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    Zachary ‘Zack’ State 

The protagonist of the series. Initially a friendly and liberal-minded stockbroker, his personality changes into that of a ruthless, manipulative sociopath after being forced to watch his girlfriend, Rose Vane. After maiming, killing and traumatising those responsible, he is sent to prison for voluntary manslaughter, where his sociopathy proves useful in helping him survive and eventually enables him to take control of the entire prison system from within.

  • Anti-Hero: Zack essentially cycles through every type of Antihero possible. At any one time, he can be anything from a kind-hearted Guile Hero to a full-blown Villain Protagonist.
  • Badass Baritone: He is described as a honey glazed baritone.
  • Beware the Nice Ones: He appears to be a charismatic young man who just wants to get on well with as many people as possible and make life better for everyone. However, if he doesn’t like you, he will take away everything you have and crush you like an insect.
  • Character Development: From a mundane and naïve young man to a cynical and ruthless manipulator and then back again.
  • The Chessmaster: Whether it’s playing criminals and law-enforcers against each other or organising a coup, Zack always gets exactly what he wants and makes everyone dance to his tune.
  • Crazy-Prepared: It is revealed in the penultimate chapter that the watch he claimed was from Rose was actually a meaningless trinket that he bought before he was arrested. He brought it into prison so that everyone would think that it was his weakness, knowing full well that someone would try to exploit it. It also turns out that Rose’s full name is ‘Rosemary’ rather than ‘Rosette’, and he had been lying about it from the beginning in order to protect her.
  • Cruel Mercy: He is a big believer in letting people live in misery and terror rather than killing them. When informed that his actions led to someone dying, he reacts with disappointment at the fact that they didn’t suffer longer.
  • Cruel to Be Kind: Zack’s approach to dealing with drug addicts is to cut off their supply and force them to go cold turkey. He also manipulates Officer Reed into becoming a drug addict himself in order to make him empathise with the inmates and demonstrate alternatives to simply arresting and punishing them.
  • Cynicism Catalyst: Seeing Rose getting raped.
  • Dark Shepherd: As a last resort, Zack can convince his subordinates to behave by threatening to use his influence to undo some of the improvements he has made to the prison. He also recruits Charlie to his side so that he can threaten rebellious inmates who have children.
  • Devoted to You: He has absolutely no interest in sex whatsoever, as he is still haunted by his memories of Rose.
  • Evil Laugh / Signature Laugh: “Heh! Hih! Hih!” Scowl.
    • He has a more shrill and manic one when he manipulates Danny’s gang, which they find rather hammy.
    • He gets a truly epic one in the final chapter while he is pretending to be a crazed pimp to save Rose from a mugger. It is such an elaborate cackle; it takes an entire page to describe it.
  • The Fettered / The Unfettered: Zack is somehow able to be both at the same time. He is ruthless when it comes to getting what he wants. However, what he wants is to impose his own concept of morality on the rest of the prison, and he is very particular about what he is allowed to do to others. He never does anything to harm good people (apart from Charlie, but this was because he was in an ethical grey-area and Zack was not entirely happy about having to do it), he uses tough love to reform salvageable or morally-ambiguous people, and he mercilessly torments the ones who are beyond the point of saving (in his own word, ‘Irredeemables’).
  • Forced to Watch: He is deliberately made to watch as Danny rapes Rose. To say it affects him is an understatement.
  • Four Eyes, Zero Soul: When he looks at you from over the top of his elliptical spectacles and smiles, you know you’ve been screwed.
  • Guile Hero: On his good days.
  • Good Is Not Nice: Of course, it is debatable how ‘good’ Zack actually is.
  • Had to Come to Prison to Be a Crook: He is genuinely responsible for the crime he was imprisoned for, but he had understandable motives for that. Once he is put behind bars, his motives become considerably more self-serving.
  • Heartbroken Badass: Realising Rose is afraid of him drives him to be as hardcore as he can possibly be.
  • Heroic BSoD: Being made to watch as the person you love is raped will do that to you.
    • He gets another one in the last few pages of the novel; this time, with the opposite effect.
  • He Who Fights Monsters: His ‘monsters’ are people he refers to as ‘Irredeemables’ (people who have no excuse for their actions and are nothing but a bad influence on the other inmates). However, he acknowledges that there are occasionally non-evil versions of these characters (such as Charlie and Big Billy). He even admits to being one himself. He still punishes these Irredeemables, but they are the only ones he has second thoughts about hurting.
  • Hurting Hero: Those who know what happened to him tend to regard him as this.
  • It Amused Me: He accepts Saif’s challenge mainly because he is bored and wants a worthy opponent.
  • Jerk with a Heart of Gold: He genuinely believes he knows what is best for the prisoners and always tries to reform them when possible. Whether this is because they are less likely to hurt him or not is open to interpretation.
  • Karma Houdini: Apart from his first offence, he is never punished for any of the crimes he commits while in prison, including theft, blackmail, smuggling, arson, hacking, poisoning, and framing someone. He even manages to swing an early release thanks to good conduct and survives the whole ordeal with little more than a slight bruise that could have been a hundred times worse.
  • Karmic Trickster: His machinations will either teach you a valuable lesson or ruin your life.
  • Kick the Son of a Bitch: Nothing seems to give him quite as much pleasure as wrecking the lives of people who refuse to repent for their crimes.
  • Knight In Sour Armor: He expects the worst from people, but it doesn’t stop him from trying to change them if possible. Usually, he can.
  • Lack of Empathy: Comes with being a sociopath. Luckily, his knowledge of psychology makes up for it.
  • Manipulative Bastard: There’s scarcely a single character in the story he hasn’t lied to, exploited or blackmailed.
  • Manslaughter Provocation: He is serving an eight-year jail sentence after mutilating the man who raped his girlfriend while forcing him to watch, stabbing one of his accomplices and killing another.
  • The Matchmaker: He helps Sbekz and Isabelle get together by arranging for a tunnel to be dug between the two gender-split sides of the prison.
  • Moral Sociopathy: Apart from self-preservation, his primary motive throughout the course of the story is to impose his own concept of morality on the prison system. Luckily, he is a big believer in prisoner rights and freedom of choice. His rule is less like a ‘dictatorship’ and more like a ‘dictablanda’.
  • Motive Decay: Played straight and then inverted. Zack starts of altruistic, but he becomes obsessed with survival once he goes to prison. Later on, his objectives become more ambitious and he seems to genuinely care about the wellbeing of the other inmates by the end. Of course, YMMV.
  • Nerd Glasses: He wears elliptical spectacles.
  • Nerves of Steel: Everyone is impressed by his ability to confront the burliest inmate around, ‘Big Billy’.
  • Nice Guy: He spends most of his life trying to learn how to make friends. Sadly, this all ends once he and Rose get attacked.
  • Nominal Hero: He never does anything virtuous unless he can justify it with a selfish motive. Of course, it is open to interpretation as to whether this is always the case, or if he is simply trying to convince himself that he is one of these.
  • Not Used to Freedom: Saif’s one victory over Zack is that he finds the outside world quite dull once he is released. He only has two uses for his sociopathy in the real world; aggressive business acumen and rescuing damsels in distress.
  • O.O.C. Is Serious Business: The only time Zack genuinely loses his temper is after he has arranged for the prison rapists to get lacerated by a hoard of violent female inmates. It serves to show just how much he despises rapists above all other types of offender.
  • Pay Evil unto Evil: His hobby. He usually only needs a single weapon; his mind.
  • Playing the Victim Card: In his first week, Zack exploits the fact that everyone thinks he’s a Naïve Newcomer and makes a logically coherent argument that convinces Bones’ gang that Harry is trying to frame him for grassing them up, when, in actuality, it is the other way around. He also uses this supposedly unpleasant experience as his blanket excuse to avoid having to take drugs with the rest of them.
  • Psychotic Smirk: If he smiles at you from over the top of his glasses, you’ll know he has completely beaten you.
  • Safety in Indifference: Zack realises that Rose is now afraid of him and everyone else probably will be too. He doesn’t break out of this slump until the end, when he realises that she is still afraid of him and he still cares about it.
  • The Sociopath: A Semi-Heroic example. He is essentially on a quest to survive in prison and, simultaneously, impose his own concept of morality on the place. Luckily, his concept of morality is an extremely liberal one.
  • Sociopathic Hero: For a nihilistic megalomaniac with a messiah complex, one cannot deny that his actions help a lot of people.
  • The Starscream: To Bones.
  • Took a Level in Badass: The timid and ineffectual Zachary is quite different from the cunning and manipulative Zack.
  • Took a Level in Cynic: Zack has a much darker view of the world than Zachary.
  • Took a Level in Jerkass: Zachary becomes a lot more cutthroat once he becomes Zack.
  • Took a Level in Kindness: As the story progresses, he becomes less concerned about remaining in charge and focuses more on trying to keep the prison the progressive and tolerant place it has become. He also saves Rose a second time shortly after his release and regains his ability to love in doing so.
  • Tragic Hero: Zack may be cruel and ruthless, but it is little wonder given what happened to him.
  • Treacherous Advisor: He becomes this to Bones and also Mc Douglass to a lesser degree.
  • Unable to Cry: Zack shuts down his emotions once he realises that he has made Rose afraid of him. He finally snaps out of this when he saves and scares her a second time, forcing him to confront the feelings he had lost touch with after so many years.
  • Unscrupulous Hero: He is not too concerned about the fallout of his plans. As he is living in a world of people he generally regards as Asshole Victims, he is perfectly willing to get his fellow inmates into trouble.
  • Utopia Justifies the Means: He is a firm believer in this. Even Viceman cannot help but acknowledge the drop in crime following the changes Zack blackmails him into implementing.
  • Villain Protagonist: From a conservative perspective. He occasionally becomes this on bad days.
  • Visionary Villain: He certainly develops lofty ambitions and is not exactly friendly.
  • Wild Card: He is extremely unpredictable, and his loyalties are rather hard to determine.
  • You Are What You Hate: He regards himself as an ‘Irredeemable’ on account of having selfish motives and not being able to give up his sociopathic ways. Luckily, he is proven wrong in the end.

    Saif Dhu Hadin 

The most notorious criminal in the entire prison and the primary antagonist of the story, despite only appearing in the last third of the book. He is the leader of the ‘Irredemables’ and Zack’s most formidable opponent. He initially intends to recruit Zack as an underling against his will, but eventually decides to seek revenge after his machinations result in him losing his fingers.

  • Big Bad: He is a criminal mastermind with a global empire and Zack’s most formidable opponent.
  • The Corrupter: He encourages people, particularly inmates, to be as self-serving as they can.
  • Crush the Keepsake: Does this to the watch that Rose gave to Zack. [[spoiler Subverted, as Zack had bought it himself to let people think it was important, just in case one of his enemy’s tried this]].
  • The Dreaded: All the other criminals steer clear of him.
  • Dystopia Justifies the Means: He prefers the den of iniquity the prison used to be before Zack’s arrival and wants to see it go back to the way it was.
  • Evil Cripple: He eventually has all his fingers cut off to prevent him from doing the same to others. He has them replaced with silver prosthetics.
  • Fate Worse than Death: He ends up spending the rest of his life in solitary confinement and loses all his fingers to boot.
  • Faux Affably Evil: Saif always appears to be cordial with new people. However, he quickly drops the pretence when they are being uncooperative.
  • Fauxreigner: Done seriously. He never reveals himself to his pawns and underlings in the criminal underworld and adopts a different name to suit whichever group of people he is dealing with, in order to make them think they are from the same country. This backfires when Zack suggests that the officials reveal to the arrested underlings like Sami that he is actually a forty-year-old American Caucasian. After which, they cannot wait to squeal on him.
  • Fingore: Micky cuts off all of Saif’s fingers in retaliation for Saif removing one of his.
  • Humiliation Conga: He has all his fingers cut off, his entire criminal network collapses, he receives a ridiculously long prison sentence and is forced to spend the rest of his life in solitary confinement.
  • I Have Many Names: He goes by a number of pseudonyms, including ‘Conniver’, ‘Napoléon Du Crime’ and ‘Hijo del Diablo’. Out of vanity, he arranges for his prison badge to read ‘K. Söze’.
  • It's Personal: His original goal is to dig up dirt on Zack in order to control him and explot his talents and assets. This all changes when Zack arranges to have Saif’s fingers cut off.
  • Longer-Than-Life Sentence: Thanks to Zack’s plans and Jeremy’s intelligence gathering, Saif ends up with a thousand-year sentence and forty life-sentences.
  • Manipulative Bastard: As a psychopath, he has had years of practice. Unfortunately for him, Zack is better.
  • Meaningful Rename: All his pseudonyms are intended to warn people of different cultures that he is dangerous.
  • Motive Decay: His plans for Zack become pettier as the story progresses. He initially wants to extort him into joining his criminal organisation and ultimately settles for emotionally breaking him out of revenge.
  • Mysterious Past: On account of him erasing all traces of himself, his true origin is unknown. It is speculated that that he used to work in black ops, but no one knows which faction he worked for if any.
  • No Name Given: His real name is never revealed.
  • Only Known by Their Nickname: Nickname(s). He goes to extreme lengths to maintain his anonymity. Even the courts don’t know his real name. He uses Saif the most often because it means ‘Double-edged Sword’, which he thinks suits him down to the ground.
  • Out-Gambitted: By Zack at every turn.
  • Overshadowed by Awesome: He has an entire underworld network, the ability to control and strike fear into even the hardest of criminals and an IQ in the 140s. He clearly has great organisation and forward-thinking skills, a ruthless streak to rival any of his enemies and the ability to manipulate his pawns with ease. Aside from the one offence out of hundreds, if not thousands, that could be successfully pinned on him, he only really made one mistake in the entire story… choosing Zack as his opponent. Against ANYONE else, he would have crushed them.
  • The Psychopath: As opposed to Zack, who is a high-functioning Sociopath.
  • Smug Snake: He is so full of himself; he even has a name-tag that reads ‘K. Söze’.
  • White Hair, Black Heart: Actual quote, ‘The darkness within his soul was hidden beneath a hood of platinum-blonde hair; ghostly white and draped lightly over his shoulders’. His face is also described as being ‘disturbingly perfect’.
  • Withholding Their Name: He has gone to great lengths to erase any record of his identity.
  • Worthy Opponent: He regards Zack as this. The feeling appears to be mutual, at least until Zack completely outdoes him and ruins his criminal career.
  • Would Hurt a Child: He controls Officer Jeff by threatening to cut off the funding needed for his daughter’s medical bills.

Other Inmates

Bones’ Gang


The ‘Irredeemable’ leader of the gang Zack joins when he goes to prison. He uses Paul and his drug connections to control his comrades. He is later overthrown by Zack and joins Saif’s team.

  • Arc Villain: He is the second major opponent Zack faces, with Harry being The Dragon and James being little more than an inconvenience.
  • Demoted to Dragon: Eventually joins Saif’s team after Zack usurps him.
  • Villainous Breakdown: Has one when Zack turns his entire gang against him by accusing him of deliberately withholding drugs from them.

    Harry Jacks 

An ‘Irredeemable’ gang member who pretends to be friends with new inmates but is really trying to get them hooked on drugs so that they can be controlled. He joins Saif’s team after Zack tricks everyone else into thinking he is a grass.

  • Affably Evil: He presents himself as being rather friendly towards the people he is secretly poisoning and gets on well with those he has already lured into chemical dependency.
  • The Corrupter: He is the reason why many of the inmates are hooked on Spice.
  • The Dragon: To Bones, at least until Zack makes everyone think that he is a grass.
  • It Amused Me: He gets bored easily. This is why he drugs people.
  • Out-Gambitted: And how!
  • Rapid-Fire "No!": Once he realises that Zack grassed up the gang, set him up as a scapegoat and is now walking away Scott free.
  • Screwy Squirrel: He secretly adds drugs to other inmates’ lunches simply to stave off the boredom of being behind bars.
  • Slipping a Mickey: He likes doing this to new inmates.
  • Villainous Breakdown: Has one when he finally works out that it was Zack who ratted the gang out to the authorities and told everyone that he was responsible.

    Devon ‘Sbekz’ Knowles 

The most computer-literate inmate. He is a former hacker who helps Zack with all his technical requirements. He hacks into the prison’s CCTV system and rigs Zack’s computer with a booby-trap to outsmart other hackers.


    Paul Sorrell 

A supplier of illicit items in the prison. Bones uses his drug connections to maintain control over the rest of his gang. He eventually starts working for Zack and is instrumental in his takeover.

  • Corrupt Corporate Executive: Used to be one prior to getting arrested for fraud.
  • Friend in the Black Market: He protects himself from harm by using his connections to procure items for the other inmates. Bones only ever demands drugs; whereas Zack’s requests are more…unusual.
  • Karma Houdini: Only because Zack has better things to do than punish a cowardly runt like him. He is also useful to have around.
  • Sycophantic Servant: He is fairly pathetic and ingratiates himself towards anyone in power.


One of the buffer members of Bones’ gang. He eventually sides with Zack.

  • The Bully: To Charlie once he finds out the truth about him.
  • Bully Brutality: When he wants to pick on someone, he really lets them have it, as Charlie finds out.
  • The Dragon: Becomes one to Zack.
  • Dumb Muscle: He is quite gullible and susceptible to Zack’s manipulations. He is also a rather strong person.
  • Heel–Face Turn: Zack convinces him and the others to turn against Bones. He also becomes more sociable once Zack cuts off his drug supply.
  • Good Is Not Nice: He may be on Zack’s side, but he is still a somewhat brutish thug.
  • Jerkass: He tends to pick on weaklings; particularly Charlie. It takes a stern threat from Zack himself to resist the urge to bully people.

Little Micky’s Gang

    ‘Little Micky’ Crane 

A violent black-supremacist who uses his younger but much bigger brother to bully the other black inmates into joining his gang. He runs against Zack in the election for prison representative. Zack eventually turns the tables on him by exposing his hypocrisy and crippling his brother. He later joins the ‘Irredeemables’ and Saif cuts one of his fingers off after he attempts to stage a coup. He later returns the favour.

  • Angry Black Man: After Zack exposes the fact that the other black inmates are only on his side because they are afraid of his brother, he completely loses his composure and resorts to threatening everyone who contemplates leaving him.
  • Arc Villain: He is number five on the list of villains Zack has to contend with and the final one before the appearance of the Big Bad.
  • Big Brother Bully: Downplayed. He is rather uncaring towards Billy and regards him as little more than an instrument of power.
  • The Corrupter: His goal is to turn all the black inmates into Angry Black Men and pit them against the white inmates.
  • Demoted to Dragon: He becomes one of Saif’s ‘Irredeemables’ after he loses an election to Zack. He doesn’t take to it very well.
  • The Dog Bites Back: In retaliation for cutting off one of his fingers, he takes advantage of the chaos and confusion caused by a scuffle Zack initiates to pin remove all of Saif’s fingers without getting caught.
  • Enemy Mine: As much as he hates Zack for removing his power, he hates Zaid even more for removing his finger. For this reason, he goes along with Zack’s plan to clip Saif’s wings (among other things).
  • Fingore: When he attempts to stage a coup and take over the ‘Irredeemables’, Saif puts him in hisplace by removing his ring finger.
  • Green-Eyed Monster: He is envious towards Zack and Saif for their ability to maintain leadership of their respective factions. He even tries to usurp Saif as the leader of the ‘Irredeemables’. It doesn’t go well.
  • Hair-Trigger Temper: He is not the most patient inmate around.
  • Malcolm Xerox: Exaggerated. He can barely open his mouth without insulting the Caucasian inmates and knows pretty much every anti-white racial slur in the book. On top of that, he wants all the other black inmates to be one too. Luckily, he is alone in his fanaticism and quickly slides into Angry Black Man territory after Zack exposes his hypocrisy.
  • Villainous Breakdown: Has one when Zack completely takes away his power.

    ‘Big Billy’ Crane 

Little Micky’s younger brother. He serves as his brothers enforcer and bodyguard and is fiercely loyal to him. He is temporarily crippled after Zack outsmarts him in a fight.

  • Big Little Brother: Hence their names.
  • Career-Ending Injury: Zack tricks him into crushing both his hands so badly that Micky can no longer threaten people with him. It is possible that this is partly an act of mercy on Zack’s part, as Micky can no longer abuse his brother’s loyalty.
  • The Dragon: To Micky.
  • Dumb Muscle: He is the biggest guy around and completely lacks the initiative to think for himself.
  • Even Evil Has Loved Ones: In addition to his brother, he also has a daughter, which is something Zack takes advantage of.
  • Papa Wolf: Zack provokes him into attacking him by threatening to use Charlie’s fictitious contacts to send someone over to ‘play’ with his daughter.
  • Punch-Clock Villain: He is an ‘Irredeemable’ not because he has selfish or sadistic motives like the others, but because he is completely loyal to his brother and even has a daughter on the outside.
  • Scary Black Man: He is Micky’s muscle and the biggest bruiser in the entire story. Even Smithy is wary of him.
  • Token Good Teammate: He is completely loyal to his friends and family and only does what Micky says because he is his brother. In fact, Zack claims that the only reason he is an ‘Irredeemable’ is because he lacks the initiative to defy his brother’s wishes. Zack even regrets having to injure him so badly and hopes that it will at least prevent Micky from using him to threaten people.
  • Undying Loyalty: To Micky, as a result of taking a promise he made to an unnamed relative a little too seriously.

    Shaun Jackson 

A black inmate who secretly tells Zack about the true reasons why all the other black inmates are supporting Micky.

  • Defector from Decadence: He does not approve of Micky stirring up racial hatred and using his brother to bully people into siding with him.
  • The Fettered: His motivation for turning against Micky.
  • Mistreatment-Induced Betrayal: He is pushed to his limits when Billy starts beating people up when they don’t agree with Micky.
  • Reverse Mole: He rats Micky out to Zack. Micky doesn’t take it well when he finds out.

Other Inmates

    Kenneth ‘Kenny’ Homolka 

The most notorious rapist in the prison. He is manipulated by Zack into digging a tunnel to connect the men’s side of the prison to the women’s. Zack betrays him and his fellow rapists and gets them all severely injured. He and several of his friends join Saif’s team of ‘Irredeemables’.

  • Arc Villain: He is the third enemy Zack faces. Subverted in that he is not actively seeking to oppose Zack and it is ultimately Zack who does most of the actual plotting and scheming in this arc.
  • Evil Redhead: His hair is a mass of ginger coils.
  • Green-Eyed Monster: He believes that female criminals have it easier and are therefore more smug.
  • Jerkass: He leaps at the idea of infiltrating the women’s prison and raping all the inmates.
  • Prison Rape: Averted. Everyone knows he’s a rapist and keeps their distance from him and his friends. Zack suggests that he and the other rapists dig a tunnel into the women’s prison, sneak over and rape them all. However, this is a trick, and all the women are fully equipped to fight back.
  • Rape Is a Special Kind of Evil: After using and abusing him and his fellow rapists, Zack tells them this in no uncertain terms. It is one of the rare instances in which he shows genuine emotion and rage.
  • Straw Misogynist: He truly believes that women are playthings and have no purpose other than to appease men’s appetites.
  • You Have Outlived Your Usefulness: A heroic version. Zack pretends to share his desire to take revenge on the female prisoners and persuades him and his friends to dig a tunnel from the men’s side of the prison to the women’s. In actuality, he was actually trying to create a system whereby male and female inmates who were in love could meet be together and was just using Kenny’s group to do all the hard labour. Once the tunnel is finished, he sends the gang into an ambush.

    Isabelle Faye 

A female inmate who is in love with Sbekz and secretly makes friends with Zack. Together, the tree of them devise a plan to create a secret tunnel between the men’s side of the prison and the women’s side, so that she and Sbekz can be together.

  • Hidden Heart of Gold: She pretends to mock Zack and the others so that she can secretly communicate with Zack.
  • Pretend Prejudice: She yells abuse at the male prisoners from her side of the prison. However, she is really giving credence to Zack’s supposed plans for revenge. In truth, she actually has a boyfriend who Zack is trying to help her meet up with.
  • Star-Crossed Lovers: With Sbekz.

    Charles ‘Charlie’ Walter 

A celibate pedophile who Zack befriends. He is used as a pawn in the schemes of both Zack and Saif.

  • Because You Were Nice to Me: He is friends with Zack because he is the only person who has ever accepted him after discovering what he is.
  • Butt-Monkey: Once he is outed deliberately by Zack, he repeatedly becomes a victim of bullying; first by the rest of the gang, then Sgt. Haig and then Saif’s group.
  • Covert Pervert: It alarms and confuses everyone when he tells them how long his sentence is (about as long as a murderer’s sentence), until they find out WHY!
  • Double Reverse Quadruple Agent: LITERALLY! After his true role in the Battle of Wits between Zack and Saif is revealed, Zack even describes him as this WORD FOR WORD!
  • The Quiet One: He is quite uncommunicative on his first day, on account of being afraid of all the inmates and not wanting to let his secret slip. Even after he opens up to Zack, he is the only one that Charlie can talk to freely.
  • Morality Pet: He serves as this to Zack. Despite being used as a pawn like all the other inmates, he is shown to be one of the few people Zack actually cares about on a personal level and only decides to deal with Haig’s menace after he beats Charlie to a pulp for no good reason. He is also one of only two people Zack feels bad about manipulating.
  • Naïve Newcomer: This leaves him wide open to Zack’s manipulations.
  • Nice Guy: Ironically, he is one of the friendliest and most loyal people in the entire story.
  • Pædo Hunt: An extremely rare protagonist version. He is serving a lengthy span for having Lolicon imagery on his computer. He professes that he has never acted on his fantasies. Still, it doesn’t stop him from being beaten and humiliated by the other inmates and prison guards. Zack is the only one who truly believes him, on account of his knowledge of psychology and his ability to distinguish between a ‘Pedophile’ and a ‘Child Molester’. He still uses him to threaten inmates with children when they don’t agree with him.
  • Undying Loyalty: To Zack. Chiefly because he is the only one who genuinely understands and accepts him. Even a psychopathic manipulator like Saif cannot drive a wedge between the two of them.
  • Unwitting Pawn: He becomes Zack’s secret weapon.
  • Vow of Celibacy: Self-inflicted on account of not wanting to harm anyone.

    Jimmy Steiner 

A lock breaking expert doing time for theft.


A murderer who pretends to fight with Smithy as a distraction to get Haig out of his office

    Jeremy Koji 

A kleptomaniacal inmate who Saif recruits in the belief that he can control him but is secretly working for Zack.

  • Allergic to Routine: He develops Kleptomania as a result of living a tediously boring life and now being cooped up in a cell all day.
  • Reverse Mole: Saif, believing he has absolute control over him, tasks him with spying on Zack and his gang. However, Zack is the one who placed him in Saif’s gang to trick Saif into revealing all his secrets.
  • The So-Called Coward: He is portrayed as a Dirty Coward, stealing Zack’s most precious treasure and running to Saif for protection. However, he is secretly looking for action and excitement and is working to destroy Saif’s operation from within.
  • Sticky Fingers: Zack actually weaponizes this.
  • Sweet Tooth: He spends most of his prison wages on bars of chocolate that he eats during his meetings with Saif. Unbeknownst to them, he is also using the wrappers to send secret messages to Zack and the police.
  • Thrill Seeker: The reason for his kleptomania and why he agrees to act as a spy.
  • Token Minority: He is the only Japanese character in the story, despite there being several Asians in the same prison. He serves as this to both Zack’s gang and Saif’s.

Law Enforcers and Officials

    Commissioner Clive Viceman 

A high-ranking and ultra-conservative government official who is technically in charge of the state’s prison system. He sends Officer Reed to spy on the inmates in order to expose their drug-dealing but ends up being blackmailed over his unethical behaviour by Zack.

  • Break the Haughty: Zack sees to this.
  • Corrupt Politician: He is keen to make a name for himself by cracking down on crime and uses some rather underhanded methods to do it, which ultimately get him into trouble.
  • Hoist by His Own Petard: His attempt to expose the level of drug dealing in prison by sending in an undercover cop is foiled when Zack uncovers the truth. He threatens to expose the officer and have him killed, thus, forcing Viceman to choose between risking charges of endangerment and breaching human rights laws and obeying Zack’s every whim.
  • Morality Adjustment: He starts to care less about being used when he sees that Zack’s method of running the prison has caused crime to drop and the ideas Zack forced him to market as his own have actually made him quite popular. This adjustment even spreads to other officials, resulting in the entire prison system changing.
  • Oh, Crap!: When he receives a call from an unknown inmate who threatens to expose the undercover officer he has working inside the prison and have him killed.
  • Out-Gambitted: If he hadn’t tried to send an undercover officer into the prison to gather evidence on drug dealing, neither he nor his agent would have wound up under Zacks control.
  • Overarching Villain: While not technically a villain, he certainly has a very conservative view of law and order and provides quite a contrast to Zack’s liberal approach to dealing with crime. There is a marked difference in the treatment of prisoners between Viceman being in charge and Zack being in charge.
  • Puppet King: A heroic version. Zack blackmails him with information regarding his undercover officer and forces him to implement a large number of changes to prison policy by claiming they are his own ideas. Ultimately, these changes cause re-offending rates to drop and life becomes much more bearable for the inmates.
  • Smug Snake: His unethical attempts to gather information about criminals proves to be his undoing.
  • Stealing the Credit: An interesting variation. Zack makes him tell everyone that the changes to the prison system that are introduced are all his idea, in order to cover up the fact that he is blackmailing him. Whilst not too happy about it at first, he gradually comes to realise that the changes are causing re-offending rates to drop, and the other officials are impressed with him. Obviously, he jumps right on-board the bandwagon.

    DC Harold Mc Douglas 

A good-natured prison warden who believes in rewarding good behaviour. Zack quickly wins favour with him.

  • Big Good: He is the closest the story has to one, as he is the most open-minded officer and frequently enables Zack if his plans are intended to improve the running of the facility.
  • Good Cop/Bad Cop: The good cop to Haig’s bad cop.
  • Nice Guy: He is a surprisingly tolerant and understanding person, considering he sees the darker side of humanity every day.
  • Reasonable Authority Figure: He is always prepared to try something new to improve the running of the prison.
  • Wardens Are Evil: Averted. DC Harold Mc Douglas is the most trusting member of the prison staff and has to periodically put Sgt. Haig in his place.

    Sgt. Dennis S. Haig 

A sadistic prison guard with ultra-conservative views. Zack frames him for drug possession and ends up an inmate in his own prison.

Jerkass: He regards the inmates as the scum of the earth and treats them accordingly.
  • Karmic Transformation: Once he gets sent to prison, he is forced to team up with the very criminals he used to despise.
  • Lawman Gone Bad: He starts of as little more than an aggressive Jerkass: with little to no patience. Later, [spoiler: once Zack changes the system to give prisoners more rights]], his hatred for the inmates builds up to the point where he starts attacking weaker inmates for trivial reasons. Eventually, he gets arrested for a crime he didn’t commit and willingly joins forces with Saif and the other ‘Irredeemables’.
  • Police Brutality: He is the most volatile prison guard and actively enjoys punishing the inmates. He nearly beats Charlie to death.
  • Throw 'Em to the Wolves: Zack gets him arrested for a crime he didn’t commit. By coincidence, he is sent to the same prison he had been working at and Zack delights in letting the other inmates pay him back for all the crap he had inflicted upon them over the years.

    James Garth / Officer Reed 

An undercover officer posing as a drug addict to infiltrate Bones’ gang. Zack steals his mobile containing information about his real identity and blackmails him into becoming an addict. He later comes to respect Zack’s good intentions.

  • Becoming the Mask: He becomes a genuine drug-addict and ultimately comes to realise that there are better ways of dealing with the problem than simply punishing those involved.
  • The Bus Came Back: He eventually leaves his prison assignment to take up a post in counterterrorism. He turns up again towards the end of the book to interrogate Sami and discovers that Zack is helping the authorities dismantle Saif’s organisation, much to his amusement.
  • Defeat Means Friendship: Once Zack has beaten him down and used him to gain control over the rest of the prison, the two of them actually start to bond. Zack even shares some private thoughts with him.
  • Friendly Enemy: He comes to regard Zack as both his friend and his nemesis.
  • Guilt-Ridden Accomplice: He almost ruins Zack’s plan when contemplates revealing his involvement to Paul.
  • Humiliation Conga: After Zack uncovers his secret, he is put through a brutal hazing, loses his chance at promotion, becomes addicted to Spice and winds up a pawn in Zack’s schemes.
  • The Mole: He is secretly trying to identify all the inmates who are dealing in Spice.
  • Oh, Crap!:When Zack reveals to him that he has stolen his mobile phone and now knows everything about him, including his real name and job as an undercover cop, he realises that Zack has him completely under his thumb.
  • Out-Gambitted: When he thinks he has everything he needs to get Bones’ gang into trouble and earn himself a promotion, Zack takes it all away from him in an instant.
  • Stockholm Syndrome: He gradually starts to see the kinder side of the sociopath who is controlling him and even learns to respect his methods.
  • Sympathy for the Devil: See above.
  • This Cannot Be!: He has this reaction when Zack convinces him that he has a gang of cronies on the outside who know his real identity and will kill him if he gets anyone into trouble.

    Officer Jeff 

A prison guard who is secretly being extorted by Saif.

  • Defeat Means Friendship: He and Zack become quite close after Zack gets all fo Saif’s cronies arrested, including Jeff himself. Understandable, as he was feeling guilty about everything he had done and was not happy about working for Saif in the first place.
  • The Dragon: To Saif, albeit reluctantly.
  • Easily Forgiven: Zack is quite understanding of him when he is arrested for his crimes and even asks him to take over his role once he is released from prison. Of course, this is partly to ensure he remains in the spotlight and cannot plan anything behind everyone else’s back.
  • The Mole: He acts as this for Saif.
  • Papa Wolf: He is devoted to his daughter, which is why he has to put up with all the torment Saif drags him through.
  • Regretful Traitor: He is deeply unhappy about having to work for Saif behind the authorities’ backs.
  • Take Care of the Kids: A non-fatal example. Zack asks him to protect Charlie once he is released from prison and unable to do so.
  • Token Good Teammate: He hates working for Saif and is actually a decent person.
  • Trapped in Villainy: Saif is supplying the funds to pay for his daughter’s medication, on the proviso that he cooperates. He is eternally grateful to Zack when he contrives a solution to his problem by using Saif’s bail money to pay the medical bills instead.
  • Welcome Back, Traitor: See Easily Forgiven above.

Outside Gangs

Danny’s Gang


A gang leader who rapes Rose while forcing Zachary to watch. Zack punishes him by turning his own friends against him, carving a lump of flesh out of his arm and threatening to cut his testicles off.

  • Arc Villain: He is the first of Zack’s opponents.
  • Hoist by His Own Petard: His own gang turns on him.
  • Humiliation Conga: His own friends turn against him in the name of entertainment, he suffers a Groin Attack, he loses a large chunk out of his arm and he is left traumatised for life.
  • Groin Attack: It would have been a LOT worse if Rose hadn’t taken pity on him.
  • Post-Rape Taunt: He calls Rose a ‘real party girl’ after he rapes her and tells his fellow gang members to cheer for her.


A female member of Danny’s gang.

  • All Girls Want Bad Boys: She hangs around with a gang of street thugs and rapists.
  • Dark Chick: She is just as perverse as her male teammates.
  • Goth: She fits in well with the boys.
  • Karma Houdini: Her fate is left unclear. Though, she was most likely arrested along with the rest of the gang.


A member of Danny’s gang with Schizophrenia and a violent personality. Zachary kills him to save Rose and himself. It is this murder that sends Zachary to prison.

  • Ax-Crazy: He is clearly psychotic.
  • The Corrupter: Zachary determines that Spike is an ‘Irredeemable’ and the worst influence on the rest of the gang.
  • Eye Scream: After being stabbed in the chest, Zachary hastens his death by stabbing him in eye, causing him fatal brain damage.
  • Insane Equals Violent: He is the most vindictive of the gang and is described as the inspiration for the others’ violence.
  • Killed Off for Real: He is one of the few characters to die in the story.
  • Mercy Kill: Zack decides that this is the only way to deal with a psychotic criminal.
  • Psycho Supporter: Towards Danny.


The dumb muscle of Danny’s gang.

  • Bit-Part Bad Guys: Apart from being Spike’s friend and one of Zack’s surviving victims, he has little relevance to the plot.
  • Dumb Muscle: Almost categorically stated.

Other Characters

    Rose / Rosemary Vane 

Zachary’s love interest who is raped near the beginning of the book. She becomes scared of his ‘Zack’ persona after he goes on a Roaring Rampage of Revenge against those responsible. She still consults with his family to see how he is doing in prison. She eventually overcomes her fear when he saves her from a mugger and reverts back to his original personality.

  • Back for the Finale: Zack accidentally meets her again after he is released from prison at the end of the book. The final chapter ends with the two rediscovering their feelings.
  • Break the Cutie: She is raped by street thugs, almost gang-raped afterwards and then sees the man she loves brutally maiming, stabbing and killing the ones responsible. Not only is she scarred for life, but no longer sees Zachary as the man she loved.
  • Damsel in Distress: She finds herself the victim of both a rape and a mugging. Zack is unable to save her from the former but succeeds in saving her from the latter.
  • Heal the Cutie: After Zack saves her a second time, this time from being killed, she sees him break down in tears and weep about what he has become. She realises that the Zachary she knew is still there and is finally able to push past her fear and return to him. The story ends with the two of them embracing.
  • Lazy Alias: Zack simply calls her ‘Rose’ when he talks about her and occasionally says that it is short for ‘Rosette’. This is all a ruse to keep her safe from any of his enemies, as her real name ‘Rosemary’.
  • Shrinking Violet: She has always been a rather shy girl, even more so after her ordeal.
  • Tears of Fear: She has plenty of reason to be afraid, and Zack is one of them.


One of Saif’s terrorist contacts.

    Unknown Mugger 

A mugger who threatens to kill Rose in the final chapter. Zack rescues her.

  • Dirty Coward: He runs away at even the suggestion that Zack has a criminal gang ready to kill at a moment’s notice.
  • Knife Nut: His weapon of choice. He would even prefer to skin a woman rather than rape her.
  • Nice Job Fixing It, Villain!: It is because of his attack on Rose that she and Zack are brought together again and can work out their issues.
  • No Name Given: His name is never mentioned.
  • Post-Climax Confrontation: He is the last threat Zack has to face.

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