Chicago, Illinois, May 7, 1927. Two men step off an eastbound train at Union Station. They carry leather bags and wear low fedora hats. Their names are Anthony Torchio and Vincent Spicuzza. They are hired killers from St. Louis. Each has been promised $25,000 to kill Alphonse Capone.
The station is crowded with travelers. Torchio lights a cigarette. Spicuzza adjusts his coat. Neither realizes they are already being watched.
Three buildings south, in the back room of the Four Deuces saloon at 2222 South Wabash, a phone rings. A man answers. He listens without speaking. He hangs up. He walks through a door into an adjoining room where five men sit playing cards.
One of them is Vincenzo Antonio Gibaldi, 24 years old, known on Chicago's streets as Jack McGurn, in the boxing ring as "Battling Jack McGurn," and to the police as "Machine Gun Jack McGurn." McGurn stands, five feet nine inches tall, 160 pounds, his dark hair slicked back with pomade. He wears a gray suit, a white shirt, and a silk tie. He owns three Cadillac cars and four Thompson submachine guns. He has killed 12 men.
Two more just arrived, the messenger says. McGurn nods. He picks up his coat. He walks out to a black 314 Cadillac parked on Wabash Avenue. Another man, Frank Nitti, follows him. They drive north.
The contract on Capone was arranged by Giuseppe Aiello. Joe Aiello controlled the Sicilian Union in Chicago's Little Italy. He wanted to be the boss. Capone controlled prostitution, gambling, and liquor distribution in Cook County. The Chicago Outfit was making $105 million a year. The Aiello faction wanted that money for itself.
On April 23, 1927, Aiello placed advertisements in newspapers across seven cities. The ads did not name Capone. They circulated through criminal networks in St. Louis, Detroit, New York, Cleveland, Kansas City, Milwaukee, and Philadelphia. The message was simple. $50,000 to eliminate a businessman in Chicago, and $25,000 per man if they worked as a pair.
By May 1, four teams had already arrived in Chicago. Four teams had already been found dead. On May 2, hitmen Samuel Valenti and James LaPorte of Detroit registered at the Morrison Hotel on Madison Street. They were found on May 4 in an alley behind 31st and Wallace, both shot in the head. .45-caliber pistol rounds. LaPorte was also hit three times in the chest with a Thompson submachine gun.
On May 5, New York contractors Michael Pizzaro and Joseph Amato were found in a Packard on South Cicero Avenue, the engine still running. Both men had been shot in the skull at close range, 9mm. McGurn killed all four men himself.
A Cadillac moves through the streets of Chicago. It is nearing midnight. The temperature is 51 degrees Fahrenheit. The sky is overcast. Nitti drives. McGurn sits in the passenger seat with a Model 1921 Thompson submachine gun on his lap. The weapon weighs 10 pounds. It holds a 50-round drum magazine. It fires 800 rounds per minute.
Torchio and Spicuzza 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. That would be suicide. They sit in the lobby of a small restaurant across the street. They order coffee. They wait.
At 1:15 a.m., a black Cadillac stops at the curb outside the restaurant. McGurn and Nitti stay inside the car. They watch the restaurant through the windshield. A third man, 21-year-old Tony Accardo, enters the restaurant. He sits at the counter. He orders coffee. He sits three stools from Torchio and Spicuzza.
Accardo is there to confirm their identities. He has photographs of both men from a paid informant inside the Aiello organization. The informant's name is Salvatore Catinia. Catinia works as a liquor distributor for Aiello. Capone pays him $500 a week to report every upcoming assassination attempt.
Accardo drinks his coffee. He leaves ten cents on the counter. He walks out of the restaurant. He walks toward the Cadillac. He leans through the window. He nods.
McGurn opens the car door. He steps onto the curb. The Thompson is hidden under a long coat. Nitti stays behind the wheel. The engine idles.
McGurn walks toward the restaurant entrance. Two officers from the Chicago Police Department's 22nd District pass on their regular patrol. They do not look at McGurn. They do not stop. The Chicago Police Department receives $68,000 a month from Capone to ignore operations.
At 1:31 a.m., Torchio stands up. He tells Spicuzza he is going to use the bathroom. He walks to the back of the restaurant. McGurn enters through the front door. He walks straight toward the counter. Spicuzza drinks his coffee. His back is to the door.
McGurn stops three feet behind him. He raises the Thompson from under his coat. He says nothing. He fires a three-round burst into Spicuzza's back at point-blank range. The noise is deafening inside the enclosed space. Spicuzza falls forward onto the counter. His coffee cup shatters.
Torchio hears the gunfire. He does not come out of the bathroom. He climbs through a window into the alley. McGurn walks through the restaurant toward the bathroom. The door is open. The window is open. He returns through the restaurant to the front door. Blood spreads across the counter. A waitress screams. Two customers lie on the floor.
McGurn exits the restaurant. He gets into the Cadillac. Nitti drives south on Michigan Avenue. They turn west onto 26th Street. They drive six blocks. They stop behind a warehouse. McGurn disassembles the Thompson. He places the parts in a canvas bag. They drive to the Des Plaines River. McGurn throws the bag into the water.
At 2:14 a.m., Anthony Tortiello runs west on 21st Street. He does not know Chicago. He is lost. He turns north onto Sangamon Street. At the intersection of Sangamon and Cermak Road, a black Cadillac approaches him. The passenger window is down. Tortiello sees the muzzle of a Thompson submachine gun. He raises his hands. Frank Nitti fires a continuous stream of bullets. Tortiello is hit nine times. He dies on the sidewalk. The Cadillac does not stop.
By sunrise on May 8, 1927, six hired killers sent by Joe Aiello were dead.
Four years before the spring of 1927, Vincenzo Gibaldi had not yet become Jack McGurn. He was 20 years old. He lived with his mother Giuseppina and his stepfather Angelo DeMory at 1041 West Taylor Street in Chicago's Little Italy. Angelo owned a grocery store. He sold produce, canned goods, olive oil, and sugar.
The Genna family controlled Little Italy. Six brothers: Sam, Pete, Angelo, Tony, Mike, and Jim Genna. They ran 400 illegal stills across the neighborhood. The stills produced raw alcohol sold to speakeasies at $3 a gallon. The Genna family was making $350,000 a month. They imposed protection fees on every business owner in the area.
Angelo DeMory sold sugar to the Genna brothers for their stills. He also sold sugar to rival bootleggers on the South Side. The Genna family discovered this in December 1922. On January 4, 1923, three Genna men visited DeMory's store. They told him to stop selling to competitors. DeMory refused. He said business is business.
On January 8, 1923, at 9:35 p.m., Angelo DeMory was closing the front door of his store. Three men approached from across Taylor Street. One carried a shotgun. Two carried pistols. They fired simultaneously. DeMory was hit six times. He died before police arrived.
Vincenzo Gibaldi was inside the family apartment above the store. He heard the shots. He ran downstairs. He found his stepfather bleeding on the sidewalk. He placed DeMory's head in his lap. DeMory died at 9:41 p.m.
Chicago police detective Frank McGorty arrived at 10:17 p.m. He questioned Vincenzo. He asked if Vincenzo knew who did this. Vincenzo said no. He was lying.
For three years, Vincenzo worked to identify the three gunmen. He changed his name to Jack McGurn. He took the name from an Irish boxer he admired. Irish fighters got better matches in Chicago rings. He fought as a middleweight. He won three professional fights. He lost one. He drew two. He left boxing in 1924.
He needed access to the Genna organization. He needed names. In April 1924, he contacted members of the North Side Gang. They were rivals of the Genna family. They were led by Dean O'Banion, Hymie Weiss, and Vincent Drucci. McGurn offered his services. He said he wanted to kill Genna family members.
The North Siders gave McGurn small tasks, like intimidation, collections, and beatings. In November 1924, the Torrio-Capone organization killed Dean O'Banion inside his flower shop at 738 North State Street. The North Side Gang declared war on Torrio and Capone.
McGurn saw his opportunity. In December 1924, he left the North Siders. He contacted Frank Nitti. He said he wanted to work for Capone. Nitti arranged a meeting. McGurn met Alphonse Capone on December 18, 1924, at the Hawthorne Hotel in Cicero. Capone was 25 years old. He controlled bootlegging operations in 12 Chicago suburbs. He employed 400 men.
McGurn told Capone he could kill. Capone asked him how many. McGurn said as many as it takes. Capone hired him.
By February 1926, McGurn had located the three men who killed Angelo DeMory. Their names were Edward "The Eagle" Baldelli, Giuseppe Gisleri, and Salvatore Greco. All three worked as enforcers for the Genna family.
On February 15, 1926, Edward Baldelli was found shot to death in his car on South Hermitage Avenue. He had been shot seven times with a .45-caliber pistol. On February 18, 1926, Giuseppe Gisleri was killed inside a billiard hall at 1436 West Taylor Street. He was shot four times in the head. On February 23, 1926, Salvatore Greco was ambushed as he left his home at 814 South Ada Street. He was hit by 12 rounds from a Thompson submachine gun.
The three murders occurred within eight days. All were carried out by Jack McGurn. The Chicago police linked the killings to the 1923 murder of Angelo DeMory. No arrests were made.
McGurn became one of Capone's top enforcers. On April 27, 1926, McGurn accompanied Capone in a five-car convoy that ambushed rival bootleggers James Doherty and Thomas "Red" Duffy outside the Pony Inn in Cicero. McGurn carried a Thompson submachine gun. Capone drove the car, while McGurn fired from the passenger window. Both Doherty and Duffy were killed. Assistant State's Attorney William McSwiggin was riding in the same car. He was killed as well.
The McSwiggin killing caused a political crisis. Capone and McGurn fled Chicago for three months.
On October 11, 1926, McGurn killed Hymie Weiss. Weiss was the leader of the North Side Gang after O'Banion's death. McGurn was positioned in a second-floor apartment at 740 North State Street, directly across from Holy Name Cathedral. At 4:07 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 "Paddy" Murray was also killed. Three other North Side gangsters were wounded.
Police found 70 empty shell casings in the apartment. The casings were .45-caliber, consistent with a Thompson. A later forensic examination revealed that the rifling marks matched a weapon known to be owned by McGurn. No arrests were made.
By May 1927, McGurn had killed 15 men. His reputation was cemented. He was feared throughout the Chicago underworld. He drove Cadillacs. He wore tailored suits. He wore diamond cufflinks. He frequented the Green Mill jazz club at 4802 North Broadway, which he partly owned. He dated showgirls and waitresses. He played golf at the Evergreen Golf Course. He was regularly photographed in nightclubs. He was untouchable.
Then Joe Aiello placed a $50,000 bounty on Capone's head. Aiello made a fatal miscalculation. He advertised the bounty widely, believing numbers would guarantee success. Instead, the wide advertisement led to leaks. Salvatore Catinia, one of Aiello's distributors, went to Frank Nitti. He offered information in exchange for money and protection. Nitti paid him. Catinia provided names, arrival dates, and photographs of every hitman Aiello hired.
This gave McGurn a list. Between May and September 1927, that list became a death sentence for at least four hitmen who arrived in Chicago. Some accounts suggest the number was higher, six, or perhaps eight. The bodies were found in alleys, in cars, and in the Chicago River. They were all out-of-town contractors. They all came for Capone. They were all killed by McGurn.
March 7, 1928, 2:43 p.m. Jack McGurn entered the tobacco shop inside the McCormick Hotel at the corner of Ontario and Rush streets. He had been staying at the hotel for six days. He ran his business from there. The hotel was in a neutral zone, away from South Side and North Side gang territories. McGurn believed this made him safer. He was wrong.
Frank Gusenberg and Peter Gusenberg had been watching him for two weeks. The Gusenberg brothers worked for George "Bugs" Moran, who took over the North Side Gang after Hymie Weiss was killed. McGurn was the one who killed Weiss. Moran wanted McGurn dead.
The tobacco shop was small, eight feet wide and 12 feet deep. It sold cigarettes, cigars, newspapers, and magazines. A clerk stood behind a wooden counter. McGurn entered from the street door. He intended to buy a cigar.
Frank Gusenberg was waiting inside. He stood near the magazine rack. He wore a long coat. Under the coat, he carried a Thompson submachine gun with a 20-round vertical magazine. Peter Gusenberg was positioned outside on the sidewalk. He carried a .45-caliber automatic pistol.
McGurn did not notice Frank upon entering. He approached the counter. He asked the clerk for a Havana cigar. The clerk turned to get the order. Frank Gusenberg raised the Thompson. He fired from six feet away. The first burst hit McGurn's chest and left shoulder. McGurn fell backward. He hit the floor. Frank fired a second burst. These rounds hit the wall. The clerk took cover behind the counter.
Peter Gusenberg ran into the shop. He fired four shots from his pistol into McGurn's body as he lay on the floor. The brothers then fled. They exited through the street door. A black Packard waited at the curb. The driver was James Clark, a North Side gangster. The Packard sped north on Rush Street.
McGurn remained on the floor of the tobacco shop. He had been hit multiple times. One bullet pierced his chest, collapsing his left lung. Another bullet lodged near his spine. A third bullet passed through his shoulder. He was bleeding heavily. He remained conscious.
Chicago patrolman Daniel O'Brien entered the shop at 2:46 p.m. He had heard the gunfire from one building 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 taken to Henrotin Hospital at 108 West Oak Street. Doctors performed emergency surgery. They removed one bullet from his chest. The second bullet lodged near his spine could not be safely removed. It remained in his body for the rest of his life.
McGurn survived. He stayed at Henrotin 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."
McGurn said. Detective McFarland did not believe him. Neither did anyone else. McGurn knew exactly who shot him. He had seen Frank Gusenberg's face. He recognized the brothers, but McGurn did not cooperate with police. He would handle it himself.
On April 17, 1928, McGurn left Henrotin Hospital. He could walk, but he moved slowly. His left arm movement was limited. He suffered constant pain from the bullet near his spine. Doctors told him he would never fully recover.
On April 19, 1928, two days after his release, McGurn was driving south on Morgan Street. It was 8:17 p.m. when James Clark and Billy Davin, two North Side gunmen, drove their car alongside McGurn's Cadillac. They fired pistols at him. The bullets shattered McGurn's driver-side window. McGurn ducked below the dashboard. None of the bullets hit him. Clark and Davin sped away.
McGurn did not report anything to police. He went to the Four Deuces saloon. He met with Frank Nitti and Tony Accardo. He told them he wanted the Gusenberg brothers killed. He wanted Moran killed. He wanted the entire North Side Gang killed.
On May 4, 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 killing was attributed to Jack McGurn. No arrests were made.
The Gusenberg brothers went into hiding. They avoided their usual locations. They changed hotels every three days. They knew McGurn would be looking for them.
Throughout the summer and fall of 1928, McGurn met repeatedly with the Capone organization. The subject was always the same, the North Side Gang. McGurn 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 gave the green light.
The plan was the St. Valentine's Day Massacre.
McGurn spent months organizing the details. He had Capone's mechanic, Joe Bergl, renovate a 1927 Cadillac sedan to resemble a Chicago police squad car. He obtained Chicago police uniforms and badges. He recruited out-of-town gunmen from St. Louis, including Fred Burke, Gus Winkler, and Fred Goetz. These men had no ties to Chicago gangs. Their faces were unknown.
McGurn arranged a fake whiskey deal to lure Moran's men to the SMC Cartage Company garage at 2122 North Clark Street. The deal was offered through an intermediary, high-quality Canadian whiskey at a reduced price, delivery on the morning of February 14, 1929.
McGurn placed lookouts in a room across from the garage. He instructed them to call the moment Moran arrived. He positioned the gunmen in the Circus Cafe, owned by Claude Maddox, two buildings away.
On the morning of February 14, 1929, at about 10:15 a.m., the lookouts made a critical error. They mistook Albert Weinshank for Bugs Moran. Weinshank resembled Moran in height and build. He also wore a similar coat. The lookouts gave the go signal.
The gunmen 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 coats. All four were armed. Two carried Thompson submachine guns. Two carried shotguns.
Inside were seven men: Adam Heyer, Albert Kachellek, John May, Albert Weinshank, Reinhardt Schwimmer, Frank Gusenberg, and Peter Gusenberg. Moran was not among them. He was running late.
The two 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 gunmen then opened fire. The Thompsons fired simultaneously. More than 70 rounds were fired in less than 10 seconds. All seven men were hit multiple times. Six died almost immediately. Frank Gusenberg survived long enough to be taken to a hospital. He died at 1:15 p.m., after police asked him who shot him. He answered: "No one shot me."
On February 15, 1929, Chicago police sergeant Thomas J. Loftus entered the SMC Cartage Company garage at 2122 North Clark Street. He came after a neighbor reported hearing what sounded like explosions from a truck. Loftus found seven bodies. Blood covered the floor. Shell casings were scattered everywhere. A dog tied in the garage barked continuously.
Loftus called for backup. Within 30 minutes, 20 officers arrived. Detective chief John Egan arrived at 12:14 p.m. and surveyed the crime scene. He counted 70 shell casings. Forensic analysis later showed the casings came from two Thompson submachine guns and two shotguns.
By 3:00 p.m., the bodies were identified: Adam Heyer, 40, an accountant. Albert Kachellek, 41, also known as James Clark, a mechanic. John May, 35, a garage mechanic. Albert Weinshank, 35, a speakeasy manager. Reinhardt Schwimmer, 29, an optician and gang associate. Peter Gusenberg, 40, an enforcer. Frank Gusenberg, 36, an enforcer.
Police questioned George Moran that evening. They asked why he was not at the garage. He said he was running late. They asked who was responsible. He answered: "Only Capone kills like that."
Police immediately focused their investigation on the Capone organization. Capone was in Miami, Florida, at the time of the killings. He had been there since February 10. He had documented meetings with the Miami state's attorney on February 14. He had a solid alibi.
Police then focused on Jack McGurn. Investigators arrested him on February 27, 1929. McGurn was charged with seven counts of murder. His lawyer was William Wurberd. At the arraignment, McGurn's girlfriend, Louise Rolfe, testified that McGurn was with her at the Stevens Hotel from February 12 to 15. She stated they were together in bed at the time of the murders. She provided detailed descriptions of their activities during that time. The press dubbed her "the Blonde Alibi."
The prosecution had no physical evidence linking McGurn to the crime scene. They had no witnesses placing McGurn in the garage. They had only suspicion and McGurn's known grudge against the Gusenberg brothers. On July 2, 1929, the charges were dropped. No one was ever convicted of the St. Valentine's Day Massacre.
The massacre caused massive national outrage. Newspapers across the country ran front-page stories. The Chicago Tribune called it the worst gangland killing in United States history. President Herbert Hoover ordered the Department of Justice to investigate crime in Chicago. The federal government began building cases against Capone and his organization.
In April 1930, Frank J. Loesch, chairman of the Chicago Crime Commission, published the first list of Public Enemies. The list included 28 men believed to be corrupting Chicago through organized crime. Capone was number one. Jack McGurn was number four.
This public notoriety destroyed McGurn's standing within the organization. Capone was arrested on federal tax evasion charges in 1931. He was convicted on October 17, 1931, and sentenced to 11 years in federal prison. Frank Nitti took control of the Chicago organization.
Nitti viewed McGurn as a liability. McGurn's face was too well known. His name appeared in newspapers regularly. He could not move without attracting attention. In 1933, Nitti pushed McGurn out of the organization's operations. McGurn received no further income from the Outfit. His assets were seized. His interests in speakeasies were withdrawn.
By 1934, McGurn was broke. He had married Louise Rolfe on December 28, 1931. They lived in a small apartment at 2638 West Washington Boulevard. McGurn had no legitimate business. He tried to establish a career as a professional golfer. He played in the Western Open golf tournament in August 1933 at Olympia Fields Country Club. He registered under his birth name, Vincent Gebhardi. During the second round, he was recognized and arrested on the golf course under the Illinois Criminal Reputation Act. He was released, but his golf career was over.
McGurn became desperate for money. He contacted Frank Nitti several times demanding to be brought back into the organization. Nitti refused. McGurn began drinking heavily. He frequented bars where he spoke openly about his past work with Capone. He bragged about the murders he had committed. He made threats against Nitti. This made him a danger to the organization.
On the evening of February 14, 1936, McGurn woke at about 7:00 p.m. in his apartment. He had slept in. It was Valentine's Day, the seventh anniversary of the massacre. McGurn dressed in a gray suit, a white shirt, and a tie. He told Louise he was going bowling with friends. He left the apartment at 8:30 p.m.
McGurn went to the Avenue Recreation bowling alley at 805 North Milwaukee Avenue. The alley was on the second floor. McGurn arrived at about 11:45 p.m. He was alone. He met two acquaintances, Robert Berman and Anthony Vaccaro, at the alley. The three men began bowling.
At about 12:50 a.m. on February 15, the building's janitor handed McGurn an envelope. Inside was a Valentine's Day card. The card depicted a poor couple standing next to a "For Sale" sign. The printed message read: "You lost your job, you lost your money, your jewels and your cars and your beautiful homes, but things could be worse. You know, at least you didn't lose your pants."
McGurn read the card. He placed it on a bench. He returned to bowling.
At 1:03 a.m., three men entered the bowling alley. They wore long coats and fedora hats. They walked directly toward McGurn. One of them called his name. McGurn turned. The three men drew pistols. They fired simultaneously. McGurn 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 exited the bowling alley. They descended the stairs to Milwaukee Avenue. They got into a waiting car and drove away. Police arrived at 1:14 a.m. They found McGurn dead. They found the Valentine's Day card on the bench. The killers were never identified. The murder was never solved.
McGurn was buried on February 18, 1936, at Mount Carmel Cemetery in Hillside, Illinois. About 200 people attended the funeral. The Capone organization, imprisoned at Alcatraz, sent a six-foot-tall floral arrangement with a card reading "From the Boys."
With the sunset of February 15, 1936, the era of "Machine Gun Jack McGurn" was over.