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Valhalla State Penitentiary

Inmates

    Donut 

Franklin Delano Donut

"Any love in this prison is awesome. Seriously, there's a lack of it. It's depressing."

A kindhearted prisoner arrested for killing his roommate in self-defense.


  • Beware the Nice Ones: Donut is the only prisoner who can accurately be described as good, but he's also one of the best fighters in prison.
  • Break the Cutie: Prison slowly but surely breaks Donut.
  • Butt-Monkey: Donut takes a lot of punishment over the course of the story, from mild ribbing to horrific beat downs.
  • Crime of Self-Defense: He killed Maine in legitimate self-defense, which he went admittedly overboard with out of panic. Donut's ignorance about Maine's actual motive and the amount of times he stabbed him results in Donut being sent to prison.
  • Crouching Moron, Hidden Badass: Donut is kind and somewhat ditzy, but he is a vicious fighter and a Combat Pragmatist who is capable of astonishing brutality.
  • Ear Ache: O'Malley cuts off his ear after stabbing him repeatedly tasks a message to Doc.
  • Failed a Spot Check: He somehow manages to miss that Simmons and Grif are a couple for five years.
  • Good Is Not Soft: He's probably the only person in the prison who can be qualified as 'good', but he's absolutely vicious in a fight.
  • Knight in Sour Armor: He develops into this over the course of Volume 2 after undergoing a Trauma Conga Line. He still tries to do the right thing, but he's a bitter cynic and viciously pragmatic when it comes to his own survival.
  • Made of Iron: He takes a lot of punishment, but always comes bouncing back.
  • NaĂŻve Newcomer: He starts off as very much at odds with prison life. He wises up after Church bluntly tells him he'll get himself killed, or worse, end up alone.
  • Nice Guy: Donut is perpetually kind and empathetic, and is almost always concerned with helping others.
  • Not-So-Harmless Villain: Wash, Delta, and eventually Church are convinced that he's this due to him murdering the Meta.
  • Poor Communication Kills: Maine's attempt to knock him out results in Donut becoming convinced he's trying to murder him and killing him in turn.
  • Prison Changes People: The more time he spends in prison, the more violent he becomes. He's warned multiple times in Volume 3 that he'll be unable to readjust to the outside world if he continues to immerse himself in prison culture.
  • Took a Level in Badass: Deconstructed. Donut slowly turns into a badass, but it's frequently pointed out that it's making him unsuited to life outside the prison.
  • Took a Level in Cynic: After going through a Trauma Conga Line in Volume 2, Donut becomes increasingly cynical and bitter about life in the prison.
  • Took a Level in Jerkass: Downplayed. After O'Malley nearly kills him, Donut becomes increasingly brooding and volatile. He's by no means a jerk, but it's noticeable enough that people start to worry about him.
  • What Have I Become?: He has this reaction after he bites O'Malley's tongue out. It triggers something of a downward spiral for Donut, and causes him to increasingly immerse himself in prison culture.

    Church 

Leonard L. Church/Alpha

A former member of Delta's crime syndicate who now runs a blackmailing ring around the prison.


  • Anti-Villain: Church is no saint, but he's got standards and he does have something of a heart.
  • Deadpan Snarker: He's always ready with some sort of snarky comment.
  • Even Evil Has Standards: He's absolutely disgusted by prison rape and refuses to engage in it.
  • Even Evil Has Loved Ones:
    • He genuinely loves his younger brother Epsilon. Keeping him safe was what motivated him into a life of crime to begin with.
    • He also cares deeply for Tucker and does his best to protect him.
    • To a lesser extent, he cares about Donut and Caboose.
  • Everyone Can See It: Pretty much everyone is aware of his crush in Tucker except for Tucker himself.
  • Friend in the Black Market: He positions himself as this after Wyoming dies.
  • Hidden Depths: Lampshaded when he reveals he read Frankenstein.
    Church: So I read a book once, big fucking deal!
  • It Gets Easier: Double Subverted in the rewrite. He claims to Donut that killing was always easy for him, but his flashbacks show that he was lying through his teeth and that this more or less applies.
  • Jerkass: He's foul-mouthed, cynical, and very ruthless and manipulative. He spent years lying to Caboose to use him as his personal muscle.
  • Jerk with a Heart of Gold: Downplayed. Church is a horrible person, but he still cares about his friends and can be surprisingly caring to those close to him.
  • Noble Demon: He's got his own sense of scruples and is against causing any unnecessary violence.
  • Protagonist Journey to Villain: His flashbacks chronicle him falling deeper and deeper into a life of crime to protect Epsilon.
  • Self-Made Orphan: He murdered his own father to stop him from killing Epsilon. It still haunts Church in the present day, even though he has no regrets about the murder.
  • Sir Swears-a-Lot: Church swears the most out of an already foul-mouthed cast. It gets to the point that the one trait people are willing to admit about him during his time of Alpha is his penchant for cursing.
  • Wrong Genre Savvy: After Tucker chews him out after finding out about Church's crush on him, Church, inspired by various romance movies, gives him a Forceful Kiss in the middle of the argument. Rather than instantly resolve it, Tucker is horrified and left even angrier at him.

    Tucker 

Lavernius Tucker

A perverted con artist and Church's right-hand man.


  • invoked Badass Decay: Invoked. Tucker starts out as one of the most feared inmates in the prison and an expert con man, but his injuries gradually catch up to him and by Volume 3, he's a blind, weak old man unable to defend himself. He lampshades it, noting that he and Donut have the opposite problem; while Tucker has grown to weak to go back to life outside the prison, Donut has become so acclimatized to the prison culture that he too cannot readjust to the outside world.
  • Blind Black Guy: After Miller blinds him during the riot.
  • Butt-Monkey: Tucker takes a ton of increasingly painful injuries over the course of the story.
  • Deadpan Snarker: He's always ready to snark at everyone near him, especially Donut.
  • Eye Scream: Miller pretty much stabs his eyes out during the riot.
  • Even Evil Has Loved Ones:
    • He deeply loves his son Junior. It's also deconstructed, since the language barrier means that for all that he cares, he doesn't actually know his son.
    • He eventually reciprocates Church's feelings for him, and begins a relationship with him. Admittedly, it's at least partially motivated by him being blinded.
  • Ignored Epiphany: Tucker regrets many of his crimes, such as stealing from C.T., kidnapping Terrence]], and inadvertently driving Jones to suicide, but he always rationalizes that it's too late to change anything and never learns from it.
  • Jerk with a Heart of Gold: Downplayed. Tucker freely admits to being a terrible person, but he cares about his friends and feels guilt for some of his crimes.
  • Now What?: He eventually realizes that he doesn't know what he'll do after parole when he starts getting close to it. He's blind, has lung problems, and prison is essentially all he knows.
  • Papa Wolf: To Junior. The entire reason he's in prison is because of a brutal campaign he went on to rescue him from Pillman.
  • Sense Loss Sadness: He gets depressed after losing his eyesight since he'll never see Junior grow up.

    Caboose 

Michael J. Caboose

A mentally handicapped inmate who serves as Church's main enforcer.


  • Affably Evil: He's almost always polite and cheerful.
  • Anti-Villain: Caboose isn't evil, but his inability to distinguish between right and wrong, his gullibility, and mental disabilities result in him being one of the lost dangerous inmates. Donut's influence helps him step out of the villain territory, for the most part.
  • Ax-Crazy: A borderline case, though he stops being this after his Heel Realization.
  • Cruel Mercy: Part of the reason he chooses to let Grif live after learning he caused the car accident that left him brain-damaged is that he recognizes that Grif wants to die so he can be with Simmons, and that denying him death that will be even more painful for him than killing him.
  • Dumb Is Good: Averted. Caboose is definitely innocent, but that's not the same as good, and he's very prone to murdering and injuring other people, even by accident.
  • Heel–Face Turn: Donut's influence slowly gets him to change his murderous ways.
  • Heel Realization: Church bluntly telling him that he's a murderer and that Church manipulated him into being his enforcer triggers one, leading to his Heel–Face Turn.
  • Kindhearted Simpleton: Subverted. He's Affably Evil, but that belies how utterly vicious he can be. He slowly steps into this territory for real due to Character Development.
  • Psychopathic Manchild: Though he's light on the 'Psychopathic' element, he's still more than willing to kill and maim at Church's behest. Donut's influence gets him to drop the 'Psychopathic' part entirely.
  • Unwitting Pawn: He's very easy to manipulate. O'Malley very quickly turned him into a pawn, and Church manipulated him into being his enforcer for years on end.

    Simmons 

Richard "Dick" Simmons

A shy, nerdy inmate.


  • Accidental Murder: In the rewrite, he and Grif were only trying to rough up their victim, not kill him. It's implied that Simmons was responsible for it because he whacked the man in the head with a baseball bat.
  • Affably Evil: He's pretty friendly, but it's made very clear that Simmons is still pretty cold-blooded.
  • The Cracker: He served as a freelance hacker before going to prison.
  • Cruel and Unusual Death: He's disemboweled by the Red Zealot.
  • Deadpan Snarker: Very prone to throwing out a sarcastic barb, especially to Grif.
  • Died in Your Arms Tonight: He dies in Grif's arms after being fatally wounded by the Red Zealot.
  • Even Evil Has Standards: He's disgusted by prison rape.
  • Jerk with a Heart of Gold: He's a cold-blooded killer, but he's very caring and protective of his friends.
  • Not-So-Harmless Villain: His nerdy, friendly personality and his and Grif's bickering makes him seem harmless, but it only belies how downright vicious the two get when slighted.

    Grif 

Dexter Grif

A lazy, crude inmate.


  • The Alcoholic: He's very prone to making pruno in his cell. He later descends into further alcoholism and drug use after Simmons is killed.
  • Butt-Monkey: Nothing seems to go right for him in Volume 3.
  • Deadpan Snarker: He has a very dry wit, and he's not afraid to use it.
  • Drowning My Sorrows: In Volume 3, he descends further into alcoholism and drug use due to his grief over Simmons's death.
  • Heroic BSoD: After Simmons dies, Grif goes into a suicidal, depressed funk which he never quite gets out of.
  • Implausible Deniability: He denies being high to Donut in spite of how blatantly obvious it is.
    Grif: Don't step on the floor!
    Donut: …Why? What's wrong with the floor? Did you spill your pruno again?
    Grif: The floor's jello! You'll sink! You step on the jello, you'll sink. You'll fall and vanish and I'll be the only non-ghost Red left except Lopez and he doesn't speak English so he doesn't really count as company.
    [An incredulous Donut walks forward]
    Grif: Donut, no! Don't do it! You have so much to live for!
    Donut: There, see? I'm fine.
    Grif: Holy shit. You're like Prison Jesus… or I'm even higher than I thought I was.
    Donut: Grif, what did you take?
    Grif: You can't prove nothing!
    Donut: You literally just told me you were high.
    Grif: That won't hold up in court.
  • Knight Templar Big Brother: He's insanely protective of Sister. He once chased Simmons up a tree for having sex with her, and he's only in prison because he accidentally beat a drug dealer to death for having caused her to nearly OD.
  • Lazy Bum: He's a card-carrying slacker who brags about how laziness is a familial trait, and can frequently be seen taking naps when everyone else is long since awake.
  • Not-So-Harmless Villain: His laziness and his and Simmons' bickering makes him seem harmless, but it in belies how vicious the two can get when slighted.
  • The Old Convict: He serves as this in Volume 3, by which point he's become one of the older inmates, and is now semi-reluctantly mentoring the new inmates.
  • Trademark Favorite Food:

    Lopez 

Lopez

A cynical inmate who only speaks Spanish.


  • Deadpan Snarker: Every word out of his mouth is some kind of snark at the idiots around him.
  • The Dragon: O'Malley temporarily gets Lopez to serve as this to him, but Lopez abandons him after it's clear that O'Malley is mo trouble than he's worth and being forced to help him mutilate Donut.
  • Only Sane Man: He's the only well-adjusted and mature inmate in the Row, and even outside of it.
  • Surrounded by Idiots: He's (probably rightfully) convinced that the rest of the inmates are all morons, which unfortunately gives him the bad habit of underestimating them too.

    O'Malley 

O'Malley/Omega

A sadistic, psychopathic serial killer and a former member of Delta's crime syndicate.


  • Asshole Victim:
    • Doc's constant drugging of him would be horrifying, were it not for the fact that O'Malley constantly rapes and tortures him for fun, and the only reason he did it was out of fear. Even when it does permanent damage to his hands, it's hard to feel a drop of sympathy for him.
    • When he finally dies at the hands of his longtime victim Doc, the only real response is And There Was Much Rejoicing. The only reason people actually care that he died is because his death sets a precedent about what guards are allowed to do to prisoners.
  • Ax-Crazy: O'Malley is psychotically violent, constantly retaliating to the simplest of slights with gruesome revenge and even murdering random people just to fuel his sadism.
  • Attention Deficit... Ooh, Shiny!: If he's bored with something, O'Malley's attention will rapidly shift to whatever he finds interesting, even if it's very self-destructive. It gets even worse when he's on the medication, which makes him unable to pay attention to anything for a long period of time.
  • Bait the Dog: It initially seems like he genuinely cares about Doc, but it quickly becomes clear that O'Malley only cares about him in terms of finding his suffering particularly enjoyable.
  • Big Bad: Of the first two volumes. O'Malley serves as the main threat, often manipulating conflict for his own ends and causing problems for all of the main characters with his sadism and ruthlessness. He becomes part of a Big Bad Ensemble in Volume 3, which ends when he dies a third of the way into it.
  • Card-Carrying Villain: O'Malley gleefully embraces what he is, and makes no bones about being pure evil.
  • Faux Affably Evil: He's funny and charismatic, but still an absolute monster with no redeeming qualities.
  • For the Evulz: O'Malley is always trying to torture people physically and psychologically because it's the only thing that gives him joy.
  • Freudian Excuse: Averted. O'Malley had very loving parents and a privileged upbringing, but he still turned into a serial killer because he liked looking at animal's insides.
  • Hidden Depths: O'Malley genuinely liked being a surgeon, even if he only did it so he could see people's insides.
  • Jerkass: Definitely. He's always doing something horrible just for kicks, and is an asshole in general.
  • Lack of Empathy: He sees everyone around him as little more than playthings that he breaks for his amusement.
  • Moral Myopia: He rapes and tortures Doc for years on end, yet acts like him leaving is the most heinous thing ever.
  • No Medication for Me: He's constantly trying (and failing) to dodge his medication because it ruins his attention span. He stops after Sheila switches him to another medication that doesn't have these negative side effects.
  • O.O.C. Is Serious Business: He panics for the first time in the entire fic when Doc kills him in the most peaceful manner possible, the way O'Malley hates the most.
  • Psychopathic Manchild: O'Malley has the temperament of a spoiled child. He's convinced that everyone else are his playthings, and his response to when they don't do what he want is to basically throw a giant, murderous tantrum.
  • Sadist: O'Malley loves tormenting people. Pretty much everything he does is to cause suffering just so he can enjoy it.
  • Tongue Trauma: Donut bites off his tongue when he tries to rape him.
  • Undignified Death: Doc forces him to have a morphine overdose and leaves him to die quietly and peacefully, the worst possible death for someone like O'Malley.
  • Villainous Breakdown: He starts panicking very quickly when Doc kills him, showing terror for the first time in his life.
  • Yandere: He's absolutely obsessed with Doc, and he gets very angry very fast whenever he things Doc is trying to leave him, which of course leads to lots of death and mutilation.

    Wyoming 

Wyoming

An elderly inmate and the main source of illegal items within the prison.


  • Dirty Prison Guard: Wyoming was initially a guard, but he was so corrupt and brutal that he was eventually locked up and imprisoned. He managed to survive in spite of his former occupation by using his connections to form a smuggling ring that became invaluable to the prison economy.
  • Friend in the Black Market: He runs a smuggling ring that pretty much every inmate buys from. He'll happily sell to rivaling factions, simply because he's secure from retribution due to being the only game in town.
  • It Amused Me: He only really helps O'Malley because he finds what he does fun to watch,
  • The Old Convict: He's the oldest and most knowledgeable inmate. However, while Wyoming is respected for his longevity, it's also an open secret that he'll betray anyone in a heartbeat and the only advice he gives is generally part of his manipulations.
  • Wild Card: He constantly switches sides at lightning speed depending on who can pay him he most, secure in the knowledge that his smuggling ring has made him too valuable to kill. He finally pushes his luck too far when he helps O'Malley cause a riot so he can escape, and Flowers guns him down.

    Miller 

Miller

The leader of the check counterfeiters who has a grudge against Tucker.


  • Anti-Villain: He's undoubtedly a bad guy, but he's not that different from Church and Tucker morally speaking and his motivations are understandable. This lessens after he gets back from prison, by which point Miller has crossed the Despair Event Horizon and become far more vicious than either of them.
  • Fingore: Caboose breaks his fingers, and Doc's incompetence at medicine mangles them further and irreparably.
  • It's Personal: He wants revenge on Tucker for driving Jones to suicide, though as Tucker points out, it would come across as more sincere if he stopped getting Jones' name wrong.
  • Politically Incorrect Villain: He calls Tucker "boy" while trying to murder him during the riot.
  • Slashed Throat: Church kills him by brutally slicing his throat open.
  • Slowly Slipping Into Evil: He becomes increasingly vile over the course of his quest to get revenge in Tucker.
  • Took a Level in Jerkass: He's much more vicious after going back to prison and more prone to unnecessary brutality.

    Delta 

Delta/"Denzel"

The former leader of a crime syndicate that rivaled the Director.


  • The Atoner: He feels some guilt over what happened to Carolina and Wash, which pushes him into befriending York.
  • Freudian Excuse: His father relentlessly trained him to follow in his footsteps, leaving Delta coldly logical and unable to do anything other than be a criminal because he doesn't know anything else.
  • Legacy Character: It's mentioned that Delta's father was also known throughout the criminal underground as Delta, and that the current Delta took over the name and identity after his father's death in order to keep his work going.
  • Odd Friendship: He develops one with York, in spite of having (unbeknownst to York) killed his wife Carolina.
  • Tyke Bomb: His father trained him and Theta from birth to be criminals. As Delta bitterly notes, he only became a criminal because he doesn't know anything else.

    C.T./Pillman 

Jake Hawke/C.T./Pillman

"I do what I'm good at, and what I'm good at is bullshit."

A career criminal working for Hargrove who shares the "C.T." alias with Connie and the leader of the Innies.


  • Arch-Enemy: To Tucker.
  • Ax-Crazy: Downplayed. He seems pretty stable, but he's a little too obsessed with tomahawks, and once attacked a guy with one.
  • Friendly Enemy: With Florida. The two are on directly opposing sides and get along like a house on fire.
  • Underestimating Badassery: He immediately dismisses the Row as weak because of their Noble Demon qualities.

    Sharkface 

Terrence "Sharkface" Hawke

Pillman's somewhat eccentric foster son.


    Locus 

Samuel "Locus" Ortez

A quiet and menacing inmate.


  • Dehumanization: He views himself as little more than a gun to cope with his murders.
  • The Stoic: He's almost perpetually calm.
  • Tyke Bomb: As a child, he was trained by Rhee Sebiel to become an expert assassin. This has unfortunately left him with loads of mental health problems.
  • The Quiet One: He's perpetually quiet, which most of the inmates find creepy.

    Felix 

Isaac "Felix" Gates

A manipulative inmate.


  • Adaptational Nice Guy: Subverted. He initially seems like a genuinely nice tattoo artist who is surprisingly not an asshole, but it quickly turns out to have been a mask.
  • Bitch in Sheep's Clothing: He acts like a harmless inmate, but it quickly becomes clear that he's a dangerous sociopath.
  • Faux Affably Evil: He's very good at playing nice, but it's all a ruse.
  • Odd Friendship: With Donut, though it's left ambiguous how genuine it truly is.

    Palomo 

Palomo

A naive, but kindhearted inmate.


  • Kindhearted Simpleton: He's naive to a truly mind-blowing degree, but a genuinely nice guy. He's only in prison because he was tricked into carrying marijuana, which he thought was lawn clippings.

    Bitters 

Bitters

A cynical inmate arrested for cooking meth.


  • The Cynic: He's a very pessimistic and blunt man who seems to view going to prison as the natural next step for him.

    Matthews 

Matthews

A nervous, friendly inmate arrested for cooking meth.


  • Berserk Button: He gets uncharacteristically angry when Grif offers Bitters drugs.
  • Generation Xerox: He bears a lot of resemblance to Simmons: a shy, awkward, but friendly nerd.
  • Nice Guy: He's surprisingly a genuinely nice person, if socially awkward.

    The Red Zealot 

The Red Zealot

The unhinged, fanatical leader of the Zealots.


  • Alas, Poor Villain: He dies asking the flag if he had failed it, and wondering why it had forsaken him.
  • Ax-Crazy: He's totally insane, and will murder anyone if he thinks the flag needs sacrifices.
  • Even Evil Has Standards: He's reluctant to go along with O'Malley's orders to kill Donut, and quietly begs the flag for forgiveness when he goes after him.

    Andy 

Andy

A pyromaniac prisoner.


  • Bus Crash: He's killed in-between Volume 2 and Volume 3 over his role in the riot. It's justified, since his last scene in Volume 2 made it very clear that the entire prison was out for his blood over his role in the riot.
  • Jerkass: Andy is an unmitigated douche who is constantly insulting people.
  • Killed Offscreen: He's murdered offscreen for his role in the riot by an unknown party.
  • Pyromaniac: He loves lighting things (and people) on fire. The only reason he participates in the riot is the opportunity to do this on a massive scale.
  • The Scapegoat: The inmates and guards collectively blame him for the massive riot in Volume 2; while Andy admittedly played a large part in it, the masterminds were O'Malley, Miller, and Wyoming. Being as the former is adept at keeping off the radar of the prison as a whole and the latter two die during the riot, Andy is left with the entire prison baying for his blood.
  • With Friends Like These...: Caboose is his friend and trusts him absolutely, which Andy exploits by lighting him on fire for fun repeatedly, and later manipulating him on O'Malley's behalf.

    Birdie 

Birdie

A former sniper and a member of the Innies.


  • Affably Evil: He's pretty laid-back and charming, which makes him very well-suited to being a drug dealer.

    Demo 

Demo

A member of the Innies.


  • Artificial Limbs: He has a batter-powered prosthetic arm after he lost his arm to explosives while in a mission with Pillman. He's still pretty bitter about it, especially since someone stole his prosthetic arm's batteries to use for the remote control and he can't buy batteries due to being, y'know, in prison.

    Santa 

Santa

A bilingual inmate.


    Andersmith 

John Elizabeth Andersmith

An inmate and a former fixer.


Staff

    Doc 

Frank "Doc" DuFresne

The incompetent but well-meaning prison doctor.


  • Break the Cutie: O'Malley's abuse gradually convinces Doc that he's worthless and should just sit down and take it so O'Malley won't lash out again. It culminates in Doc losing his pacifism and murdering O'Malley in cold blood.
  • Butt-Monkey: Life is pretty much hell for Doc, especially since O'Malley will always step in to ruin things whenever things look like there going well for him.
  • The Dog Bites Back: He finally snaps after O'Malley tortures Wash just to get back at him and forces him to have a drug overdose, then leaving him to die quietly and peacefully, the way he hates the most.
  • Heel Realization: After O'Malley gives him a "The Reason You Suck" Speech about how dangerously incompetent he is at medicine, Doc leaves his position, feeling it's for the best.
  • Nice Guy: He's incompetent, but he genuinely cares about helping people and always means well.
  • Prison Rape: In spite of not being an inmate, O'Malley frequently subjects him to it.
  • Secretly Selfish: Doc's desire to become a doctor is motivated more by wanting to feel useful and be liked than anything else.
  • There Are No Therapists: Averted. Hr's rehired as the prison therapist, and while he' still incompetent, he actually does do wonders for Wash's mental health.
  • Thou Shalt Not Kill: As a pacifist, Doc is deeply opposed to violence or killing. Eventually, though, he snaps and murders O'Malley.
  • Wide-Eyed Idealist: He starts off as one. O'Malley gradually beats it out of him.

    Wash 

Washington

A disturbed, cynical guard.


  • Jerk with a Heart of Gold: In Volume 3, he's mellowed out into being this. He's still cold and blunt, but he's stopped brutalizing the prisoners and has become a pretty good friend to Doc and York.
  • Kick the Dog: Wash repeatedly endangers Donut's life throughout Volume 2 just so he can see how he killed Maine.
  • My God, What Have I Done?: He's horrified when O'Malley reveals he's been raping and torturing Dic for years, since Wash was the one who dragged him back to the prison.
  • Took a Level in Kindness: He's mellowed out greatly in Volume 3, thanks to Doc's therapy sessions.

    Sarge 

Sarge

The deranged warden of the prison.


    Tex 

Ally "Tex" Church

Church's cynical, tough ex-girlfriend.


  • Anti-Hero: She's corrupt and hypocritical, but Tex is legitimately committed to doing the right thing and does her best to keep violence from breaking out in the prison.
  • Dirty Prison Guard: She smuggles in items for Church after he takes over Wyoming's operation and she helps Tucker and Caboose break Donut's leg after he betrays Church.
  • The Dreaded: She's one of the most feared guards alongside Wash because she will not hesitate to beat the crap out of unruly prisoners.
  • Hypocrite: She calls out Church on killing Miller in self-defense, but as he points out, it's not that different from how she allowed Donut's leg to be broken.
  • One-Steve Limit: Averted. She has the same last name as Church and Epsilon.

    Flowers 

Captain Butch Flowers/Florida

The cheery head of the prison guards.


  • Affably Evil: He's cheerful, friendly, a good friend, and absolutely committed to the idea of rehabilitation. He's also a ruthless and brutal killer working for the Director.
  • Combat Pragmatist: He won't hesitate to use a Groin Attack to win a fight.
    Flowers: You always forget to guard the crotch, Hawke.
    C.T.: That's a coward's move.
    Flowers: No, it's a pragmatic move.
  • Friendly Enemy: With Pillman. The two are on directly opposing sides, but they get along like a house on fire.
  • Hypocrite: He's shown at one point hectoring at honesty, when he is in fact The Mole for the Director.
  • Jaded Washout: Florida is stewing with anger and resentment about how his talents are wasting away while he serves as The Mole at the prison.
  • The Mole: He and South are keeping an eye on the prison for the Director. Florida is more than a little bitter about it.
  • Vitriolic Best Buds: With Sarge.
  • Walking Spoiler: It's hard to talk about him without revealing he's a spy for the Director.

    York 

York

A reasonable guard and Wash's best friend.


  • Nice Guy: Deconstructed. He's friendly and personable, but he also enables Wash's abuse of Donut because of his loyalty to Wash and his fellow guards.
  • Reasonable Authority Figure: Downplayed. He's affable enough and is surprisingly concerned with the prisoners' welfare, but he still covers up Wash's brutality.

    South 

South

A bullying guard.


  • Even Evil Has Standards:
    • She does regret handing Wash over to Delta's syndicate to be tortured.
    • She's horrified when North brutally beats Grif and sends him, Donut, and Caboose into the SHU simply because he accidentally broke her nose.
  • Jerkass: She's absolutely self-centered and a bullying asshole in general.
  • The Mole: She's keeping an eye on the prison on the Director's orders.

    North 

North

South's more reasonable brother.


    Sheila 

Dr. Sheila Filss

The prison doctor after Doc's resignation and Henderson's death and Lopez's wife.


  • Action Girl: She knocks a zealot out with a single blow in spite of having been stabbed by the man.
  • Combat Pragmatist: She knocks a zealot out using a bedpan she happened to be holding.
  • Deadpan Snarker: It's subtle, but she definition a penchant for wry quips.
  • Nice Girl: She's very compassionate and empathetic to her patients and goes above and persons to help them, even if they are prisoners.
  • Undying Loyalty: To Lopez, to the point of having herself assigned to the prison just to stay with him. To a lesser extent, she has this to Caboose, sticking with him long after any other doctor would have abandoned him.

    Niner 

Niner

The warden after Sarge is fired.


  • Redeeming Replacement: To Sarge. While he was an incompetent buffoon, Niner is very much on the ball and runs a very tight ship.
  • Wardens Are Evil: Averted. She's competent and pragmatic, but refuses to tolerate any prisoner abuse up to a point and does her best to keep the level of deaths in Valhalla down.

    Kimball 

Vanessa Kimball

The prison's compassionate social worker.


    Doyle 

Donald Doyle

The prison's accountant.


    Henderson 

Walter Henderson

The prison doctor after Doc resigns.


  • Logical Latecomer: Much of his limited screentime is spent questioning the prison's idiosyncrasies.
  • We Hardly Knew Ye: He's only around for one day before the Zealots disembowel him.

    Stassney 

Stassney

"God bless the prison code."

An eccentric guard.


  • Cloudcuckoolander: Stassney is just weird, constantly rambling about random topics and refusing to break up fights between inmates because they're shirtless and he thinks it's hot.

Outside

Delta's Gang

    Sigma 

Sigma

Delta's right-hand man.


    Gamma 

Gary/Gamma

A consummate liar and con man.


    Meta 

Maine/Meta

Formerly one of the Director's men, he serves as the gang's muscle.


  • Mistaken for Murderer: What caused his death. His attempts to knock Donut out were interpreted as a murder attempt, and Donut stabbed him to death in perceived self-defense.
  • Noble Demon: He's a ruthless brute, but he deeply cares for the rest of the gang and, to an extent, Donut, and he has a strong sense of loyalty.
  • Poor Communication Kills: His attempts to knock Donut out after Epsilon arrives gets him killed when Donut mistakes it for a murder attempt and reacts appropriately.
  • Undying Loyalty: He is unendingly loyal to Delta's gang, even deciding to go along with Epsilon's doomed plan to rescue Church in spite of being well aware it likely won't end well for them.

    Epsilon 

Eddie Church/Epsilon

Church's younger brother.


  • Adaption Personality Change: Justified. In canon, Epsilon was essentially a revival of Church and had the same personality as him; here, Epsilon has a vastly different characterization as Church's semi-innocent brother.
  • Morality Pet: He's one of, if not the only person in the world that Church treats kindly.
  • Nice Guy: He's rather sweet-natured and empathetic.

    Theta 

Theta

Delta's brother.


The Director's Crime Syndicate

    The Director 

Leonard Church/The Director

The leader of a powerful crime syndicate.


    Carolina 

Carolina Church

The Director's daughter and Tex's sister, who serves as one of his henchmen.


  • Well Done Daughter Girl: Carolina is bitterly aware of how the Director's favorite daughter is Tex, which motivates her to participate in his operations.

    The Counselor 

Aidan Price/The Counselor

The Director's right-hand man.


    Dr. Grey 

Dr. Grey

A deranged doctor working for the Director.


Others

    Hargrove 

Malcolm Hargrove

A wealthy businessman who secretly moonlights as a crime boss.


  • Greater-Scope Villain: He hasn't had much direct involvement in the plot, but he's the one who owns the prison, and the ripple effects of both his crimes and shady business practices often comes trickling down unto the prison.

    Sister 

Kaikana "Sister" Grif

Grif's perverted sister.


  • Cloudcuckoolander: Sister is… out there, to say the least.
  • Shipper on Deck: For Grif and Simmons. She's very eager for them to get married, and thinks that she'll become an aunt because of it.

    Max Gain 

Detective Max Gain

A detective.


  • Mauve Shirt: He appears in each of the main characters's flashbacks before Caboose murders him.

    Connie 

Connie/C.T.

A bartender and con artist who mentored Tucker.


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