath, Hanley and the O`Donnells sped off with McSwiggin and Doherty, who both died in Klondike`s car. Duffy was left behind and was taken by a motorist to West Suburban Hospital, where he died the following morning.

It was later revealed that the Capone gang and the O`Donnell brothers had had a tiff and were on the verge of open warfare. Rumor has it that Capone was behind the gun or in the car that the gun was fired from, and to witness for himself the firepower of the Tommy Gun. 

Tensions between the Westside O’Donnells and the Capone gang were eased when Capone left town for a while until the heat died down.

William "Klondike" O'Donnell, William "Three-Fingered Jack" White, Murray "The Camel" Humphreys, Marcus Looney, and Charles Fischetti.

William “Klondike” O’Donnell, William “Three-Fingered Jack” White, Murray “The Camel” Humphreys, Marcus Looney, and Charles Fischetti.

In October 1926 a peace conference took place between warring factions in the Chicago Beer Wars, where they would secure a fragile peace. William “Klondike” O’Donnell and his brother Myles attended the conference. 

Other notable names in attendance were, Vincent “Schemer” Drucci and George “Bugs” Moran from the North Side Gang, Ralph Sheldon attended, Joe Soltis and Frank McErlane were represented, although both Frank McErlane and Joe Soltis were in prison at the time. Al Capone was represented by Tony Lombardo. They agreed to peace but it didnt last long, within months they were back at it again.

The Westside O’Donnell’s allied with Capone, with “Klondike” O’Donnell becoming a vital part of the labor racketeering and taking over the unions along with Murray Humphreys, Marcus Looney, George “Red” Barker and “Three Finger Jack” White to name but a few. All of these men and more were busted in a Chicago hotel executive suite in 1932, they were believed to be overseeing the corruption of unions.

Towards the end of the 1920’s and into the early 1930’s the mobsters branched out from bootlegging, gambling and prostitution into labor racketeering


Dean O'Banion

Dean O'Banion

Dean Charles O’Banion

Al Capone’s interaction with Dean O’Banion would have been complex, at this stage of his career Capone was still one of John Torrio’s top lieutenants, so his dealings with O’Banion would have been more like John Torrio’s personal messenger or emissary. John Torrio’s eyes and ears.

It would seem that this is where Capone would learn the importance of peace and profit over needless mob warfare or reacting on impulse and anger. John Torrio’s patience would rub off on Al Capone. 

Interestingly, like other young mobsters of the time in New York, such as Salvatore Lucania better known as Charles “Lucky” Luciano, Frank Costello, Meyer Lansky, etc, they would see the importance of doing business and being allies with mobsters of other ethnic backgrounds like Irish, Jews, Polish etc.

John Torrio had a plan for Chicago, he called for the other mobs to sit down and agree to divide Chicago into territories among themselves. For the most part, the territories were accepted by all, for some reason the Southside O’Donnells either did not take part in the agreement or did take part for a while then split from the agreement early on. The Southside O’Donnell’s, were not related to the Westide O’Donnell’s, went to war with the Soltis / McErlane gang, who were backed by Torrio and Capone.

Edward “Spike” O’Donnell & Frank McErlane

In January 1924 John Duffy sometimes known as John Dougherty, a mobster from Philadelphia who had moved to Chicago and did some work for O’Banion’s Northside Gang killed his wife. 

Duffy, who was in a panic began to reach out to people in the hopes of getting out of town, reportedly, O’Banion agreed to help Duffy and arranged to meet at The Four Deuce’s, Al Capone’s place on South Wabash Avenue. John Duffy was last seen alive outside the Four Deuce’s getting into a car by eyewitnesses, who said they had seen him getting into a Studebaker with two men. John Duffy’s body was found the following morning on a snowbank in Chicago.

Police began their investigation naturally by focusing on Al Capone, The Four Deuces was the headquarters of Al Capone’s mob operations. It was a furniture store on the first floor, under the name of “Al Brown”, but actually had a saloon on the first floor, gambling on the second and third floors, and a brothel on the top floor, and Duffy was last seen outside it. Soon though, the suspicion turned to O’Banion’s gang.

John Torrio coveted the Gold Coast territory, which was Dean O’Banion’s, and came to a compromise with O’Banion’s gang, agreeing to a sharing of profits in breweries and casinos. O’Banion accepted the deal but continued hijacking shipments, angering Torrio and Capone as some of the booze that was being hijacked belonged to them. Al Capone was incensed by what he saw as an insult and asked Torrio to care of it but to keep the peace with O’Banion, Torrio refused to deal with it.

Despite the uneasy peace between the gangs, O’Banion did work with Torrio by getting some of his gang to work with Torrio and Capone in trying to influence the results of the mayoral election in 1924, making sure that the right candidate won. During that election, Al Capone’s brother Frank was shot and killed in outbreaks of violence throughout the city.

Frank Capone - Al Capone's brother

Frank Capone

In return for his help, Torrio gave Dean a piece of Cicero’s beer rights and a 15% in a casino called The Ship. O’Banion accepted but cheated Torrio by moving some Cicero speakeasies into his North Side and not sharing the profit. When Capone protested, Torrio tried to reason with O’Banion to abandon this course of action in exchange for some South Side brothel proceeds. O’Banion flatly refused, as he hated prostitution.

O’Banion made matters worse one night at The Ship casino, with “Schemer” Drucci, Hymie Weiss, Frankie Rio, Frank Maritote, and Al Capone. As they were counting the night’s takings and dividing the profits, Al Capone brought to attention that one of the Genna brothers, Angelo, had an I.O.U for a hefty sum of money. 

O’Banion, who was already in dispute with the Genna Brothers, made an issue of it and it was suggested that O’Banion let it go to keep the peace. Angered, O’Banion refused and demanded a telephone and got Angelo Genna on the phone to pay in full the $30,000 debt he owed to The Ship.


“To Hell with them Sicilian’s”

The "Terrible" Genna's Left to right Sam, Angelo, Peter, Tony and James.

Left to right  Sam, Angelo, Peter, Tony and James.

Famous last words, not quite, there are differing views on what O’Banion said exactly but it was some combination of the quote above, maybe with some racial slurs. Nonetheless, the words were taken as they were meant, at this point the Genna’s wanted to get rid of Dean O’Banion immediately but John Torrio wouldn’t allow it, Torrio knew that Mike Merlo, President of Unione Siciliana wouldn’t allow such a thing to happen, Merlo was powerful and influential in the Sicilian American community and preferred peace and profit over violence.

In what became the final insult Dean O’Banion tried to trick Torrio, by telling him that he was leaving the rackets and bootlegging and that he wanted to sell his stake in Sieben’s brewery on North Larabee Street.

In reality, it’s believed that Dean O’Banion had gotten a tip-off that the brewery was to be raided by the police and federal agents. O’Banion knew that John Torrio already had a charge for violating the Prohibition Laws and another violation would land Torrio a mandatory prison sentence. In the raid on Sieben’s Torrio, O’Banion and Louis “Two Gun” Alterie were all brought in by Police. It was the final straw for Torrio and O’Banion.

Al Capone was not present at Sieben’s Brewery as he was keeping a low profile since “Ragtime” Joe Howard had been murdered.

After the Sieben’s Brewery raid O’Banion and Louis Alterie went to Colorado to lie low for a while, a move that would become pivotal in mob history. On this trip to Colorado, O;Banion witnessed for himself the Thompson submachine gun, or Tommy Gun. Impressed by what he saw, O’Banion brought some Tommy Gun’s to Chicago. Its thought that O’Banion gave one of these to mobster Frank McErlane, a move that would shape mob warfare in the future. William McSwiggin was believed to have been killed by a mobster shooting a Tommy Gun

The Tommy Gun became so widely used it became known as the Chicago Typewriter, or lesser known as the Chicago Piano.

Dean O'Banion shot

An Illustration of the scene of Dean O’Banion’s Murder / Chicago Tribune

Soon after Dean O’Banion returned to Chicago, he was murdered in Schofield’s flower shop on the 10th of November 1924, Frankie Yale, although some say it was Genna gangster Samoots Amunata, was said to have extended his hand to O’Banion for a handshake in the famous “Death Grip”, while two gunmen, the “Murder Twins” or “Killer Twins” Alberto Anselmi, and John Scalise opened fire, killing O’Banion. 

A simple basket of roses near O’Banions casket had a condolence card attached that was sent from Al Brown, a Used Furniture Dealer, Al Brown being an alias for Al Capone. Capone was known for sending flowers to rival mobsters’ funerals. It’s not clear if John Torrio sent flowers or if Capone or Torrio attended the funeral, presumably they did, as is customary in gangland. 

Interestingly, Frankie Yale, Alberto Anselmi, and John Scalise all died on the orders of Al Capone years later. It was rumored that Scalise and Anselmi were plotting with Joe Giunta and possibly Joe Aiello to take over Chicago. Yale was killed in a car chase with mobsters who were using a Tommy Gun.

Giovani John Scalise & Alberto Anselmi - The Murder Twins

Giovani / John Scalise & Alberto Anselmi, The Murder Twins

Anselmi, Scalise, and Joe Giunta were murdered at a lavish banquet that was being held. At some point during the banquet, the three were held at gunpoint, beaten, and finally shot several times each in the head, legs, and chest. Their bodies were found dumped in Douglas Park, or as it is now known, Pulaski Park.

There have been many different iterations of the same story where Capone beat them with a baseball bat or future Outfit boss Tony Accardo beat them with a baseball bat, and that is how he got the name “Joe Batters”. However, it’s not clear if Al Capone was even in attendance at the banquet at the time. 

Dean O’Banion’s murder would shape Chicago’s gangland dramatically and would lead to a period of all-out mob warfare, culminating in the St. Valentine’s Day Massacre in 1929.

Al Capone winking at the camera

Al Capone

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Ralph Sheldon

Al Capone and Ralph Sheldon in Hot Sprongs, Arkansas

Al Capone (left) and Ralph Sheldon (right) in Hot Springs, Arkansas.

The Sheldon Gang, led by Ralph Sheldon was a bootlegging gang during Prohibition Era Chicago, in the early years the Sheldon gang was allied with the Soltis / McErlane Gang and battled against the Southside O’Donnells in the Southside Beer War. 

There had been an uneasy truce between the gangs until about 1923 when war broke out between the Soltis / McErlane, backed by John Torrio, and the Southside O’Donnells.

The gang war eventually ended when Edward “Spike” O’Donnell was forced to leave Chicago after being wounded by Frank McErlane in what was one of the first recorded uses of the Tommy Gun or what would become known as the “Chicago Typewriter” on September 25, 1925.

Thompson Sub Machine Gun, Tommy Gun, Chicago Typewriter, Chicago Piano

The Thompson Sub Machine Gun, Tommy Gun, Chicago Typewriter

Afterward, the Sheldon Gang split from the Soltis / McErlane gang and allied with Al Capone. One possible reason for the split was that the Soltis / McErlane gang was becoming too friendly with the Northside Gang, especially after Dean O’Banion’s murder. 
Danny Stanton

Danny Stanton

Ralph Sheldon formed a partnership with Danny Stanton, a former slugger who worked for one taxi company that fought with another, in the Chicago Taxi Wars. Danny Stanton was also a decorated WW1 veteran. They became known as the Sheldon / Stanton gang, they took much of the former Ragen’s Colts members with them. Ragens Colts was a street gang and political club that was involved in the Chicago Race Riots of 1919.

The Sheldon / Stanton Gang quickly became a major alcohol suppliers in Chicago’s Southwest Side and one of the main suppliers to Al Capone.

The Sheldon’s main rivals were the Saltis-McErlane Gang and the Southside O’Donnell’s. In October 1925 Frank McErlane used his favorite new gun again in an attack on the Sheldon gang, a saloon that was a hangout for the Ragen’s Colts gangsters. This led to a strange three-way gang war breaking out, both the Southside O’Donnell’s and the Sheldon / Stantan gang fought the McErlane / Soltis gang. The O’Donnell and Sheldon / Stanton gangs didn’t fight each other, however.

Edward "Spike" O'Donnell
Edward "Spike" O'Donnell
Ralph Sheldon

Edward “Spike” O’Donnell

Frank McErlane

Ralph Sheldon

As time went on Ralph Sheldon became ill with Tuberculosis and had to leave Chicago due to his health. While Sheldon was away, his gang, which was now solely run by Danny Stanton, discovered that Al Capone had been paying Ralph Sheldon bonus money to give to his men, but Sheldon had been pocketing that money for himself. Naturally, his men were furious, and Hugh “Stubby” McGovern shot Sheldon when he returned. Thus Sheldon left Chicago again.

The Stanton Gang was eventually absorbed by Al Capone’s Chicago Outfit. 

Hymie Weiss - The Only Man Capone Feared

Earl "Hymie" Weiss

Earl J. “Hymie” Weiss

After the murder of Dean O’Banion in 1924, “Schemer” Drucci and “Hymie” Weiss became obsessed with getting revenge on John Torrio and Al Capone in retaliation.

On January 25, 1925, it is believed that Drucci, Weiss, and Moran pulled up alongside Al Capone’s car and opened fire, they missed Capone however.

Twelve days later there was an attempted assassination attempt on John Torrio later. It’s believed that “Schemer” Drucci was the getaway driver while “Bugs” Moran and Hymie Weiss blasted John Torrio, leaving him seriously wounded, this was enough for John Torrio and left Al Capone as the Boss of Chicago. When John Torrio recovered he went to jail for a prohibition violation, he retired from crime and went to live in Sicily after he finished his sentence.

John Torrio leaves hospital having survived an attempt on his life. He hides the scars of the gun blasts

John Torrio leaves hospital having survived an attempt on his life.

The Northside Gang managed to wipe out most of the Genna Brothers gang in revenge for O’Banion’s murder, Mike Genna was killed by police, and the remaining Genna Brothers fled back to Italy. 
Weiss and Drucci shoot out with Capone gunmen

Chicago Tribune

None of this went unanswered though Vincent “Schemer” Drucci and Earl “Hymie” Weiss survived an assassination attempt in broad daylight in August 1926. “Schemer” Drucci and Hymie Weiss were having a late breakfast in the Congress Hotel and were attacked as they were leaving by Al Capone’s gunmen, who were waiting across the street.

A gunfight raged up and down the street with dozens of shots being fired by the attackers, while Drucci and Weiss returned fire, one onlooker was hit in the leg by shrapnel or a stray bullet. “Schemer” Drucci added to the drama by hopping on a car running board, waving a gun at the driver, and ordering them to follow the escaping attacker’s car. One Capone gunman was later arrested and was identified as Paul Valerie, better known as Paul “The Waiter” Ricca.

Drucci was arrested and claimed that it was a robbery and that the attackers were trying to rob him of $13, 200 he had in his pocket.

A month later on 20th September 1926, one of the most spectacular mob hits in Chicago took place, the attack on the Hawthorne Inn, Al Capone’s headquarters in Cicero

Scene from the 1967 movie The St. Valentine’s Day Massacre

Mobsters from the North Side Gang led by Weiss, Drucci, and Bugs Moran, rolled up in a convoy of four to six cars and they let loose with a volley of bullets from machine guns and shotguns into the hotel but Capone is thrown to the ground by his bodyguard Frank Rio and was unharmed.

Some say about 200 to 1,000 rounds are poured into the Hawthorne Hotel. A man and woman were injured but the target Al Capone escaped.

In recent times it has been discovered that the attack was coordinated with mobsters from the McErlane / Soltis gang from Chicago’s South Side. They had once been allied with Torrio and Capone. Frank McErlane, who was one of the leaders of that gang, arranged from prison with his brother Vincent to coordinate with the Northside Gang.

The war between Capone and the North Side Gang reached a peak in October 1926. A peace conference was arranged between the warring parties, although Al Capone didnt attend in person, Tony Lombardo was his emissary. Peace was on offer if O’Banion’s killers, believed to be Scalise and Anselmi, were handed over or killed, through Lombardo on the telephone Capone refused, reportedly saying “I wouldn’t do that to a yellow dog!”. 

Earl “Hymie” Weiss was murdered less than two weeks later.

Earl Hymie Weiss lies dead outside Schofields flowershop

Hymie Weiss Murder Scene

Later in October 1926 Hymie Weiss, the only man that Capone truly feared was gunned down outside Schofields Flowershop. Schofields was significant because it was also the location where Dean O’Banion was murdered almost two years previous. Schofields was also the headquarters of the Northside Gang, now run by Weiss, it had remained there.

The assassination of Hymie Weiss was an impressive operation involving at least two separate hit teams stationed in different buildings directly across the street from Schofields. The technique used to get Weiss was named the “Rented Ambush”, where gunmen hired apartments near where their targets would be and killed them at the best opportunity. There were bullets lodge, which still bears the scars, in the walls of the Holy Name Cathederal across the street.

At 4 O’clock on the 11th of October 1926, as Weiss was leaving the court to return to Schofields Flowershop, gunmen opened fire with a machine gun and an automatic shotgun from buildings across the street. Some witnesses say they saw gunmen on the ground too, who were shooting at Weiss

Hymie Weiss had been at the trial of Joe Soltis, one half of the Soltis / McErlane Gang, who at the time were believed to have been seeking an alliance with the Northside Gang, Weiss was found with the jury list of Soltis trial in his pocket.

Weiss and one of his men Paddy Murray were fatally shot, William O’Brien, who was an attorney was hit four times but managed to stagger to hide at a stairwell. An investigator who worked with William O’Brien was wounded along with Weiss’ bodyguard Sam Pellar.

In October 1926 a peace conference took place between warring factions in the first Chicago Beer War, where they would secure a fragile peace.

Vincent “Schemer” Drucci and George “Bugs” Moran represented the North Side Gang having assumed control of the gang after the deaths of Dean O’Banion and Hymie Weiss.

William “Klondike” O’Donnell and his brother Myles were from the West Side O’Donnell’s.

Ralph Sheldon was present, representing his faction that had split from the Soltis / McErlane Gang.

The Soltis / McErlane were represented, although both Frank McErlane and Joe Soltis were in prison awaiting separate trials at the time.

The South Side O’Donnells didn’t attend or take part in the peace conference.

The Genna Brothers Gang, who were once a rival outfit to the North Side Gang, had been all but wiped out at this stage.

Peace held for a while but the shootings and killings within the gangs continued. The peace pact broke down within a couple of months and so, the second Beer War began. 

After the attempted hits on Capone, mostly by the Northside Gang, in revenge for Dean O’Banion’s murder, Capone began to take his security seriously. Al Capone’s car, a 1928 Cadillac Model 341A Town Sedan, had a Police siren, bulletproof glass, and police radio.

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"Bugs" Moran & The St. Valentines Day Massacre

George “Bugs” Moran took over the Northside Gang after “Schemer” Drucci was killed by a police officer in 1927. Moran and Capone were by now, bitter enemies. 

Moran picked up where the others had left off. After the tit for tat the Northsiders decided to go after one of Capone’s top gunmen. On March 7th in 1928 its believed that the Gusenberg brother’s, Moran gangsters pulled off an attempt on the life of “Machine Gun” Jack McGurn in the McCormick Hotel. Witnesses say they saw a car pull up outside the smokeshop in the hotel, two men got out and ran into the smokeshop and opened fire on McGurn, wounding him and another customer.

The peak of the warfare seen a carefully planned and executed ambush played out to make sure that George “Bugs” Moran and his top men were dead, thus eliminating Capone’s main rival, Moran never made it to the location that day, and he survived, although seven unlucky victims didnt survive

Throughout the gang war, both had survived several assassination attempts. On one occasion, Moran, Weiss, Drucci, and some of their men drove a convoy of cars past the Hawthorne Hotel where Capone and his men were having lunch and sprayed the building with lead, miraculously no one was killed and few had minor injuries.

A plan was hatched where they would try to trick Moran into thinking he was buying a shipment of hijacked booze from Canada, the drop-off point was to be the SMC Cartage Company garage at 2122 North Clark Street, a property belonging to Moran. The idea behind the plan was to kill Moran and his men while they were all in the building together.

SMC Cartage Company scene of the St. Valentine's Day Massacre

SMC Cartage Company warehouse at 2122 North Clark St

At 10.30 am Moran’s gang had been preparing to meet the incoming shipment but in a twist of fate, George “Bugs” Moran was running late that morning. Moran pulled up in his car just in time to spot a quartet, including two dressed as police officers enter the building, thinking it was a raid on the building he quietly moved on.

A police car had arrived outside the building with two men dressed in uniform and two more in civilian clothes. Inside the building were six of Moran’s men. The last to arrive was Albert Weinshank, as Weinshank made his way into the warehouse, he was grabbed by the two police officers and they forced him inside. Believing the gangsters were being raided, as they were gangsters they knew the drill so they lined up against the wall with their backs to the police.

The seven victims of the St. Valentines Day Massacre
When they were in line, before they knew what hit them, armed with Thompson machine guns the assassins opened fire, emptying an entire 20-round box magazine, and a 50-round drum into them. They even continued shooting even after the gangster’s bodies had dropped to the floor. The men dressed as police officers escorted the assassins out of the building, under the guise of arresting them, and fled the scene.

Six of the gangsters died instantly but one remained alive, although barely, Frank Gusenberg was taken to hospital but died later that day, but not before the police could talk to him. As soon as he had arrived at the hospital and been stabilized by doctors, the police questioned him and wanted to know how he had gotten 14 gunshot wounds, and who had shot him. He replied “No one shot me,” Frank Gusenberg died three hours later.

The victims that day were brothers Frank & Pete Gusenberg, long time members of the Northside Gang, John May, Albert Weinshank, Adam Heyer, Albert Kachellek aka James Clark. Also there was Dr. Reinhardt Schwimmer, who liked to hang around with gangsters but wasnt one himself. 

St. Valentine's Day Massacre victims

Vicitms of the St. Valentine’s Day Massacre

“Bugs” Moran the intended target never even made it inside the warehouse and so survived

Highball a German Shepherd, that belonged to John May, the youngest person to be killed in the St. Valentine’s Day Massacre. Highball was the only eyewitness inside the garage where the massacre happened. And endured the whole incident. When police arrived, Highball was found chained, trembling, and howling. Sadly Highball was so traumatized he had to be put down.

No one was ever charged for the crime and no actual suspects were named, although there are plenty of guesses as to who it was. Some of the suspects included:

Gus Winkler & Fred “The Killer” Burke, who were both former members of the Egan’s Rats, a gang from St. Louis, Machine Gun Jack McGurn, John Scalise, and Alberto Anselmi. All of which were certified killers and could have easily pulled this off. Some evidence, from the wife of Gus Winkler, says that she saw both Gus Winkler & Fred Burke dressed in uniforms on the morning of the massacre, these were prime suspects, though they were never arrested.

In the fallout of the St. Valentine’s Day Massacre, George “Bugs” Moran stated, “Only Capone Kills Like That”. Having heard what Moran had said, Al Capone responded with “The Only Man That Kills Like That Is Bugs Moran”

After the St. Valentine’s Day Massacre George “Bugs” Moran held on for a while with a much weakened Northside Gang. Eventually, Moran faded away from bootlegging in Chicago altogether. Moran continued his life of crime, getting picked up by police for petty crimes. He was arrested for robbery in 1939 and sent to prison until 1944. “Bugs” Moran was arrested again in 1945 and sent to prison for 20 years, he died in prison in 1957, ironically outliving Al Capone. 

The "Terrible" Touhy's

Of course, this article wouldn’t be complete without mention of the “Terrible Touhys”.


Some of Roger Touhy's brothers

Some of Roger Touhy’s brothers. From left to right Joseph, James, Thomas and Ed. 

Four of the “Terrible Tuohys”, from left to right, are Joseph, James, Thomas, and Ed. Not pictured are John and Roger Tuohy. The Touhy’s father was a patrolman in the Chicago Police Department, while their mother died in a house fire when they were younger.

Roger Touhy, one of the “Terrible Touhys” was the most notable name among five of the six Touhy boys who became part of a bootlegging gang.

Touhy’s territory was in Northern Chicago where he had partnered with Matt Kolb, who was formerly partnered with Marty Guilfoyle. Touhy and Kolb were pulling in an estimated $1 million a year from beer sales alone. Naturally, this attracted Al Capone’s attention.

"Terrible" Roger Touhy

“Terrible” Roger Touhy

The Touhy’s challenged Capone’s outfit’s moves to muscle in on their territory that Capone considered to be “Virgin Ground”. Both sides went to war, losing many men in reprisals and counter-reprisals. In 1927 John Touhy was killed in the Lone Tree Inn, possibly by Capone gunmen.

Joeseph Touhy was killed in 1929, Joeseph and a group of his men were breaking up a Capone speakeasy, that Capone had set up within Touhy’s territory. That didn’t stop Capone from continuing his take-over, nor did it stop the Touhy’s.

Trying to strong-arm Touhy did not work either, some reports suggested that Capone sent his goons to talk to Touhy, Touhy arranged for locals to come to his hangout, look menacing, and be armed with all kinds of guns, giving the appearance of the Touhy gang being “bigger” than they really were.   

The charades, however, didn’t take away from the Touhy’s ability to fight Capone. In 1932 the Touhys ambushed Charles “Red” Barker, one of Capone’s top union men, outside a hotel in Northwest Chicago. Apparently, William “Three Finger Jack” White, Claude “Screwey” Maddox, and William “Klondike” O’Donnell all narrowly avoided being hit. 

Subsequently, the Touhys went on the offensive leading to a string of ambushes and murders throughout 1932. This offensive for the most part was met with firstly political and official pressure, the Chicago Police shut down every Touhy speakeasy and operation in the Northwest Side of Chicago.

Al Capone was brought to trial and sentenced during his 1931 tax trial. Capone’s Outfit was now under the control of Frank Nitti, who had a different style of leadership, Nitti preferred to handle things that didn’t attract the spotlight. 

In 1933 everything changed for the Touhys, Roger in particular. 

"Terrible" Roger Touhy in jail

Roger Touhy

The crime that put “Terrible” Roger Touhy and his gang in prison, behind bars was the one he didn’t commit, the alleged kidnapping of Jake Factor, half-brother of the make-up artist Max Factor. It is believed that Nitti and the company put Factor up to the job of falsely accusing them.

This miscarriage of justice lasted years. The drama didn’t end there, Touhy and some prisoners managed to escape prison escape prison, and go on the run, being caught and sent back to prison, then ended in Touhy’s parole. However within weeks of his release from prison, “Terrible” Roger Touhy was gunned down.

“Terrible” Roger Touhy lies on his sister’s front porch having been shot in 1959, Touhy would die of loss of blood hours later on the operating table.

"Terrible" Roger Touhy lies on his sister front porch, after being shot

Roger Touhy after being shot

Touhy and his bodyguard Walter Miller, a retired detective were confronted by two or three men, who were armed with shotguns, Touhy was shot in the left leg above the knee and the right leg below the knee. Walter Miller was hit three times in the arm, but Miller did manage to return fire, it’s not clear if any of the attackers were injured.

As Touhy was in the hospital, he told medics and police,


“I’ve been expecting it. The bastards never forget.”

The Untouchable's

Elliot Ness Prohibition Agent

Elliot Ness

In the aftermath of the St. Valentine’s Day Massacre, the authorities clamped down on gangsters, especially in Chicago. because of the rampant corruption in Chicago with bribes being paid off to the police, politicians, and judges, the Federal government eventually stepped in and set up a multi-agency task force, with the Justice Department and the Treasury Department launching investigations for gangsters to pay tax.

A unit of Prohibition agents was set up, which included the famous Elliot Ness who led a team of agents, they earned the nickname, The Untouchables, because they weren’t as easily bribed and corrupted as the local police and authorities. The Untouchable’s main task was to take down Al Capone, they succeeded in getting Capone on thousands of Prohibition violations, however, the government decided not to pursue the Prohibition violations and instead pursued income tax violations.

Capone would be on the receiving end of the law for most of 1929 & 1930. Capone was arrested on the 27th of March 1929 by FBI agents, leaving court. In May 1929 Al Capone was arrested for carrying a concealed weapon, for which he was sentenced to 1 year in Eastern State Penitentiary in Philadelphia. After he was released in 1930 Capone was named Public Enemy Number One.


In June 1930 Al Capone was indicted on 22 counts of tax evasion and 5,000 prohibition violations. Capone would stand trial in 1931 and was convicted on five counts of tax evasion, the judge decided to pursue the tax evasion charges as he deemed them more serious than the prohibition violations. 

Al Capone was sentenced to 11 years in prison and given a $50,000 fine, plus any court costs in October 1931. He was also held liable for $215,000 in tax arrears on an estimated $1,038,654 earned from 1925 to 1929.

Capone’s underboss, the next in line to take over from Capone, was Francesco Nitto better known as Frank Nitti. Nitti had been in charge of all the money flowing through the Capone Organization. Under Nitti the Outfit would start branching out, they would no longer just focus on alcohol, gambling, and prostitution and move into labor racketeering and unions.

Frank Nitti "The Enforcer"

Frank Nitti

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The Board of Director's

William "Klondike" O'Donnell, William "Three-Fingered Jack" White, Murray "The Camel" Humphreys, Marcus Looney, and Charles Fischetti.

William “Klondike” O’Donnell, William “Three-Fingered Jack” White, Murray “The Camel” Humphreys, Marcus Looney, and Charles Fischetti.

In 1932, a police raid managed to apprehend Al Capone’s Board of Directors. Chicago Chief of Detectives, William Shoemaker, who was looking to arrest William “Three Finger Jack” White stumbled across a meeting of the biggest names in Chicago’s gangland on the fourteenth floor in one of Chicago’s finest skyscrapers at No.1 La Salle Street, surprising Detective Shoemaker as much as it did the gangsters.

The scene was described to the media by Detective Shoemaker like this; the gangsters were meeting like the presidents of banks, in an expensive directors’ suite. At the head of the large mahogany table was Murray “The Camel” Humphreys, who was one of Al Capone’s trusted lieutenants. Next to Humphreys, to his right was sitting William “Klondike” O’Donnell the Southside Beer Baron. On Humphreys’ left was sitting Marcus “Studdy” Looney a labor racketeer and business agent for the Teamsters Union.

Along the sides of the table were other racketeers and union business agents such as Thomas Cullen, John O’Brien, Joe Marino, Sam Alex, William Martin, and Charles Sullivan, a labor racketeer and brother-in-law of the recently deceased Charles “Red” Barker. 

Charles Fischetti a labor racketeer and a former bodyguard of Al Capone’s. At the bottom end of the table was sitting William “Three Finger Jack” White. In the center of the table was a gold frame with the photo of Charles “Red” Barker.

“Red” Barker had been gunned down on the street by the Touhy Gang with a total of 18 bullets lodged in him. In gangland tradition, Barker had a huge send-off, with estimates of up to four thousand mourners and curious on-lookers. 

This group was in charge of the union take-over when the Outfit branched out from gambling, alcohol, and prostitution into labor racketeering among other more “legitimate” rackets.

A surprised Detective Shoemaker walked into the room and was greeted by Murray Humphreys, sitting in his chair at the top of the table “Ah, how do you do. We meet again”. Shoemaker searched Humphreys and found a gun, as he searched the rest of the members of the board he found a gun on Charles Fischetti, another when he searched William “Three Finger Jack” White, and a fourth gun in a drawer in the desk.

The entire board of directors plus all of their bodyguards were brought down to the station, where Shoemaker was thinking of what charges should be brought against them, he knew they were up to something they shouldn’t be but wasn’t sure what it was. “I understand they’ve gone into the labor rackets”

In a separate raid across town on the Westside in a “political” club the police arrested other Outfit mobsters such as Sam “Golf Bag Sam” Hunt, “Machine Gun” Jack McGurn, Tony Accardo, Rocco de Grazio, and four other gangsters.

Samuel McPherson aka Sam Golf Bag Hunt
Anthony "Tony" Accardo
Machine Gun Jack McGurn

Sam “Golf Bag” Hunt

Anthony ” Tony Batters” Accardo

“Machine Gun” Jack McGurn

In The End

Al Capone in Florida
Al Capone was sentenced to 11 years in prison and given a $50,000 fine, in 1931 and went to prison in 1932, he was sent to Atlanta at first and then onto the newly opened Alcatraz prison in California, where he was stabbed by another inmate, though Capone wasn’t badly hurt. 

While he was in prison Capone was diagnosed with syphilis, by 1939 his condition was deteriorating and so was paroled.

Al Capone spent the rest of his life living in Florida, where he died in 1947, surrounded by his wife Mae, his son “Sonny”, also living in Miami with them was Mae’s brother Daniel Coughlin and his wife. Daniel would act as a part time chauffeur for Capone. 

Frances “Sonny” Capone would live a normal law abiding life, he married an Irish woman and teenage sweetheart by the name of Diana Ruth Casey. It appears that “Sonny” somewhat struggled with shaking his fathers legacy, for example, used his fathers old aliases, Brown, to enroll into university and at different times throughout his life. “Sonny” died in California in 2004.


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Owen Forsyth

Web Designer, Teacher, Artist, Writer, 3D, Modeling & Visual Effects, DJ

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