Submitted by Steve
Leo orders Richard and Pronge to kill Mickey, one of DeMeo’s associates. DeMeo finds out Richard was one of the killers and is kicked out of the mob. Leo refuses to pay Richard for the hit, so Richard kills him. After his daughter is injured in a hit-and-run accident, Richard thinks Pronge is responsible and kills him. Before he can kill DeMeo, Richard is caught by the police and sentenced to two life terms, and he will serve them in the same prison his brother is at. Neither his wife nor his daughters ever visit him in prison.
In 1964, Richard Kuklinski (Michael Shannon) is working for the mob dubbing porn films for them before they are distributed. His family, including his wife Deborah (Winona Ryder), thinks he dubs Disney movies. This isn’t the only secret Richard is keeping from Deborah. As a child, Richard was constantly beaten by his father, leading to him becoming a violent man. This is shown by Richard slitting the throat of a man who insulted him following a game of pool. Another secret is that Richard’s brother Joseph (Stephen Dorff) is serving a life sentence for raping and murdering a 12-year-old girl. When the head of the Jersey City mob, Roy DeMeo (Ray Liotta), shuts down the porno business, he offers Richard another job, this time as a contract killer. He is given an impromptu audition for the job when DeMeo gives him a gun and is ordered to kill a homeless man. Richard, after some hesitation, does so, and is given the job. Richard never tells Deborah of his new job, creating another secret he is keeping from her.
As the years go by, Richard is racking up the kills, and he earns the nickname “The Iceman”, because he freezes his victims to obscure their time of death. It’s now 1975, and following a hit, Richard meets Robert Pronge (Chris Evans), who goes by the nickname “Mr. Freezy” because of his cover job of driving an ice cream truck. Pronge was also hired by DeMeo for the same job. After that hit, Richard lets a young prostitute escape, and Pronge tries to kill her, but Richard stops him, and the girl gets away. Richard tells Pronge that he refuses to kill women and children because he has a reputation to uphold. He also doesn’t kill women and children because he doesn’t want to be like his brother. The next day, DeMeo suspends Richard for not killing the witness.
While under suspension, Richard’s violent behavior increases. He had been able to sate his violent tendencies by killing, but he can’t do that now since he’s suspended. One day, while driving with his family, Richard accidentally bumps another car, and the driver gets out and insults him and Deborah. Richard then chases the man for several blocks before Deborah and the kids can calm him down. That night, she tries to talk to him about his increasingly frequent loss of his temper, and he proceeds to smash up the house. He’s also becoming paranoid, thinking that someone may be trying to kill him. One time, he sees an ice cream truck, and he thinks it may be Pronge coming to kill him. That’s what led to the car accident.
With no contract money coming in, and his behavior becoming reckless because he can’t kill, Richard approaches Pronge about working together. Pronge, who is a freelance hitman, agrees to the partnership, and they decide to split the payments they make on hits ordered by DeMeo’s boss, Leo Marks (Robert Davi). It’s at this time that Richard learns that Pronge killed the prostitute Richard let get away, on orders from DeMeo. In 1986, Leo orders Richard and Pronge to kill Mickey, one of DeMeo’s associates, and they do the job. DeMeo learns that Richard was one of the killers, and he kicks him out of the mob. Richard then goes to collect the $50,000 contract, but Leo refuses to pay him because DeMeo knows he ordered the hit. After Leo threatens his family, Richard snaps and he kills him. A short time later, one of Richard’s daughters is seriously injured in a hit-and-run accident. Richard thinks Pronge was involved, so he goes to the park where Pronge usually parks his ice cream truck and kills him.
Richard has one loose end left: kill DeMeo. He meets with a hitman from another crime family to get the cyanide he needs to do the job. However, the hitman is actually an undercover cop, and Richard is arrested. It’s at this time that Deborah and the daughters finally learn that Richard is actually a hitman. He is eventually given two life sentences, and he is sent to the same prison his brother is at. The movie ends with Richard admitting to a reporter that the only thing he regrets his putting his family in danger. Title cards at the end reveal he died in prison in 2006, before he could testify against the Gambino family, and that foul play is suspected. It is believed he killed over 100 people in the 22 years he was a hitman. Neither Deborah nor either of his daughters ever visited him in prison.