Characters affiliated with the Association and its subsidiaries.
All spoilers are unmarked.
Chayne's husband and the CEO of Paradise Association.
- Affably Evil: Incredibly cheerful and charismatic — until he casually lets a bit of his veiled hatred for Mint slip and is further revealed to have made a deal with the original Chayne Summers under enigmatic circumstances to kill or otherwise use Mint.
- The Atoner: Explored; he wants to be this, but he admits he can't make up for what he's done.
- Corrupt Corporate Executive: Although he does at least mean well if Aria is anything to go by, Mason's business practices are highly, highly questionable to say the least, with the cover-up of things like horrible human experimentation and the enforcement of a "shoot first ask questions later" policy with those infected by the Phantom being just a few of the things his tenure as CEO of Paradise Association has led to.
- Even Evil Has Loved Ones: Ruthless and amoral as he is, Mason genuinely loves his daughter Aria and his wife Chayne, and it's the death of the latter that fuels what's implied to be a very intense grudge towards Mint.
- Evil Redhead: A man with bright ginger hair who's also the CEO of a highly amoral supercorp with its own paramilitary, and beyond that a broken, grieving, spiteful monster towards Mint.
- Final Solution: To Australia after the outbreak of the Phantom; after the Phantom had spread across Australia to a point where those remaining on the island couldn't be saved without allowing the spread of the Phantom further, Mason ordered a series of airstrikes to kill everyone still in the country and reduce it to a bomb-out hellhole.
- Greater-Scope Villain: For the entire first half of the series, Mason simply serves as a background presence, with the measures he takes to find a cure to the Phantom and his sanction of his monstrous wife's proposed experiment allowing the plot of Before Heaven and From Heaven's Door to happen alongside the creation of all the runaways, and his extremist policies push the Big Bad of The Touch of Heaven, Jango, to measures that lead him going off the deep end. It's only until The Ambition of Hell where he finally steps down from this position and makes his first onscreen presence — and shortly after this, the true Big Bad, beyond even him, reveals herself.
- Happily Married: Used to be this with Chayne. The apparent death of his daughter Aria started to put strain on this until Chayne made a HeelFace Turn as a result of her grief and estranges herself from her husband. Aria does eventually come back, but by that time, Chayne is long dead.
- Minor Major Character: Has only appeared in one chapter thus far in The Ambition of Hell with little truly revealed about his motivation and true personality, but him being the CEO of the Association makes him in one way or another responsible for almost everything that's happened in the series.
- Totalitarian Utilitarian: Mason's motto, and as a result, the Association's, is "for the greater good." This is a fairly reasonable stance to take in a world ravaged by an incurable, lethal disease capable of spreading like wildfire — but it does not justify wiping out millions of people and covering up horrible experiments in the process.
- Villain with Good Publicity: Downplayed. Mason is noted to be an extremely controversial figure in the world of the Phantom for the actions he's facilitated through the Association — which only worsens as the Association is forced to try and explain more and more — but Mason has kept his position for over fifteen years, and Mint suspects it's almost entirely because Mason is extremely charismatic.
- Well-Intentioned Extremist: The CEO of an entire group of well-intentioned extremists; Mason has ordered millions of deaths to save billions, and the stress of which coupled with the loss of his wife and (for a time) his daughter are heavily implied to have broken him.
- You Killed My Father: Double-subverted; Mason seems to hold no ill will towards Mint for the murder of his (omnicidal) wife even though Mint fears it, but later abruptly lets it slip that he hates Mint and the rest of the world for it.
Charles' wife, the Vice President of Red Clover, and Jenny's mother.
- Abusive Parents: Not to Jenny or Jason, but for all intents and purposes, Tara is Tango's mother and they make sure to let Tara know — which doesn't stop Tara from letting Tango know to their face that she doesn't want anything to do with them.
- Broken Bird: By the time of The Radiance of Heaven, Tara's devolved into a quiet, apathetic woman with seemingly no more true motivation to cure the Phantom as a result of the Association crumbling and her becoming one of the lightning rods for all the people's hatred in the wake of Mason's disappearance, as well as her daughter Jenny returning from seeming death only to have been replaced an alternate personality.
- Chekhov's Gunman: One of the very first characters to ever be physically described as her face is one of the few memories Tango retains in the beginning of From Heaven's Door, but her true importance as Tango's mother and one of the highest-ranking members of the Association doesn't come to light until much later.
- The Ghost: Up until The Touch of Heaven, Tara's only physical appearance in the series was through a painting and a recurring memory of Tango's.
- I Have No Son!: Tragically forms this attitude by the time of The Radiance of Heaven. When Tango finally returns, Tara so adamantly refuses to accept that Tango is now in her daughter's body that she disowns Tango, somberly telling them she just wants Jenny back.
- Intergenerational Friendship: Forms one with Mint; despite being a few decades the latter's elder, Mint and Tara bond as Mint is one of the last living links to Jenny she has up until Tango's return in Radiance, although there's no indication the friendship suffers in spite of that and Tara's thoughts on Tango.
- Outliving One's Offspring: Although Jenny/Tango is still very much alive, Tara and Charles' first child, Jason, died of the Phantom scant months after it broke out, something which serves to motivate them both into using Jenny in the program as a hope to divine a cure to the Phantom.
- Parents as People: Implied to have been a very good mother to Jenny, but the stress of her job put significant stress on her relationship with both her and Charles.
- That Thing Is Not My Child!: Tara views the "Tango" personality with disdain and aversion, having attempted to motivate them to extract their neurochip and bitterly telling them to their face they are not her daughter.
- Well-Intentioned Extremist: Comes with the territory of working for the Association, but she is noticeably significantly less extreme than many of her colleagues, leaving the P.A.R.A.D.I.S.E. program in disgust once her daughter comes into legitimate harm.
The chief of security of Haven's military division, the security bureau, on behalf of the Association.
- Anti-Hero: Jones is rough, stern, and willing to hand a young woman to a potentially dangerous raider but at the same time, he has full reason to believe said young woman is a dangerous fugitive putting the security of the entire town at risk and he makes sure to note that Tango won't be in any legal trouble despite harboring her. Compared to the rest of the Association, Jones is a saint, and other characters speak highly of him long after his death.
- Four-Star Badass: A decorated soldier responsible for curbing dangerous civil wars in the past. Unfortunately, Jones never gets much a choice to show it due to Jango completely blindsiding him with the powers of the Never-becoming and killing him as a result.
- Happily Married: To his wife, Amanda; while we never see them onscreen together, Jones keeps a photograph of his family on his desk at all times and cheerfully gushes over them to Miles when he's prompted.
- Hero Antagonist: To Tango; while Jones means entirely well for Haven, his attempt to pass Celia over to Jango for what he believes is the sake of the town's protection puts him at odds with Tango, who decidedly needs Celia to try and pacify Jango through alternative measures and can't talk to Jones telepathically due to Jones having a metal plate in his head.
- Posthumous Character: Surprisingly enough for such a relatively minor character, Jones' legacy is felt long after his death in The Touch of Heaven, with his wife Amanda and his son Ruby becoming firm allies of the heroes and a feast held in his honor in The Ambition in Hell.
- Reasonable Authority Figure: While an Obstructive Bureaucrat to Tango, Jones is entirely in the right to do his job and never does a single immoral thing in his post, even making sure to let Tango know that neither they or their friends are to come into any harm despite valid criminal charges being able to be placed against them. From his viewpoint, Celia is a danger to Haven.
- Surprisingly Sudden Death: Alongside Pleasance, Jones dies startlingly fast when Jango unveils the powers of the Never-becoming, quickly taking out Jones before he can even get a move in and massacring the rest of his men.
A bureaucrat in the Association, and the caretaker of Mint and Tango after Tango returns to Earth.
A smug, uppity higher-up in the Association.
- Break the Haughty: The termination of the Association and his prodigious position with it clearly shakes Nascor.
- Jerkass: Nascor cultivates a nasty reputation and he's despised by almost everyone, even in the Association itself. The little we see of him holds up this reputation, though the Association's eventual fall seems to humble him a bit.
- Obstructive Bureaucrat: Nascor bit part as the closest the Association has to a head has him assume this. Nothing he does serves to improve the Association's standing and his reaction to the attack on Yonkers by the Children of Heaven is to adopt a "not my problem" attitude towards it and bark orders to Yvette.
- Pet the Dog: As much of a tightwad as he is, he does seem sincere in bidding Tara and Jenny farewell in their future endeavors.
An employee of the Association in Haven and Miles' mother.
- My Beloved Smother: Debbie is suffocating to Miles and overly concerned with him, likely as a result of the nature of her job and her husband's death.
- Nervous Wreck: Even worse about this than her son, having a panic attack and throwing an utter fit when Miles goes missing and being responsible for a significant amount of Miles' own neurotic behavior herself.
- Outliving One's Offspring: Debbie is revealed to have survived the massacre of Haven early on in Heaven & Hell but tragically, Miles did not.
The manager of the P.A.R.A.D.I.S.E. Program, the CEO of Red Clover a division of the Association responsible for the events of From Heaven's Door and Tango's father.
- Anti-Villain: Barely a villain at all; the extent of Charles' evil deeds stop at signing up Jenny to an experiment to be exposed to energies she's naturally immune to anyways albeit, without her consent with everything following that, including covering up Jenny's subsequent rape, literally forced on him by Chayne and Ash.
- Archnemesis Dad: Subverted. For a few chapters, Charles is made out as a monster who sold out Jenny to be raped and used for a horrible experiment, but every single part of this was manipulated as part of Chayne and Ash. Charles' actions still permanently shatter his relationship with Tango and Jenny, tragically.
- The Atoner: Has become this by the time of From Heaven's Door, with the consequences of having signed up his daughter for the program have spiraled into events that utterly destroy him and every relationship he has, leaving a pitiful shell who merely yearns for things to go back the way they were while utterly hating himself for having had a part in it all in the first place.
- Big Bad: Seemingly this for From Heaven's Door, made out to be behind Red Clover and, consequentially, everything the runaways go through. That's what it seems, at first; Charles has long given up on the project and all of his worst actions are at pressure from either Paradise Association, Ash, or Chayne.
- Defiant to the End: Even when Pluto is crushing Charles' neck into paste, Charles simply tells Pluto to "save it" when he tries to gloat and dies refusing to beg or whimper before Pluto, instead letting himself cry a few simple tears of pride for his daughters.
- Forced into Evil: Charles has utterly no say in what happens to the applicants and his own daughter during the P.A.R.A.D.I.S.E. program, overseeing the horrible program solely because Chayne and Ash are using Jenny as leverage.
- Go Out with a Smile: Even when he's had his throat crushed into paste, Charles still has a small smile on his face after he's killed.
- HeelFace Turn: For as little of a heel he was in the first place, Charles definitively switches sides after Chayne and Ash are defeated.
- I Did What I Had to Do: This is his motivation for a lot of his more questionable deeds revolving around the P.A.R.A.D.I.S.E. program, including signing up Jenny for the program against her will but this motivation stops dead when Ash violates Jenny and forces his compliance after he attempts to sever ties with the program by threatening her life. From that point forward, everything Charles does is just as a figurehead and pawn of Chayne and Ash.
- Luke, I Am Your Father: The major twist in From Heaven's Door is that the mysterious Director is actually Tango's father and the CEO of Red Clover itself.
- Orcus on His Throne: Leaves all the direct work to his subordinates and doesn't even directly appear until halfway through From Heaven's Door. There's a good reason for this; Charles is infected with the Phantom to a point where he can barely move.
- Outliving One's Offspring: Charles lost his first son, Jason, to the Phantom years ago. This is a major, major factor in the lengths he takes to try and find a cure to the Phantom, having been utterly destroyed by his son's death and even volunteering his own daughter, whom he finds out is immune, so nobody ever has to experience the grief he did when Jason died.
- Put on a Bus: Charles isn't seen onscreen during The Touch of Heaven or The Ambition of Hell, remarked to have been flown into a quarantine zone and kept alive through the donation of Aria's blood.
- Reluctant Mad Scientist: Although he's directs the P.A.R.A.D.I.S.E. program itself willingly, although hesitantly, the only reason he's overseeing the lethal aspects of the experiment and the deaths of the applicants is because Ash promises to kill Jenny if he doesn't.
- Secretly Dying: It's not revealed until he's finally seen in person in From Heaven's Door that he's infected with the Phantom, and it's all but explicitly stated he's keeping it a secret from his coworkers in Before Heaven. By the time of The Touch of Heaven, it's no longer a secret but the dying bit has been put on hold as the effects of the Phantom are frozen by Aria's blood.
- Tragic Villain: Charles was once a completely upstanding man with a happy family who was forced to increasingly desperate measures after his son died and his responsibilities as the CEO of Red Clover grew. When it was time to commence the P.A.R.A.D.I.S.E. program and he was forced to use his own daughter, Charles did so extremely hesitantly, putting immense strain on his relationship with both his daughter Jenny and his wife Tara, the former of whom furiously chewed him out on to which he had no defense. After this? Not only is Charles infected with the Phantom Jenny is raped and tortured into catatonia by Ash, who then forces a furious Charles to continue the program and oversee dozens more deaths of completely innocent people against his will by threatening to murder Jenny. By the time Tango reaches him, all the unnecessary pain, death, and manipulation has destroyed Charles and every relationship he once had, leaving him a sad, broken shell near death who's completely given up on everything he once strove for.
- Well-Intentioned Extremist: A textbook example of this, and he's only been forced into the extremist category; Charles is desperate for a cure so nobody has to experience the grief he and Tara had to face after his son Jason died, even reluctantly volunteering his own daughter for a potentially dangerous experiment against her will. Once Ash has his way with Jenny, however, Charles snaps and tries to break off from the project and only continues when Chayne and Ash hold Jenny's life over his head as motivation for him to continue. When Tango finally finds him, Charles is just a broken old man who's choices have utterly destroyed him.
The supervisor of the two-month pre-simulation process and one of the chief executives of the P.A.R.A.D.I.S.E. program.
- A God Am I: Intends to become a god with Heaven's energies with the intention to recreate humanity. She ends up getting her wish for all of a few minutes.
- Alas, Poor Villain: Mint, at the least, seems to regard Chayne's death as this; Chayne dies without ever coming to peace with her grief over the loss of her daughter and her misanthropic hatred of humanity, which Mint considers a "forlorn tragedy" as they destroy Chayne.
- Bad Boss: Her experiments with Tango end up catching and likely killing or perhaps worse the other members of Red Clover in the process, and she casually brushes off Ash being driven to vegetative insanity a few minutes before the experiment starts.
- Big Bad Duumvirate: In this with Ash for From Heaven's Door, hijacking this position from the Director after he gives up on the project. While Ash is mostly the one who dirties his hands the most and is the one actually manipulating the Director, the plan is all Chayne's and she's ultimately the final one to be fought.
- Brainwashing for the Greater Good: It's why the entire story even begins...the Heaven Project, brainwashing, all to allow Chayne to rise to the top and remake the world.
- Broken Pedestal: Admits that she looked up to the Director for the longest time, and ended up disappointed when he didn't have the heart to finish the project.
- The Chessmaster: Manipulates events so that no matter what happens, the portal to Heaven will end up opening. If she hadn't let Jilton into her service, she would have won and comes within a hairsbreadth of victory even with Jilton's presence.
- Crazy-Prepared: Aside from the sheer persistence of her own manipulations, Chayne also happens to have a body double she utilizes just in case there ends up being a threat to her own physical well-being. Surprisingly, the body double ends up being a good idea.
- Dragon-in-Chief: To the Director. While Charles is ostensibly responsible for running the program as a whole, Chayne is directly ordering Ash and does most of the dirty work herself. Ultimately, it turns out the Director's already given up on the project and Chayne's been using him as a figurehead the whole time, leaving Chayne to backstab him and take control of the project herself.
- Even Evil Has Loved Ones: She dearly loved her daughter. One of her most humanizing traits.
- Even Evil Has Standards: Chayne's furious reaction to Ash's rape of Jenny might be construed for fury Ash nearly derailed their entire scheme in a blind, drugged lust, but her inner monologue shows she's decidedly repulsed by it on a moral level as well, with the possibility of Ash's Parental Incest towards his son horrifying her further.
- Faking the Dead: Believed dead for a brief time after her body double is gunned down.
- Famous Last Words: Be quiet! You can't comprehend this! You can't comprehend me!
- Faux Affably Evil: She's excellent at putting up a cheerful, professional facade in public, but once her true intentions are revealed, she addresses everyone with the callousness she really considers everyone with.
- Freudian Excuse: Her daughter Aria was supposedly lynched after she caught the Phantom virus and her home was destroyed by a mob that also happened to consist of Chayne's friends. This incident drove Chayne to misanthropic grief and convinced her humanity was violent, thus pushing her to the extremes she undertakes in the story.
- Go Mad from the Revelation: Realizing she is still flawed and all-too human despite her newfound power drives Chayne to snap.
- Hidden Depths: As shown in Before Heaven, Chayne's character goes far beyond simple misanthropy. Chayne's grief over her daughter is shown in greater detail in her POV chapter, including breaking down over a picture of her daughter (made worse by Ash's attempt to console her) in private and admitting to herself she still regrets everything she is about to do.
- Hypocrite: Albeit an unconscious one, as a god-like being in Heaven, Chayne proclaims herself a god and free of everything she's dubbed flaws. Mint points out Chayne isn't free of imperfections, as her own grief for her daughter something she's previously ruled as a flaw is still deep within her. The realization of this in her perfect state is what causes Chayne to finally snap.
- In Their Own Image: Her ultimate goal is to simply destroy and recreate Earth anew to her picture of paradise.
- Ironic Death: Mint uses the very energies Chayne sought to make herself a god to obliterate her.
- Misanthrope Supreme: Her defining motivation is her absolute hatred for humanity as a whole, which motivates her into trying to destroy mankind so she can recreate them free of what she deems flaws.
- Motive Rant: Gives one to Mint in the final confrontation, which also serves to reveal her own past.
- Non-Action Big Bad: Ash does most of the heavy lifting for her, and Chayne remains waiting in the background for much of the story.
- Omnicidal Maniac: Her ultimate goal is to utilize Heaven's energies into destroying all humanity and becoming a god so she can create the world more to her liking. She briefly decides to let all humanity die once she's defeated the first time.
- One-Winged Angel: After physically passing through the Boundary into Heaven, the energies of Heaven turn her into a towering, seraphic god-like being dubbed the Black Queen of Heaven.
- Pet the Dog: As callously as she speaks of his (apparent) death later, Chayne does truly seem sincere and personable with Jackson Winters during their talk in the Nest, urging him to ease Jenny's anxiety and father issues as she knows she'd trust Jackson more to do so and cluing in she's genuinely regretful for not being able to tell Jackson of her Evil Plan.
- Red Baron: The Black Queen of Heaven.
- The Sociopath: Subverted. Although she's still a callous human being with little a care for the applicants or even her own subordinates, unlike Ash, it turns out Chayne had a daughter she cared for once, and it was her death that triggered Chayne's Start of Darkness. Chayne mentions she's learned to suppress her empathy for others, but regardless, Chayne still grieves for her daughter deep, deep down, and it's this fact that Mint uses to defeat her. Before Heaven shows she still grieves in private, to the point of breaking down over a picture of her daughter but decides it's too late to chance anything anyways.
- The Starscream: Backstabs the Director once he gives up on the project and takes matters into her own hands.
- Suicidal Cosmic Temper Tantrum: Decides to drag all humanity with her to the grave after she's foiled. After being powered up from Heaven's energies, Chayne quickly forsakes that and returns to her original goal.
- Sunk Cost Fallacy: Gone too far, can't stop now.
- Taking You with Me: After Jilton betrays her in the climax, Chayne decides to withhold the information on how to shut down the portal to Heaven, reasoning that if she can't recreate the world, all of humanity should die with her.
- Tragic Villain: Although her tragic past is hinted at in From Heaven's Door, it's Before Heaven that truly shows her as this. Chayne used to be a completely normal, pleasant human being with a husband and daughter she both loved dearly. After the Phantom arose in Australia, Chayne dedicated herself to helping to curb and stop it. After her daughter was murdered in a lynch after catching the Phantom, however, something in Chayne snapped and she was driven to depression further worsened by her association with Ash at that point which eventually caused her to shut herself away from her husband and gradually turn into the misanthropic, delusional woman who appears on page. Her POV chapter in Before Heaven still shows she truly regrets having to unleash such disaster on the world she's just trying her absolute best to ignore those feelings.
- Villain Ball: Chayne likely would have won if it hadn't been for the fact she happily let Jilton an established traitor and someone who'd previously killed her body double under full assumption it was Chayne herself onto her side without suspecting anything. Predictably, Jilton derails the entire plan once she's close to Chayne.
- Villainous Breakdown: Suffers two of them. The first is when Jilton betrays her, causing her to snap and try and doom all humanity out of spite, which ends with Chayne literally diving into the portal once it starts to close. Once Heaven powers her up, Chayne regains her cool, only to suffer an even larger breakdown once Mint points out even as a god, she's flawed, causing Chayne to devolve to angry protesting as Mint overwhelms and kills her.
- Well-Intentioned Extremist: Despite her twisted way of doing it (i.e. allowing Heaven to spill into Earth, annihilating humanity and twisting the universe into an eldritch nightmare) Chayne truly does seem to believe things would be better under her control.
- Xanatos Gambit: An absolute master of pulling these off, all correlating to her plan to open the portal to Heaven. If the Director opens the portal as part of the program, everything goes to plan. Circumstances make the only person immune to Heaven's energies barely functional? Emotionally manipulate their father into using them anyways. Said father gives up on the project? Chayne simply takes control of the project herself. Even when Jilton betrays her, Chayne simply decides to use her position to drag humanity with her by refusing to close down the portal, and once she becomes a god through Heaven's energies, Chayne simply resumes her original goal.
The other chief executive of Red Clover and the first Red Clover official met in the story.
- Addled Addict: In a bizarre instance of this, Ash is addicted to the energies of Heaven as a result of connecting his own mind to the world. This does not have a good effect on his already-loose sanity, to the point where Ash is barely functional at the best of times, forgets things at random, and abuses other drugs for the sole purpose of staying lucid. Ultimately, the energies consume him.
- A God Am I: Fancies himself a god alongside Chayne and is willing to wipe out all life on Earth to achieve godhood with Heaven's energies.
- And I Must Scream: His final fate, trapped within Heaven in eternal agony while his body becomes a mindless vegetable.
- Ax-Crazy: A textbook example. He's a barely-functioning psychopath with horrid impulse control and a constant urge to hurt everyone around him, and by the end, he's devolved to trying to wipe out all humanity purely because he hates everyone.
- Bad Boss: Ash verbally and even physically abuses his own compatriots at any given point, and has no hesitation in seeing them all exposed and likely slaughtered by the energies of Heaven when he attempts to tear open a portal to Heaven alongside Chayne.
- Be Careful What You Wish For: Ash sneers that he wants to murder every living person on Earth to experience his "perfect universe" in Heaven for eternity with nobody to bother him. He gets his wish in the end — his mind hurtling through Heaven ripped from his body, for all eternity, beyond even the purest state of agony known to man.
- Big Bad Duumvirate: With Chayne in From Heaven's Door. Ash is still the first to be defeated plot-wise and Chayne is technically his superior, but when the Director gives up on the project, both Ash and Chayne take over responsibility of opening the portal together. Chayne treats Ash as more of an equal than an associate (although she's nevertheless apathetic to his fate).
- Cloud Cuckoolander: A particularly dark interpretation of this, as his eccentricities are incredibly disturbing and he only acts the way he does due to literally having been driven insane from Heaven's energies.
- Cold-Blooded Torture: Or as Ash would call it "fun times."
- Eye Scream: Suffers this at the hands of Tango, and tries to burn their face with hydrochloric acid later in retribution for it.
- Fate Worse than Death: His mind is devoured by Heaven's energies, where it will exist in torment forever.
- Faux Affably Evil: Ash tries to be civil when it best suits him, although he does a horrible job. Other times, he just doesn't bother.
- Hate Sink: Ash is unbelievably vile, and represents the worst factors of the Heaven Project. While others in the group are well intentioned, Ash cares solely for his own gratification and the pain of others.
- It's All About Me: His underlying motivation and defining trait. Ash seeks stimulation alone and is willing to screw over anyone if it's to his benefit, conveniently forgetting about the effects later due to his own broken mind. This is ultimately what fuels his omnicidal tendencies as well, as the only reason he decides to help Chayne kill off all humanity is that he believes people are hogging too much room in his life and tainting his perfect universe, to the point where Ash calls out the people he's screwed over on being single-minded and simple.
- Jerkass: A complete asshole of a human being and one of the most vile characters in the series, with exactly zero redeeming traits about him. His single attempt to be sincere with Chayne only makes things worse and he decides not to bother when she reacts.
- Kick the Dog: An absolute master of this. Probably one of his cruelest moments is forcing the Director to continue the project and oversee the deaths of the other applicants by threatening to torture Jenny to death if he doesn't do as he says and telling Chayne it'd be funny to him to kill Jenny afterwards regardless.
- Laser-Guided Karma: Let's face it. The guy who did so much in pursuit of opening the path to Heaven? Gets exactly what he earned...
- The Man Behind the Man: To Director Charles. Chayne is mostly hesitant to confront Charles on using his own daughter in the simulation, as it turns out due to her own issues with her late daughter but Ash is more than happy to force Charles into running the simulation under the threat of Jenny's life, ultimately meaning everything Charles does can be traced back to Ash.
- Obviously Evil: A man who looks like a "goblin shark coming out of a garbage bag" always seen in a trench coat who spends most of his page time cursing up a storm, physically and verbally abusing everyone around him, and generally being as contemptuous and horrible as he can be. Pretty trustworthy fellow.
- Omnicidal Maniac: Alongside Chayne, Ash is planning to wipe out all humanity with the energies of Heaven and become a god. Unlike Chayne, Ash isn't planning on bringing anyone back, and devolves to a state where he's willing to murder Chayne herself so he can have his perfect universe to himself.
- Pet the Dog: Rather astoundingly subverted. Ash's one attempt to be sincere with Chayne by trying to comfort her over her daughter's death has him only makes things worse through his horrible attempt to reassure Chayne and he ultimately decides not to bother once Chayne rightfully snaps at him.
- Rape Is a Special Kind of Evil: His rape of Tango/Jenny is one of the more personal and loathsome acts in the series and is a major reason Ash is as despicable as he is
- Sadist: Ash loves to inflict pain on others and picking on those who are weaker than him. Jilton even remarks the only things he finds funny are things of the ilk of Vlad the Impaler sticking people's heads on spikes.
- Sanity Slippage: Although never exactly the most balanced or controlled individual in the first place, Ash hooking his mind to Heaven has a gradual but nasty effect on his already loose sanity; throughout From Heaven's Door, Ash becomes more and more dependent on the stimulation Heaven's energies have on him and him continuing to allow his mind to drift through Heaven fractures his mind more and more as a result, leading to him forgetting things at random, his sadistic and violent tendencies being amplified, and what little impulse control he has dying as a result. By the time his mind is almost completely taken by Heaven, Ash has gone almost completely nuts and rants about how he just wants to kill everyone to have his "perfect universe" with Heaven alone.
- Serial Killer: Ash makes a hobby of purchasing slaves from traffickers, with a preference for children, for the sole purpose of raping and torturing them to death, with many, many victims behind him.
- Serial Rapist: Has raped countless people during his life; while his only explicit victims are Jenny and his son Andrew, Ash is established to regularly purchase prostitutes from traffickers to rape, torture, and murder them at his whim, and Harlow Grave suspects he may have done similar to the other applicants as he did to Tango judging by some of their reactions to his presence.
- Sir Swears-a-Lot: Just about everything he says is sandwiched between a stream of curse words.
- Small Role, Big Impact: Ash is a relatively minor character in the Cycle as a whole, but as Jenny's rapist and torturer and one of the most sickening figures in the series, his actions have repercussions long after he's gone.
- The Sociopath: An extremely low-functioning example; he doesn't care about anyone or anything and only lives to gratify himself, doing remarkably stupid things over the course of the story to achieve that.
- The Starscream: He wants to backstab Chayne and the rest of the Heaven Project for his own benefit, even if it does not work to that at all. Nobody ever said he was a particularly intelligent traitor.
- Stupid Evil: Ash is resoundingly moronic despite his apparent brilliance in neurosurgery, exacerbated even further when he connects his own mind to Heaven and what little impulse control he has withers and dies as a result.
- Token Evil Teammate: Exaggerated; Red Clover and the overarching Association is already cabal of extremists and mad scientists, but they're generally all working for the greater good at the end, with even Chayne's actions for the sake of what she sees as a greater good. By contrast? Ash is a sneering, sociopathic monster who's easily the worst person in their employ and the most vile character in the series before Heaven and Hell get involvde, possessed of absolutely none of his colleagues' redeeming traits and existing purely to make everything and everyone around him miserable for the sole sake of his own stimulation.
- To the Pain: In Before Heaven, Ash illustrates his plans for Jenny should Charles not fold to every little detail:"I'll take her away. To some horrid, decrepit fuckin' place you'll never see her again, the rankest shit-hole in the world. I think my uncle's old fuckin' cabin out in the forest he sold to me would be a good start. Haven't cleaned out the fuckin' please in years. I'll chain your kid to the fuckin' wall and every day, I will visit a new torture upon her. Trust me, man I got some sick ideas. I'll thrust glass into her unmentionables. I'll ram needles up her nails and break every single one of her fingers. I'll gouge out her eyeballs make her choke one down and eat the other myself. I'll burn off her fuckin' face with hydrochloric acid, make her swallow the damn stuff. And, yeah, I'll be fuckin' her every day of every week, I will fuck her so hard she will fuckin' bleed. And I will fuckin' destroy you, Charles Chayne and I will pin the deaths of the applicants on you and you will never walk a free man again. And every day, for years to come, I'll be rapin' and beatin' and torturin' your kid, Charles. Over and over and over until one day, she just dies from the shock of it. Wouldn't that be fuckin' nice, Charles, old buddy?"
- Too Dumb to Live: Ash does things with absolutely no regard to the consequences, hooking up his own mind to another dimension purely to experience its effects on his mind with no care for his mental health in the process. Predictably, this is what does him in.
- Would Hurt a Child: Willing to rape and brutally murder the young Mint for nothing more than a giggle. Heaven and Hell confirms he's an outright pedophile as well.
One of the scientists in employ of Red Clover.
- Ascended Extra: Gets a bit more screentime to talk and be developed in Before Heaven.
- Even Evil Has Standards: For as much of an unbearable asshole he is, Harlow is horrified when he learns that Ash raped Tango and utterly disgusted when Charles and Chayne cover it up for the purpose of keeping the P.A.R.A.D.I.S.E. program going.
- Impaled with Extreme Prejudice: Dies in From Heaven's Door after Tango defiantly sticks a knife into his neck after he offers a cash reward for Tango being let go from the project.
- Jerkass: Harlow is a smug, contemptuous jackass under a fairly shallow guise of concern and civility, and he's fully complicit in an experiment that will result in the deaths of every applicant he talks down to.
- Well-Intentioned Extremist: The perfect example of the Association's corrupt morals in exchange for the greater good; willing to experiment and sacrifice one-hundred people for the potential of gaining revolutionary knowledge and the cure to the Phantom from Heaven. Jackson even remarks he's the spitting image of everything wrong with the Association.
A guard under the employ of Red Clover.
- Back for the Dead: Reggie returns to join the main cast in Radiance and even becomes a member of the main party for a short while despite the risks. He learns the hard way the sorts of trouble he's gotten into.
- The Bus Came Back: Rather unexpectedly during The Radiance of Heaven where it's revealed he survived the collapse of Paradise and is now a roommate of another ex-guard named George.
- HeelFace Turn: Downplayed. Reggie was barely a heel, even when he was employed under Red Clover, but when he comes back in The Radiance of Heaven, Reggie's no longer associated with the Association and is a firm ally of the heroes.
- Surprisingly Sudden Death: Gunned down almost instantly during the Battle of Yonkers.* Put on a Bus: Entirely absent alongside Jackson for The Touch of Heaven, but returns for Heaven & Hell.
- Token Good Teammate: To Red Clover in From Heaven's Door; Reggie's just a grunt and a security guard, but he takes pity on Tango and looks the other way when their friends expose the truth of Red Clover's conspiracies and lets them escape.
- What Happened to the Mouse?: Reggie's fate at the end of From Heaven's Door is explored and it's hinted he's killed alongside the rest of Red Clover's faculty by Chayne and Ash. Turns out he managed to escape and he reappears in The Radiance of Heaven.
- What Measure Is a Mook?: Explored. Instead of just being another faceless mook in Red Clover's employ, Reggie actually bothers to have a conversation and connect a bit with Tango, which Tango immediately notes puts him leagues above the monstrous heads of Red Clover.
The son of Amanda and Donald Jones, and Mint's roommate in The Ambition of Hell.
- Action Survivor: The least experienced of any of Tango's True Companions and the least capable in a combat situation, but Ruby still remains totally fearless and survives the overall events of the series.
- Affectionate Nickname: Snowflake for Mint.
- Best Friend: Becomes this to Mint when they become roomates over the Time Skip.
- Covert Pervert: Mint seems to sarcastically insinuate Ruby has a tendency to peer down their shirt. Ruby, of course, denies it.
- Deadpan Snarker: Ruby is extremely snarky, although generally in a playful manner, and he and Mint spend a lot of their mutual screen time seeming to snipe at each other and bash everything they can think of.
- Early-Bird Cameo: Ruby's briefly seen in a photograph alongside Amanda before he's properly introduced in The Ambition of Hell.
- Eye Scream: Ruby has his eyes ripped out in the Garden of Eden, permanently rendering him blind. Ironically, it doesn't seem to bother him that much once the shock of it wears off.
- The Insomniac: Though apparently not literally, Ruby has an extremely disjointed sleep schedule that he proudly admits he does nothing to fix, regularly staying up the entire night.
- Lazy Bum: Outside of his job, Ruby seems to not really do much except lounge around in his room and play video games.
- Let's Get Dangerous!: The least qualified of Tango's True Companions to be anywhere near the danger zone, having none of the powers the immunes have or the experiences the others do. Even in spite of this, he ends up shooting Leviathan's host dead when his mother is injured.
- Major Injury Underreaction: Downplayed. Ruby getting his eyes scratched out puts him in incoherent shock for what's at least a few hours, but when that clears, Ruby is surprisingly accepting about no longer being able to see, teasing Mint that he still has better vision than them.
- O.O.C. Is Serious Business: Ruby is normally a nonchalant, snarky jokester, but when the subject of Alice, the previous identity of his best friend, being the one to have murdered his father is revealed, Ruby drops it completely.
- Platonic Life-Partners: Mint may be romantically involved with Tango and both sides make it clear they're not even remotely interested in each other romantically, but Ruby is Mint's closest friend and partner otherwise. Even in the epilogue when they're still firmly platonic, Lavender still notes that Mint and Ruby are quite physically attached to each other regardless.
- Sad Clown: Heavily implied. Ruby always has a barb and a joke ready for every occasion, even in moments when it clearly doesn't fit, but beneath that Ruby's still a young man dealing with the trauma of having his father killed in Haven, with his humor clearly being his main coping mechanism.
- She Is Not My Girlfriend: Makes this attitude clear when it comes to Mint — though unlike many other instances of the trope, he's undeniably telling the truth.
- Vitriolic Best Buds: With Mint. There's not a single moment that goes by without Ruby and Mint slinging barbs at each other, but they're as close as can be.
- You Are Better Than You Think You Are: Instead of ripping apart Mint for Alice's actions in Haven lik they expect him to, Ruby frankly tells them "I don't give a shit about Alice" and instead encourages Mint to tell him more about themself.
The wife of Donald Jones and the mother of Ruby.
- Action Girl: Amanda very quickly proves herself worthy of her militaristic husband's legacy when her first reaction to a nightmarish Eldritch Abomination in her son's apartment is to blow clean through it with a shotgun.
- Happily Married: To Donald Jones. Years after his death, Amanda is still singing his praises and holding a feast for what would have been their twentieth anniversary in his honor.
A gunrunner friend of Reggie's in the current day.