Warden

His absolute rule and domain over Superjail causes numerous problems, as he thinks up twisted ideas that invariably wreak havoc on everyone. No matter how absolutely ridiculous his schemes are, they all seem perfectly rational to him. In spite of his recklessness, he is still nonetheless a technical genius, as shown in his ability to plan out and build Superjail in the first place, along with various inventions and mechanisms (including Jailbot). He does occasionally exhibit an underlying sense of morals and dedication on certain occasions, such as his vow to help his inmates and save them.[6]

The Warden is extremely narcissistic, to point that he has apparently committed all of the Seven Deadly Sins of Narcissism[7] and has exhibited many, if not all, the traits related to it. Due to his narcissism, he automatically loves anything of his likeness, even going as far to design Superjail's various buildings and weapons with his likeness, and getting excited when he sees things with his face on them.

The Warden's behavior may have started when his father died and he inherited his father's jail at a young age. Trauma, and being exposed to such an environment at an early age, might have caused a stunt to his emotional development. Having had a less-than proper childhood, thanks to his father's abuse, even in his adulthood he is very immature and exhibits childish tendencies, and The Mistress even refers to him as an "overgrown man-child" in "Ladies Night.

Dark side

Despite his usual cheerfulness, The Warden is notable for easily slipping into pure evil. He appears to enjoy the killings which occur on a regular basis at Superjail and has stated that he never misses an execution.[8]

In "Combaticus", he discovers a deadly combat arena while exploring an underground cave and gathers all the inmates to battle each other to the death, offering freedom to the last one alive.

In "Time-Police Part 1", it is revealed that if he proceeds with the idea of making Superjail a franchise, he will eventually declare world war and conquer the whole planet, enslaving and killing millions of innocent people.

In "Burn Stoolie Burn", when he gains the ability to manipulate fire, he goes insane and starts a mass burning rampage through Superjail, completely losing control over his prison, staff, and inmates. Eventually, he destroys the entire prison and the volcano it is located in, transforming the prison into what is essentially hell on Earth, as he rules over fiery and demonic creatures.

Relationships

Employees

Jared

Jared is essentially the Warden's whipping boy and is often subject to the Warden's abuse, which he often accepts without hesitation. He thinks that Jared needs to calm down most of the time and clearly cares little, if at all, about his feelings, mental health, and physical well-being. Most of the time, the Warden thinks that Jared is incompetent, and in the rare moments wherein he does agree with him, this is usually related to his own gain or praises about him.

Nonetheless, they occasionally do get along, such as in "Uh Oh, It’s Magic", where they team up together to defeat Prison Peedee, and on certain occasions it is shown that the Warden consider Jared to be a friend.

Alice

The Warden recruited Alice from her job at her previous jail, where he immediately took a liking to her ruthlessness towards prisoners and her "ravishing" appearance.[9] He makes frequent advances on her throughout the series, all of which have proven unsuccessful. It is shown that he apparently sleeps with a miniature Alice doll at night, and in "Dream Machine" he is depicted dreaming of going on a date with her.

Jailbot

The Warden created Jailbot and takes great pride in him, describing his creation as his "finest hour".[9] The Warden often sends Jailbot on missions to collect new inmates or protect him from various objects and things, and he is completely dependent on Jailbot to run and provide maintenance for Superjail. In fact, he is completely lost without Jailbot, to the point of not knowing where the bathroom is.[10] Jailbot does nearly everything for the Warden, even getting him ready for the day.

Jailbot sees the Warden as a father figure, as seen in the episode "Dream Machine". The Warden is extremely upset in "Jailbot 2.0" when Jailbot breaks down, even bursting into tears and considering Jared's initial suggestion of replacing Jailbot as a "sacrilege"; by the end of the episode, he is relieved when Jailbot is fixed and affectionately refers to him as his "buddy".

Prisoners and other characters

The Mistress

The Warden and The Mistress, who is essentially the Warden's female counterpart, are bitter rivals. He wagered with the Mistress in "Ladies Night" that his prisoners were more civilized than her female prisoners, a bet that he ends up winning thanks to interference from the Twins. The Mistress ends up getting bitten by one of the Spanish flies released by the Twins and in a completely aroused state, she has sex with the Warden. The next morning, he gloats upon winning and declined the winnings and stated that the ladies were "too unrefined for such a high-class establishment like Superjail", if only to aggravate her even further.

In "Stingstress", the Warden and the Mistress are set up to become the "super couple" of Superjail by Jared and Sharice in order to bring Superjail to peace (since it had been taken over by the Mistress) and therefore bring them together. The Warden and Mistress almost have sex for a second time, but this time around the Warden was more interested in making animal balloons with the condoms he was given instead of actually partaking in the act.

Following the Mistress' conversion to a hippie-type figure she seems to have a more lax attitude towards the Warden, though he still resents her.

The Twins

Aside from the pilot episode, the Warden makes no mention of The Twins and is either oblivious to their activity in Superjail or chooses to overlook their interferences. Only briefly do they make an appearance in front of him in the episode "Combaticus". He also witnesses The Budding of The Warbuxx, but says nothing and acts like it is completely normal.

Ash

In "Burn Stoolie Burn", after the Warden mistakenly believes that Ash wanted to help the Warden (Ash was, in reality, stealing the Warden's safe with a group), he decides to allow Ash to help put up new wallpaper in his room instead of much more life-threatening tasks involving head-lice that can eat him. Soon afterwards, Ash starts becoming one of the Warden's more favored inmates even to the point that not only does the Warden give Ash a VIP ride in the hot air balloon and cling to Ash when he thinks he is about to die, but the Warden even gives Ash his own pony and burns down his own jail (along with Ash) to stop him from being beat down by the other inmates.

The Warden, before burning down his jail, describes Ash as an "innocent soul." In exchange for his kindness, Ash teaches the Warden how to create fire out of nothing. In "Superhell!", Ash later teaches the Warden how to put out the fire by thinking of his worst memories, though after the events of the episode the Warden has seemingly lost his memory of his friendship with Ash.

The Warden's father

As a young child, the Warden constantly tried to impress his father, but instead of earning praise, the older man would instead get angry at him. There is evidence of both verbal and physical abuse as seen in "Time-Police Part 1", where the Warden's father would yell at him and throw his toys. However, despite this the Warden appears to have no grudges against his father and even cried when he unintentionally caused his death and sent him to the orphanage.

In a deleted scene, it is shown that the Warden seems deeply depressed about how his father yelled at him and died before he could apologize (though he probably wasn't going to), a sign that he does not blame his father for the things that happened between them, but instead blames it on himself. He thinks his father would be proud of his Superjail if he were alive, which supports the fact that he still longs for his father's approval.

Jarum

Jarum was the assistant of the Warden's father and possibly became the Warden's caretaker of the orphanage after his father's death. The specifics of their relationship, however, are unknown.