Henroin

### Goals

* Destroy Angel Dust and Arckniss' relationship, and corrupt the latter into becoming a mobster and his right-hand man (both succeeded).
* Transform Angel Dust into a competent gangster (failed)
* Kill Angel Dust (failed)

## Characteristics

### Species

* Human (formerly)
* Spider-Scorpion Sinner

### Abilities

* Spider physiology
* Scorpion physiology
* Semi-Immortality
* Nigh-Invulnerability
* Regeneration
* Enhanced strength
* High intelligence
* Charisma
* Marksmanship
* Intimidation
* Manipulation
* Natural weaponry
* Vast wealth and influence
* Authority

## Professional status

### Occupation

* Boss of an unnamed mafia
* Kingpin
* Owner of *Annie's*

## Relationships

### Family

* Unnamed father
* Annie (deceased)
* Angel Dust (disowned son)
* Arackniss (son; erased)
* Molly (daughter)

### Friends

* Various mafia associates
	+ Vito Corleone

### Minions

* Spider mafia
	+ Arackniss (erased)

### Enemies

* Angel Dust
* Cherri Bomb (erased)
* Moxxie
* The Insurgency

## Other

### Headcanon voice(s)

Christopher Walken

"*My dear friends, brothas, sistas, and all... We havin' fun? Good... It has come to my attention that a, uh... New band, if you will. has descended upon Pride. Call themselves, uh, 'the Insurgency'. (chuckles) Ain't that cute? Lil' rebels with their fancy guns tryin' to overtake the establishment. (chuckles weakly and facepalms) Ah, signore dammi forza... Ya see, these jokas, they think of themselves, as, as like lions. But, in reality, they're just jackals. Hyenas, even, Or whateva's in the jungle these days. Fuckin' lowlife scavengers. But, thin is, when all the lil' creatures of the wild start pokin' the big guy, the lion... He shows them who tha fuckin' king is. Ya follow me? If they even think'a showin' their faces around me, I'll gouge their fuckin' eyes out with my stinger 'ere, and decorate my office with their heads. To remind them who's really one in control. 'Cuz that's what lions do... S'too late to be scared. These are confusin' times, my friends. But if you leave everythin' to me, we - all of us - will live like lions. But enough chit-chat... Who's up for some cannolis?*"
— Henroin's speech to his mafia regarding the Insurgency.

**Henry**, known in Hell as **Henroin**, **the Satanfather**, or **The Scorpion**, is a recurring character in *Hazbin Hotel: Journey to the Light*.

He serves as the overarching antagonist of Angel Dust's storyline.

He is a terrifying, ruthless, widely feared mafia don and businessman who stands as Hell's most powerful and reputable drug Kingpin. He is the Satanfather of a massive mafia clan of spider demons and territory based in Pentagram City. He is also the husband of Annie, the father of Arackniss and Molly, and the disowned father of Angel Dust.

## Biography

### Background

In the early to mid-1900s, Henry led a criminal life as a gangster involved in a range of illegal activities, including mafia executions, loan sharking, and drug trafficking, primarily dealing in heroin. During this time, he entered into a marriage with a woman named Annie and together they raised three children: Salvatore, Anthony, and Molly. Henry took it upon himself to groom his two sons to become proficient in the art of violence from the moment they were born, raising them to believe that being a mafioso was part of normal life. He was a stern, menacing, and sometimes abusive father to Salvatore and particularly to Anthony. In stark contrast, he showered Molly with affection, indulging her desires and even purchasing her a boutique at one point.

At a significant juncture in Anthony's formative years, Henry subjected his son to a harrowing experience, compelling him to witness the brutal assault and ultimate demise of a rival mafia don. The violence inflicted upon the don was so extreme that his identity became utterly unrecognizable, and his life was mercilessly extinguished by being encased in cement shoes and submerged in water. Seeing the victim die such a terrifying death in a watery grave left an indelible mark on Anthony, causing him to develop a profound fear of drowning. Despite the overwhelming distress it caused him, Anthony felt compelled to endure the ordeal under the relentless pressure of Henry, who derived twisted satisfaction from the spectacle as he callously laughed on.

During therapy sessions with Charlie, Angel Dust claimed that his father was physically and emotionally abusive even before he discovered that he was gay. However, after Anthony became the underboss of his mafia and kill several of the mob's enemies, Anthony began to stop caring and fully embrace the lifestyle. Henry openly favored Salvatore over Anthony, while his relationship with Anthony was barely cordial.

Henry bought Molly her own boutique when she was 24. He was devastated by her murder at the hands of a rival mafia, which also contributed to the early death of his wife, Annie, who died of a stress and grief-induced stroke shortly afterward.

Eventually, Henroin died at an unknown point in time and was reborn in Hell, where he was able to rise to the ranks and regain his reputation as a drug lord and mafia boss, obtaining the status as a criminal Kingpin. He later founded an Italian restaurant which he named after his wife, Annie. He also reconnected with Arackniss, quickly appointing him as his right-hand man, while Angel Dust was nowhere to be found.

Through means unknown, Henroin discovered Angel's sexual orientation and was outraged. When Angel finally found his father and brother, Henroin viciously assaulted him, beating him "black and blue" in Angel's words, and was ready to permanently kill him with a blessed revolver until Arackniss protested against it. As Angel laid in a pool of blood, Henroin threatened that if Angel ever stepped foot near him or his brother, he would kill him once and for all, before storming off, leaving his battered son to fend for himself and disowning him. Henroin and Arackniss never saw Angel in person again after that.

Angel Dust blames his father for every unfortunate thing that has happened to him in Hell, claiming that, if his father did not disown him, he would have never become involved with Valentino and exploited for 70 years.

### Events of *Hazbin Hotel: Journey to the Light*

#### Season 5

In "My Brotha Arackniss", Henroin makes a speech at his estate to his fellow mob bosses, associates, and hired guns, addressing the appearance of the Insurgency and the threat they pose they present to Hell itself. Henroin laughs off the Insurgency and proclaims that they are not as big a threat as they claim, and boldly proclaims that he will kill them if they make any move against him.

Henroin then commences a party where he enjoys drinks with his pals, and engages in a poker match which he wins easily (in no small part thanks to his servants making threatening gestures at his opponents). While drinking liquor and enjoying cannolis, Henroin is questioned by an associate about the absence of his son, Arackniss. Henroin tells he sent Arackniss to an anonymous business deal, unaware that his son had been captured by Sir Pentious, Loopty Goopty, and Lyle Lipton.

In "A Behemoth of Fun", on a stormy night in his manor, Henroin is in his office, giving tips to an associate on how to export people before Arackniss storms into the manor begins arming himself with weapons, enraged that Angel Dust had broken Henroin's "truce" with him, remaining completely ungrateful to Angel saving him. Henroin inquires the source of his son's anger and where Arackniss has been this entire time, to which Arackniss tells him about what had happened with Angel Dust. He continues, telling his father that he could have sworn he saw Angel with Molly while scoping out the hotel. In response, Henroin calmly tells Arackniss to come over to him, before punching Arackniss in the face for speaking Molly's name, telling his son that she was too good for Hell and threatening to kill him for suggesting otherwise.

After properly disciplining Arackniss and returning to his office with his son, it is revealed to Henroin by one of his hired guns that they had spotted Angel with Moxxie, who Henroin knows as being the son of his associate, Crimson. Henroin and Arackniss begin conspiring a plot to kill two birds with one stone as Henroin orders his receptionist to schedule a meeting with Crimson to deal with their common enemies.

In "Metatron, the Voice of God", Henroin and Arackniss found themselves at their estate, conducting a precarious deal with Rough Cut, a rather unremarkable mafia boss of modest standing. Despite Rough Cut's recent gesture of goodwill by eliminating a rival gang that had been plaguing Henroin, leveraging his superior wealth and influence, the Satanfather astutely presented Rough Cut with a lopsided offer. He essentially proposed that Rough Cut accept a subordinate role or face certain demise. When Rough Cut, refusing to bow to such terms, held his ground Crimson, who had surreptitiously arrived at Henroin's estate, coldly executed Rough Cut with a single gunshot to the back of the head. Amused by Rough Cut's death, Henroin and Crimson quickly catch up on each other's lives.

After a brief exchange of updates on their respective criminal ventures and the sharing of sinister execution methods, Crimson declares that they get down to business, and the two bosses engage in a tense, but cordial exchange. Henroin acknowledges Crimson's reputation for fearlessness and they exchange banter about their respective qualities. Crimson confides in Henroin about his son, Moxxie, who has become uncooperative and threatens his criminal empire. Henroin criticizes Crimson for letting a woman, who wiped out half of his resources, slip through his fingers. They also discuss a recent attempt to marry into Crimson's family that went awry. Henroin suggests that they deal with these problems together, and to illustrate his point, he presents a photo of Angel Dust and Moxxie together, implying that they can eliminate this perceived threat and kill two birds with one stone. Crimson eagerly expresses a willingness collaborate on this dark endeavor.

In "What a Tangled Web We Weave", Henroin and Crimson had joined forces; taking advantage of their alliances, they temporarily merge their mafia organizations to orchestrate significant heists and mass killings across the Pride Ring. These criminal activities yielded millions in funds, which they discussed and agreed to divide between them. While enjoying their excess over Italian food and wine, Henroin and Crimson discuss terms for their agreement. Henroin pledged a substantial sum to Crimson for assisting him in eliminating Angel Dust and then proceeded to propose an ongoing partnership. He offered to "borrow" some of Crimson's men in exchange for a one-year, monetary financial aid. Crimson displayed noticeable displeasure, resenting Henroin's advantageous position. In an attempt to reconcile, Crimson suggested that Henroin extend his support to dealing with the entire I.M.P, ensuring protection for his business. After reaching an accord and sealing it with a handshake, Crimson specified that Moxxie was his to deal with, prompting Henroin to assert his ownership over handling Angel Dust. Subsequently, they coordinated their respective mobs to apprehend Angel and Moxxie.

As Angel Dust and Moxxie found themselves bound and confronted by their mutual fathers, the atmosphere in Henroin's mansion was tense and charged with misunderstanding and prejudice. Crimson claims that he was right about Millie being Moxxie's "beard", believing that he and Angel Dust were lovers. Angel and Moxxie, find some amusement in the situation despite its severity, using it to mock Crimson and Henroin. They took the opportunity to educate their parents about sexual orientations, with Moxxie emphasizing that bisexual individuals can have platonic friendships with another male, something Crimson and Henroin refuse to believe. Moxxie stood up for himself, defending the legitimacy of his relationships and identity. Not tolerating their mockery, Henroin silenced Angel with a punch, giving him a black eye. When Angel defiantly threw more mockery at Heroin, Henroin spitefully intended on poisoning Moxxie with his stinger, though Crimson intervened, asserting his authority and indicating that Moxxie was his responsibility. Henroin announced his plan of a public execution of both sons to send a message. Henroin decreed that if Moxxie and Angel were so close, then they could rot together, having his men confine them in a large cage.

In "The Family Jewels", Henroin has a melancholic dream of reuniting with Annie and Molly, his wife and daughter. Upon awakening, he enters his massive study, taking a seat at his piano and performs "Storia d'amore" for a few minutes until Crimson walks into his office. Crimson admonishes Henroin for indulging in his daydream and urges him to focus on their tasks. Despite refusing to reveal his vulnerability, Henroin complies, shutting the piano closed and agreeing to concentrate on the work at hand.

As Henroin dons a suit for his son's execution, memories flash through his mind. In one vivid recollection, he revisits a moment from Angel Dust's childhood when Anthony and Salvatore engaged in a spirited boat race. Annie, Henroin's wife, noticed his lack of enthusiasm and confronted him about it. Henroin saw the race as trivial, feeling out of place as a mafia boss at a children's event. Playfully, Annie encouraged him to embrace the importance of enjoyment and cherishing their children. When Anthony and Salvatore triumphed in the race, Henroin couldn't contain his pride and joy, cheering them on. Overwhelmed with emotion, he scooped up his sons, proudly declaring them as his "boys."

As the dreaded moment arrives, a horde of mafia enforcers from Pride and Greed flock into Henroin's mansion. Even a crew from 666 News descends to televise the impending public execution of Angel and Moxxie. Henroin contemplates the whereabouts of Arackniss, who was on a mission with Alessio to eliminate Millie. However, Crimson redirects Henroin's attention, emphasizing the greater priorities at hand, a point Henroin concedes.

Stepping onto the stage in front of the imposing assembly of mafia personnel, Henroin delivers a speech about instilling fear and displaying uncompromising resolve. He then presents the bound Angel and Moxxie to the crowd. Moxxie is restrained by Crimson's shark henchmen, while Angel is cast at Henroin's feet. In a climactic and tense moment, a goon hands Henroin an angelic handgun, and he takes aim at Angel's head. Angel is visibly petrified, struggling to maintain composure, attempting to display bravery in the presence of his father. However, before Henroin can squeeze the trigger, the mansion's doors burst open, revealing the unexpected entrance of Arackniss, Fergus, Husk, Millie, and most significantly, Molly.

At Crimson's command, several mobsters raise their weapons, targeting the group. However, upon seeing Molly, Henroin's instincts kick in, and he shouts at them to lower their arms, a directive they immediately heed. Astonished, Henroin descends from the stage, his eyes wide with disbelief at the sight of Molly. Overwhelmed by emotion, Molly rushes into her father's embrace. Henroin, revealing a vulnerable side, holds Molly close, grappling with the surreal possibility that this might be a dream. He queries why she's in Hell, and Molly discloses that "Anthoyn" needed her help. Frustrated, Crimson urges Henroin to halt the sentimental moment and proceed with the execution, but Millie intervenes, silencing him.

In a final plea, Molly passionately tries to reach out to Henroin, reminding him of the love and bond he initially shared with Anthony as his father, recounting cherished memories of their time together. She emphasizes that Anthony being true to himself and whom he loves doesn't diminish their familial connection. Henroin is clearly affected by this, and after a moment of contemplation, he acknowledges his love for Anthony in the past, but his expression darkens as he expresses profound disappointment in Anthony's choices and the shame it brought to their family and his status. He stands firm in his decision to confront Anthony's actions and not overlook what he perceives as an insult to their values and heritage. Henroin summons one of his goons to hold Molly back as he takes aim at Angel, only for Arackniss to leap up and grab his father's wrist, redirecting Henroin's aim. Henorin furiously throws Arackniss to the ground, asking him if he has lost his mind. Just then, a portion of the ceiling in Henorin's mansion explodes as Cherri Bomb enters, having come to Angel's rescue Angel.

As chaos erupts with the clash between the mafia and Cherri Bomb, Henroin prioritizes Molly's safety and instructs his men to escort her out of the escalating battle. Meanwhile, Angel and Moxxie seize the opportunity, breaking free from captivity thanks to Cherri and Millie's intervention. Reunited and armed, they join forces, laughing amidst the bedlam as they exact vengeance on the mafia that nearly took their lives away. Arackniss joins the fight, leading to a conversation with Angel where they bond over their mutual love for Molly. Seeing Crimson attempt to run away, Moxxie and Millie join together and chase after him, killing Crim in an extremely anticlimactic way following a boat chase.

Soon after Moxxie and Millie leave, Angel and Cherri join forces to fight the mafia, rekindling a small portion of their previous, chaotic friendship. Angel tries to tell Cherri this might be the last time they can raise some Cain, but Cherri tells him to shut up and live in the moment. Cherri and Angel's massacre is halted when the Insurgency storms into the mansion, having followed Cherri to the location and knowing of the very public event. In a fierce battle, Izzi finally gets to confront Angel Dust, where it is revealed that Angel knows all about Izzi through Cherri. Angel fights Izzi himself, but he proves to be a formidable opponent, overpowering Angel effortlessly while mocking him for pursuing a path of redemption. Witnessing Angel in grave danger, Molly undergoes a transformation, embracing a more feral form, and attacks Izzi, clawing his face in a desperate bid to protect her brother. Molly manages to blind Izzi's single eye with her claws, but Rum intervenes, pulling Molly close and holding a blessed switchblade to her throat. However, Arackiss saves his sister by leaping onto Rum and biting him in the neck, poisoning him as Rum deliriously makes a sexual remark.

The battle takes a drastic turn as Izzi, now wielding Stolas' grimoire and harnessing its magical power, manages to ensnare Cherri, Angel, and Moxxie effortlessly. However, Arackniss intervenes, attempting to wrestle the grimoire from Izzi's grasp, disrupting the spell. In the chaos of their struggle, Striker unexpectedly appears and ruthlessly attacks Arackniss, stabbing him in the leg and causing him to collapse in agony. As payback for Izzi killing Stolas when he was meant to, Striker callously kills Arackniss with a swift shot to the head from an angelic revolver, leaving Molly and Angel stunned and horrified.

In the midst of the chaos and tragedy, Izzi's fury is directed at Striker, as Arackniss was seemingly his to kill. Seizing the moment, Cherri joins the fray, attacking her father with relentless force, only stopping when the Insurgency fires at her. Meanwhile, Henroin arrives at the gruesome scene after fighting off Insurgency soldiers, witnessing Molly crying over Arackniss' lifeless body as Angel stood in stunned silence. Succumbing to a tidal wave of emotions. Overwhelmed by grief, he cradles his son's lifeless body, breaking down in tears for the first time.

Blinded by sorrow and rage, Henroin redirects his fury towards Angel Dust, unable to listen to Molly's attempts at reasoning. Following their earlier confrontation with Crimson, Millie and Moxxie rush to aid Angel, but Henroin's anguish-fueled aggression knows no bounds. He effortlessly swipes Moxxie aside and inflicts a venomous wound on Millie, leaving her poisoned and in need of urgent help. In a desperate attempt to save Millie, Moxxie carries her away from the chaotic battlefield, seeking desperately for a way to alleviate the effects of the venom.

In the grip of fury and grief, Henroin unleashes a brutal assault on Angel, blaming him for Arackniss' death. His goons restrain Molly, preventing her from intervening. With relentless determination, Henroin uses his tail to strangle Angel, seeking revenge for the loss of his son. However, Angel summons the strength to retaliate, managing to shoot Henroin in the abdomen with his father's blessed pistol. Severely weakened, Henroin's grip loosens, and Angel seizes the opportunity. He swiftly deals with the goons restraining Molly and tackles his father to the ground. Overwhelmed by his emotions, Angel unleashes a torrent of pent-up feelings, tackling Henroin and mercilessly punching and pistol-whipping his father, blaming for the deaths of Arackniss, Molly, and Annie in life, attributing their demise to Henroin's cruelty and unwavering loyalty to the mafia lifestyle over his own family. Tearfully, Angel confesses his own guilt, acknowledging their family could have been perfect if Henroin had not corrupted him and Arackniss into terrible people. Angel then puts the blessed handgun to Henroin's head, but after suffering a flashback of Henroin putting a gun to his head after discovering his sexuality, an emotional Angel throws the gun away in disgust, refusing to kill his father. Witnessing the aftermath of the vicious beating, Molly intervenes to prevent Angel from taking Henroin's life. Molly holds her emotionally shattered brother close, comforting him as he collapses in tears.

Regaining his strength and witnessing the harrowing scene unfold, Izzi seizes the opportunity to retrieve a blessed grenade. With malicious intent, he tosses the grenade towards Henroin, Molly, and Angel, aiming to kill all three with the ensuing blast. As Izzi leaves, Cherri Bomb spots the incoming danger and rushes in, leaping pushing Angel and Molly out of harm's way, getting them just out of the way of the blast as the grenade detonates.

In the wake of the devastating explosion, Angel and Molly struggle to regain their senses but eventually recover from the disorientation. They witness the aftermath, where Cherri bears the brunt of the blast, her left arm severely scarred from her courageous act. Overwhelmed by concern, Molly rushes to Henroin, who is badly injured with his flesh burned and fur singed. Henroin, in a state of delirium and pain, mistakes Molly for Annie in his final moments. As Molly pleads with him to hold on, the weight of the situation hits her deeply. Despite Henroin's past cruelty towards her brothers, Molly is unable to hold back her tears as she mourns over his lifeless body. Meanwhile, Angel is left in stunned silence, trying to grapple with the complex emotions that this moment of tragedy evokes.

## Personality

"*You wanna talk about trauma?! When I was 24, my pa put a revolver to my head and said (imitating Henroin) 'if yer a fag, I'll paint the walls with yer brain!' (normally) So, naturally, I went out to the nearest bordello and fucked the first guy I saw.*"
— Angel Dust about Henroin.

"*My daddy's... Complicated. He's a very traditionalist kinda guy, y'know? He's a terrible man who did horrible things ta some good people. He loves power, wealth, and control, and doesn't care which poor bastard's life he has ta destroy to geddit. And ta top it off, he manipulated and used all of us, his own family, his associates, and othas to gain it until he was the last of us to be six feet above. (tearing up) I'll always love 'im fer the nice things he did fer me, fer all of us, but his hate and greed destroyed our lives, and we'd all just be betta off without 'im.*"
— Molly about Henroin.

Henroin epitomizes the archetype of a classic mob boss, exuding an outward charm that conceals a dark, chilling, and ruthless nature. Despite his affable facade, he harbors a deep-seated hostility and cruelty that taint his character. His disdain for his homosexual son, Angel Dust, is rooted in both personal prejudice and concern for his own reputation. Henroin clings steadfastly to traditionalist values, subjecting Angel to a harrowing childhood marked by relentless mockery for his reluctance to embrace the mafia lifestyle. He shamelessly compared Angel unfavorably to his brother and exhibited an utter disregard for their safety, thrusting them into perilous roles as underbosses in his criminal empire.

Henroin's malevolence extends to his sadistic enjoyment of violence, frequently orchestrating mafia executions, including chilling methods like drowning and live burials. Shockingly, he encouraged his own children to witness these horrors, displaying a chilling apathy towards the psychological trauma inflicted on them. His extreme homophobia reached a horrifying climax when he discovered Angel's sexual orientation, leading to a brutal assault that nearly claimed his son's life. Only the intervention of Arackniss prevented a tragic outcome.

Henroin's imposing presence belies a surprising duality. In moments of good humor, he emerges as a charismatic, jovial, and downright hilarious figure. He revels in hosting extravagant mob parties, engaging in spirited card games, and sharing laughter with his business partners. Loyalty holds paramount importance within his clan, and he fosters camaraderie among his associates, often addressing them as "brothers" and "sisters" to forge unshakable bonds and unwavering allegiance. However, this genial façade conceals a chilling reality: Henroin is unhesitant about eliminating those who disappoint him, a fact that both garners respect and instills fear among his henchmen. His ability to wield charm as a potent tool of manipulation is uncanny. Even in the midst of his comedic antics, he maintains an aura of terror. Henroin revels in the knowledge that he can send shivers down the spines of those around him and derives amusement from wielding his sadistic sense of humor to intimidate associates into yielding in card games. Paradoxically, he fancies himself somewhat of a family man, a facet of his character that adds a sinister layer to his refusal to accept his son Angel Dust's homosexuality, making his actions all the more despicable.

In a manner akin to his son Angel, Henroin holds Italian cuisine in the highest regard, bordering on obsession. His approach to managing restaurants mirrors his mob boss mentality, with the belief that merely refraining from eliminating important patrons constitutes the basic tenet restaurants should uphold. Henroin and his family share a refined palate, making them unapologetic food snobs who recoil in horror at the sight of improperly prepared or gimmicky dishes, such as the sacrilegious inclusion of pineapple on pizza, the desecration of pasta noodles through cutting, and their general disdain for American pizza as a whole.

According to Angel, the one redeeming quality in Henroin's character is his genuine sense of humor. He finds solace in sharing jokes with his associates, although these jests tend to veer into the morbid and macabre realm. For instance, he playfully alludes to the idea of wiping out his associates and their entire families should they best him in a card game, a grim jest that exemplifies his dark and twisted sense of humor.

In a stark contrast to his otherwise irredeemable nature, Henroin demonstrates a capacity for genuine love and affection, primarily directed toward two individuals in his life. His deep and unwavering love for his wife, Annie, is evident through his actions, such as naming his restaurant in Hell as a tribute to her memory. He brooks no disrespect when it comes to her legacy, fiercely protecting her honor.

Similarly, Henroin's love for his daughter, Molly, shines through in their shared history. During their time together, he doted on her, and there is a sense of approval for her kind-hearted nature, as he affectionately referred to her as a "good girl." Nevertheless, his expressions of love and concern for his family often took a twisted and toxic form, stemming from a place of emotional ineptitude that hindered his ability to articulate his feelings appropriately. Molly astutely noted that Henroin consistently prioritized his own desires over the well-being of his family, despite his love for them. This self-centeredness ultimately played a role in the tragedies that befell his family, indirectly contributing to their untimely deaths. The fact that he outlived all other members of his family and died a natural death serves as a stark testament to his inherent selfishness, casting a shadow over his complex and often contradictory character.

Henroin's character is indeed complex, revealing a set of standards that, while twisted and morally skewed, add another layer to his persona. He maintains a personal rule that he will not directly harm or kill women, a somewhat unconventional code of conduct in the criminal world. However, this principle does not absolve him of violence entirely, as he opts to delegate any acts of murder or brutality against women to his hired enforcers, revealing a disturbing willingness to use others as instruments to carry out his dark intentions.

## Appearance

Henroin is a formidable and imposing demon, bearing a striking physical presence that is both awe-inspiring and terrifying. His massive form combines the features of a scorpion and a spider, resulting in a nightmarish amalgamation of dark grey fur, ominous long eyebrows, and an eerie countenance. His visage is dominated by eight piercing red eyes, devoid of pupils, which exude an otherworldly aura. In a nod to his son, Angel Dust, Henroin's hair adopts a distinctive and extravagant swooshing style, adding a touch of eccentricity to his otherwise fearsome appearance. However, his most defining attributes lie in his lower half, where six scorpion-like legs grant him an unsettling mobility, and a long, retractable scorpion tail, complete with a menacingly sharp stinger, serves as a potent weapon, ready to strike at a moment's notice.

The only things he wears in terms of clothing is a red tie and a black trilby with a red band.

## Powers and Abilities

### Natural Powers

* **Immortality**: As a sinner, Henroin lives forever as an undead soul.

### Unique Powers

* **Enhanced Strength**: Henroin possesses impressive physical strength, partially due to his massive size. His strength was best displayed during his beatdown of Angel Dust, where he disfigured Angel by pistol-whipping and punching him, easily held him in the air by his neck, casually throw him into a car's windshield with enough force to total said car, and was punching him with such force that it was creating splits in the concrete ground that Angel was laying on. Fergus, a fallen angel who can effortlessly torn apart metal and broke walls, noted that even he would not want to earn Henroin's wrath or get into a fight with him.
* **Retractable Scorpion Tail**: Henroin possesses a large scorpion tail which he can retract into his body.
* **Venom Generation**: Henroin can infect other sinners and demons with a potent venom using his spider-like fangs or his scorpion tail. The venom is capable of severely intoxicating others and giving them the same effects of being on heroin.

### Abilities

* **Cunning Intelligence**: Henroin is a criminal mastermind who controls a sizeable part of Pentagram City's underworld, organizing dealings and occasionally turf wars. Upon being reborn in Hell, he rose back to power fairly quickly and amassed an army of other criminals to help him in his goals, making them submissive through loyalty, charisma, or fear.
* **Intimidation**: Henroin is widely regarded as one of the most frightening sinners in Hell due to his ruthlessness and lack of morals. Angel Dust suffers from recurring nightmares as a result of his experiences with his father, and Fergus claimed that Henroin was a "big man" that even he would not mess with. Henroin simply moving his hand was enough to make Arackniss squirm and close his eyes in clear fear. He was able to win a poker game against several other mafia members by making them fold after he subtly threatened to kill them if they beat them.
* **Natural Weaponry**: Henroin can use his claws, scorpion-like appendences, and spider-like fangs to attack and injure his enemies. He also sports a venomous scorpion tail which he can use to infect other demons, or simply use it to impale them.
* **Influence:** Henroin is the boss of a powerful mafia family and organizing many criminal activities such as drug deals, weapon trafficking, kidnapping, homicides and turf wars. He seems to be particularly involved in the drug world, building an immense drug market and arriving to produce almost all substances of Pentagram City.

## Relationships

### Family

#### Annie

Annie is Henroin's wife. While not much is known about their relationship, Henroin appears to deeply love his wife, naming his restaurant in her name and passionately calling back to their time together.

#### Angel Dust

"*You think it's fuckin' funny that my precious 'son', and yer brother, prances around like a dainty little fairy in fishnets while all tha putzes in Hell ogle his backside like he's a piece of meat? Think I'm gonna sit on my ass and act like a fuckin' comedian and let that happen? Nah. Not my son. Not eva. (slowly goes into his full demon form, violently using his stinger to stab a television advertising Angel Dust) **Not**. **My**. **Son**.*"
— Henroin about Angel Dust.

Henroin's relationship with his disowned son, Angel Dust, is steeped in profound animosity and disdain. He regards Angel as an irredeemable source of embarrassment, one that tarnishes his reputation as a mobster. While Henroin's disapproval of Angel seemed to have existed for some time, it reached a devastating climax when he discovered Anthony's involvement as a gay prostitute. This revelation triggered an eruption of fury, culminating in a brutal and near-fatal assault on his own flesh and blood. Only the intervention of Arackniss prevented the ultimate erasure of Angel's existence.

In the present day, Henroin's strategy regarding Angel is one of deliberate ignorance. He actively silences any mention of Angel's name through murder, and vehemently refuses to acknowledge him as his son. This drastic measure arises from his belief that having a son like Angel undermines his authority and standing within the criminal world, where credibility and intimidation hold immense value. Henroin's unwavering determination to distance himself from Angel paints a chilling portrait of their fractured relationship, defined by violence and rejection.

#### Arackniss

Arackniss is Henroin's son, protégé, and underboss. Henroin exhibits a clear preference for Arackniss over Angel Dust, recognizing in him the potential to ascend as a successful crime leader. This favoritism is marked by a deep trust in Arackniss, often entrusting him with high-stakes negotiations despite his son's volatile temper.

However, Henroin's approach to mentoring Arackniss is characterized by unrelenting brutality and an absence of forgiveness. He has no reservations about subjecting his son to beatings and even threatening to end his life in response to mistakes. This harsh treatment is rooted in Henroin's desire to toughen Arackniss and maintain an unyielding facade of strength in front of his criminal associates. The notion of showing "weakness" is anathema to him, and he believes that this harshness is a necessary means of survival in their ruthless world.

The mention that Henroin subjected both Angel Dust and Arackniss to brutal physical punishments during their upbringing highlights the unforgiving environment they were raised in. This upbringing serves as a testament to the ruthless and uncompromising nature of Henroin's character, molding his sons into individuals who must navigate a perilous world fraught with violence and danger.

#### Molly

Molly is Henroin's daughter. Henroin's relationship with his daughter, Molly, stands in stark contrast to his interactions with his sons. While he ruled over his sons with fear and subjected them to abuse, he held a deep and genuine love for Molly. His affection for her was evident in the lengths he went to protect her from the darker aspects of his mafia business, shielding her from its influences as much as possible.

Henroin's love for Molly manifested in extravagant displays of affection. He indulged her every desire during her lifetime, treating her to memorable experiences such as trips to the carnival and even gifting her a boutique for her birthday. These gestures of generosity underline the depth of his love for his daughter, and the bond they shared.

The devastating loss of Molly, marked by her tragic murder, had a profound impact on Henroin. He was forever changed by her death, and the void left by her absence is palpable in Hell. His enduring grief and longing for Molly serve as a poignant reminder of the complex and multifaceted nature of Henroin's character, revealing a tender and compassionate side that contrasts sharply with his ruthless persona in the world of crime.

### Allies

#### Crimson

Crimson is one of Henroin's associates. Henroin and Crimson seem genial and professional with each other, breaking bread, and discussing and sharing methods of "disposal" and execution. Henroin admires and praises Crimson for his ruthless nature and the fact that the imp is willing to do the most horrible things for the sake of toughening Moxxie. He also calls Crimson "unique" for the fact that he does not seem to be afraid of Henroin.

Still, despite seemingly respecting Crimson, Henroin appears to view the imp as a lesser, as he reminds Crimson of the financial failings his empire has endured, and leverages Crimson into a deal by offering him financial support, much to Crimson's irritation.

## Quotes

### Season 1

"*Listen ta me, you goddamn faggot. If you eva show yer sissy, fairy face ta me or yer brother again, I'll fuckin' kill you.*"
— Henroin in a flashback, saying his last words to Angel Dust before disowning him.

### Season 5

"*I got this one case, a rat had been squealin' to the feds, so one of my men took him for a lil' swim. ...Only he couldn't swim.... and he was wearin' concrete shoes! (he and his associates laugh raucously)*"
— Henroin joking with his associates.

"*So ya threaten his family, dumbass! And if his gums don't start flappin', we'll break his kid's legs, and if that don't get 'im to talk, his wife and kids sleep with da fishes. [...] Who the fuck do ya think yer workin' with? [...] Ok, then get tha fuck on it. Goddamn amateurs...*"
— Henroin while on a call with one of his underlings.

"***Arackniss**: That stupid fuckin' fairy! He's **DEAD** now! It's fuckin' over!
**Henroin**: (appears suddenly behind Arackniss) What are you cryin' about, Sal?
**Arackniss**: (he jumps in surprise) Jesus, Pa! it happened! IT FINALLY FUCKIN' HAPPENED! Anthony wants ta fuckin' die again! He broke yer truce, seee?!
**Henroin**: Hmm. Seems problematic...
**Arackniss**: A-a-a- And get this, Pa! I've been scopin' out that hotel, and I coulda sworn I saw... Molly. (Henroin begins glaring) With my own fuckin' eyes! For all I fuckin' know, it coulda been Anthony in drag again, but-
**Henroin**: (sternly) Sal. C'mere. (Arackniss slowly slowly approaches Henroin, who punches him as soon as he gets close enough) **Keep her fuckin' name outta yer goddamn mouth**. (he looms over Arackniss, who crawls to the corner in fear) Molly was an angel. She was good enough for the Lord's light... Unlike you. (he presses the stinger of his scorpion tail against Arackniss' face, just inches from his eye) If you keep talkin' shit about her, yer gettin' sent to Anthony as an example as what I'm gonna do ta him. Capiche?
**Arackniss**: (he quivers in fear) Y- Yes, Pa. I- I get tha message...
**Henroin**: (he begins walking away) To my office. Now.*"
— Henroin intimidating Arackniss.

"***Henroin**: (laughs dryly) Would you look at that? Anthony's been loungin' about with Crimson's boy! (laughs loudly and facepalms) Oh, what a tangled web we weave...
**Arackniss**: (laughs) That's rich, boss. Well, y'know what they say; fags of a feather fuck together. (he bursts out laughing before Henroin slams his fist on his desk, sending Arackniss to the ground, having misread Henroin's mood)
**Henroin**: **YOU THINK THIS IS FUNNY, YOU FUCKIN' STRONZO**?! (Arackniss flinches in fear) S'all a fuckin' game to you, huh? You think it's funny that my precious 'son', and yer brother, is out there prancing around like a dainty little fairy in fishnets, lettin' all tha putzes in Hell ogle his backside like he's a piece of meat? Think I'm gonna sit on my ass and act like a fuckin' comedian and let that happen? Nah. Not my son. Not ever. (he looks slowly goes into his full demon form, violently using his stinger to stab a television advertising Angel Dust) **Not**. **My**. **Son**.
**Arackniss**: (analyzing the stinger and television) Hmm... Say... Crim's gonna wanna know about this, seee? I heard he and his boy ain't on tha best of terms at the moment. If we get him involved, we can have our way with both of those faggots, seeeee?
**Henroin**: That... Might be the wisest thing you've said all day, boy. But, let me do tha talkin'. Just shut yer fuckin' yap, and watch and learn from tha boss. (to his receptionist) Tell Crim I have a proposition he might like. And step on it! (the receptionist runs off)*"
— Henroin and Arackniss conspiring.

"***Rough Cut**: Henroin! How's life my dude?
**Henroin**: It's goin' swimmin'ly, thanks to you. I hear you decided to take down our competitor. Thanks fer that... I'm assumin' you came here for yer payment. Why else would ya come? (Henroin and Rough Cut both laugh) Alright. Let us say that I wanted a "personal" touch added to your product and in exchange, I would be willin' to do whateva you ask, within reason, of course, and make a large sum of money... In theory, of course. What would your answer be?
**Rough Cut**: What kind of 'personal touch'? What's with the fancy-schmanzy word play?
**Arackniss**: He's sayin' he's gonna rob ya, batty boy!
**Henroin**: (he whips Arackniss into a wall with his tail casually) I'm a man of my word, so you'll get 'payment'. But... ya know me. I pay, but not with cash. You get a choice. Eitha ya work for me, or ya die. Which'll it be?
**Rough Cut**: (he sighs and shakes his head) Henny, I thought you were my guy, my main man! (goans) Guess you really can't trust anybody in this goddamned pit. You don't wanna go and make an enemy of me, my friend.
**Henroin**: (Arackniss moves to aim his gun at Rough But, but Henroin stops him with one gesture of his arm, laughing) A funny guy, eh? Well yer lucky we've broken bread several times by now or youz woulda been sleepin' with the fishes a while ago. (to Arackniss) Son, kill the yardie if he doesn't do what I say.
**Rough Cut**: (he sighs) I'm assumin' this deal non-negotiable?
**Henroin**: 'fraid so, pal. It's an offa you can't refuse.
**Rough Cut**: Well, jokes on you, bredren, 'cuz I'm refusin' it.
**Henroin**: (laughs) I love jokes! Ya ever hear the one about the Jamaican sonuvabitch who was so fuckin' stupid and desperate to die, he couldn't tell he was bein' set up despite his many years in the business? That he couldn't see the barrel of the gun... Right behind his head? (just as Rough Cut turns around, he is shot in the head by an unseen figure, who turns out to be Crimson; Henroin cackles as Rough Cut's body slumps to the floor) Fuckin' amaterues...
**Crimson**: (he hands his pistol to Alessio for him to clean up, cackling) It's not everyday I get ta blow some poor schmuck's face off up close and personal. Oh, wait, it is! (he and Henroin share a laugh as Crimson sits down and they shake hands)*"
— Henroin's deal with Rough Cut.

"***Henroin**: How's life treatin' ya, Crim?
**Crimson**: It's treating me... Well enough... So what did you need my presence for? I heard we've got some business to be done regarding some... common enemies. I flew all the way from Greed for this job so let's not keep our customers on the bench long.
**Henroin**: (he chuckles) Indeed, my friend. (he sits in a chair across from Crimson) Oh, yer a unique fella, aren't ya, Crim? There ain't many like ya out there, I'll give ya that. Folks who got the balls the do things that most are too pussy to do themselves. Most folk, they'd be quakin' in their boots, pissin' their pants at the sight of me. But you, you ain't. You ain't afraid of me, are ya?
**Crimson**: I've got balls of steel, what can I say? (he grins, clearly pleased with himself) How 'bout you?
**Henroin**: Ah, it takes more than just steel balls to run a mafia, my boy. It takes smarts, leadership, a lack of ruths, respect, power, charm, and a whole lotta violence. I got all that covered, how 'bout you?
**Crimson**: I got all that and then some. (he laughs) You've seen it all before. Let's get down to business, see?
**Henroin**: Of course. You're my boy, Crim. Ya know I'd neva let ya down. So believe me when I say that this deal is a great opportunity ya can't refuse, especially in lieu of recent... Familial complications.
**Crimson**: (sighs) My son, Moxxie, is... Uncooperative... He's refusing to cooperate with the family, and it's costin' me my whole empire. Can you believe that shit? I put my dark soul into building my family into what it was, and then he thinks he's too good for us and runs off to hide behind his satandamn beard!
**Henroin**: (groans) That 'beard' wiped out half of your reserves, friend... Right in front of ya. You let some dizzy dame kill your men, and ya didn't even try to fight 'er?
**Crimson**: I didn't expect her to get that far, man! (he grits his teeth as Alessio refills his glass) She's just one of many pains in my ass that I need to get rid of... I need 'er gone, for good, before she does any further damage.
**Henroin**: (he begins smoking a cigar) And, uh, let's not ferget that jabroni who tried to marry into yer family. Alls it takes is a tacky suit to pull a wall over your eyes, huh? No background check or nothin'.
**Crimson**: (eyes widen) Are you sayin' I'm gullible?!
**Henroin**: I'm an honest man, Crim. That was... A pretty fuckin' big mistake. And look what it cost ya. A mafia on the wrong side of the grass, all ova a fag weddin'.
**Crimson**: Listen 'ere... That sorry sonuvabitch got what was comin' to 'im for tryin' to swindle me. **Anyone** who's EVA crossed eitha went to the blocks, or is livin' out their existence as a satandamn momento on my wall! So, did you call me 'ere to bust my balls, or are you gonna propose we do somethin' about all of this? (Henroin nods to one of his goons, who places a photo of Angel Dust and Moxxie together in front of Crimson he picks up the photo and analyzes it with a hint of fury before a twisted smile forms on his face) I'm listenin'...*"
— Henroin and Crimson scheming together.

"***Crimson**: Hahaha! I had a feelin' that dumb broad was just a beard! What kinda pathetic freak are ya, Mox?! Datin' some drug-addicted whore like Angel Dust!
**Moxxie**: W-Whuh? ...Crim, we're not... (Moxxie's eyes widen) You... do know that bisexual men can have platonic male friends, right?
**Henroin**: That's the biggest piece of bullshit I've ever heard.
**Crimson**: EXACTLY! (to Moxxie) You think I'm stupid! You seriously think gays like you are capable of befriendin' another guy and **not** wantin' to get in his pants?!
**Angel Dust**: Ay, Mr. Fuhgeddaboudit, me and Mox is like brothas. Trauma brothas, ta be exact.
**Henroin**: (Henroin uses one of his scorpion legs to stomp on Angel's foot, impaling it) What trauma, Anthony? Havin' to wear a suit instead of a frilly dress? Havin' a meltdown decidin' which fedora goes with yer eyes? Having to frantically removin' all that fuckin' makeup when I came for a visit?! (Henroin removes his leg from Angel's foot; he leans in and blows cigar smoke in Moxxie's face) You must be a special kinda stupid to try and get close to Anthony, sonny. (Henroin laughs) Eh, who am I kiddin'? You two deserve each other. Yer both disgraces to the mafia. Me 'n' Crim run a mafia, not a gay pride parade.
**Angel Dust**: (snickers) Wait a minute... (Angel bursts out laughing) Youz thinks we're lovers?! (Angel and Moxxie share a look before mutually bursting into laughter)
**Moxxie**: Classic!
**Angel Dust**: (to Moxxie) Oh, brotha! They's, they's thinks we's-! (Angel and Moxxe go down on the floor from laughing) Oh, shit! That's fuckin' rich!*"
— Henroin and Crimson confront Angel Dust and Moxxie.

"***Henroin**: What's the problem here?
**Amelia**: (to Simon; whispering fearfully) Simon, please...
**Simon**: So-
**Giulia**: (she covers his mouth, stammering nervously) N- Nothing's wrong, sir! He's just being dumb!
**Simon**: (he removes Giulia's hand) There's no pineapple on our pizza!
**Arthur**: Aaaand here we go. (he puts an empty plate on his head like a helmet as Megara hides behind Manco fearfully)
**Henroin**: ...Kid, pineapple don't belong on pizza. Tha hell's wrong wit' you?
'**Simon**: Why not? It's soooo sweet and nutritious! Also, why were my pasta noodles not broken in half?
**Henroin**: (his eyes twitches) You- You don't **break** pasta noodles in half! You kids are killin' me! The fact you even wanted a goddamn pizza prepared that way, I see it as an insult to my wife's memory!
**Simon**: This is **totally** how pizza should be made. (Henroin frowns deeply) Aw, what's wrong? (in a bad Italian accent, pinching his fingers) Am I breakin' yer wife's ball- (Manco frantically covers Simon's mouth, laughing nervously to Henroin)
**Henroin**: (after a pause, he leans into Simon's face menacingly) Listen, sonny... I spent 10 years in the kitchen makin' the finest Italian cuisines with my pa. I buried ten people alive just to open my first restaurant, and I've put hundreds of demons in cement shoes fer sayin' the same shit yer spewing right now. I didn't invest half my life - both of them - in this business fer you little assholes from America to fuckin' tell me how to run a goddamn restaurant. I get it. Yer young. You fucked up. I geddit. So, the next set of words to come from yer mouth better be an apology... Or else the only thing you and yer pals are gonna be eatin'... Is **lead**.
**Simon**: ...What's 'America'?
**Henroin**: (he slowly leans off the table) ...Unbelievable. (walks away, whispering to himself) Get tha fuck outta 'ere...*"
— Henroin is disrespected by Simon.

"***Employee**: That kid is bustin' yer balls. What are we gonna do?
**Henroin**: Got a gun?*"
— Henroin joking with his employee.

"*This kid is outta control... I think someone needs to put 'im in line.*"
— Henroin about Simon.

"***Molly**: Daddy, listen **please**. Anthony IS your son... You used to push him on the swing, remember? You helped him learn how to ride a bike... We would go on all those vacations to Italy, have picnics and you would fish with him. When he won that game of bocce with the otha kids, he cried when you cheered for him. (laughs tearfully) He would beg ya to do macaroni art with him and you would try to turn your back... but ya couldn't. He's yer SON, and who he loves has no bearing on that...
**Henroin**: (looks away from Molly for a second, before facing her) I did. I did love him... (his expression darkens) **But he let me down**. He disgraced our family and culture and I'm not gonna sit on my ass like a vagabondo and let his degeneracy slide. Not now, not **eva**.*"
— Molly fails to appeal to Henroin.

"*Ti ho proposto la proposta di matrimonio sul ponte vicino alla casa di Madre Maria nell'estate del 1902. Abbiamo vissuto felici e contenti, come in una fiaba. (to Molly) Annie! Oh, mio caro. Stavo ricordando la nostra vacanza in Spagna. Molly ci ha fatto impazzire con i suoi scherzi. Anthony e Salvatore hanno fatto volare insieme quell'aquilone e gli abbiamo comprato la loro Vespa. Eravamo seduti sotto l'ombrellone mentre provocavano il caos in città. Hanno riso insieme per la prima volta. La nostra famiglia era così perfetta, come in una fiaba.*"
— Henroin's delirious, dying words.

## Trivia

* Henroin's mannerisms and way of speaking is patterned after American actor Christopher Walken.,
* His sinner name is a portmanteau of his true name "Henry", and the drug heroin.
	+ Henroin earned his name from sinners due to heroin being his most marketed drug.
* His theme song would be "I Wan'na Be Like You" by Christopher Walken.
* Angel Dust claims that, in life, Henroin considered selling him in order to pay off debts.
* One of Henroin's associates bares a resemblance to Marlon Brando's portrayal of Vito Corleone from *The Godfather*.
* He, along with most of his family, is Catholic.
* He owns a restaurant that is named after his wife, Annie, showing that he owns some legitimate businesses alongside his less than legal enterprises.