"How do you shoot the devil in the back? What happens if you miss?"

- Verbal Kent (Usual Suspects - 1995)


Gangsters inhabit a ruthless world where violence and murder are necessary adjuncts to keeping order and getting ahead and for this reason there is usually a significant body count in a gangster flick. Made-men are called for; contracts are taken out, buttons are pushed and people are whacked, clipped and iced - sometimes by the people they trust the most. Bodies are buried in the desert, some in the marshes others are left out in public to be found as messages.


However, there tends to be no greater turning point in our favourite gangster movies than the hits that go wrong. Nothing seems to fuel our gangster anti-heroes' fervour more than an attempt on their lives. This list compiles the most significant failed assassination attempts and the resulting consequences of the botched hits…

The Most Significant

Failed Assassination Attempts

5. Butch Coolidge – Pulp Fiction


The Set Up: Has a hit ever gone so badly for a hitman? Butch Coolidge was an aging boxer. For his final bout he was paid handsomely to throw the fight by LA crime boss Marcellus Wallace “Repeat after me, in the fifth my ass goes down”. Butch however had other ideas and was not about to let his ass go down in the fifth. Once word got out the fight was fixed, Butch’s odds went thought the roof, and he laid several large bets on himself. When Butch won the fight (killing the other fighter in the ring) Wallace wanted him dead. “If Butch goes to Indo-China, I want a n1gger waiting in a bowl of rice ready to pop a cap in his ass.” He put his top hitman, Vincent Vega on the job. Vega was presently without a partner as Jules Winnfield had retired from the business, so Wallace went with him to Butch’s apartment. 


Armed with Mac 10 automatic machine pistols, they found his place empty and so they staked-out his place, in the event that he came back. Vega waited, while Wallace left to go and get coffee and donuts. Butch, as it happened, did come back; to collect his gold watch. He assumed his apartment was empty, but he discovered a machine gun lying in his kitchen. He picked it up just as hitman Vega, unsuspectingly exited the bathroom. When Butch saw him he didn’t hesitate; he pulled the trigger and killed Vega.


What Happened Next: Fleeing the scene in his Honda Civic, Butch saw Wallace returning with the coffee and donuts and ran him over. Wallace got up and pursued him down back lanes and into the Mason Dixie Pawn Shop. The store proprietor Maynard and his brother Zed were twisted deviants and tied Butch and Wallace up in their basement and abused the crime boss. Butch escaped and killed Maynard but left Zed for Wallace to finish off with a pair of pliers and a blow torch. Wallace thankful to Butch for saving his ass (*coughs*) cancelled the hit on him - so long as he left LA and never returned.

Gangster Movie - The Godfather Part 2
Gangster Movie - Carlito's Way


The Set Up: Nikolai Luzhin was a chauffeur and enforcer for a Russian Mafia family in London led by an old, vor Semyon . He helped to clean up and dispose of the dead body of Soyka - a captain of another Russian Mafia family - murdered on the orders of Kirill, the loose cannon son of Semyon. When Soyka’s brothers came looking for revenge they mistake Nikolai for Kirill.


Sat in a Turkish sauna wearing nothing but a towel and his vory tattoos, Nikolai was unaware of Soyka’s brothers entering. Both brothers were armed with linoleum knives and the first brother slashed him across the chest. Repelling the attack he walked straight into the second brother who gave him a beating, before he pulled out his linoleum knife. At this point Nikolai's Russian FSB training kicked in and he knocked him to the ground. When the first brother came back at him with the knife, Nikolai was able to guide the knife into the second brother’s chest – leaving him for dead. Incensed by his brother’s fate the first brother fought on, but in a tense battle on the floor Nikolai was able to grab hold of the stray knife and while pointing it up, pushed the brother’s head back on to it. The second brother with a knife in his chest was not quite done and in one final desperate attempt he found the strength to remove the knife, but Nikolai was able to block the weak stabbing attempt and instead took the knife and stabbed him in the eye until he was finally dead.


What Happened Next: Kirill’s father and mob boss, Semyon was responsible for sending the brothers after Nikolai instead of his son. Semyon was unaware that Nikolai was a Russian FSB agent who had infiltrated his family and was about to bring him down on charges of rape of a 14 year old. Still undercover Nikolia was able to take over as boss of the mafia family.

6. Nikolai Luzhin - Eastern Promises

7. Tony Soprano - The Sopranos


The Set Up: One of the major plot points in Season 1 was Tony’s own Mother, Livia Soprano and his uncle, Corrado ‘Junior’ Soprano, plotting to kill him. In the penultimate episode of the season it all came to a head when Rasheen Ray and Petite Clayborn were given the contract to execute the hit.


On his way to another therapy session (his prescription Lithium was making himhallucinate) Tony stopped to buy a newspaper and some orange juice. When he returned to his burgundy Chevrolet Suburban he saw in the reflection of the car window Clayborn approaching and drawing down on him with a Glock. Clayborn's first shot hit the bottle of 


orange juice, spilling the contents in to the street (a not too subtle  nod to The Godfather knocking over the oranges) and as Tony scrambled to get into the car a second shot hit the driver window. Tony jumped in to the driver seat just as Clayborn reached in with the gun to shoot him. Through the broken window Tony grabbed his arm stopping him from shooting.


The second gunman, Rasheen came around the other side of the vehicle and took a shot at Tony as he wrestled with Clayborn. The shot missed Tony, but hit Clayborn plumb in the head. Tony then grabbed hold of Rasheen and his SIG-Sauer and dragged him along the street as he drove off in the Suburban; Rasheen eventually fell away. In the euphoria Tony was clearly elated about not only surviving the hit but being able to fight off the gunmen as he shrugged off the lithium fog, before he veered off the road and crashed into a parked car


What Happened Next: Tony learned the truth about his mother’s and uncle’s involvement in the hit, but Livia Soprano faked a stroke. Although initially Tony considered smothering her with a pillow he was not able to bring himself to kill his own mother, but considered her dead in his eyes. Junior was arrested by the FBI before Tony could take action against his uncle, however the bodies of other members of Junior’s crew started to pile up starting with Junior’s consigliere Mikey Palmice.

8. Michael Sullivan  Road to Perdition


The Set Up: Michael Sullivan was an enforcer for Prohibition era Irish mob boss John Rooney. When Sullivan’s son Michael Jr witnessed his father and Rooney’s son Connor kill some men, Connor wanted to silence the Sullivan boy (for good). He killed Sullivan’s wife and younger son which forced both Michael Sr and Jr to go on the run. The Chicago mob, with close business ties to John Rooney agreed to hide and protect Connor from Sullivan’s attempts to kill him and assigned hitman Harlen Maguire to find and kill them. Maguire first tracked them down to a roadside diner, but Sullivan got wind of Maguire’s intent and left quickly, slashing the hitman’s tyres to ensure he couldn’t follow them.


The second attempt was a closer call. Sullivan was lulled into a trap when he visited Rooney’s accountant Alexander Rance. Maguire burst into the room with his Winchester Model 1897 and started lighten up the place. Rance was killed in the ensuringcrossfire and when Sullivan shot a whiskey decanter Maguire copped a lot of the shrapnel in his face leaving him disfigured. Sullivan quickly left while Maguire was left clutching his face.


What Happened NextFollowing the first encounter with Maguire and realising Rooney has sanctioned a hitman to kill him, Sullivan began robbing all the banks that were storing mob money, which he planned to exchange for Connor Rooney and kill him.


After the second failed attempt, Sullivan escaped from the ambush with the accountant’s ledgers. He discovered from the books that Connor Rooney had been embezzling his father’s ill-gotten money. However, even when faced with the (old) news that his son was stealing from him, John Rooney refused to give up his son and Sullivan was forced to kill him. Following the death of John Rooney, the Chicago mob ended their protection of Connor and Sullivan was finally able to kill him.

Gangster Movie - Scarface

9. Gyp Rosetti - Boardwalk Empire


The Set Up: This botched hit is the second of two on this list in which the target is naked and fends off the assassin with his cock lolling about (the first was Nikolai Luzhin). Gyp Rosetti is the main antagonist in Season 3 of Boardwalk Empire and probably the greatest character to light up the prohibition show. In retribution for being frozen out of the liquor deals and perceived insults from Nucky Thompson, Gyp held Tabor Heights hostage, a small village on the main road between Atlantic City and New York so he could intercept Nucky’s liquor trucks on their way to Arnold Rothstein. Rothstein ruthless as ever wanted to end the stand-off and sent a young Benjamin ‘Bugsy’ Siegel to assassinate Gyp. 


Posing as a paper boy Rosetti’s men allowed Bugsy into the small hotel Gyp was staying in. Gyp was initially caught off guard as he was engaged in an asphyxiation  session with a local waitress. He was alerted to the approaching danger when Bugsy shot the guard stationed outside the hotel room. Gyp struggled to reach for his gun as his kinky shenanigans had a belt tied tightly around his neck and the other end tied to the bed post. Bugsy burst in to the room, but Gyp held the waitress up in front of him, to take the bullets and she died naked on the bed, before he is able to finally return fire. Bugsy fled the hotel giggling like an idiot and shot two more guards as he made his escape before unnecessarily shooting the real paper boy.


Gyp, still naked, ran down the hallway in pursuit, but is unable to catch Bugsy as he jumped into a waiting getaway car. The scene lingered on a butt-naked Gyp Rosetti, the belt still fastened around his neck, as he surveyed his dead men and the bloodied naked body of the waitress.


What Happened Next: Gyp Rosetti, a man who can find an insult in the most innocent of comments was incensed by the attempted hit. He left Tabor Heights and headed back to New York. There he convinced mob boss Joe ‘The Boss’ Masseria to provide him with more men to kill Nucky Thompson and Arnold Rothstein and then take over Atlantic City bootlegging activities. The Italian was successful in taking over AC, but he lost the resulting gang war in which dozens of men on either side were killed including Rosetti.

Gangster Movie - Once upon a Time in America

10. Joey Cussack - A History of Violence

Gangster Movie - The Untouchables


The Set Up: Tom Stall took Joey Cussack out to the desert and killed him or at least he thought he did. Ok I admit this failed hit is a little on the... how shall it put this... existential side, but it works... stick with it for a minute.


Joey Cussack was a gangster from Philly, he was very accomplished at killing people; he liked to drink hard, play hard and had sociopathic tendencies. The final straw came when he bust up a made-man’s joint, killed his men and ripped the guy’s eye out with barbed wire. Before any pay back could be dished out he faked his own death, but he went a step further. He killed the personality that was Joey Cussack and became Tom Stall. 


As Stall he became the owner of a restaurant in a small Indiana town, he had a wife and two kids: a teenage son; and a young daughter. He spent the best part of two decades as Mr Middle America – a soft spoken man who went to church on a Sunday and paid his taxes on time. Tom Stall only realised that Joey was not dead when two dangerous men entered his restaurant and threatened his staff. Stall unwittingly let out Cussack, who in the blink of eye and with the accomplished flourishes of an artist brandishing his brush across a canvas skillfully executed both men.


What Happened Next: Tom Stall’s worst fears were realised. The press coverage of his heroism was noticed by gangsters back east who came calling – notably the made-man who had his eye removed with barbed wire, Carl Fogarty. Stall was made to face his past when he admitted to being Joey and killed the gangsters who came looking for him. To kill Joey Cussack once and for all, he travelled back to Philadelphia to face his brother who had risen to become a mob boss and killed him.

Gangster Movie - The Sopranos
Gangster Movie - Gangs of New York

11. Ray - In Bruges


The Set Up: Perhaps the oddest failed hit on this list involves Ray and Ken from In Bruges. Ray was new to the hitman life and in one of his first jobs he accidently killed a young boy. He was advised by his crime boss, Harry, to go on the lam with his partner Ken, in Bruges – it’s in Belgium – and wait for Harry’s call with further instructions.


When the call finally came, Harry ordered Ken to kill Ray (because even accidentally, it’s unforgivable to kill a child). Harry even stated he’d kill himself at once if he ever killed a child. With a heavy heart Ken attempted to follow through on the order. He found Ray sitting alone on a park bench. He screwed the suppressor on to his newly acquired Berretta and walked up to Ray from behind. As he was about to squeeze the trigger with the gun firmly pointed to the back of Ray’s skull, Ray who thought he was all alone in the park, pulled out his own gun, a Smith and Wesson Model 60 and put it against his temple. He was still racked with guilt over killing the little boy and was ready to end it all and blow his own brains out. In a strange turn of events instead of completing the hit or better yet allowing Ray to take his own life, Ken felt obliged to step in and prevented Ray from killing himself.


What Happened Next: Ken told Ray to get on a train and leave Bruges and never come back. Ken then rang Harry to let him know that he disobeyed his order and allowed Ray to live. Harry immediately travelled to Bruges to kill Ken for his insubordination. A quirk of fate brought Ray back to Bruges and Harry killed himself by throwing himself from a tower to alert Ray below that Harry was going to kill him. Harry, in pursuit of Ray accidently killed a dwarf dressed as a school boy (on a film location set) and thinking he’d shot a child is true to his word and he killed himself. The fate of Ray is left vague and we never find out whether the bullet wounds he sustained from Harry were fatal.

Who survived - who missed - and who give the go ahead

Edited Image 2014-10-21-9:58:39


The Set Up: At the beginning of The Godfather Part II, Michael had moved the family out to Lake Tahoe, Nevada and was still trying to legitimise the family business. He hosted a large shindig at his lake-side compound in honour of his son’s First Communion, replete with dignitaries and a brass band. Later that night Michael walked into his bedroom and picked up a drawing his son Anthony has left for him of a car. His wife Kay noticed that the drapes had been opened, but before Michael even had time to consider why, gun shots shattered the windows and filled the room. He grabbed his pregnant wife off the bed and pulled her to the floor. When the gunfire eventually stopped Michael was seriously pissed. “In my home! In my bedroom, were my wife sleeps! Where my children come and play with their toys.” Michael later shouted at Frankie ‘Five Angels’ Pentangeli in a manner only Al Pacino can muster. 


What Happened Next: As a result of the attempted hit, Michael handed over the reins of the Corleone family to Tom Hagan, the only man he trusted as he tried to find out who ordered the hit. Michael later discovered his business partner Hyman Roth was responsible, partly to bump Michael out of the casino business and partly for retribution for killing his close friend Moe Greene. Business is business at the end of the day, but the real sickener for Michael is when he learned that that the insider that made the hit possible was his own brother Fredo and we all know what happened to poor Fredo…

4. Michael Corleone  The Godfather Part 2

Gangster Movie - The Godfather


The Set Up: Tony had a major falling out with his employer Frank Lopez, boss of the biggest cocaine cartel in Miami. Tony agreed to an unauthorised $18 million deal with the Bolivian cartel and Frank was furious about it. Frank and Tony saw the future of the business differently. Frank’s motto is to fly straight and remain low-key – Tony wanted to expand and dominate. To retain control, Frank ordered the hit on Tony.


Tony was sat in the Babylon night club alone at a VIP table. He’d not had a good night: he’d had the major bust up with Frank Lopez; corrupt cop Detective Bernstein had shaken him down for 25-large a month; and he’d just caught his kid sister getting hot and heavy in the 


club bathroom with some guy. Tony’s miserable puss stood out amongst the other happy-faced club revellers as they enjoyed the entertainment. Only two other faces in the crowd were similarly unmoved by the cabaret. These two men were sat with Mac 10 automatic pistols hidden under napkins waiting for the opportune moment to release holy-hell on Tony.


Tired of the inane comedian the hitmen rose to their feet and fired their automatic weapons, somewhat wildly, in Tony’s direction. The Cuban’s reactions were cat-like as he dove to the floor. From the floor Tony shot at the legs of the hitmen through tables and killed one the assassins. The second gunman was finished off when a lighten rig fell from the ceiling on top of him. Tony escaped in his Porsche 928 with only a shot to his left shoulder - although it did ruin his $800 suit.


What Happened Next: Later that night Tony confronted Frank Lopez over the attempted hit and killed him, along with bent copper Bernstein. This allowed Tony to become the number one drug kingpin in Miami and he began earning upwards of $10 million a month from cocaine imported through his Bolivian connection Alejandro Sosa. 

3. Tony Montana – Scarface

Gangster Movie - American Gangster


The Set Up: The attempted hit on Irish Political boss Leo O’Bannion in the Coen Brothers’ classic Miller’s Crossing is a beautiful 4 minutes of cinema. O’Bannion refused the request of Italian mob boss Johnny Casper to kill bookie Bernie Bernbaum, for selling out his fixed boxing matches; consequently Casper went to war and sanctioned a hit on O’Bannion.


On the night of the attempted whacking Leo O’Bannion was sat on his bed dressed in his pyjamas and red silk robe listening to a pressing of Danny Boy on his phonogram when two assassins with Thompson Submachine Guns silently broke in to his house downstairs. 


One of the assassins slit the throat of O’Bannion’s guard and the lit cigarette of the dead man fell on to his newspaper and set it alight. The fire quickly spread as the gunmen made their way upstairs and along the hall towards O’Bannion. Wisps of smoke made their way up through the waxed oak floorboards alerting the Irish mobster to the impending danger. He sat up, stepped into his slippers, stubbed out his stogie and just as the gunmen entered his room he grabbed his Colt New Service pistol from the bedside table and slid under the bed. Feathers filled the air as the gunmen unloaded the Tommy guns into the bed. O’Bannion shot one them in the ankle and as he fell to the ground O’Bannion put another in his head. The other gunman fled the room in order to regroup; O’Bannion used the opportunity to prise the submachine gun from the clutches of the dead man and ran across the hall to another bedroom and with the agility of a gymnast half his age vaulted out the window down to the ground. The gunman then entered the room looking for him. O’Bannion let rip, up through the window, peppering the assassin’s body with bullets. The gunman’s finger was frozen to the trigger of his Tommy gun and sprayed his own array of bullets around the room as he went into what can only be described as his death dance.


Driving down O’Bannion’s affluent leafy suburban street the would-be getaway car for the assassins showered more gunfire in O’Bannion’s direction. However with a menacing calmness he turned his Thompson submachine gun towards the car and casually pursued it on foot, streaming wave after wave of large .45 ACP cartridges their way. Stood in the middle of the street, still dressed in the slippers and red silk robe he killed the occupants as the car veered into a tree and became engulfed in flames.


Smug and satisfied stood in the night air, Tommy Gun still smoking, he reached in to his robe pocket and pulled out another stogie and popped it between his teeth – Danny Boy still belting out from the phonogram.


What Happened Next: Leo O’Bannion might still be an "Artist with a Thompson", but the very fact that Casper’s men were able to get so close to him showed he’d lost his touch and it turned the war against him. O’Bannion lost the backing of the Police Chief and Mayor who turned their allegiance to Johnny Casper. More alarming, the fallout sent his loyal lieutenant Tom Reagan over to Casper too. 

2. Leo O'Bannion – Miller's Crossing


The Set Up: The Godfather, Don Vito Corleone, expected trouble. When he refused to front Vigil ‘The Turk’ Sollozzo $2 million for a drugs racket he knew there’d be reprisals, particularly as The Turk had the backing of the Barzini’s and Tattaglia’s two of the other crime families in New York. However, he failed to smell a rat when he learned his regular driver Paulie Gatto had called in sick and his son Fredo had to drive him home instead. Leaving his legitimate place of work, Genco Olive Oil, Fredo got into the Cadillac Fleetwood 60 and waited as his father went across the road to buy some fresh fruit from the grocer. 


Two suspicious men then appeared from around the corner before running towards the Don, pistols drawn. The Godfather saw them and made a dash for the car, upsetting baskets of fruit as he went, sending oranges tumbling into the street. Fredo with all the grace of a drunken chimpanzee trying to peel an orange while wearing mittens fumbled his Smith and Wesson and was able to offer no protection to his pop. The gunmen put “Five bullets in his Sicilian hide” from their respective Colt Detective Special and Berretta. Fredo crumpled into a heap on the curb and cried like a child, believing his pop was dead. Alas the Don is made of stern stuff and made a full recovery.


What Happened Next: The death of the Don was supposed to be viewed as ‘business’ and Sonny Corleone who was ‘hot’ for The Turk’s drugs business idea would take over the family and invest in the operation. Instead this became the singular factor which put Michael Corleone on the dark path towards becoming the most ruthless and feared mob boss in the country. Many deaths occurred as a consequence of the attempted hit on the Godfather, including: Sonny; The Turk; Police Chief McCluskey; Apollonia; Carlo Rizzi and eventually Moe Greene and the heads of the other New York Families.

1. Vito Corleone – The Godfather

Gangster Movie - The Departed
Gangster Movie - Miller's Crossing

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