Jack Cayman

Jack Cayman is a cyborg bounty hunter who stars in MadWorld as well as Anarchy Reigns.

Appearance
Jack is a hulking muscle bound man with a arms bigger than his head, a cybernetic right arm that has a chainsaw attachment on it and a permanant scowl on his face. He wears goggles on his head, wears fingerless biker gloves, a biker jacket and matching leather looking pants.

In Anarchy Reigns we see his outfit in color, and he adds sets of chains to around his left arm, belt and around his boots.

MadWorld
Jack has had a variety of jobs in his earlier life including being a mechanic, a cop, a marine and a bounty hunter.

At some point Jack began to enter the DeathWatch games, although his motivation for doing so originally is unknown. By the time he enters the 2019 DeathWatch, he has already won three of these murder tournaments, including the last known held one in 2001.

Back then he grew tired of killing and vowed to never enter DeathWatch again, but with the organisers of 2019's DeathWatch dragging innocent civilians into the mix via a deadly sickness and forcing them to slaughter one another for a chance at the vaccine, Jack returns working alongside the Ministry of Justice and his partner Amala to put down the games for good.

At some point between 2001 and 2019, Jack had his entire body surgically altered, becoming 75% mechanical, and even going so far as to have his face and eye color altered so as to not be recognised by the DeathWatch organisers.

Jack's rampage goes on and he quickly becomes an audience favourite, his success doing immeasurable damage to the DeathWatch organisers finances as audience members bet on him winning causing huge payouts. Due to his popularity, DeathWatch comittee members cannot have him silently killed off screen either, and put a huge bounty on Jack's head instead, planning to film his death to boost the ratings in by the books DeathWatch matches.

Jack instead continues to win.

Anarchy Reigns
Jack is a member of The Chasers guild, an elite team that deals with cases regular police are not prepared to handle: kidnappings, disappearances, and fugitive apprehension.

He had adopted an orphan girl by the name of Stela Fitzgerald and was set on raising her. Unfortunately during a hostage situation, Stela was killed by a BPS agent, Maximillion Caxton, in an accidental friendly fire scenario. Torn up by her death, Jack visited her grave when he was approached by the daughter of the man who shot Stela, requesting he help her track her father down. Despite Jack's insistance that this would be a terrible idea due to his hatred of the man, she offered him a huge sum of money and broke down in tears, enough to make Jack consider taking the job.

When the game begins, Jack is in a bar trying to retrieve any information he can about the whereabouts of Max, when the Strike One unit lead by Nikolai Dmitri Bulygin arrives and starts threatening the bar-bot with violence. Jack tells him to leave the bar-bot alone. Nikolai's partner Sasha Ivanoff tells Nikolai that she has found some information on Max's whereabouts. When Jack attempts to grab Nikolai to get that information, Nikolai attacks him, knocking him to the floor and leaves with Sasha and Leonhardt "Leo" Victorion, who looks at Jack with curiosity before going.

As Jack gets up he notices Big Bull and his gang have been eyeing him up too, and after leaving the bar he is soon cornered by Big Bull's men. Jack defeats them all effortlessly but Big Bull now wants to 'Lock Horns' with Jack. After Jack defeats Big Bull too, Big Bull announces Jack as one of his brothers and the fight was part of entering the brotherhood. Jack is confused but indifferent and leaves.

Before long Jack has a group of Drones, robotic soldiers, sent after him to kill him. Big Bull arrives in the nick of time and manages to hold off most of the drones before being injured and needing to escape himself, however this saves Jack's life, allowing him to continue searching for clues to Max's location.

Trivia

 * Jack Cayman isn't Jack's birth name. His old name was erased when he faked his own death.
 * Jack is a heavy chain smoker, but gave up smoking in memory of his daughter, Stela Fitzgerald.
 * Jack has a fondness for eating raw onions, chowing down on them to recover his health.
 * Jack's allies seem to shift slightly between the two games he stars in. In MadWorld the Black Baron is the final boss, but the two seem to be on reasonably good terms in Anarchy Reigns having just a friendly rivalry instead. Likewise Big Bull is one of Jack's opponents in MadWorld and is killed by Jack, but returns with a vitriolic friendship towards Jack, wanting him to become his brother in arms.
 * It's unexplained whether or not Anarchy Reigns is a sequel to MadWorld. Despite the deaths of many of the characters who reappear in Anarchy Reigns such as Big Bull, Black Baron and Rin Rin, they (especially the Baron) continuously came back after being killed off within MadWorld making it unclear. Jack's backstory is mostly consistent in both titles.