Goodfella, Tommy DeSimone


Thomas Anthony DeSimone was born on May 24, 1950. He was an Italian_American mobster that worked as an associate of the Lucchese crime family of New York. He had several nicknames, but a couple stood out and fit Tommy nicely; “Two-Gun Tommy” because he always had two guns, and “Tommy D”.

Tommy had three siblings, a sister named Dolares and two brothers, Robert (imprisoned for life)  and Anthony DeSimone. Both Robert and Anthony were associates for the Gambino crime family. His brother Anthony was murdered in 1979 and Robert died in . His grandfather was Los Angeles mob boss Rosario DeSimone in 1922, and his uncle Frank DeSimone was the Los Angeles crime family mob boss in 1956.

Tommy became involved with a Lucchese crime family crew headed by capo Paul Vairo in 1965. He was fifteen years old, skinny and naïve. Jimmy Burke was a family friend of the DeSimone’s and knew Tommy as he grew up. When he was ready, Jimmy took him in handing him a few rackets to get his feet wet so-to-speak.

DeSimone quickly became known for having a quick temper and a huge appetite. He would drink almost an entire gallon of whole milk each day. Friend and fellow Lucchese associate Henry Hill described Tommy as a “pure psychopath”. He committed his first murder at the age of 18 when he shot Howard Goldstein in cold blood as he walked down the street. Henry Hill was with him and said, “That was cold-blooded, Tommy!” DeSimone replied, “Well, I’m a mean cat.”

DeSimone would kill several more times in his short life. In 1970 he killed a made man with the Gambino crime family named “Billy Batts” Devino. As portrayed in the movie Goodfella’s Devino made fun of DeSimone for once being a shoe shine boy. Devino was a feared gunmen and had killed several people, but Tommy had earned respect as well and didn’t take verbal punishment from anyone. A couple of weeks later Devino was drinking at Hill’s bar when he instructed Jimmy Burke and Henry Hill to keep Devino occupied until he returned. DeSimone returned just after closing where DeSimone, Burke, and Hill killed Devino. They buried his body upstate.

Goodfella’s Joe Pesci acting out the scene of Spider’s death.

DeSimone’s third murder was also portrayed in the movie Goodfella’s. According to Henry Hill, this reenactment is very accurate to what actually happened when DeSimone shot and killed Michael “Spider” Gianco. Spider and insulted DeSimone a week before and DeSimone retaliated by shooting him in the foot. When Spider returned to his job as a bartender, he and DeSimone exchanged more words. When Burke jokingly gave Spider money for having the guts to stand up for himself, Tommy pulled out his .38 caliber revolver and shot Spider three times in the chest. Hill checked his pulse and announced he was dead. Burke, who was in charge of the crew told Tommy he would have to dig the hole to hide the body himself. Tommy agreed, and Spider was never seen again. Since the making of the movie there has been speculation that Hill made up Michael “Spider” Gianco as law enforcement looked for the body where Hill stated it would be and found nothing. Furthermore there are no records or birth certificate related to Michael Gianco, and in the neighborhood where he purportedly lived and worked, no one had ever heard of him. Unless a body is found, that death will remained unsolved as Hill, who died on June 25, 2012 was the last person alive who could prove a murder took place.

DeSimone killed several other people after Spider; a warehouse foreman named Stanley Diamond who DeSimone was just supposed to rough up, and Gotti protégé Ronald “Foxy” Jerothe on December 18, 1974. To Jerothe’s disapproval, DeSimone had dated Jerothe’s sister. When Jerothe found out about it, word got back to Tommy that Jerothe had said he was going to kill him. Acting on the threat, DeSimone went to Jerothe’s apartment, knocked on his door, and when Jerothe opened the door, DeSimone stuck a .38 caliber pistol in his face and shot Jerothe between the eyes killing him instantly. DeSimone’s fifth murder occurred when Burke ordered the murder of hisbest friend Dominick “Remo” Cersani. Burke had learned Remo was working with the NYPD and planned to set up Burke in a sting. When Burke found out about the set-up he and DeSimone traveled to Remo’s place, asked him to “go for a ride”, and was subsequently killed by DeSimone by choking him with a piano wire. They buried Remo next to Burke’s bar and a bocce ball court next door. It’s been said, everytime DeSimone and Burke would play someone on that bocce ball court they would say “hey Romo how ya doing?”

DeSimone was alleged to have taken part in the December 1978 Lufthansa heist from JFK International Airport where $6,000,000 dollars was taken from a warehouse. After the heist DeSimone was ordered to kill Parnell “Stacks” Edwards for failing to hide the delivery truck. DeSimone was told he would become a “made” man when he completed the hit. He found out where Stacks was hiding and shot him several times in the head and chest.

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On January 14, 1979 DeSimone’s wife, Angela reported him missing. She said she last saw Tommy “a few weeks earlier” when he borrowed money from her. It been said he was killed on January 6, 1979 when Martin Krugman, the person responsible for telling Henry Hill about the Lufthansa money went missing. Several scenarios have come to light describing why Tommy was murdered.

Some say it was because he killed “Billy Batts” Devino and Ronald “Foxy” Jerothe, both members of the

Tommy DeSimone shortly before he went missing.

Gambnio’s without proper permission as mandated by the commission. The penalty for the perpetrator is death. Another scenario is DeSimone was killed by Burke as DeSimone had killed or ordered to be killed almost everyone involved in the Lufthansa heist. A final scenario is given by Henry Hill when he said Tommy was killed by the Gambino family for the two killings. The Gambino’s only found out about the killings after DeSimone had tried to rape Hill’s wife, who was having an affair with Paul Vario while Hill was in prison. Vario told the Gambino’s that DeSimone was responsible and sanctioned his hit. Henry claimed that in “the week after Christmas” that he and Jimmy Burke had gone down to Florida to straighten out a drug deal gone bad. Tommy had remained behind in New York because he was going to be made. When Jimmy called to see if the ceremony had occurred (the code phrase was to ask if Tommy had seen his godmother yet), Burke was told that it had been called off due to a heavy snowfall. The next day, Burke listened in and found out that DeSimone had been murdered; he slammed the receiver down and began crying, as depicted in the film Goodfella’s.

Chicago Outfit

The Chicago Outfit is that city’s branch of the American Mafia. Its modern organization dates to the beer

Alphonse Gabriel “Al” Capone, the most powerful leader of the Chicago Outfit

wars of Prohibition and its most notorious leader, Al Capone. It has a seat, along with the Five Families of New York City, on the Commission that governs the Italian mob in America.

The Outfit’s roots reach back to the early 1900s and an influx of Italian immigrants to Chicago. Street gangs, some of them Italian in background, controlled various criminal activities in the city.

At the same time, extortionists practiced the “Black Hand” scheme imported from Italy. This involved threatening residents with violence unless money was paid. Extortion letters were stamped with a hand in ink, hence the name. Many Black Hands worked independently, but some joined forces, forming organized criminal syndicates.

 But the Chicago Outfit truly came into its own in the 1920s. Giacomo “Big Jim” Colosimo, who ran hundreds of brothels, had solidified power over large portions of the underworld during the Black Hand era. He welcomed his nephew, Giovanni “Papa Johnny” Torrio, to the scene, and in 1919 Torrio introduced a new face: Alphonse “Scarface” Capone.

Prohibition took effect in 1919, but Chicago, like other cities, simply sent its liquor underground. Torrio urged his boss to go into the booze business, but Colosimo refused. To remove this impediment, Torrio had Colosimo killed. What followed were the “beer wars,” the most violent episode of organized crime in American history.

Charles Dean O’Banion founded the North Side Gang. His main nemisis was Johnny Torrio and Al Capone

Before Prohibition, the Outfit had focused on gambling and prostitution. Now that bootlegging had joined the repertoire, frequent bouts of murder followed. Torrio’s gang controlled the South Side and the Loop but soon began to expand into the Gold Coast, where Dean O’Banion and the Irish-American North Side Gang ruled.

For a while the two sides managed a truce, but it didn’t last long. O’Banion scammed Torrio out of half a million dollars, and Torrio retaliated. On November 10, 1924, O’Banion was murdered in his flower shop. His death resulted in all-out urban warfare.

 Tommy-gunfire raged back and forth. The North Siders tried to kill Torrio but failed. The experience jarred him, and he retired. He handed the reins of the Outfit to Capone, whose fortunes soared.

Then, in 1929, after five years of gunfire between the North and South sides, Capone made a move intended to cripple his enemies. It had the opposite effect. On February 14, he sent a group of men to a garage on North

 Clark Street, where they unloaded their guns into seven members of the North Side Gang. The “St. Valentine’s Day Massacre” drew so much negative publicity the city was forced to crack down on organized crime.

The federal government joined the effort, prosecuting Capone for tax evasion. He went to prison, and his criminal enterprise suffered without him, but it didn’t die. In fact, it soon bounced back and began to spread its wings.

 After Capone left in 1932, control of the Outfit passed to Frank “The Enforcer” Nitti, a former bodyguard who had risen to become a leader of the organization’s bootlegging operations. But the real decisions were made by his underboss, Paul “The Waiter” Ricca.

When Prohibition ended in 1933, the Outfit was forced to focus on other criminal enterprises, such as prostitution, labor racketeering and especially gambling. Under Nitti and Ricca, it also began to expand. The organization set up shop in Wisconsin, Missouri, Los Angeles and Las Vegas, where it eventually took over control of legal casinos from the Five Families.

These expansion tactics led to a major scandal and a raft of indictments in 1943, when the FBI caught Chicago gangsters shaking down the movie industry in Hollywood. Nitti was set to take the blame, but he had served time before, was severely claustrophobic, and decided he couldn’t handle prison again. Instead he shot himself in the head while wandering a Chicago rail yard.

Ricca formally became boss and appointed Tony “Joe Batters” Accardo his lieutenant. Together they ran the Outfit for the next 30 years, though their titles and roles changed. After Ricca’s death in 1972, Accardo led the Outfit for another 20 years. Accardo is considered one of the smartest bosses of the American Mafia: Over a criminal career that spanned 70 years, he spent only one night behind bars.

The Outfit grew to encompass most mob operations in the Western United States during the Ricca-Accardo years. It reached its peak during the 1960s, when Accardo’s flashy front man, Sam “Momo” Giancana, attempted to orchestrate the assassination of Fidel Castro for the CIA and briefly had an affair with a woman who was also sleeping with President John F. Kennedy. Giancana was kicked out of the Outfit in 1966 and murdered in 1975.

His job as titular head of the Outfit was filled by Joey “Doves” Aiuppa, who held that position until his conviction in 1986 for skimming profits from Las Vegas casinos. Though he spent 11 years in prison, he had his revenge: He allegedly ordered one of the most famous hits in Mafia history, the murders of Michael and Tony “The Ant” Spilotro, who were beaten, strangled and buried in an Indiana cornfield in retaliation for the mismanagement of the casinos. These killings, and the Las Vegas history that led to them, were depicted in the movie Casino.

After Aiuppa went to prison, control of the Outfit was handed to several other mobsters, while James “Little Jimmy” Marcello acted as front man. In the years to follow, the organization began to lose much of its power in Chicago and the Western United States. Las Vegas went legitimate, labor unions began to purge themselves of gangsters, and federal trials sent large numbers of Mafiosi to prison for long terms.

The Outfit was dealt perhaps its most crushing blow in 2007. The FBI managed to flip several high-ranking members in an operation dubbed ” Family Secrets,” one of the most successful federal investigations of organized crime. The resulting trial ended with the conviction of five men on charges of conspiracy and racketeering for crimes that included several murders. Another six pleaded guilty, two died before trial and a ninth was too ill to face prosecution. Marcello was convicted in part for the murder of the Spilotro brothers. The Outfit has dwindled in recent years, but it isn’t dead. As the Family Secrets investigation demonstrated, racketeering is still at the heart of its operations. It doesn’t have the reach it once did, but it remains a major part of the world of crime in Chicago.

Anthony Strollo – A Reputation for Switching Sides

Anthony Strollo, most notably known as Tony Bender, was born June 18, 1899 in New York City. He had two brothers, Emilio and Dominick. His playground as a young man was Manhattan, where he worked as bootlegger and enforcer for Joe Masseria.

Early in his mafia career Strollo earned a reputation for switching sides when it appeared he might be on the losing end. Carl Sifakis writes in The Mafia Encyclopedia, “Within the councils of the underworld it was no secret that Bender’s loyalty was always for sale to the highest bidder. He changed colors and sides like a chameleon.”

During the Castellammarese War when it was clear that Masseria was going to lose the war, Strollo aligned himself with Maranzano. As a capo to Maranzano, Strollo took part in the planning of several murders.

After Maranzano was murdered by the Luciano crime family, Strollo became a capo for Luciano and his underboss Vito Genovese.  Genovese and Strollo became close friends, with Genovese standing up as best man in Strollo’s wedding.

For a number of years the Luciano crime family was the most powerful family in New York. Strollo gained considerable power as well having control over the Greenwich crew and major illegal gambling in Lower Manhattan. It wasn’t until things changed in 1936 with Luciano’s conviction that the good life for Strollo would begin to unravel. Shortly after Luciano was imprisoned for what appeared to be the rest of his life, his close friend and new acting boss, Vito Genovese was indicted for murder.

 Having no choice Genovese fled the United States for Italy leaving Strollo to “hold things together”. But it was not to be. Genovses’s chief rival Frank Costello pushed Strollo aside and appointed himself the acting boss, and Willie Moretti as his underboss. Strollo maintained a position in the family but with virtually no power. He was also stripped of his Greenwich rackets.

Genovese fought extradition from Italy to the United States for nearly 9 years. In 1946 Genovese returned from Italy having beat the indictment and was allowed back into the Costello crime family as a capo and given the Greenwich gambling rackets once controlled by Strollo and most recently the deported Joe Adonis.

For nearly ten years Genovese and Strollo worked the Greenwich rackets waiting for their time to take back the family from Costello. During that time, Strollo was the mastermind behind several murders on behalf of Genovese’s methodical march to taking over the family from Costello.

Costello was released from prison in 1957 and shortly after Genovese made the move to take control of the Costello family. He enlisted Strollo to set up the murder like he has several times before.

On May 2, 1957 Strollo met Costello at Chandler’s restaurant for an early dinner. During dinner he learned of Costello’s plans for later in the day consisting of several meetings later in the night.

When Costello was walking to the elevator in the lobby of his Manhattan apartment building he was shot in the head by Genovese gunman Vincent Gigante. Unfortunately, Gigante tipped Costello off to the assassination attempt by yelling, “This is for you Frank, prior to pulling the trigger. Costello reacted to the scream by turning his head slightly causing the bullet to graze his head. He fell to the ground and Gigante fled thinking he murdered Costello. Though he survived the murder attempt, Costello immediately stepped down as boss of the Costello crime family relinquishing control to Genovese.

In 1959 Strollo continued to set up murders for Genovese. One day he learned that “Genovese had marked his best friend, Little Augie Pisano, for murder- even Genovese was tenderhearted enough originally to try not to involve Bender-Bender cheerfully volunteered to set up the hit. He broke bread with Little Augie in a Manhattan restaurant while gunmen took up positions in Little Augie’s car to shoot him after he left.”

Through the years, Genovese used murder to take what he needed and created several enemies as he did. Eventually a conspiracy grew to finally end Genovese’s ruthless pursuit to the top of the mafia commission and it included his most trusted confidant, Anthony Strollo.

A secret meeting was held with Gambino boss Carlo Gambino, Meyer Lansky, Frank Costello, and Lucky Luciano who hatched a plan to use Genovese’s drug trafficking as a way to end his reign. Strollo aligned himself with the men and helped set Genovese up that would eventually send him to prison for the rest of his life.

Vito Genovese

Vito Genovese

Though Genovese was sent to prison on a 15 term, he continued to control the family. With time on his hands Genovese used it to figure out how he was captured. He suspected he was set up, but was unsure of how or whom was involved.

At some point, Genovese concluded that Strollo was part of the plot to set him up. After all it was Strollo was stressed to Genovese to give himself up because he would likely only get a short sentence. It was this knowledge that helped Genovese come to the conclusion that his old friend was part of the plot. As boss of the family, Genovese had the means to have Strollo killed and put the wheels in motion.

Sifakis wrote, “On the morning of April 8, 1962, Bender left his home. His wife told him, “You better put on your topcoat. It’s chilly.”

Bender demurred. “I’m only going out for a few minutes…””

He walked down the sidewalk from his home and was never seen again.

Carlo Gambino – American Mafia Made Man at 19 Part 1 of 4

     “Don” Carlo Gambino was born on August 24, 1902 in Caccamo, a province of Palermo Sicily. He had two brothers, Gaspare who was never involved in the Mafia, and Paolo who would eventually work alongside his brother in the American Mafia.

     In Italy, Gambino’s family belonged to the Honored Society, an Italian version of the Black Hand in the United States. The Black Hand was a less organized version of Italian gangsters, most of which immigrated to the United States.

     In 1921 Gambino illegally boarded a ship headed for the United States. It’s been said he ate nothing but anchovies and wine during the month-long trip. Once in the United States he joined his cousins, the Castellano’s in New York City. The Castellano’s were already affiliated with the D’Aquila gang, and quickly introduced Gambino as a new member. By the end of 1921 at the age of 19, Carlo Gambino became and “made man” of the American Mafia.

Jewish Gangster Meyer Lansky

Around the same time Gambino also became close with an Italian and Jewish gang called the “Young Turks” in New York. The gang included notables such as, Frank Costello, Albert Anastasia, Frank Scalise, Settimo Accardi, Tommy Lucchese, Joe Adonis, Vito Genovese, Meyer Lansky, Bugsy Siegel, and Mickey Cohen. The Turks were led by Charles “Lucky” Luciano, the future creator of the mafia Commission.

     After several years of fighting for territory among the different gangs in and around New York, two men emerged holding the most power. Giuseppe “Joe the Boss” Masseria and Salvatore Maranzano a Palermo bore mafioso who recently arrived in the United States. Maranzano quickly inserted himself in extortion and gambling operations that directly competed with Masseria. On October 10, 1928 Masseria had rival Toto D’Aquila, once the most powerful mobster in New York, murdered clearing the way for him to become the “Boss of Bosses”. However, Maranzano and the Castellammarese Clan he brought with him from Palermo, stood in his way.

     In 1930, Masseria flexed his muscle and went after Marranzano’s then boss, Nicola “Cola” Schiro demanding a $10,000 tribute. Schiro, fearing for his life against the more powerful Masseria paid the tribute, and fled New York leaving Maranzano as the gang’s new leader. It was this move that set the wheels in motion for the start of one of the largest gangland wars in history; the Castellammarese War.

     By 1931, Masseria had begun to eliminate Maranzano’s Castellammarese Clan. His goal was to weaken Maranzano and take over New York. However, Maranzano would not go down without a fight and declared war on Masseria and anyone else who aligned themselves with him.

     Gambino and Alfred Mineo the new leader of the D’Aquila gang aligned with Masseria. Half of the Young Turks joined as well, with the others aligning with Maranzano.  The Castellammarese Clan included Joe Bonanno, Stefano Magaddino, and the Profaci crime family, which included Joseph Profaci and Joseph Magliocco. Former Masseria allies Gaetano Reina, boss of the Reina family and Tommy Lucchese also joined the Castellammarese and Maranzano.

     The war went on between these two factions for nearly 4 years. It was the height of prohibition where profits were large; however the war almost completely destroyed many of the New York family rackets. Luciano and members of the Young Turks from both sides began to realize the war needed to stop and stop soon or much of what they took so long to build in New York City would be lost. During the war many of the Jewish and Irish crime families became the dominant families in New York. Meyer Lansky, a Jewish mobster and close confidant of Luciano felt that Masseria and Maranzano were old-school mafioso who were too greedy to see the riches that could be had by working with non-Italians. Gambino and the Young Turks agreed and decided to end the war and form a national syndicate led by Charles Luciano.

     On April 15, 1931 Masseria was murdered by Luciano associates Albert Anastasia,

Joe “the Boss” Masseria dead with an Ace of Spades in his hand. This card was likely planted.

Joe Adonis, Vito Genovese, and Bugsy Siegel while dining at Nuova Villa Tammaro restaurant in Coney Island. With Masseria out of the way, Marranzano declared himself the Boss of Bosses and with the help of Luciano’s vision, re-organized the New York gangs into five Mafia families. Vincent Mangano was promoted and took over Masseria’s Mineo family. Young Turk, Albert Anastasia became his underboss and Gambino was promoted to Capo.

     On September 10, 1931 Maranzano was murdered by Luciano gunmen ending his reign as Boss of Bosses. With Maranzano gone Luciano called a meeting of all the bosses in New York and the United States. During this meeting many of the bosses including Al Capone of the Chicago Outfit expected Luciano to declare himself Boss of Bosses. However, Luciano had another idea and during the meeting laid out his plan to create The Commission, a ruling panel of crime family leaders which would mediate conflicts between the families. The leaders nominated Luciano, Joe Bonanno, Joe Profaci, Tommy Gagliano, and Vincent Mangano as its inaugural members.

     With a seat on the Commission, the Mangano family set out to become one of the most powerful mafia families in the country. Gambino quickly became one of the family’s top earners and controlled several illegal rackets including loansharking, illegal gambling, and protection.

“Machine Gun” Jack McGurn – St. Valentines Day Massacre

     “Machine Gun” Jack McGurn was an Italian-American born in Licata, Sicily population 39,000 on July 2, 1902. His birth name was Vincenzo Gibaldi, however he had other variations such as Vincent Gebardi, and Vincenzo Demory.

At four years old he and his mother, Giuseppa Verderame, just 24 years old according to the ships manifest arrived at Ellis Island on November 24, 1906. They arrived, just the two of them, and awaited Jack’s brother and father who would arrive later in the year.

As a teenager McGurn grew up in the Chicago slums having to fight his way in a difficult neighborhood. He changed his name to “Battling” Jack McGurn and took up a career in boxing. The name McGurn, is Irish, and at the time Irish boxers got better bookings than Italians. He boxed from 1921 to 1923 and was referred to as the local 147 pounder from the West side.

McGurn didn’t run with the local street gangs, he focused on boxing, worked part-time and minded his own business. It wasn’t until his stepfather was assassinated by gang extortionists on January 28, 1923, that McGurn turned to a life of crime. Three men were responsible for his stepfather’s slaying, and McGurn took it upon himself to avenge the murder and killed all three. This act provided his introduction to Capone in late 1923 as a recruit for the Circus gang, a Capone subgroup run by Claude “Screwy Moore” Maddox.

McGurn’s specialty in the Circus gang was as a bodyguard and killer. Capone noticed these attributes and used McGurn as his personal bodyguard. McGurn can be seen everywhere Capone went, football and baseball games, and nightclubs. It’s been said that McGurn was not only a ruthless killer but also kept intelligence on Capone rivals having uncovered several murder plots before any attempts took place.

On September 5, 1929, gangsters and professional hit men Edward Westcott and Frank Cawley were found killed in a Chicago suburb. Both men had Buffalo Nickels pressed into their hands.

On December 12, 1930, Rudolph Marino and his brother Sam were found dead; murdered gangland style. Both men also had Buffalo Nickels pressed into their hand, and although there is no proof, the Buffalo nickel is said to be a calling card of a McGurn hit.

Although feared, McGurn was also the occasional target of assassination. In one such situation members of the deadly Northsiders gang almost cut McGurn in half by machine gun fire as he walked through the smoke shop in the McCormick hotel. The hitmen spotted McGurn from the street; both ran in one with the Thompson machine gun and the other a 45 caliber automatic revolver. The Thompson machine gun cut through McGurn’s right lung, chest, and arm as he dove for cover behind a partition wall. Fearing return fire the hitmen fled leaving McGurn to hobble to his feet and back to his hotel room, number 906 where he asked a bell boy to find a doctor.

After McGurn recovered he was once again placed at Al Capone side. Capone welcomed him back with a plan to rid themselves of the Northsider’s and Bugs Moran gang once and for all. Their meeting was the beginning plans of the St. Valentine’s Day massacre.

On February 14, 1929 five members and the North Side gang were lined up against

Police re-enactment of the shooting using the same garage, and wall, the men were killed one day earlier.

a garage wall and executed. Two of the shooters were dressed as uniformed police officers while the others wore suits, ties, overcoats and hats, according to the witnesses who saw the “police” leading the other men at gunpoint out of the garage after the shooting. Bugs Moran escaped the slaughter arriving late to the meeting.

McGurn was questioned immediately after the slaying and provided an alibi stating he was in a hotel with his girlfriend Louise Rolfe who claimed they spent the entire day together. McGurn was charged in the case but never brought to trial due in large part to his alibi.

In April 1930 chairman of the Chicago crime commission published a nationwide list of public enemy’s that were corrupt in Chicago and its suburbs. Machine Gun Jack McGurn was fourth on the list. The notoriety McGurn received from the list cause the Outfit to turn their backs on him. The spotlight was too great. Having nowhere to turn McGurn, an avid golfer since youth, attempted a career as a professional. He had been a silent partner in a golf course on Western Avenue for many years and played well.

McGurn and brother Anthony after being pulled off the golf course and placed in a police lineup.

On August 25, 1933 the Western Open Golf Championships began at Olympia Fields Country Club a southern suburb of Olympia Fields Illinois. McGurn entered the competition using an alias, Vincent Gebhadi where he carded a 13 over par 83 on his first day. The next morning the name Gebhardi was published on a list of golfers set to tee off for day to when an alert police officer noticed the name as an alias for McGurn. The police chief was notified who subsequently sent two sergeants and five uniformed officers to arrest him. McGurn was arrested on the seventh green; however he politely requested to finish the round. The officers agreed and became part of his gallery escorting him until he finished a 16 over par 86, 14 strokes above making the cut. With his cover blown McGurn’s golf career was all but over. He played with his brother Anthony and was arrested on the course several times after that.

On February 15, 1936, McGurn entered a bowling alley at 805 Milwaukee Ave. with two so-called friends. Upon setting up his bowling game another man entered and yelled for everyone to stand still.

He said, “You move and you die.”

The two men accompanying McGurn, and the third man subsequently formed a semi circle around him, pulled out their guns, and fired. McGurn was hit several times; three in the head and once in the back before collapsing to the floor; payback for the massacre of the North Side gang seven years earlier.

“Machine Gun” Jack McGurn after he was shot and killed.


Contrary to popular belief, there was no Valentine card found on his body, however left at the front desk a note states “you lost your dough and handsome houses, but things could be worse you know at least you haven’t lost your trousers”.

On March 2, 1936, less than a month after McGurn was gunned down his brother Anthony was shot by three men in a Chicago pool hall after stating he knew who killed Jack.

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