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Detective Jack "Iron Jack" Rafferty, also called "Jackie-Boy", is an antagonist who appears in the Sin City comics, as well as the Sin City film, where he was portrayed by Benicio del Toro. He is Shellie's abusive former boyfriend, and was once a decent cop. However, after years on the force, he seemingly ended up being corrupted and worn down from the job.
He was portrayed by Benicio del Toro who also portrayed Dario in License to Kill, Aaron Hallam in The Hunted, the title character in The Wolf Man, DJ in Star Wars, The Collector in Thor: The Dark World and Swiper the Fox in Dora and the Lost City of Gold.
A drunken Rafferty is paying a visit to his old girlfriend Shellie while she just had a night with Dwight. She wants nothing to do with him, but when he threatens to break down the door to her apartment, she lets him in out of fear, along with his pack of equally drunk friends. He wants her to call some stripper and waitress friends of hers and hit the town with him and his "troops". After she refuses, Rafferty strikes Shellie in the face after claiming he had never hit a woman in his life.
While relieving himself in the bathroom, he is accosted by Dwight, who had been hiding behind the shower curtain the whole time. Dwight threatens that if he does "ever so much as think [Shellie's] name... I'll cut you in ways that [would] make you useless to a woman.". Dwight then shoves his head in the unflushed toilet.
Humiliated, Rafferty and his friends run off to Old Town, pursued by Dwight. After evading a police squad car by entering Old Town, Rafferty tries to pick up Becky, who rebuffs him. He finally loses what patience he has and pulls his gun on her. This cues Miho, to cut off his hand with a Swastika-shaped shuriken. She then jumps on his car and slices up his gang, then comes for him. While the wounded Rafferty is distracted by Dwight, Miho throws a metal rod into his gun's barrel. When he tries to shoot Dwight, the gun backfires causing the barrel to lodge itself in his skull. Finishing the job, Miho purposely botches the decapitation, causing blood to spew from his neck, similar to "a Pez dispenser".
Dwight and the Old Town girls then discover that Rafferty is actually a "hero cop" and his death would shatter the Truce between Old Town and BCPD, leaving them open to a hostile takeover by the mob. Realising this, Dwight offers to get rid of the bodies. Unfortunately, since there isn't enough room in the trunk of the scrapheap car they supply him with, Jack's body sits in the front with Dwight.
As his frustration rises and the instinctive bottling of his rage and fear that is his weakness begins afresh, Dwight begins to hallucinate and imagines that Rafferty is talking to him, mocking him at every turn. This interferes with Dwight's driving and he attracts the attention of a motorcycle cop. At the mocking suggestion of Jack, Dwight slams on the brakes, driving the gun barrel further into Rafferty's head as he slams against the dashboard. The cop, believing Jack is merely stone drunk, tells Dwight that he is simply driving with a busted tail-light, and lets him go with a warning.
As Dwight is about to dispose of the bodies at the Santa Yolanda Tar Pits, Irish mercenaries attack and cut off Jack's head to give to the mob. Miho pulls Dwight out of the tarpits and then pursue and kill the mercenaries, retrieving the head.
Back in Old Town, he calls the mobsters, offering to exchange the head for Gail. They agree, and the exchange is made. However, Dwight has packed the head with a mercenary's grenades and detonates it. The head explodes, eliminating Rafferty's head, the evidence, and the Old Town girls hiding on the rooftops to shower the mobsters with bullets, killing them all.