My Grandfather’s Cousin was killed at The St. Valentine’s Day Massacre



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From The Mob Museum

The St. Valentine’s Day Massacre occurred about 10:30 a.m. on February 14, 1929, inside the S.M.C. Cartage Company garage at 2122 North Clark Street on the north side of Chicago.

Seven men associated with George “Bugs” Moran’s bootlegging operation were waiting inside the garage, presumably for a meeting to buy a hijacked shipment of Canadian whiskey at a good price.

But four men, two wearing police uniforms, pulled up in a police car, entered the garage and ordered Moran’s men to line up shoulder to shoulder against a wall of the garage. They did not put up a fight because they believed they were being subjected to a police raid.

Chicago investigators re-enact the Massacre. Courtesy of John Binder Collection

The men opened fire with two Thompson submachine guns and a shotgun. All seven were shot dead. A German shepherd dog named Highball, tied to a car bumper in the garage, was not killed.

Victims of the St. Valentine’s Day Massacre in a garage on Chicago’s North Side. Courtesy of John Binder Collection

The killers undoubtedly had hoped to kill Moran himself, but he was not among the seven victims. Moran was supposed to be there, but was late for the meeting, saw the police car and walked on by along with two associates. If they had been on time for the meeting, one can assume that 10 men would have perished in the Massacre.

Five of the seven victims were bona fide gangsters. Peter Gusenberg, 41, and Frank Gusenberg, 37, were top enforcers for the Moran gang, as was Albert Kachellek, 42. Adam Heyer, 40, was Moran’s business manager, and Albert Weinshenker, 36, managed various businesses for Moran.
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Reinhardt Schwimmer, 29, was an optician who enjoyed hanging out with hoodlums. John May, 35, was an auto mechanic who did repair work for Moran.

Frank Gusenberg, who had 22 bullet wounds, did not die immediately. He was rushed to the hospital, where police questioned him. In classic gangster fashion, he refused to say much. One account has him saying that “police” were responsible for the shooting, which is consistent with the fact that two of the assailants wore police uniforms. Gusenberg died three hours after the shooting.

From Wikipedia:

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 TorrioAl Capone organization, later known as the Chicago Outfit.

History of the North Side Gang

Early history

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.[which?]

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.


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 Streetrestaurant 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 byMike 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

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 Anthony 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

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

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.


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