Chicago, Illinois, May 7th, 1927. Two men step off the eastbound train at Union Station. They carry leather valvelas and wear fedoras pulled low. Their names are Anthony Tokyo and Vincent Spikusa. They are professional killers from St. Louis. Each has been promised $25,000 to murder Alfonso Capone.

The station is crowded with travelers. Tokyo lights a cigarette. Spikers adjusts his coat. Neither man knows they are already being watched. Three blocks south in the back room of the four deuces saloon at 2222 South Wabash Avenue, a telephone rings. A man answers. He listens without speaking. He hangs up.

He walks through a door into an adjacent room where five men sit playing cards. One of them is Vincenzo Antonio Gibbaldi, age 24, known on Chicago streets as Jack McGurn. Known in boxing rings as battling Jack McGurn, known to police as machine gun Jack McGurn. Mcghern stands. He is 5’9 in tall, 160 lb, dark hair sllicked back with pomade.

He wears a gray suit, white shirt, silk tie. He owns three Cadillacs and four Thompson submachine guns. He has killed 12 men. Two more came in, the messenger says. McGurn nods. He picks up his coat. He walks out to a black Cadillac Series 314 sedan parked on Wabash. Another man, Frank Niti, follows him. They drive north.

The contract on Capone was put out by Jeppe Aleo. Joe Aleo controlled the Sicilian Union in Chicago’s Little Italy. He wanted to be boss. Capone controlled prostitution, gambling, and alcohol distribution across Cook County. The Chicago outfit generated $15 million annually. Allello wanted that number for himself.

On April 23rd, 1927, Aello placed advertisements in newspapers across seven cities. The advertisements did not mention Capone by name. They circulated through criminal networks in St. Louis, Detroit, New York, Cleveland, Kansas City, Milwaukee, and Philadelphia. The message was simple.

$50,000 for the elimination of a Chicago businessman. 25,000 to each man if working in pairs. By May 1st, four teams had already arrived in Chicago. Four teams had already been found dead. On May 2nd, hitmen Samuel Valente and James Leaport from Detroit checked into the Morrison Hotel on Madison Street. They were discovered on May 4th in an alley behind 31st and Wallace, both shot in the head. 45 caliber pistol rounds.

Leaport had also been shot three times in the chest with a Thompson submachine gun. On May 5th, New York contractors Michael Bizaro and Joseph Amato were found in a Packard sedan on South Cicero Avenue. Engine still running. Both men shot through the skull at close range. 9 mm. McGurn had killed all four himself.

The Cadillac moves through Chicago streets. It is nearly midnight. The temperature is 51°. The sky is overcast. Niti drives. McGurn sits in the passenger seat with a Thompson submachine gun model 1921 across his lap. The weapon weighs 10 lb. It holds a 50 round drum magazine. It fires 800 rounds per minute.

Tokyo and Spacuza take a taxi from Union Station to the Lexington Hotel at 2135 South Michigan Avenue. This is Capone’s headquarters. They do not go inside. This would be suicide. They sit in the lobby of a diner across the street. They order coffee. They wait. At 1:15 a.m., a black Cadillac pulls to the curb outside the diner.

McGurn and Niti remain in the vehicle. They watch the diner through the windshield. A third man, Tony Akardo, age 21, enters the diner. He sits at the counter. He orders coffee. He sits three stools away from Tokyo and Spicot. Akardo is there to confirm identity. He has been provided photographs of both men by a paid informant inside a Yellow’s organization.

The informant’s name is Salvatore Katainer. Kataina works as a liquor distributor for a yellow. He is being paid $500 per week by Capone to report all incoming assassination attempts. Akardo drinks his coffee. He leaves a dime on the counter. He exits the diner. He walks to the Cadillac. He leans through the window. He nods.

McGurn opens the car door. He steps onto the sidewalk. The Thompson is hidden under a long coat. Niti remains behind the wheel. The engine idles. McGurn walks toward the diner entrance. Two patrolmen from the Chicago Police Department’s 22nd precinct walk past on their regular beat.

They do not look at McGurn. They do not stop. The Chicago Police Department receives $68,000 monthly from Capone to ignore his operations. At 131 a.m., Tokyo stands. He tells Speckers he is going to use the washroom. He walks to the rear of the diner. McGurn enters through the front door. He walks directly to the counter.

Specker is drinking coffee. His back is to the door. McGern stops 3 ft behind him. He lifts the Thompson from beneath his coat. He does not say anything. He fires a three round burst into Spike’s back at point blank range. The noise is deafening inside the enclosed space. Spuza falls forward onto the counter.

His coffee cup shatters. Tokyo hears the gunfire. He does not come out of the washroom. He climbs through a window into the alley. McGurn walks through the diner to the washroom. The door is open. The window is open. He goes back through the diner to the front door. Blood is spreading across the counter.

A waitress is screaming. Two customers are on the floor. McGurn exits the diner. He gets into the Cadillac. Niti drives south on Michigan Avenue. They turn west on 26th Street. They drive six blocks. They stop behind a warehouse. McGurn dismantles the Thompson. He places the components in a canvas bag.

They drive to the Desplains River. McGurn throws the bag into the water. At 2:14 a.m., Anthony Tokyo is running west on 21st Street. He does not know Chicago. He is lost. He turns north on Sangamon Street. At the intersection of Sangamon and Surerach Road, a black Cadillac pulls alongside him. The passenger window is down.

Tokyo sees the barrel of a Thompson submachine gun. He raises his hands. Frank Niti fires a sustained burst. Tokyo is hit nine times. He dies on the sidewalk. The Cadillac does not stop. By sunrise on May 8th, 1927, six hired assassins sent by Joey Yellow are dead. Four years before the spring of 1927, Vincenzo Gibbaldi was not yet Jack McGurn. He was 20 years old.

He lived with his mother, Juspena, and his stepfather, Angelo Deorei, at 1041 West Taylor Street in Chicago’s Little Italy neighborhood. Angelo owned a grocery store. He sold produce, canned goods, olive oil, and sugar. The Jenner family controlled Little Italy. Six brothers, Sam, Pete, Angelo, Tony, Mike, and Jim Genna.

They operated 400 illegal stills throughout the neighborhood. The stills produced rockg alcohol sold to speakies for $3 per gallon. The Jenners generated $350,000 monthly. They demanded protection payments from every business owner in the district. And Angelo Deere sold sugar to the Jenner brothers for their stills.

He also sold sugar to competing bootleggers on the south side. The Jenners discovered this in December 1922. On January 4th, 1923, three Jenner enforcers visited Deere’s grocery store. They told him to stop selling to competitors. Demory refused. He said business was business. On January 8th, 1923, at 9:35 p.m.

, Angelo Deorei was locking the front door of his grocery store. Three men approached from across Taylor Street. One carried a shotgun. Two carried pistols. They fired simultaneously. Demori was hit six times. He died before police arrived. Vincenzo Gabaldi was inside the family’s apartment above the store. He heard the shots. He ran downstairs.

He found his stepfather bleeding on the sidewalk. He held Dimuri’s head in his lap. Dimuri died at 9:41 p.m. Chicago police detective Frank McGorty arrived at 10:17 p.m. He questioned Vinenzo. He asked if Vinenzo knew who did this. Vinenzo said no. He was lying. For 3 years, Vinenzo worked to identify the three shooters.

He changed his name to Jack McGurn. He took the name from an Irish boxer he admired. Irish fighters received better bookings in Chicago rings. He fought as a welterweight. He won three professional fights. He lost one. He earned two draws. He quit boxing in 1924. He needed access to the Jenner organization. He needed names.

In April 1924, he approached members of the North Side gang. They were rivals of the Jenners. They were led by Dean Oanyan, Haimey Weiss, and Vincent Druchi. Mern offered his services. He said he wanted to kill Guenners. The Northsiders gave him small jobs, intimidation, collection work, beatings.

In November 1924, the Torio Capone organization killed Dean Oanyan inside his flower shop at 738 North State Street. The Northside gang declared war on Torio and Capone. McGern saw opportunity. In December 1924, he left the Northsiders. He approached Frank Niti. He said he wanted to work for Capone. Niti arranged a meeting.

Mcghern met Alfonso Capone on December 18th, 1924 at the Hawthorne Hotel in Cicero. Capone was 25 years old. He controlled bootlegging operations in 12 Chicago suburbs. He employed 400 men. Mcern told Capone he could kill. Capone asked how many. Mcern said as many as necessary. Capone hired him.

By February 1926, McGernn had located the three men who killed Angelo Deorei. Their names were Edward, the Eagle, Baldelli, Jepp Gizleri, and Salvatore Greco. All three worked as enforcers for the Denner family. On February 15th, 1926, Edward Baldelli was found shot to death in his automobile on South Hermitage Avenue.

He had been shot seven times with a 45 caliber pistol. On February 18th, 1926, Jeppe Guestleri was killed inside a pool hall at 1436 West Taylor Street. He was shot four times in the head. On February 23rd, 1926, Salvatore Greco was ambushed while leaving his home at 8:14 South Adah Street. He was shot 12 times with a Thompson submachine gun.

All three murders occurred within 8 days. All three were committed by Jack McGurn. Chicago police linked the killings to the Angelo Demori murder of 1923. No arrests were made. McGurn became one of Capone’s primary enforcers. On April 27th, 1926, Mcghern accompanied Capone in a fivecar convoy that ambushed rival bootleggers James Doati and Thomas Red Duffy outside the Pony Inn in Cicero.

Mcghern carried a Thompson submachine gun. Capone drove. McGurn fired from the passenger window. Doi and Duffy were killed. Assistant states attorney William Mcwigan was riding in the same vehicle. He was also killed. The Mwigan murder created a political crisis. Capone and McGurn fled Chicago for 3 months.

On October 11th, 1926, Mcghern killed Haimey Weiss. Weiss was the leader of the northside gang after Oanyan’s death. McGurn positioned himself in a secondf flooror apartment at 740 North State Street, directly across from the Holy Name Cathedral. At 40:07 p.m., Weiss exited his car and walked toward his headquarters.

McGurn opened fire with a Thompson submachine gun from the apartment window. He fired 35 rounds. Weiss was hit 10 times. He died on the sidewalk. Patrick Patty Murray was also killed. Three other northside gangsters were wounded. Police recovered 70 spent shell casings from the apartment.

The casings were 45 caliber, consistent with a Thompson. A forensic examination later matched the rifling to a weapon known to be owned by McGurn. No arrests were made. By May 1927, McGurn had killed 15 men. His reputation was established. He was feared throughout Chicago’s underworld. He drove Cadillacs.

He wore custom suits. He carried diamond cufflinks. He frequented the Green Mill Jazz Club at 4,8002 North Broadway, which he owned partially. He dated chorus girls and waitresses. He played golf at Evergreen Golf Course. He was photographed regularly in nightclubs. He was untouchable. Then Joe Aello placed the $50,000 contract on Capone.

Aello made a critical miscalculation. He advertised the contract widely, believing numbers would guarantee success. Instead, the wide advertisement created leaks. Salvatore Cainer, one of AEL’s distributors, went to Frank Niti. He offered information in exchange for money and protection. Niti paid him. Kainer provided names, arrival dates, and photographs of every hitman hired by a yellow.

This gave Mcghern a list between May and September 1927. That list became a death sentence for at least four assassins who arrived in Chicago. Some accounts suggest the number was higher. Six, perhaps eight bodies were found in alleys, in cars in the Chicago River. All were out of town contractors. All came for Capone. All were killed by Murn. March 7th, 1928.

2:43 p.m. Jack McGurn walked into the smoke shop inside the Hotel McCormick at the corner of Ontario and Rush Streets. He had been staying at the hotel for 6 days. He was conducting business from there. The hotel was in neutral territory away from Southside and Northside gang zones. McGurn believed this made him safer. He was wrong.

Frank Gusenberg and Peter Gusenberg had been tracking him for 2 weeks. The Gusenberg brothers worked for George Bugs Moran who had taken control of the North Side gang after Haimey Weiss’s death. Mern had killed Weiss. Moran wanted Mghern dead. The smoke shop was small, 8 ft wide, 12 ft deep.

It sold cigars, cigarettes, newspapers, and magazines. A cler stood behind a wooden counter. McGurn entered through the street door. He intended to buy cigars. Frank Gossenberg was waiting inside. He stood near the magazine rack. He wore a long overcoat. Beneath the coat, he carried a Thompson submachine gun with a 20 round vertical magazine.

Peter Gussenberg was positioned outside on the sidewalk. He carried a 45 caliber automatic pistol. McGurn did not see Frank immediately. He approached the counter. He asked the clerk for Havana cigars. The clerk turned to retrieve them. Frank Gusenberg lifted the Thompson. He fired from 6 ft away.

The first burst struck McGurn in the chest and left shoulder. McGurn fell backward. He hit the floor. Frank fired a second burst. These rounds hit the wall. The clerk dove behind the counter. Peter Gussenberg ran into the shop. He fired four rounds from his pistol into McGurn’s body as he lay on the floor. Then both brothers ran.

They exited through the street door. A black Packard sedan was waiting at the curb. The driver was James Clark, another northside enforcer. The packard drove north on Rush Street. McGurn lay on the floor of the smoke shop. He had been shot multiple times. One bullet entered his chest, collapsing his left lung. Another bullet lodged near his spine.

A third passed through his shoulder. He was bleeding heavily. He remained conscious. Chicago police patrolman Daniel O’Brien entered the shop at 2:46 p.m. He had heard the gunfire from one block away. He found McGurn on the floor. O’Brien called for an ambulance. He asked McGurn who shot him. McGurn said nothing.

The ambulance arrived at 2:54 p.m. McGurn was transported to Henrottton Hospital. At 108 North Oak Street, doctors performed emergency surgery. They removed one bullet from his chest. The second bullet, lodged near his spine, could not be safely extracted. It remained in his body for the rest of his life. McGurn survived. He remained in Henin Hospital for 38 days.

Chicago police detective Sergeant Thomas McFarland visited him six times. Each time, McFarland asked the same question. Who shot you? Each time, McGurn gave the same answer. I don’t know, Mern said. Detective McFarland did not believe him. Neither did anyone else. McGerman knew exactly who shot him. He had seen Frank Gusenberg’s face.

He recognized both brothers, but McGur did not cooperate with police. He would handle the matter personally. On April 17th, 1928, McGurn was released from Henroin Hospital. He could walk, but he moved slowly. His left arm had limited mobility. He was in constant pain from the bullet near his spine.

The doctors told him he would never fully recover. On April 19th, 1928, 2 days after his release, McGurn was driving south on Morgan Street. It was 8:17 p.m. James Clark and Billy Davin, two northside gunmen, drove alongside McGurn’s Cadillac. They fired at him with pistols. The shots shattered McGurn’s driver side window.

Mcghern ducked below the dashboard. None of the shots hit him. Clark and Davin’s car sped away. McGurn reported nothing to police. He went to the Ford deuces. He met with Frank Niti and Tony Aardo. He told them he wanted the Gussenbergs dead. He wanted Moran dead. He wanted every North Side gangster dead.

On May 4th, 1928, Billy Davin was found shot to death in an alley behind 4216 West Madison Street. He had been shot five times in the face. The murder was attributed to Jack McGurn. No arrests were made. The Gutenberg brothers went into hiding. They avoided their usual locations. They changed hotels every 3 days.

They knew McGurn would be searching for them. Throughout the summer and fall of 1928, Mcghern met repeatedly with Al Capone. The subject was always the same, the North Side Gang. Mcghern presented a plan. He told Capone he could eliminate Moran and his top men in a single operation. The plan was elaborate.

It required precision. Capone authorized it. The plan was the Saint Valentine’s Day massacre. McGurn spent months organizing the details. He had Capone’s mechanic, Joe Burgle, refurbish a 1927 Cadillac sedan to resemble a Chicago Police Department patrol car. He obtained Chicago Police uniforms and badges.

He recruited out of town shooters from St. Blaua, including Fred Burke, Gus Winkler, and Fred Gol. These men had no connections to Chicago gangs. Their faces were unknown. McGurn arranged for a phony whiskey deal to lure Morren’s men to the SMC Cartage Company garage at 2122 North Clark Street.

The deal was presented through an intermediary, highquality Canadian whiskey at a discounted price. delivery. On the morning of February 14th, 1929, McGurn positioned lookouts in a room across from the garage. He instructed them to call the moment Moram arrived. He stationed the shooters at the Circus Cafe owned by Claude Maddox two blocks away.

On the morning of February 14th, 1929, at approximately 10:15 a.m., the lookouts made a mistake. They identified Albert Weinhank as Bugs Moran. Wine shank resembled Moran in height and build. He wore a similar coat. The lookouts made the call. The shooters left the circus cafe. They drove to the garage in the fake police car.

Four men entered the garage. Two wore police uniforms. Two wore long overcoats. All four carried weapons. Two had Thompson submachine guns. Two had shotguns. Inside the garage were seven men. Adam Hy, Albert Cashell, John May, Albert Wine Shank, Reinhardt Schwimmer, Frank Gusenberg, and Peter Gusenberg.

Moran was not present. He was running late. The men in police uniforms ordered the seven to line up facing the north wall. The seven complied, believing it was a routine police raid. They placed their hands on the wall. The shooters opened fire. The two Thompson guns fired simultaneously.

Over 70 rounds were discharged in less than 10 seconds. All seven men were hit multiple times. Six died almost instantly. Frank Guzenberg survived long enough to be transported to a hospital. He died at 1:15 p.m. He was asked by police who shot him. He said, “Nobody shot me.” February 15th, 1929. Chicago Police Sergeant Thomas J.

Loftess entered the SMC Cartage Company garage at 2122 North Clark Street. He had been summoned by a neighbor who heard what sounded like truck backfires. Loftus found seven bodies. Blood covered the floor. Spent shell casings were scattered everywhere. A dog chained in the garage was barking continuously.

Loftus called for backup. Within 30 minutes, 20 officers arrived. Chief of Detectives John Egan arrived at 12:14 p.m. He surveyed the scene. He counted 70 shell casings. Forensic analysis later revealed the casings came from two Thompson submachine guns and two shotguns.

The bodies were identified by 3PM Adam Haer, 40 years old, bookkeeper. Albert Coachellic, 41 years old, also known as James Clark, mechanic. John May, 35 years old, garage mechanic. Albert Weinshank, 35 years old, speak easy operator. Reinhardt Schwimmer, 29 years old, optometrist and gangster associate.

Peter Gusenberg, 40 years old, enforcer. Frank Gusenberg, 36 years old, enforcer. George Moran was questioned by police that afternoon. He was asked why he was not in the garage. He said he had been delayed. He was asked who was responsible. He said only Capone kills like that. Police immediately focused on Al Capone.

Capone was in Miami, Florida at the time of the murders. He had been there since February 10th. He had documented meetings with the Miami District Attorney on February 14th. He had a confirmed alibi. Police next focused on Jack McGurn. Detectives arrested him on February 27th, 1929. McGurn was charged with seven counts of murder.

His attorney was William War Corbett. At the arraignment, McGernn’s girlfriend, Louise Rolf, testified that McGernn had been with her at the Stevens Hotel from February 12th through February 15th. She stated they were in bed together during the time of the murders. She provided detailed descriptions of their activities.

The press called her the blonde alibi. Prosecutors had no physical evidence connecting McGurn to the scene. They had no witnesses placing Mcghern at the garage. They had only suspicion and McGurn’s known grudge against the Genenberg brothers. On July 2nd, 1929, the charges were dropped. No one was ever convicted for the St.

Valentine’s Day massacre. The massacre generated national outrage. Newspapers across the country ran front page stories. The Chicago Tribune called it the most brutal gangland slaying in the history of the United States. President Herbert Hoover ordered the Department of Justice to investigate Chicago crime.

The federal government began building cases against Capone and his organization. In April 1930, Frank J. Lo, chairman of the Chicago Crime Commission, published his first public enemies list. The list named 28 men believed to be corrupting Chicago through organized crime. Al Capone was number one. Jack McGurn was number four.

The public notoriety destroyed McGern’s position within the outfit. Capone was arrested on federal tax evasion charges in 1931. He was convicted on October 17th, 1931 and sentenced to 11 years in federal prison. Frank Niti assumed control of the Chicago outfit. Niti saw McGurn as a liability.

McGern’s face was too wellknown. His name appeared in newspapers regularly. He could not operate without drawing attention. In 1933, Niti removed McGurn from outfit operations. McGurn received no further income from the organization. His assets were seized. His speak easyy interests were revoked. By 1934, Mghern was impoverished.

He had married Louise Rolf on December 28th, 1931. They lived in a small apartment at 2638 West Washington Boulevard. McGurn had no legitimate employment. He attempted to establish a career as a professional golfer. He played in the Western Open in August 1933 at Olympia Fields Country Club. He registered under his birth name, Vincent Gibb Hardy.

During the second round, he was recognized and arrested on the golf course under the Illinois Criminal Reputation Law. He was released, but his golfing career ended. McGurn became desperate for money. He approached Frank Niti multiple times requesting reinstatement into the outfit. Niti refused. Mern began drinking heavily.

He frequented taverns where he talked openly about his past work for Capone. He bragged about murders he had committed. He made threats against Niti. This made him dangerous to the organization. On the evening of February 14th, 1936, McGurn woke at approximately 700 p.m. in his apartment. He had overslept.

It was Valentine’s Day, the 7th anniversary of the massacre. McGurn dressed in a gray suit, white shirt, and tie. He told Louise he was going bowling with friends. He left the apartment at 8:30 p.m. McGern drove to the Avenue Recreation Bowling Alley at 85 North Milwaukee Avenue. It was a second floor establishment.

McGurn arrived at approximately 11:45 p.m. He was alone. He met two acquaintances, Robert Beerman and Anthony Vicaro, at the alley. The three men began bowling. At approximately 12:50 a.m. on February 15th, the building’s janitor handed McGurn an envelope. Inside was a Valentine’s Day card. The card depicted a destitute couple standing beside a forale sign.

The printed message read, “You’ve lost your job. You’ve lost your dough, your jewels and cars and handsome houses, but things could still be worse. You know, at least you haven’t lost your trousers. McGurn read the card. He placed it on a bench. He returned to bowling. At 10:03 a.m., three men entered the bowling alley.

They wore overcoats and fedoras. They walked directly toward McGurn. One of them called his name. Mcern turned. The three men drew pistols. They fired simultaneously. McGern was hit seven times. Three bullets struck his head. four struck his back and torso. He fell face down on the bowling lane. He died within seconds.

The three gunmen walked out of the bowling alley. They descended the stairs to Milwaukee Avenue. They entered a waiting automobile and drove away. Police arrived at 1:14 a.m. They found McGurn dead. They found the Valentine’s card on the bench. The killers were never identified.

The murder was never solved. McGurn was buried on February 18th, 1936 at Mount Carmel Cemetery in Hillside, Illinois. Approximately 200 people attended the funeral. Al Capone, imprisoned at Alcatraz, sent a 6-ft tall flower arrangement with a card reading from Al. By the time the sun set on February 15th, 1936, the era of machine gun Jack McGurn had ended.