North Side Gang

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The North Side Gang, also known as the North Side Mob, was the dominant Irish-American criminal organization (although a large number of Polish-Americans were members as well) within Chicago during the Prohibition era from the early-to-late 1920s and principal rival of the Johnny Torrio-Al Capone organization, later known as the Chicago Outfit.

History of the North Side Gang[edit]

Early history[edit]

Like many other Chicago-based Prohibition gangs, the North Side Gang originated from the Market Street Gang, one of many street gangs in Chicago at the turn of the 20th century. The Market Street Gang was made up of pick pockets, sneak thieves and labor sluggers working in the 42nd and 43rd Wards. The gang especially distinguished itself during the newspaper "Circulation Wars" of the early 1910s between the Chicago Examiner and the Chicago Tribune. As sluggers for a newspaper, the Market Street Gang would beat up newsstand owners who did not carry that publication.

It was during the Circulation Wars that future North Side leader Dean O'Banion, then a member of the juvenile satellite Little Hellions, who would develop valuable contacts with politicians and journalists. O'Banion and other members of the North Siders would be mentored by safecracker Charlie "The Ox" Reiser, O'Banion was one of the many Market Streeters to become a bootlegger.

Prohibition[edit]

With the start of Prohibition, the North Siders quickly took control of the existing breweries and distilleries in the North Side of Chicago. This gave them a near monopoly on the local supply of real beer and high quality whiskey; their rivals only had supplies of rotgut liquor and moonshine. Based on the North Clark Street restaurant McGovern's Saloon and Cafe, the North Side Gang would soon control the working-class neighborhoods of the 42nd and 43rd Wards within months. In addition to bootlegging, the gang continued to burglarize local stores and warehouses and run illegal gambling operations. Unlike the rival South Side Gang, however, they refused to traffic in prostitution. O'Banion strengthened his political protection by helping his politician friends commit election fraud. O'Banion also ran a publicity campaign in the North Side with large-scale donations to orphanages and charities as well as food and loans to the poor and unemployed.

The old hostility between Irish and Italian gangs combined with O'Banion's refusal to sell portions of North Side distilleries to the South Siders, raised tension between the North and South Siders. During several meetings arranged by Torrio, O'Banion would often insult the Italians. O'Banion was also secretly hijacking South Side beer shipments and selling them back to their owners. However, the North Side Gang also ran into trouble with other ethnic gangs; in 1921, O'Banion shot Ragen's Colts member Davy "Yiddles" Miller after he insulted a North Sider at a local opera.

Although O'Banion and Weiss were arrested and charged with burglary in 1922, the North Side Gang enjoyed considerable protection from the Chicago police department. At one point, O'Banion threw a lavish banquet for Chicago politicians and police officials. Attendees included Chief Detective Michael Hughes, Police Lieutenant Charles Evans, County Clerk Robert Sweitzer, Public Works commissioner Colonel Albert A. Sprague, and a host of both Democrat and Republican politicians. Dubbed the "Balshazzar Feast" by the press, it was later investigated by reform Mayor William E. Dever.

In 1924, Chicago police assisted the North Side Gang in robbing the Sibly Distillery, which had been under federal guard since the beginning of Prohibition. Escorted by Police Lieutenant Michael Grady and four detective sergeants, North Siders looted the distillery in broad daylight, taking 1,750 bottles of bonded whiskey worth approximately $100,000. Although Grady and the other police officers were later indicted for this crime, they were quickly dismissed.

Relations between the North and South Side gangs continued to fester. In early 1924, O'Banion agreed to an alliance with Torrio and Capone that was brokered by Mike Merlo. However, the alliance began to founder when O'Banion demanded that "Bloody" Angelo Genna pay a $30,000 gambling debt from losses at the co-owned gambling casino The Ship. This demand contravened an agreement allowing Angelo and other gang members to run up debts there. In the interest of maintaining harmony, Torrio persuaded Genna to pay his gambling debt.

However, Torrio himself would soon lose patience with O'Banion. It happened when O'Banion offered to sell Torrio the valuable Sieben Brewery. On May 19, 1924, while Torrio was inspecting the property, O'Banion arranged for the police to raid the place and arrest Torrio. After his release from custody, Torrio acceded to demands from the Gennas to whack O'Banion.

On November 10, shortly after the death of Merlo, three unidentified men entered the Schofield Flower Shop owned by O'Banion and shot him dead. This was to be the beginning of a five-year gang war between the North Side Gang against Johnny Torrio's Chicago Outfit that would end with the St. Valentine's Day Massacre in 1929.

War with the Chicago Outfit[edit]

After the death of Dean O'Banion, Hymie Weiss assumed leadership of the North Side Gang and immediately struck back at his rivals. On January 12, 1925, Weiss, Bugs Moran, and Vincent Drucci, attempted to kill Torrio's lieutenant, Al Capone at a Chicago South Side restaurant. Firing at Capone's car, the men wounded chauffeur Sylvester Barton, but missed Capone entirely. Capone, startled by the shooting, ordered his famous armoured car to be created. Moran then decided to kidnap one of Capone's trusted bodyguards, torture him for information before finally executing him and dumping the body.

On January 24, shortly after the assassination attempt on Capone had taken place, Weiss, Moran, and Drucci ambushed Torrio as he returned from shopping with his wife. Both Torrio and his chauffeur Robert Barton were wounded several times. As Moran was about to kill Torrio, the gun misfired; the gang members were forced to flee the scene as the police arrived. After narrowly surviving this attack, Torrio decided he wanted out. Retiring to Italy, Torrio passed leadership of the Chicago Outfit to Capone.

Weiss and the North Siders then went after the Genna Family, allies of the Chicago Outfit. First, "Bloody" Angelo Genna was shot to death after a car chase by Moran. Next, Mike "the devil" Genna was shot down by police when he turned his gun on them after a fierce shootout with the Northsiders. Then Drucci went and killed Samuzzo "Samoots" Amatuna, a Genna family backer trying to hold the Genna's intact. Then finally Tony Genna was murdered (although it was rumored that Capone, not Weiss, ordered this hit). At this point, the remaining Genna family fled Chicago. The North Siders and Capone took the spoils.

The Northsiders under Weiss, Drucci and Moran[edit]

Soon after Dean O'Banion's death, the North Siders had formed a "governing council" with Hymie Weiss emerging as leader. Although the loss of O'Banion was a great shock, the gang had now reached its zenith of power: the Genna family was destroyed, Torrio had been scared out of the rackets, and Capone was on the run. The North Siders expanded their business and strength and plotted another attack on Capone.

The second North Side attack on Capone shocked the police, fellow gangsters and especially Capone. A fleet of North Side cars, with Moran in the lead car, drove to Capone's hotel in Cicero. While Capone and his bodyguard were drinking downstairs, the North Siders drove by the lobby and opened fire with their Thompson submachine guns. The shooting reduced the hotel to shreds and left everybody running for cover. Capone and his bodyguard were forced to take cover on the floor. Once the attack was over, Capone, terrified and aching for a moment's peace, sent word to the North Siders that he wanted a truce. A truce was made, which did last for a while, but inevitably began to come apart.

Some time later, Capone struck back at the North Siders by gunning down Hymie Weiss and several associates. Drucci and Moran now assumed joint leadership of the North Side Gang. The two gangs traded killings and bombings for several more months until a peace conference was held.

Moran and Capone both appeared at the meeting along with many other mob bosses. During the conference, Capone complained that "they were making a shooting gallery of a great business". He also stated that "Chicago should be seen as a pie and each gang gets a slice of the pie." The two gangs agreed to make peace. This peace would last for a while. It was the only time in Chicago when gunfire ceased and calmness occurred. No killings occurred that were a result of gang war. Vincent Drucci was killed during this time, but it resulted from a brawl with police. Moran now became the sole boss of the North Side Gang.

The gangland peace soon turned into a Cold War as both sides fell victim to temptation. Moran would regularly hijack Capone's beer shipments, naturally aggravating Capone. Capone retaliated by burning down Moran's dog track. A few days later, Capone's own dog track went up in smoke. Moran was the prime suspect.

Open warfare started again between the two gangs. Moran ordered the execution of two union leaders who were powerful allies and personal friends of Capone. This act prompted Capone to order a decisive blow against Moran that would turn into the most memorable gangland killing in American history: the St. Valentine's Day Massacre.

St. Valentine's Day Massacre[edit]

On February 14, 1929 four unidentified men, two of them dressed as Chicago police officers, stormed into a North Side Street garage and ordered six members of the North Side Gang and a friend of a gang member to stand against a wall. The gunmen then pulled out machine guns and gunned them all down. The only survivor, Frank "Tight Lips" Gusenberg, died hours later at a nearby Chicago hospital refusing to name his attackers. However, the primary target of the gunmen, Bugs Moran, leader of the North Side Gang, was not at the garage and escaped harm. Strong circumstantial cases can be made for almost a dozen individuals as being one of the four gunmen, but it remains unknown to this day exactly who those four gunmen were.

Known as the St. Valentine's Day Massacre, the attack effectively left the five-year gang war between Al Capone and Bugs Moran in a stalemate. The brazenness of this crime resulted in a Federal crackdown on all gang activity in Chicago that eventually led to the downfall of both Moran and Al Capone.

Aftermath[edit]

Although Bugs Moran survived the St. Valentine's Day Massacre, several experienced North Side gunmen had been lost. The North Side Gang continued to control the 42nd and 43rd Wards and managed to thwart a takeover attempt by Frank McErlane in 1930. As the decade progressed, the power of the North Side Gang slowly declined. In 1936, Jack "Machine Gun" McGurn, mastermind of the massacre, was killed and Moran was one of the prime suspects, along with Frank Nitti of the South Side mob, as McGurn had become more trouble than he was worth to protect to the former "Capone Gang".

Moran and the North Side Gang eventually lost control of their gambling operations to the new National Crime Syndicate. Since the repeal of Prohibition, gambling had been the main source of North Side income. The gang limped along until the end of the 1930s when Moran left the Chicago underworld. The North Side gang disappeared and the Chicago Outfit, successor to the old South Side gang, took control of the North Side territories.

North Side Gang members[edit]

Bosses[edit]

Other Members[edit]

NamePortraitLifeComments
Jack "Two Gun" AlterieLouisAlterie.jpg1886-1935A leading gunman during Chicago's bootleg wars, Louis Alterie was one of the more colorful figures in the Northsiders. A western enthusiast, Alterie reportedly carried two Colt. 45 revolvers on a gun belt and owned a ranch in Colorado that was frequented by other gang members. After publicly challenging O'Banion's killers to a gunfight, the mayor of Chicago publicly slapped Alterie. To cool things off, Alterie left Chicago at the request of Bugs Moran. After several years in exile, Alterie returned to testify against Ralph Capone in 1935. Alterie was murdered soon after his return.
Barney BertscheNo image
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A later member of the Northsiders, Christian P. "Barney" Bertsche ran prostitution and gambling dens in Chicago's North Side. Following the syndicate takeover of his operations by Capone after the truce agreement at the Hotel Sherman conference in 1926, Bertshe allied with Moran in the hopes of regaining control over his criminal operations.
James ClarkNo image
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1887-1929Born Albert Kachellek in Krojoencke, Germany, Clark was a bodyguard and brother-in-law of George "Bugs" Moran. One of the seven victims of the St. Valentine's Day Massacre.
John DuffyNo image
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d. 1924Duffy was hired muscle from Philadelphia who was sometimes used by the North Siders. After murdering his newlywed wife during a drunken argument, he was taken for a "one way ride", allegedly by O'Banion himself, and his body found in a snowbank outside of Chicago.
Frank and Peter GusenbergNo image
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1892-1929 (Frank)
1888-1929 (Peter)
Peter was the older brother of Frank Gusenberg. Both were top gunmen for the Moran gang. Both died in the St. Valentine's Day Massacre.
Adam HeyerNo image
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1889–1929Also known under the alias Frank Meyer, Adam Hayes, John Snyder, and Frank Snyder, Heyer was a North Side Mob accountant and business manager. One of the seven victims of the St. Valentine's Day Massacre.
John MayNo image
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1893-1929May is not considered by most researchers to have been a gang member in the conventional sense of the word - he was disassociated with the gang sometimes for months on end, only accepting jobs from them when he desperately needed money (he had a wife and seven children). May was an occasional strongarm for the Moran gang (though it is believed he never carried a gun) but was, most frequently, simply a car mechanic working on a per diem basis. He had the misfortune to be working on a North Side Gang vehicle on Thursday, February 14, and was one of the victims of the massacre.
William "Willie" MarksNo image
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Labor racketeer and a lieutenant under George Moran and, as a bodyguard, was with Moran at the time of the St. Valentine's Day Massacre. Marks, Moran and Ted Newbury avoided the massacre, either by seeing the "police" car pull up to the garage as they approached it themselves, or simply by being a few minutes late.
Dan McCarthyNo image
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A hijacker and "labor slugger" for the North Side Mob, Daniel J. "Dapper Dan" McCarthy was tried and acquitted on three separate murder trials. A "business agent" for Chicago's Journeyman Plumbers' Union he assumed control of the organization by murdering its president Steve Kelleher at Al Tierney's Auto Inn.
Samuel "Nails" MortonNo image
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1894-1923A veteran of World War I, Samuel Morton was an early lieutenant of Dean O'Banion and served as his right-hand man during the early years of Prohibition. Following Morton's death in a riding accident, several gang members took the offending horse from its stables, led it to a field, and killed it.
Ted NewburyNo image
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d. 1933Longtime Chicago rumrunner and lieutenant under George Moran during the final years of Prohibition. Defected to the Chicago Outfit following the St. Valentine's Day Massacre. Newbury was later killed by Capone successor Frank Nitti for conspiring to murder Nitti. Newbury's body was found in a roadside ditch in Indiana on January 7, 1933.
Billy SkidmoreNo image
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1879-1944Underworld bail bondsmen and scrap-iron dealer loosely associated with the North Side Gang through his gambling operations and political connections. Convicted of tax evasion in 1941, Skidmore died in prison three years later.
Albert "Gorilla Al" WeinshankNo image
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1893-1929Weinshank had worked as a speakeasy operator for Moran, and later ran a string of cleaning and dyeing stores for the North Side Gang. His build, choice of clothing, and even vague physical resemblance to Moran is theorized to be the reason that the St. Valentine's Day Massacre began with his arrival at the Clark Street Garage ahead of Moran himself.
Jack ZutaJack Zuta.jpg1888-1930Originally an accountant and political "fixer" for the Chicago Outfit, he switched sides during the gang war with the Northsiders. He fled Chicago in 1930, after an attempt on his life, but was eventually killed several months later in a roadhouse outside Milwaukee, Wisconsin.

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