Gerald Fitzgerald "Fitz", Sr. is an African-American Zen Buddhist who suffers from post-traumatic stress disorder, who works as an officer for Paradise Police Department. Before working at Paradise P.D., Fitz worked for Chicago Police Department. Gerald is later revealed to suffer from Dissociative Identity Disorder (DID), where a traumatic incident that killed many hostages back when he worked at Chicago P.D., created a split personality he was unaware of known as The Kingpin, who led an evil drug corporation called The Legion of Dooooom and in turn became the corrupt mayor of Paradise. He is voiced by Cedric Yarbrough.
- 1 Biography
- 2 Appearance
- 3 Personality
- 4 Relationships
- 5 Trivia
- 6 Gallery
Not much is known about Fitz's childhood, other than a brief flashback shown in "Task Force". As a kid, Fitz was playing with a paper boat in the rain and watched it go down the gutter. When he went down there to look, a pedophile clown came up behind him and flashed his uncircumcised dick at him, which mentally scarred him for life and gave him a crippling fear of clowns that he never got over.
As an adult, Gerald Fitzgerald worked as a police officer for the Chicago Police Department. There, he was the best police officer in town. He was able to bust every criminal he got on the case of, except for one elusive bastard; The Kingpin. The Chicago Kingpin was the town's most notorious criminal, as he had never been caught and Fitz was hell-bent on becoming the one to finally stop him.
Trauma & Recovery
Gerald Fitzgerald is shown to suffer from PTSD, after suffering from a very traumatic experience. The details of which had been long unspecified until the episode "Operation DD" gave full clarity to the story.
As explained in the flashback: On December 25th, 2014, Fitz was in a hostage negotiation with The Kingpin at the Bomb Factory. The Kingpin demanded $1,000,000 cash, a stealth bomber piloted by Mike Ditka as a getaway vehicle, and most importantly of all, a Chicago-style deep-dish pizza. The latter would be the most difficult to acquire, given that it was Christmas day and all pizza stores would be closed for the holidays.
20 minutes later, Fitz gathered together everything The Kingpin asked for. He entered the Bomb Factory with the pizza but The Kingpin was unsatisfied with what he got. Instead of getting the deep dish he asked for, all he got was a stack of three Hot-N-Readies from Little Caesar's, which Fitz shook up in the box, in hopes that it would be passable. The Kingpin was unimpressed and pressed the button, blowing the Bomb Factory, and everyone in it, to shrapnel. Everybody died, except for Fitz, who was protected by the extremely hard and inedible crust of the pizza.
Although Fitz survived, this trauma gave him severe PTSD and he had to be locked up in a mental hospital just to keep him from going insane in public. Fitz dealt with crushing guilt, over the fact that he was responsible for the deaths of the hostages, which drove him mad in the hospital and led to his brain getting split up into multiple personalities. One of these personalities was an impersonation of The Kingpin, who would occasionally seize control of Fitz's body, swearing revenge on him and all cops in general for giving him an inadequate pizza.
Thester Carbomb IV worked as Fitz's psychologist and tried to help Fitz get over his kingpin persona, by hypnotizing him and creating a mental prison in his head called Pussyland, which he planned on trapped the kingpin inside of. Little did Thester know, The Kingpin was taking over Fitz's mind every night until the day he dominated Fitz completely and then used his body to physically pretend to be recovered and then escape the mental hospital, continuing about his life under the guise of being Fitz. However, The Kingpin wasn't 100% dominant of Fitz and could only control his body at night. During the day, Fitz was in full control of himself.
As his normal self, Gerald Fitzgerald decided to quit his job at the Chicago P.D. and take some time off to relax. During his time off, he took up meditation to help him calm his nerves and put an end to his PTSD. He also got a piccolo, which he would always carry around to keep himself calm.
In "Black & Blue", Fitz began to tell this story before being cut off. Most of what he said matched up with the real story, such as it taking place at a Bomb Factory on December 25th, 2014. However, he also mentioned a shark breaking loose in said factory. This story element was nowhere to be found in the flashback.
When he left his job in Chicago, and went to work at Paradise Police Department in Paradise in 2016, he was still suffering from PTSD, and he needed to use Asian meditation rituals, such as Zen Buddhism and the use of a piccolo to keep himself calm.
Gerald was hired at Paradise PD in 2016, shortly after the death of former officer, Blackie Chan. Gerald's primary purpose for being hired was so he could fill the newly empty position, that Blackie once held.
The quality of Gerald's performance as a police officer had sharply declined since then, as now he was too afraid to fight any actual crimes and his from work either by lounging around in his car, goofing off with friends, or most prominently, doing things like meditating or playing his piccolo. Whenever his incompetence was brought to attention, Gerald would just use his PTSD as an excuse.
In "Welcome to Paradise", Randall's son, Kevin Crawford started working at Paradise P.D. and he soon became Gerald's friend. Unlike the rest of the cops at Paradise P.D., Gerald considered Kevin to be an equal and he treated him with dignity and respect, despite the latter's constant fuckups and bullshittery.
While working at Paradise PD, Gerald secretly ran an illegal business, that sold drugs. Two of his workers, Terry Two-Toes and Santa Claus, invented Argyle Meth, which then became the company's best selling resource. Terry was touted as the leader of the business, so that the cops of Paradise PD would think that he led the entire company. In case people realized that there were people of higher power than Terry, Gerald also touted Santa Claus as the "secret bigger bad", making it harder for people to discover the ultimate headmaster of the business.
At the end of "Welcome to Paradise", Terry Two-Toes was caught and arrested. While being held in the police department's prison cell, Randall said that they'd interrogate him tomorrow, for more information on the argyle meth business. Gerald could not let him spill the beans about him being behind all of it, so in the middle of the night on September 25th, 2018, he shot Terry Two-Toes, and planted a forged suicide note on him, and stole the surveillance footage, so that nobody would know he did it, and people would assume that Terry killed himself. The next day, Randall saw the scene and was led to believe exactly what Gerald wanted him to believe. Randall was stupid and decided not to look any deeper into the situation. However, Kevin knew something was amiss, and made it his separate goal to find out what really happened.
Gerald has a crippling fear of clowns. His fear is so bad, that in "Task Force", he got scared into a coma, after he was bombarded by a gang of clowns in a creepy old carnival in the middle of the night. This lasted until "Christmas in Paradise", where it was revealed that he was faking his coma the whole time. At the time of the coma, Kevin found stolen footage and learned that a member of Paradise PD shot Terry. Unfortunately, the tape was not clear enough to reveal who it was. Since the culprit's plan was still taking place, during Gerald's coma, Kevin was quick to rule him out, getting on the case of everyone else. Afterwards, all signs pointed to Dusty Marlow, successfully framing him and letting Gerald off the hook. With Gerald in the clear, and Santa Claus recently murdered by Dusty, Gerald was now ready to take all the argyle meth money for himself and continue his plan to take over Paradise. He also intends to kill Kevin for being the only cop to actually investigate in the Argyle Meth case.
After coming back from his coma, Gerald Fitzgerald's body was completely taken over by his alternate personality of The Kingpin and became a full-time villain, although he still pretended to be a good guy in front of Paradise P.D. in order to maintain trust. As The Kingpin, Fitz worked with Thester, who posed as his sidekick and they started an evil meth company called The Legion of Dooooom.
Although The Legion of Dooooom was initially planned as a company for selling argyle meth, shortly after it's launch, houndstooth meth began sweeping the streets of Paradise. The new drug rendered argyle meth obsolete and gave Fitz some competition. Fitz took the case so that he could stop the criminals, discover the houndstooth meth kingpin and take over the drug business for himself. The houndstooth meth kingpin turned out to be Cop Bot and Fitz defeated him and stole the recipe for houndstooth meth. After obtaining the recipe and making houndstooth meth, himself, The Legion of Dooooom's new goal was to sell houndstooth meth and profit off of it and fund Fitz's evil plan, Operation: D.D..
In "Flip the Vote", Fitz ran against Karen Crawford for mayor of Paradise in the 2020 Paradise Mayoral Election. Ironically, Karen was the one doing unethical and illegal things to win the election, while Fitz and The Legion of Dooooom played by the rules. Arguably, the only thing Fitz did wrong was withholding information about himself being The Kingpin, although he did promise to release the information about The Kingpin when he became mayor. In the end, the only person to vote on election day was Kevin, who voted for Fitz, letting him win. Immediately upon becoming mayor, Fitz revealed that he was the mayor and that as mayor, he'd be abolishing the police. Fitz and the rest of The Legion of Dooooom shot at the cops of Paradise and ran them out of town.
In "Operation DD", Fitz finally revealed what "Operation: D.D." stood for. It stood for "Operation: Deep Dish" and he would be turning the city of Paradise into a giant Chicago-style deep-dish pizza as revenge for not getting one back in 2014, (still believing himself to be the embodiment of The Kingpin). After covering the town in pizza sauce and cheese, he set a timer for 10 minutes, which would eventually fire a nuclear missile at Paradise to cook the pizza to a crisp.
Kevin used a brain device to transport himself inside of Fitz's brain so that he could get to Pussyland and help him escape. When they got out, an imaginary version of The Kingpin showed up to put Fitz back in his brain dungeon, saying that he was in control of his mind. Fitz didn't have the strength to fight The Kingpin, blaming himself for letting all of the hostages getting blown up at the Bomb Factory. However, Kevin told him that all of the people he killed were Instagram influencers, including Logan and Jake's fictional triplet brother, Chaz Paul. Fitz now felt as though he had the right to fight The Kingpin but still thought he was too powerless. Kevin told Fitz that since this is in his imagination, he can do whatever he wants. Fitz got the idea to transform into a giant, all-powerful, godlike being that was a combination of every superhero and villain from the Marvel/DC universes and he used his powers to blow The Kingpin to smithereens in a giant nuclear explosion.
After destroying The Kingpin, Fitz finally had full control over his own body again and regained consciousness. Now that Fitz was back to normal, he joined the cops in their mission to disarm his previously fired missiles. Fitz went to disarm the missile with his retinal scan but as The Kingpin, he had previously disabled the disarming device, leading to the nuclear missile blasting Paradise to a perfectly cooked pizza, just as planned.
For three months after the blast, Fitz lived in the sewers with everybody else. When he came back out, he was shocked to see the remains of his city. Fitz apologized for what he did, while he was the kingpin but Kevin let him know that is wasn't his fault, even though Randall said he was entirely to blame. After this atrocity took place, Fitz tried to do the best he could to put his life back together again.
Marriage and Parenthood
Fitz found out that during his time under the kingpin persona, he got married to the Dolphin Queen and they were still together to this day, making them an official couple. Fitz was freaked out by the fact that he was fucking a fish and went to go get a divorce. However, just before he could tell her this, she told him she was pregnant. After hearing he'd be having a child, Fitz suddenly had a change of heart and tried to make things work with his unconventionally unionized new wife. When she gave birth to their kid, Fitz named him Junior and was blind to the fact that it was so clearly the child of Dolphin Queen and Bullet.
Gerald Fitzgerald is an African-American man with short, black hair and a black mustache. He wears a blue police uniform with darker blue pants and black shoes.
Gerald Fitzgerald is a stereotypical black man, who enjoys doing "black" things like listening to rap music, following the lives of black celebrities, and reminiscing about the glory days of 1980's basketball. He outright rejects doing "white" things, as he tries to distance himself from indulging in "Caucasian culture". Despite this, he's still a fan of Michael Bublé. Fitz suffers from psychiatric disorders and has a bad case of PTSD, from an incident that occurred the previous police station he worked at. Because of this, he needs to do therapeutic to calm himself down like playing the piccolo and meditating. All of these things are Asian centric, like Zen Buddhism and Hindu shit, adding a little Oriental culture into his mostly Afrocentric multicultural pool of interests. Fitz also has a sexual fantasy about a magical world called "Pussyland", which is a land made out of female genitalia that he flies to on a blimp.
Fitz suffers from post-traumatic stress disorder, multiple personality disorder, and dissociative identity disorder, due to a traumatic incident that took place on, December 25th, 2014 at the Bomb Factory, where he was negotiating in a life-threatening hostage situation with a crime boss known only as "The Kingpin", who nearly killed him and succeeded in killing several hostages. Fitz's PTSD is so bad, that he can't handle leaving his station to fight crime anymore, as this would only bring back his horrifying memories again. As a form of therapy, Fitz needs to engage in Zen Buddhist practices such as meditation to keep himself calm and level. His most important form of therapy, however, is playing his piccolo. Without it, Fitz will be put on edge and will be very stressed out and terrified.
Multiple Personality Disorder
Fitz has multiple personality disorder and dissociative personality disorder, which give him other personas, which are triggered by fear. His personalities can be very dangerous as many of them are representative of criminals and evil people and once they come out, Fitz is powerless to stop them. The only way to keep these alternate personalities at bay is to keep himself calm and timid with meditation and other therapeutic practices. In "Black & Blue", Fitz had his piccolo confiscated, making him a nervous wreck and allowing for his stress and terror to take over his body, splitting him into two personalities, Officer Fitzgerald, a law-abiding police officer, and G-Fitz, a murderous thug. He would switch back and forth between the two personas and get into arguments and even physical fights with himself, inflicting self-harm and indulging in delusion.
The most impactful alternate persona, Fitz had suffered from, however was The Kingpin, which was an impersonation of the real-life, Chicago Kingpin, who he fought with back in Chicago. The trauma and guilt Fitz suffered from the incident in Chicago fractured his brain into two personalities. One was his own personality and the other one was an impersonation of The Kingpin. His Kingpin persona would occasionally take control of his body at night, though it would lie dormant during the day. This alternate persona fully took over Gerald's body when he was put into a comatose state brought on by his intense fear of clowns. While The Kingpin dominated Fitz, the original Fitz was trapped in a the mental prison of Pussyland. This lasted until the events of "Operation DD", where Kevin helped intercept Fitz's brain and team up with him to take down The Kingpin and reclaim his own body, which he succeeded in doing. Since then, Fitz has had full control over his own body and is now free to be his true self.
As The Kingpin, Fitz is a vile, grim, hateful, and malevolent man, whose goal is to get revenge on his original personality by nuking all of Paradise into a giant pizza, killing everyone in it, even himself. In order to fund this project, Fitz started up the Argyle Meth company, where he profits off of distributing illegal drugs across all of Paradise. All of the proceeds would go to Operation: D.D., which was a project that would see his possessing nuclear weapons, pizza toppings, and other preliminary components to his ultimate plan. Fitz was of course, two-faced, pretending to be his original self, whenever he was around the Paradise P.D. in order to maintain his cover. Aside from drug dealing and nuking the city, Fitz committed several other heinous acts of villainy, such as three separate murder attempts on Kevin, Dusty, and Randall, stealing money from the Catholic Church, and becoming a corrupt mayor who turned Paradise into a hellish dystopia.
- Randall Crawford - Randall is Fitz's current boss. Fitz is an obedient worker who follows Randall's orders and is one of the few workers who actually demonstrates competence. Despite mostly being a dutiful deputy, in "Ass on the Line", Fitz said that "sometimes a good soldier needs to know when not to take orders." and decided to defy Randall, when he was going insane over the case of the murdered ass person. The only real problem Randall has with Fitz is that the latter's PTSD often makes him too afraid to fight crime or even wield a gun. However, "Black & Blue" made it obvious that it's much worse for the team if Fitz actually uses a dangerous weapon, as it only made him shoot himself and give Paradise P.D. a bad name. Fitz is often offended by Randall's racist comments about black people, which will cause him to squint his eyes at him angrily. However, since Randall is his boss, there's not much Fitz can do to get revenge on him. During the majority of Season 2, when Fitz was under the control of The Kingpin, he worked as a mole at Paradise P.D. and secretly hated Randall and hoped to take him down. In "Who Ate Wally's Waffles?", Fitz ordered a lorry bomb to be placed under Randall's car as a murder attempt. In "The Father, The Son, and The Post-It Note", Randall found out that Fitz was The Kingpin and lost all faith in him as a cop. Fitz had Randall kidnapped and locked in the crackhouse so that he wouldn't spill his secret, as would be continued in "Flip the Vote". In "Operation DD", Thester explained to Randall that "The Kingpin" was just an alternate persona that took over Fitz's real personality, which made Randall like Fitz again but not before defeating him in an ultimate showdown to defeat his evil persona and free his true self from his mental prison. After Fitz was returned to normal, Randall became immediately annoyed by his regular self and sarcastically asked if they could have his evil persona back. However, he soon decided to deal with it.
- Kevin Crawford - Fitz has become good friends with Kevin, ever since the latter joined Paradise P.D.. Kevin even considers him to be his best friend. In "Karla", Fitz and Kevin went to the bar together as drinking buddies. This episode also demonstrated how much Fitz cares for his friend. When Fitz heard that Kevin was being abused by his girlfriend, he encouraged him to break up with her or at the very least, seek help. In "Task Force", Kevin told Fitz to look behind him to see a parade but by the time he looked, the parade left and all Fitz saw a skywriter spell out "Will You Marry Me?". Thinking that Kevin was proposing to him, Fitz seriously told Kevin that he would think long and hard about his offer. In "Parent Trap", Kevin demonstrated his care for Fitz, when he visited his comatose companion every day in the hospital and would not leave his side until he woke back up again. In "Christmas in Paradise", Fitz turned out to be The Kingpin and said that he hated Paradise P.D. but the cop he hates most of all was Kevin because he was too smart for him and he needed to take him out first. Throughout Season 2, Fitz would secretly target Kevin and try to kill him while working at the Legion of Dooooom. However, he would also keep his cover by pretending to be his friend, when he was working alongside him at Paradise P.D. In "Flip the Vote", Kevin refused to believe that Fitz was The Kingpin, only to have his heart broken when he found out the truth. In "Operation DD", Kevin used a brain device to enter Fitz's brain and free him from his Pussyland prison.
- Bullet - Fitz and Bullet are partners who don't always get along. In "Ass on the Line", Fitz reminded Bullet how he went in blackface at a Halloween party but Bullet said that it was perfectly okay for him to do that because he was technically "partly black", as he was a German Shepherd who was one sixteenth pitbull. In "Meet the Jabowskis", Fitz and Bullet both cut work together to go have a fun little skip day together. However, things all went south, when a guy crashed his car and died, leaving behind a briefcase full of millions of dollars. Fitz and Bullet needed to wait one day before they could legally cash it in. In the meantime, the two of them suspected each other would run off with the money, keeping it all for themselves, so they both rented an apartment at the Super Seedy Motel and stared each other down. This stare down soon turned into an all-out brawl, where they both attacked each other until Fitz was knocked unconscious and robbed by Bullet. In the end, they were both mistaken for a gay couple and needed to pretend to be one so that Randall wouldn't know they were skipping work that day. In "Operation DD", Bullet called out Fitz for how stupid his plan to turn Paradise into a giant pizza was.
- Gina Jabowski - Fitz is quite unnerved with Gina, seeing her as a crazy bitch. In "Meet the Jabowskis", Fitz even assumed she had BBCD (Bitch Be Crazy Disease), which would soon turn out to actually be true later, when Dr. Funtlichter diagnosed her with just that. In "Black & Blue", Gina was sick and tired of Fitz paying the piccolo instead of doing any actual police work and demanded that he use a gun like a regular cop. Fitz used the cop and shot himself in the leg and Gina leaked his dash cam footage of this incident to the public in an attempt to get him fired. In the end, Gina realized that Fitz was much safer off with the piccolo instead of a gun and allowed him to use his piccolo again.
- Dusty Marlow - In "Welcome to Paradise", a cutaway gag featured Fitz meditating while his partner, Dusty got beaten up by criminals. Later, Fitz hid behind Dusty as a human shield when Terry Two-Toes and his minions shot at them. In "Black & Blue", Dusty's ass served as a green screen for Fitz's news report, which really grossed him out. Later, Dusty and Gina both helped Fitz escape the media by having Dusty dress as an Islamic transgender NRA supporter, who got analraped by the Trump-supporting Fitz, while he performed an abortion on the pro-life, pro-gay, Nazi Gina. In "Police Academy", Dusty saw that Hopson was wearing chains and assumed that he was making fun of Fitz's ancestors. In "Paradise Found", Fitz visited Dusty while he was in prison and made sure he wasn't catching on the the fact that he was really The Kingpin. Dusty found one of Fitz's hairs at the scene of the crime, which frightened Fitz, before Dusty brushed it off as nothing. In "Operation DD", after finding out that Fitz was the kingpin, Dusty fought his army of flipper people by dying, going to Hell, and possessing a horse to fight them.
- Stanley Hopson - Fitz is annoyed by Hopson's outdated anti-black racism. In "Welcome to Paradise", Hopson pulled over and arrested Fitz, despite being a fellow police officer. Fitz just rolled his eyes about this and claimed that this was the third time this happened that week. In "Police Academy", it was implied that Hopson once mocked Fitz's ancestors by dressing up in chains and pretending to be a black slave. In "Tucker Carlson is a Huge D**k", when Fitz asked for the day off, Hopson assumed he was doing this for the black holiday, "Ashy Wednesday".
- Thester Carbomb IV - Thester is Fitz's therapist, who uses hypnotism and manipulation to help him overcome his mental and psychological disorders, such as his PTSD and Multiple Personality Disorder. When Fitz developed the dangerous alternate persona of The Kingpin, Thester used hypnotism to create a mental prison to lock him inside of. When The Kingpin escaped and locked Fitz's true self in the prison, he pretended to be his sidekick so that he could play along with his evil plans and get into his head. Thester acted like an incompetent, bumbling moron who always fucked up all of The Kingpin's plans, most likely as a way to hinder his evil plans but he needed to make sure it was done to make it look like these destructive actions were acts of stupidity instead of heroism. All in all, Thester is a good friend of Fitz's, who is ridiculously dedicated to helping him.
- Agent Clappers - In "Big Ball Energy", Agent Clappers threatened to discover the houndstooth meth kingpin and defeat him, making him appear as an antagonist to Fitz, despite him doing very little to solve the problem. However, in "The Father, The Son, and The Post-It Note", it was revealed that Agent Clappers was actually an ally to Fitz who was pretending to be a hero, thus explaining his incompetence and slowness to stop him. In "Operation DD", Agent Clappers got scared when Fitz introduced real nukes in his plan and opted out but Fitz wouldn't let him and threatened to deface his family portrait if he tried to leave. Agent Clappers snuck behind his back and freed his prisoners so that they could defeat him, turning him from a fake hero into a real hero. When Fitz found out about Clappers' betrayal, he got his fingerprints all over his family photo, driving Clappers to suicide. It should be noted that all of this took place while Fitz was "The Kingpin". After being restored to his original self, Fitz had several interactions with Clappers, while he was in disguise, not knowing who he was. In "Fetal Attraction", Fitz worked with Clappers in disguise as Officer Cloppers, not knowing he was trying to betray him. Fitz and Cloppers hit it off with a conversation about 80's basketball. Soon enough, they became great friends, playing basketball and sharing Mike Tyson memes. Fitz said that when he met Cloppers, this was the first time he felt happy since his wife left him. Cloppers was so happy to have made a friend as true as Fitz, that he actually regretted having to betray him but he later turned back on his word. In "PARAD-ISIS", Fitz had his first direct interaction with Agent Clappers, when he saw him out of disguise and was properly introduced to him. Agent Clappers explained his backstory about The Legion of Dooooom and said how he was "Officer Cloppers" too, which blew Fitz's mind. Clappers put Fitz in a Mutifier to turn him into a hideous mutant as an act of revenge for mutating him but Fitz reversed the effects of the mutifier and made it demutate Agent Clappers, turning him back into his normal self and making him thank Fitz for helping him. Agent Clappers decided to forgive Fitz and Fitz forgave Clappers back and they made amends and went their separate ways.
- Frank Flipperfist - Frank is one of Fitz's most prominent workers at The Legion of Dooooom. In "Flip the Vote", Frank helped Fitz by introducing Flipper People to the company as people who could elect him as mayor. Frank also helped Fitz have sex with the Dolphin Queen, so that he could marry his way into the flipper family.
- Jerry Flipperfist - In "The Father, The Son, and The Post-It Note", Jerry dressed as a sexy altar boy but Fitz did not think he was very attractive. Later in the episode, Fitz was overjoyed when Jerry stole all his stolen money back from the Catholic Church and started kissing him passionately, as though he was attracted to him.
- Pat Robertson - Fitz was initially confused as to why Pat was a member of The Legion of Dooooom but when Pat blamed the September 11th, 2001 terrorist attacks on the LGBT community, he understood why he was there. In "The Father, The Son, and The Post-It Note", Pat helped Fitz rob the Catholic Church by bringing Jesus Christ in to terrorize the Catholic Priest.
- Edna Dorsaldigits - Fitz is annoyed by Edna's incompetence. In "Flip the Vote", Edna was supposed to get Fitz elected mayor by helping him get the popular vote. However, she misheard him and instead got him a Popular Goat, which Fitz was unhappy and rather annoyed with.
- The Kingpin - Back when Fitz worked for the Chicago P.D., The Kingpin was his biggest enemy. He was an elusive bastard who could always narrowly escape arrest no matter how much Fitz tried to catch him. Fitz obsessed over him and studied his behavior and mannerisms, until he knew him inside and out, hoping that someday, this would help him catch him. Finally, on December 25th, 2014, Fitz had The Kingpin in his grasp, when the latter was holding people hostage at the bomb factory. Fitz had a plan to catch The Kingpin by giving him a faulty getaway vehicle, failed to meet The Kingpin's demands of giving him a Chicago deep-dish pizza, leading to The Kingpin blowing up the whole factory, killing all the hostages, and getting their blood on his hands. Fitz got PTSD from this and was so overrun by guilt, that he developed multiple personality disorder and had The Kingpin as one of his personalities. Because Fitz knew so much about him from his studies, Fitz was able to perfectly replicate the idea of who The Kingpin once was and eventually, in a way, become him. Initially, Fitz was able to control his Kingpin persona by trapping him in a mental prison, but in "Task Force", Fitz got scared into a coma and lost control of him, getting his true personality trapped in the mental prison, while The Kingpin took over his body. By developing his personality, Fitz allowed for the now deceased Kingpin's plans to posthumously continue to fruition through him as a vessel. In "Operation DD", Fitz was able to escape his mental prison and in his head, his mental self fought his mental version of The Kingpin to the death and finally defeated him, once and for all.
- Karen Crawford - Fitz does not really care for Karen. In "Black & Blue", Karen arrested Fitz for shooting himself, which Fitz, of course, thought was absolutely ridiculous. In "Flip the Vote", Fitz ran against Karen in the 2020 mayoral election, creating even more bad blood between them. The two of them hated each other and resorted to dirty tricks, unethical ploys, and downright illegal actions to beat each other in the election. In the end, Fitz won and Karen was so upset about this, she drank her pain away until she O.D.ed. In "Operation DD", it is presumed Karen forgave Fitz for beating her because it was then she found out he was under the influence of The Kingpin and he had just then recovered from his mental state and gone back to his normal self.
- Cop Bot - In "Big Ball Energy", Cop Bot created a recipe for houndstooth meth that became so popular, it trumped Fitz's argyle meth in sales, giving The Legion of Dooooom a run for it's money. Fitz tracked down Cop Bot and requested a team up. Cop Bot obliged and gave him the recipe. Fitz snatched the recipe and betrayed Cop Bot by shooting him in the chest. However, since he was made of metal, this failed to kill him. After realizing he'd been betrayed, Cop Bot strangled Fitz for revenge. Luckily for Fitz, Dusty broke in and accidentally crushed Cop Bot to death.
- Miss Geraldine - Gerald Fitzgerald does not treat Miss Geraldine with too much respect. In "Paradise Found", Fitz strapped a bomb to her, trapped her in a Captain Crunch costume, tied chainsaws to her hands, and sent her flying into a costume store, where she almost died. All Miss Geraldine could remember from the fact was that a black guy did it. In "The Father, The Son, and The Post-It Note", Fitz planned to break into Miss Geraldine's House, attack her, and steal her money. However, Miss Geraldine donated her money to the Catholic Church so there was no need.
- Dolphin Queen - Fitz first met the Dolphin Queen, while he was still under the influence of his kingpin persona. He met her in "Flip the Vote", when he was taken down to Flipperville to marry her, thereby green carding all of the flipper people into Paradise. Although their wedding didn't go off without them first having some wild and animalistic sex. Fitz obviously didn't love DQ back and only did this to win himself an election but Dolphin Queen took their marriage very seriously, as seen later on, when she called him, accusing him of seeing other dolphins. After that, DQ was a certified member of The Legion of Dooooom until it was disbanded. In "Fallout", Fitz had his first interaction with Dolphin Queen upon returning to his normal self, when he woke up with her in bed with him, jerking him off. He really did not want to be married to her but before he could file a divorce with her, DQ announced that she was pregnant and Fitz felt obligated to stay with her even if he didn't like her. Upon the birth of their child, Junior Fitzgerald, Fitz completely changed his tune on her and decided he loved her after all and stayed committed to making their marriage work. Their marriage lasted until "The World According to LARP", when Agent Clappers sent DQ away and forged a "Dear John" letter from DQ to break them up, which broke Fitz's heart.
- Junior Fitzgerald - Fitz is a loving father to Junior and has been ever since he was born in "Fallout". Fitz is a protective father, who likes playing with his son and teaching him about the world. As revealed in "PARAD-ISIS", Fitz knew from the very start that Junior wasn't actually his biological son, as he was actually born of Dolphin Queen and Bullet but he didn't care and still loved him as a son anyway, considering Bullet to be Junior's "baby daddy".
- Hobo Cop - In "Welcome to Paradise", Hobo Cop was teamed up with Fitz as his partner. Originally, Fitz was not happy with Hobo Cop because he thought he was disgusting and stupid. However, when Hobo Cop single-handedly bolted head first into an armed robbery at Sniffles Pharmacy and bodyslammed a robber into the trash just to save Betty without getting a single scratch on him, Fitz admired Hobo Cop's bravery and wanted to learn more about him. Hobo Cop decided to teach Fitz "the way of the hobo" and gave him some sensei training. Fitz became enamored with the vagabond lifestyle and started living under his highway with him. In the end, Fitz became friends with Hobo Cop, worked alongside him happily, and protested to have him stay on the team. In "Paradise Found", Hobo Cop was a minor employee at Fitz's Dippin' Dots Factory, working as a street vendor for Dippin' Dots.
- A running gag associated with him is his obsession with the fictional world of Pussyland, which is accessed by flying a blimp. He mentioned this in "Meet the Jabowskis" and "Task Force". In "Parent Trap", he went into a coma and had a dream about flying a blimp and finally coming here.
- In "Operation DD", we learned that Pussyland was used as a mental prison for his Kingpin persona, that his psychologist, Thester created to trap him. However, when The Kingpin took over, he trapped Fitz in Pussyland, symbolized by Fitz's arrival in Pussyland, in the aforementioned episode, "Parent Trap".
- Another running gag associated with him is something called "Fitz Bitz", where he will break the fourth wall to give an "important PSA" on a certain subject matter.
- Fitz is a fan of Michael Bublé.
- In "Task Force", it was revealed that Fitz had a crippling case of coulrophobia, (fear of clowns), which is caused by a traumatic childhood incident he had, where he was flashed by a pedophile clown. This fear was so bad that when he was bombarded by clowns at the Happy Trail Circus, he got scared into a coma and lost control of his own mind.
- Fitz also has kinemortophobia (fear of zombies), as he mentioned in "Paradise PD Meets Brickleberry".
- Fitz has anal warts.
- He believes Kevin is the smartest cop in the PD and the biggest threat to his plans.
- Fitz is a delphinophile, which is a form of zoophilia that means he is sexually attracted to dolphins. In "Flip the Vote", Fitz got married to and had sex with the Dolphin Queen and although he didn't appear to like it, it's important to note that he was in his Kingpin persona at the time. After recovering, Fitz found out he was married to the dolphin and ended up actually loving her. He got into a committed relationship with her. He had copious amounts of sex with her in "Trigger Warnings" and was truly heartbroken when she "dumped" him in "The World According to LARP".
- During his time as The Kingpin, Fitz got an "I'm the Kingpin" tattoo on his penis, as revealed in "Top Cops".
- Fitz's favorite song is the Mortal Kombat theme song being played over songs by Michael Bublé and Celine Dion.
- He is the PD counterpart of Denzel Jackson from Brickleberry.
- In the episode "Parent Trap", this was joked about, when Kevin addressed him as "Denzel".