Oswald Chesterfield Cobblepot, known as The Penguin to most is the former umbrella-boy of Fish Mooney, one-time underling of Salvatore Maroni and spy for Carmaine Falcone, until Fish exposed him to Maroni. Following that, he ran a nightclub as part of the Falcone Crime Family and acted as Falcone's right-hand man. However, he soon betrayed Falcone, almost killing him. After the Falcone-Maroni gang war, he took over Falcone's organization and became an influential and powerful gangster. Later, Penguin lost his position of power when Theo Galavan killed and murdered his mother driving him out of his seat as kingpin of Gotham's underworld causing Oswald to help murder him with Jim Gordon. Oswald was then made an inmate of Arkham Asylum after his men abandoned him and was tortured by Hugo Strange. He was then released, encountering his father Elijah Van Dahl. However, while staying with his father, Oswald's step-mother and step-siblings plotted to kill him out of jealousy. Instead, Elijah was the one who died, at the hand of his step-family. This crime was soon discovered by Oswald, Causing him to have a psychotic break and murder his step family in revenge, returning to his true self as The Penguin. Making a return as the kingpin of Gotham's criminal underworld gaining the support of many of Gotham's citizens in the war against Hugo Strange's monsters and running a campaign to become Mayor of Gotham. After suffering a betrayal at the hands of Edward Nygma and Barbara Kean who took control of his criminal empire, he survived a failed attempt on his life and planned his revenge against them alongside Ivy Pepper.
Born as the son of Gertrud Kapelput and Elijah Van Dahl, Gertrude left Elijah without even telling him she was pregnant. Oswald Cobblepot was then raised solely by his mother after his birth and was told his father died when he was young. It is implied that he was bullied as a child from a statement "Oswald, don't listen to the other children" which he said his mother said to him. She used to sing to him at night and tell him that some day he would be a great man, developing his desires for power and to move up in the world. He eventually entered the criminal underworld through Fish Mooney and her gang, where he received the nickname "Penguin", which he despised.
Ambition of a Traitor
Oswald Cobblepot was tired of being a lackey of Fish Mooney. He quickly sold her out to Crispus Allen and Renee Montoya of his own free will. Fish soon finds out and severely injures Cobblepot. After his assault by Fish, Falcone met him after saving James Gordon and Harvey Bullock and made a deal with him: in exchange for a secret he has, Falcone would assign Gordon to kill Cobblepot in hopes of persuading the detective into sparing him with the knowledge he was one of the few police officers with a moral compass, he would return to Gotham in secret and work his way into Maroni's grace as a snitch. Falcone agreed and asked for the secret Cobblepot has: Fish and Nikolai are secret lovers with plans to overthrow Falcone. Fish was supportive of Nikolai only so she could then take the position from him, and become the Queen of Gotham.  James Gordon is then assigned by Carmine Falcone to dispose of the traitor. Gordon tricks Harvey Bullock by pretending to kill Cobblepot, who drops into the river. He resurfaces once the cops are gone, however, and proceeds to murder a fisherman for his sandwich in a crazed rage of hunger.. He then sets out to create his own criminal empire.
Later, he was in the countryside after walking for a while, and he attempts to hitch-hike his way back to Gotham City. He is picked up by two jocks in an SUV, and is grateful for their help. However, they make fun of him and ask him if anyone has ever told him that he walked like a penguin; infuriated, Cobblepot broke a beer bottle and stabbed the man in the passenger seat before taking over the SUV. Hiding the body in a garbage bag, Cobblepot drove to a small trailer park and rented a small trailer for $100. He attempts to call the surviving kid's mother to get $10,000 in exchange for his release, but she does not believe him, and he, in turn, confronts the hostage once she hangs up. While it is not certain of this hostage's future, it is safe to assume his death.
Oswald later arrived back in Gotham via bus. While waiting at a street corner he was recognized by a thug, who sought to capture and take him to Fish Mooney. As the man dragged him through a tunnel, Cobblepot disabled and murdered him with a pocket knife, took his money and used it to buy himself a tuna sandwich. He later took a job at a restaurant where he met and befriended Sal Maroni. He later made a surprise visit to Gordon.
Gordon angrily confronted him on returning to Gotham and putting him, his fiancé and Oswald at risk but reluctantly takes Cobblepot on as an informant when he tells Gordon about an upcoming gang war involving Arkham Asylum, and gives him information that helps him thwart an assassination attempt on Mayor Aubrey James. Cobblepot hires a gang of thugs to rob the restaurant so he can save the restaurant's money and endear himself to Maroni. Sure enough, Maroni promotes him to restaurant manager after the original restaurant manager was killed during the robbery. Cobblepot later visits the thugs he hired and kills them with poisoned cannoli. After their deaths, Oswald left with the money.
Sal Maroni makes plans to rob a casino owned by Carmine Falcone. Carmine Falcone meets with the mob leaders on his side to detail about what to do with Sal Maroni. Sal Maroni later watches the news of the "Viper" drug where he thinks that they might be of good use. Oswald tells Sal Maroni that he knows the janitor there that might be of help to them. Sal Maroni claims that "Penguin" is a good name for him. Oswald reveals his real name and how he used to work for Fish Mooney until Carmine Falcone's men tried to kill him. Sal Maroni then pins Oswald's head to the table. Sal Maroni later sends his right-hand man to pick up James Gordon at the police station where Sal Maroni wants to see him about Oswald Cobblepot. James Gordon is brought to Sal Maroni at his restaurant where he wants to get confirmation about Oswald's story about Carmine Falcone to determine who is telling the truth. Sal Maroni hears from Jim Gordon about his investigation on Thomas and Martha Wayne and how he covered up Oswald's death to fool Carmine Falcone, Fish Mooney, and the Gotham City Police Department. Sal Maroni sees that Oswald is right and spares his life while letting James Gordon go. Sal Maroni states to James Gordon to keep their meeting private and that he might call on him again. After James Gordon leaves, Sal Maroni plans to use Oswald Cobblepot in their fight against Carmine Falcone. Later that night, Oswald and Sal await their men to come back from their heist at the casino. Upon the heist being complete, Sal has Frankie drive off.
When he returns home, Oswald's mother continues to suspect he is involved with a woman. Denying this, Oswald does mention that he has made friends with James Gordon. He then takes a bath and converses with his mother while soaking in a clawfoot bathtub. Meanwhile, having been identified as the perpetrator in Oswald's murder, Gordon is arrested and brought back to the Gotham City Police Department where he protests his innocence and Harvey Bullock is also apprehended when he comes to his defense. Suddenly, Oswald arrives, which shocks everyone.
Cobblepot leads Maroni's men to a warehouse owned by Falcone's underling, Nikolai, killing him and his fellow operatives inside. Cobblepot then stabs Frankie Carbone with the help of two Maroni operatives which he brought them over to his side. Cobblepot then meets with Falcone, and a flashback reveals that Cobblepot offered to be Falcone's spy when he was caught informing on Mooney.
Oswald attempts to make amends with Fish by offering her a broach as a gift. She accepts the gift, but then stabs him in the arm with it to punish him for snitching on her, claiming that he "hasn't suffered enough". Oswald then kidnapped Timothy, the young man who replaced him as Fish's personal assistant. He pressured Timothy into spilling Fish's secrets, although Timothy had very little access to secret information. After finishing the interrogation, he ordered Timothy killed to preserve the peace between the mobs and then limped out of the room. Oswald later confronted Fish's spy, Liza, and threatened to tell Falcone that Liza was spying on him. He ultimately agreed not to, but left Liza with the knowledge that he knew her secret.
Oswald was later brought before Falcone, believing Maroni behind the attack on his money vault. Cobblepot states that Maroni didn't commit the armory robbery, as there is a mole working for someone else, possibly for Fish Mooney. When he sees Liza enter the room, he immediately has his answer but remains silent as Falcone assigns him to find the mole. Oswald later tells his driver that he's not ready to rat out Liza yet, labeling her a "time bomb.
In his time in Maroni's ranks, he's given power enough to extort the fishermen on the mob boss's turf but is arrested by the GCPD after trying to squeeze more protection money out of them. He is eventually bailed out by Maroni, who makes it clear that he initiated the arrest himself to remind Oswald of his reach and teach him a lesson about hubris.
While dining at a restaurant with Maroni and several other gangsters, Falcone called him and ordered him to go see him. But before he could so, Jack Buchinsky caused an electric shock that forced Maroni and the other gangsters (including Oswald) to go to the GCPD for protection. The Electrocutioner then orchestrated another electric shock, this time much more powerful. Before Buchinsky could kill Maroni and his gangsters, Gordon stopped him and Aaron Danzig. After the Electrocutioner problem was solved, The Penguin went to Falcone's place, where Carmine reveals that Fish "captured" Liza and in turn for her return to Falcone, Falcone must leave Gotham. Oswald changes the plan when he reveals that Liza is a mole, Falcone sends Victor Zsasz and some henchwomen to get rid of Fish's thugs, Falcone then captures Fish and Butch Gilzean.
Oswald then became a high-ranking member of Falcone's gang and changed the nightclub's name to Oswald's and pink neon fish was replaced by a blue neon umbrella. Oswald however, was faced by Fish and Butch who escaped Falcone's torturer, Bob. Before they could do something ugly, Zsasz arrived and captured Butch but Fish escaped. Oswald also helped Gordon when Gordon wanted Arnold Flass arrested for murder, he had Gabriel interrogate Derek Delaware for information. Gabe then gave the info to Gordon. 
Fish revealed to Maroni that Oswald was a spy for Falcone, because of that Maroni had Oswald and him taken to a trip in a shack owned by Maroni in the woods. Oswald attempted to kill Maroni, only to find that the gun had no bullets. Oswald was nearly killed by Maroni when the latter ordered Duffy to destroy a car with Oswald in. Duffy was coerced to release Oswald under the threat of Falcone killing him.
Owning a Nightclub
Penguin tried to convince Don Falcone of Maroni's threat to his life, however, Falcone continues to talk about the re-decoration of Fish Mooney's club, much to Oswald's frustration. Falcone then tells Penguin that he has decided to give the club to Penguin as a reward and that he would deal with Maroni. Later Penguin arrives at the GCPD to bring Detective Gordon and invitation to the grand re-opening of the nightclub, but he has an awkward encounter with Edward Nygma who attempted to give him a riddle to answer though he was dismissed. When Jim arrived, he turned down Oswald's offer of attending the nightclub and though Penguin offered to help him with his case, Gordon rejected the offer telling him he didn't want him coming to the GCPD again. Offended, Penguin tells Jim that he shouldn't treat him that way and that he'd one day soon he'd need his help. Later, Penguin was visited by Don Maroni, much to his surprise, there the Don makes his intentions clear to not hurt Penguin, due to a deal he made with Falcone. However he warns him that the second Falcone was out of the picture, so was he.
When a drunkard dared to boo his mother, Penguin viciously attacked him in front of everyone. Later, the club continued to tank under Penguin's management. Falcone sent Victor Zsasz with a solution to the problem. At Penguin's surprise, he brings Butch Gilzean, who spent two weeks being tortured by the Zsaz to break his will, and to help Penguin run the nightclub.
Penguin later begins to have trouble getting alcohol for the club after running out, as the booze was controlled by Maroni who hated him with a passion. That night, thanks to unexpected help from Butch Gilzean, Penguin manages to steal alcohol having police officers "confiscate it".
Gordon and Bullock visit's Oswald's to ask the Penguin for his help and he is pleased to assist them after Jim promises him a favor and five minutes alone with Loeb's files. Gordon, Bullock, and Penguin reach an old farm located on the outskirts of the city where the Penguin had heard Falcone tell Loeb on the phone, that the farm was safe. There they are welcomed in by an elderly named Jude and Marge, under the guise of being a security team sent to check out the farm's security. Unexpectedly, the elderly couple, having figured out that they were not who they claimed to be, opened fire against them however they managed to subdue them quickly, leaving Penguin to watch them while they checked the attic. Later, the elderly couple managed to escape Penguin. Oswald later met with Marge and Jude after letting them go the previous day, with the promise of helping them escape the wrath of the commissioner. Unfortunately for them, he could only procure one ticket to Arizona, and gave the two the ultimatum of deciding who would get it. Marge strangles Judge, and afterward, Penguin shoots her with a shotgun. 
After being freed from Maroni, The Penguin plotted the assassination of the Italian Crime Lord in a bar called Lidia's. Oswald then convinced Lidia to hand over the bar to him while she still tending to the bar. Oswald hired the hired killer Connor to kill Maroni, he had Butch hide some guns at the bar after Butch was brainwashed by Zsasz.
Sparking the War
- "I'm King of Gotham!"
- —Oswald Cobblepot after killing Fish
When Maroni, his hitman Tommy Bones and some other gangsters were eating at Lidia's, Connor arrived and attempted to shoot Maroni, but found out that his gun had no bullets. Maroni's men then killed Connor. Oswald revealed that it was intentional as he wanted Maroni and Falcone to kill each other so he could take over. It worked, a bloody war began.
Cobblepot then attempted to murder Falcone at the hospital, but Falcone was saved by Gordon, who in turn saved both Cobblepot and Falcone's lives by killing Maroni's hit men. Gordon, Bullock, Falcone, Gilzean and Oswald then went to an old warehouse owned by Carmine, Falcone claimed that everyone who knew about the warehouse were dead. He was wrong, Fish knew about it and she was surely alive. She had arrived in Gotham just as the war reached its ending point. Fish overwhelmed them and tied them. She then called Maroni to make a deal. After Maroni offended Fish, she shot Maroni in the forehead, killing him instantly. A shootout ensued and Fish eventually won. The Penguin was however freed by Butch during the skirmish. When Fish was talking to the captives, Oswald arrived with a war machine gun and massacred all of Fish's thugs, finishing the last thug with a pistol. Falcone revealed to Jim and Harvey that he had retired. Penguin eventually found Fish in the rooftop and fought her. While they were fighting, Gilzean shot both in the legs, The Penguin then knocked Butch out and punched Fish, eventually pushing her into the river, killing his nemesis once and for all. He then shouted "I'm the king of Gotham!".
King of Gotham
The Penguin then began the life as a crime lord kingpin, collecting debts. After Gordon was discharged of service by Loeb, the Penguin said that he would convince Loeb to reintegrate him if he collected a debt from Odgen Barker, whom owed money to Falcone's former organization now Penguins who Jim killed in the process. He then intimidated Loeb to reintegrate him threatening his life. He later appears with several of his thugs gahtered in his main hall drinking, Harvey Bullock walks in. Bullock says that he will always be seen as Fish's umbrella man and that he wants revenge for Fish's death. Bullock is then held at gunpoint by Oswald's bodyguards and exits the room. Oswald angrily smashes his glass, but quickly calms down and asks for another drink.
Oswald was blackmailed by Theo Galavan to carry out acts out of his interest for him by holding his mother in captivity. Oswald and Butch murdered Janice Caulfield and he had Zsasz murder Randall Hobbs, though Zsasz was intercepted by the GCPD managing to escape and failed. He was later confronted by Gordon, who knew about the murders. Oswald said that Gordon had dirt on his name since he collected a debt for him and killed an innocent man. 
After Penguin killed Janice Caulfield and failed to kill Hobbs, he returns to Galavan and asks for his mother's release, stating that he would still do Galavan's bidding. Theo denies and tells him to leave. Penguin is now determined to take down Galavan and get revenge on him. Butch advises him to kidnap Tabitha and trade her for Cobblepot's mother but Penguin doubts that Theo loves Tabitha as much as Penguin loves his mother. Theo later sends Tabitha to Cobblepot to give him a list of multiple buildings owned by Wayne Enterprises which Theo wants burned down. Theo also wants Cobblepot to steal an old knife out of a safe in one of the buildings. He arranges for Cobblepot to receive Bunderslaw's eye which is needed to open the safe. Penguin is able to get the knife and burn down the buildings. However, as he plans to find out what drives Theo in order to destroy him Penguin meets Edwige, an old associate of Butch to find out the history of the knife. Edwige tells him that the knife is the Wayne Family Crest which was used 200 years ago by an ancestor of Bruce Wayne to cut off the hand of Caleb Dumas after the latter was accused of raping Celestine Wayne. The angered Waynes forced Dumas and his entire family into exile where the Dumas changed their name to Galavan. Penguin learns that Theo is a descendant of the Dumas and wants revenge on the Waynes. Penguin is glad because this means Theo is driven by emotion and thereby vulnerable. He then plans for Butch to seemingly change sides, claiming that Cobblepot is too mad to serve, and get into Galavan's business, but in reality plans for Butch to search for Oswald's mother. To not give Theo the opportunity to doubt Butch's story, Penguin cuts off one of his hands.
Not knowing of Butch being reprogrammed by Tabitha, Theo sent Butch back to Cobblepot as a double agent and set a trap for him. Butch tells Cobblepot of his mother's location, and Cobblepot goes to the spot with his man, only to be confronted by Theo and Tabitha. Cobblepot orders his man to shoot Theo and Tabitha only to be betrayed by Butch. Cobblepot then pleas for mercy, asking Theo to let his mother go and he will die in her place instead. Tabitha lets Cobblepot's mother leave, only to throw a knife at her in the back. Cobblepot ends up taunting Theo for being a coward and never do the dirty work himself, tricking Theo to get close enough for Cobblepot to stab him in the neck and escaping. Cobblepot later raids Theo's Mayor victory party with the rest of his men, only to be confronted by Jim and wounded by Tabitha.
Empire in Ruins
Cobblepot later encountered Nygma in a forest while Nygma was trying to bury his girlfriend's body. Cobblepot was hiding in an abandoned trailer in the forest and asked Nygma to help him before passing out from the previously inflicted gun shot by Tabitha.
When Oswald woke up, Nygma wanted to get some advice from Cobblepot for how to be a murderer, only to be rejected by Cobblepot who states that he is not interested in giving advice. Cobblepot lost his will to extract revenge or fight as he sees that he is the reason for his mother's death. Nygma suggests that love is a weakness and now that Cobblepot's mother is dead, and Kristin is dead, they are both free man with nothing to lose, making them powerful. This sparks Cobblepot's will again to recover and take revenge.
After failing to convict Theo for kidnapping Ex-Mayor James, Jim was kidnapped by policemen that Theo brided. Theo fought Jim in a duel and won, and told the policemen to kill Jim slowly. The policemen were then shot by Gabe after Theo left, and rescued by Cobblepot.
Cobblepot brought Jim to Nygma's place along with few men still siding with Cobblepot and they prepare to strike at Theo's apartment. Selina later joins the team and gave them a secret passage into the apartment. They busted into the place before Bruce is sacrificed by Father Creel. Later, Captain Barnes arrives to arrest Theo and stop Jim for doing anything stupid but was later knocked out by Cobblepot. Jim and Cobblepot later takes Theo somewhere near the sea. Cobblepot beats Theo with a bat repeatedly, and Theo pleas to Jim for a swift death and Jim shoots him in response. Cobblepot puts an umbrella through Theo's throat afterward.
Sent to Arkham
After the death of Theo, Cobblepot is left with nobody and wanders the streets. He is later arrested by Barnes. Cobblepot confesses to the murder of Mayor Theo and claims no one else is involved so that Jim and Nygma will not be arrested as well. Cobblepot also claims that he is insane, which is why he killed the Mayor. He is later sent to Arkham Asylum and greeted by Hugo Strange. After a brief session with Dr. Strange, Cobblepot was told he will be treated with proper techniques, which the idea of it terrifies Cobblepot.
When Jim visited Arkham Asylum to set up a trap for Mr. Freeze, Cobblepot tells Jim that he needs to help Cobblepot to get out because they are doing terrible things to him. But Jim replies coldly that Cobblepot is insane, as he claimed, and so he needed treatment. This angered Cobblepot, causing him to yell out that Jim was the one who killed Theo as he is being dragged away.
After some therapy, Cobblepot turned a lot gentler, calmer, and lost all violence tenancy through only a small amount of sessions. He is declared sane again and is freed by Dr. Strange, who claims to have bigger plans for Cobblepot after his release.
Meeting his father
While at his mother's grave, Oswald met his long-lost father Elijah Van Dahl. While at Elijah's house, Oswald learned that Gertrud used to work as a cook for Elijah where they had been forbidden to make love. Upon Oswald meeting his stepmother, Grace, and stepsiblings, Charles and Sasha, Elijah holds a toast to their family.
Oswald and Elijah start to bond. Oswald learns Elijah is sick and that he has a hole in his heart that continues to get bigger. Oswald eventually gathers up the courage to tell Elijah about his violent past. Elijah tells Oswald his past doesn't matter. This comes as a complete shock to Grace and her children. Grace tries to get Sasha to seduce Oswald, but he rejects her advances. Elijah becomes really sick and doctors announce that his condition is getting worse. Elijah tells Oswald that they will have many more years together. Elijah announces he wants to rewrite his will and leave everything to Oswald. As Elijah and Oswald have a drink, Elijah collapses and starts foaming at the mouth. The wine is spilled, revealing there was acid in it.
After Elijah's death, the Van Dahls wish to do away with Oswald, however after Oswald begs them to let him stay, they decide to keep him around as a free maid, assuming that Oswald would commit suicide after the trauma he has experienced. So Oswald is allowed to stay and cooks and cleans after the Van Dahls, who treat him poorly and insult his late mother. One day, Oswald comes across the decanter that contained the poison used to kill Elijah. This, coupled with his poor treatment and memories of Elijah's death, caused Oswald to awaken from the conditioning he received at Strange's hands at Arkham. No longer inhibited by Strange's conditioning, he murders Charles and Sasha offscreen. That night, Oswald serves Grace dinner. Grace inquires as to where Charles and Sasha are and asks Oswald to ring the dinner bell. Oswald replies that he doubts they would hear it. He then reveals he knows all about their plot to kill Elijah. He then draws a knife on Grace, who screams out for Charles and Sasha to help her. Oswald tells her they will not come. Grace asks where they are, to which Oswald implies they are the very meal she has on her dinner table. Oswald then kills Grace by stabbing her to death.
A day later, Oswald sits in the mansion watching a newscast in which Theo Galavan, now going by the name Azrael, drops into the frame. Oswald flashes a smile, which quickly contorts into one of rage before saying "Hello, old friend".
The next day, as he's getting dressed, Oswald declares that there is nowhere to hide for Galavan and that he's coming for him. He's later seen paying his respects to Tabitha, who's in critical condition after getting stabbed by Theo. Butch believes him to be there to murder Tabitha, to which Oswald replies that he does have reason to do so, as she's the one who stabbed his mother in the back, however, she's really not the person at fault, and that Galavan is, as Tabitha was just following his orders. Oswald states that he was affected by Galavan because he ordered his mother's death. Butch was affected by Galavan because Tabitha's life is on the line because of him, and of course, it's because of this that Tabitha herself was affected as well. Oswald proposes that the two of them reunite, if only for the purpose of killing Galavan. Butch agrees, and the two of them go to Wayne Manor, where Theo is seen attempting to kill Bruce Wayne, who is flanked by Alfred and Jim.
Oswald surprises them all, telling Gordon that he should know by now that bullets don't kill the monster in front of them, and says to Theo that his last umbrella was stuck in his throat, and he's thinking of shoving another somewhere else. Oswald then addresses Gordon once more, saying that one thing he learned dealing with Theo is that you always need the right tools. Butch then lifts an RPG launcher to his shoulder and fires a rocket at Theo, who dies instantly. With that, Oswald and Butch depart into the night.
Oswald then decides to turn his attention to Strange, seeking revenge for what Strange did to him while in Arkham. He and Butch take down a bus which they believe contains Strange, only to discover that that is not the case. Oswald is mortified to discover Fish Mooney, very much alive. It' isn't really made clear if Fish uses her new power to render Oswald unconscious or if Oswald passes out from unbridled fear. Butch also catches a glimpse of Fish, and retreats with his men. Oswald remains unconscious as a homeless woman later opens the back door of the bus, ergo accidentally unleashing Strange's experiments into Gotham City.
Gaining public support
Being spared by Fish confused Oswald, causing him to go over the nights events over and over again in his head. Six months following the incident, he arrived at the police precinct during a press conference, accusing Nathaniel Barnes of lying to the people of Gotham. Oswald then told the reports he was present when the 'monsters' escaped Indian Hill, and urged them to find the main instigator, Fish Mooney. Once done, he crosses paths with Jim who is now working as a bounty hunter and points out his surprise that he hasn't found Fish yet. But Jim replies that Oswald hasn't made it worth his while, something in which Oswald agrees with.
He stops by the new nightclub run by Barbara Kean known as The Sirens where he has made her an offer to protect it, but she turns him down. She is also in partnership with Tabitha whom Butch still has a crush on, causing Oswald to send him to the bar due to the awkwardness. He then tells the pair to spread the word that he wants Fish Mooney, and will pay a million dollars to whoever can bring her in: alive or dead. Oswald and Butch then depart, but not before Oswald reveals that Butch has been pick-pocketed by Selina Kyle.
Oswald stops off at Arkham to visit Nygma, bringing him a gift which is said to be an almost unsolvable puzzle box, however Nygma solves it within seconds. Nygma apologises to Oswald for abandoning him months previously after his release from Arkham, but Oswald makes clear that he has forgiven him. Oswald talks about his troubles with Fish, but Nygma reminds him that "Penguins eat Fish".
After Barbara and Tabitha ran into some trouble with mobsters demanding protection, which lead to two of the mobsters being killed and the ringleader badly beaten by Barbara. It transpires that Butch is involved, as he hoped that Tabitha would run back to him for protection. Annoyed, Oswald shoots the last remaining mobster dead, and informs Tabitha that the only reason she is still alive is because of Butch, but once he gives the word he will kill her in retaliation for her killing his mother.
Oswald holds his own press conference, informing the people of Gotham that he has been warning the police about Hugo Strange's monsters and Fish Mooney, however they said that Fish wasn't real and saying that the escapees were victims that need their help. He tells them that despite the GCPD recently just trying to apprehend Mooney, she ended up escaping. Oswald tells them the city is being invaded by the monsters, and urges the people of Gotham to help kill every single monster, which results in him getting a round of applause and public support.
Back at his mansion, Oswald and Butch watch a news broadcast about a hostage situation at an old mansion lead by Fish. Gathering a crowd of people, they arrive at the mansion during a police standoff, much to the anger of Barnes, who states that Bullock and Gordon have been held hostage. During the chaos Oswald gets a phone call from Gordon who tells him that Fish is escaping into the woods with Hugo Strange. Pleased, Oswald orders the crowd to storm the mansion, before going off on his own. He confronts Fish and holds her at gunpoint, and demands to know why she allowed him to live. Fish explains that she couldn't kill Oswald, due to how much he had come along and that turned him from an umbrella boy to the terror of Gotham, from Oswald to the Penguin. Almost tearful, Oswald decides to spare her life and allow her and Strange to escape. He returns back to the crowd where they have killed two of the monsters and are burning them. Oswald is then lifted up in the air and hailed by the crowds, showing their full support for him.
Trusting with the newfound support by the people of Gotham Oswald decided to use his influence to run for Mayor of Gotham against Aubrey James, confident in his abilities his campaign gained a lot of support. Aubrey James reluctant to accept the fact the a criminal such as Penguin himself could win the election attempted to disuade him even threatening him to which Oswald replied by showing his own force holding him and his men at gunpoint but assured him he did not want to kill him as the election would be dull without an opponent although acknowledging he required some more assistance.
Blackmailing Arkham's head warden into releasing Edward Nygma into his custody and arrives at Arkham's gates to find Nygma unexpectedly awaiting his arrival. Continuing his campaign to become Mayor of Gotham Oswald has Butch pay off numerous higher ups in order to secure his victory much to Edwards suspicion and later his disapproval upon discovering it. Waiting for the news of the elections it is revealed by Butch that Nygma had been taking all the money back from the higher ups of Gotham and had cost him the election, threatening his life Edward drew his attention to the television revealing that in fact Oswald has won the election in a landslide to which Edward said that he always believed in him. Oswald accused Butch of not truly believing in him, and appointed Edward as his chief of staff, much to Butch's anger and jealousy.
Mayor of Gotham
During a conference Oswald unveiled a statue of his late mother. The conference was attacked by a new incarnation of the Red Hood Gang who shot up the statue and decapitated it. Angered, Oswald ordered his men to find the leader of the gang and bring him his head. During this meeting, Oswald mentioned he would be throwing a party at The Sirens. The location of the Red Hood was discovered and Oswald along with Edward, Victor Zsasz and a couple of other goons went to the location to deal with them, only to find Butch standing over their bullet ridden bodies, having "dealt" with them. Pleased, Oswald holds another conference stating the Red Hood have been dealt with, and congratulates Butch whom he has now softened up to again. But secretly, Edward isn't certain things are what they seem.
At the Sirens nightclub Oswald is greeted by Bruce, who thanks Oswald for saving him from Galavan. During the night Oswald is attacked by Butch who is donning the red hood mask, but it turns out his bullets were filled with blanks (as part of a setup between Edward and Zsasz). Zsasz shoots Butch in the back and Oswald berates him for his betrayal. Tabitha intervenes to rescue Butch, who proceeds to break free and attack Nygma nearly strangling him to death but Oswald then attacks Butch and knocks him out and has him brought into police custody. Later that night Oswald comforts Edward at his mansion and embraces him. Despite Butch's arrest, he escapes from his police escort with the help of Tabitha.
Oswald realizes he's fallen in love with Edward and reveals so to his house maid that he plans to confess his feelings. Making attempts throughout the day to confess his love to no avail he finally builds up the courage to ask Nygma to discuss something over at the mansion that evening to which Ed agrees by offering to pick them up a bottle of wine. But this plan is scuppered the next morning after assuming Edward was kidnapped and tried to file a missing person report but was reliefed when Edward arrives. However, Ed reveals he has met a woman named Isabella whom he claims he has fallen in love with.
Jealous, Oswald arrives at the library where Isabella works and drops that Edward was sent to Arkham for murder and killed his last girlfriend Kristin Kringle, whom Isabella has a strong likeness to. But this plan fails when Isabella accepts Ed's past and reveals she is not afraid of him with it, and kisses Edward at the mansion, much to Oswald's envy and frustration.
Oswald later on manipulated Ed into breaking it off with Isabella when he began to worry about her safety afraid he might hurt her as he did with Kristin and asked Oswald to do it for him by paying her a visit but to do it gently. Oswald arrived at Isabella's apartment and told her it was over between her and Nygma but she persisted she wasn't going to let him go which infuriated him leaving him to threaten her and leave with his final warning. Reporting back to Ed on the situation, knowing she would persist Oswald had Gabe cut her brake wires in secret anticipating her route and leading her to her death hurtling towards a passing train killing her.
The death of Isabella makes Ed distraught, seemingly doing nothing but mope about her death. While Oswald is getting his portrait painted he, tells Ed to try and get over her death by finding closure. Edward then goes to the railroad cross where Isabella died and discovered from a blind homeless man heard her screaming before the crash. Ed takes matters into his own hands and goes to the repair shop where Isabella`s car has been towed, and discovers the cut brake wires.
He storms into the mansion carrying the brake wires to Oswald. Before Ed has a chance to say anything, he shows Ed his portrait and that he was included in the background. Edward goes on to tell Oswald that he knows who cut the brake wires. Oswald tenses up, and is seemingly scared for a moment before Ed says Butch did it to get revenge on him.
Barbara confronts Oswald over the location of Tabitha and Butch who have gone missing, although Oswald denies any knowledge of their whereabouts. In actuality they are being tortured by Edward, who believes that Butch is responsible for kill Isabella. However he ends up sparing them when he comes to realization that Butch wasn't responsible, although Tabitha ends up losing a hand in the process during the torture session.
Edward begins to suspect that Oswald is responsible for killing Isabella after Barbara informs him that Penguin is in love with him. Edward tricks Oswald into making it clear he is in love with Edward, causing Edward to leave. Edward then quits his role as chief of staff, much to Oswald's devastation who - despite not able to be officially Edward's lover - still wanted to remain his best friend. After Edward leaves Oswald, he secretly plots his downfall with Barbara, Butch and Tabitha, with the plan to make Oswald suffer terribly before his death. Seemingly being abandoned by Nygma, Oswald under worry for his whereabouts began to lose focus as Mayor and his reluctance to rely on Edwards replacement. After seemingly seeing his father appear to him as an apparition he was informed that his father's remains were stolen.
Finding them hidden in his office closet Oswald suspects Edwards replacement and bludgeons him to death in his office, leaving him nervous during an interview for fear they discover he is still a murderer and ruin his reputation as mayor, once again his fathers "spirit" appeared crossing the room and in a rush Oswald openly insults the people of Gotham on live television in an effort to speak with his father, not finding him anywhere in proximity he is having his reputation ruined by Nygma in secret.
Barbara attempts to comfort him by revealing that not only is he losing his grip as Mayor but also as Gotham's ruling crime-lord he needs to show his men that he has not been weakened by his mayoral status and still holds full control. Under Barbara's manipulation she has Tabitha threaten one of Oswald's most loyal underlings Tommy Bones into pretending they hold Nygma hostage are the ones who wish to take his power. After this Penguin vows vengeance against Bones and orders his men to find Nygma at all costs. But then receives a phone call from Nygma himself telling him his whereabouts.
When Oswald arrives with the little men he was able to spare Edward reveals himself by gunning down Oswald's men in front of him and having him tied to the remains of Isabella's car while waiting to have acid poured on him, pleading with Ed and claiming that he did it for love he is abandoned by him and left to die. Being released by a confused police officer Penguin returns to his mansion intent on contacting reinforcements and cementing what's left of his rule and find Ed but his cut short by the intrusion of Tabitha and Butch who take him to the Sirens where Barbara interrogates him on Nygma's whereabouts but to no avail as neither does Oswald know or care to tell them if he did as he realizes now that even after all that had been done to him by Ed's hand he still loved him. Edward reveals himself to have been listening all along, Penguin wishes Barbara luck at the head of the table and is dragged off to be killed.
On the docks Penguin makes his final plead against Ed only to once again be rejected, claiming that he was the one who made him into what he is and that Edward Nygma would be nothing without The Penguin but Edward reluctant to give in states that he loved Isabella and he killed her shooting him and pushing him into Gotham Bay watching as he sunk to the bottom.
Plans of Revenge
Oswald having barely survived the gunshot wound was found floating in Gotham River by Ivy Pepper who hid him and nursed him back to health over the course of a few weeks. Attempting to befriend him he rejects her and dismisses her obsession with plants as being a freak and has her contact any loyal remnants of his crew. Gabe arrives at the abandoned estate where Ivy had been hiding Penguin but Ivy sensed that he couldn't be trusted to which again Oswald dismissed her leaving her to run off by herself. Oswald is soon betrayed by Gabe and tied up to be auctioned off to the highest bidder and killed properly, Ivy is caught by one of Gabe's men and tied up alongside Oswald.
While Gabe and his men are distracted Ivy offers Penguin another chance to be nice to her to which he agrees, using her perfumed scent she has one of the men untie them and kill everyone apart from Gabe. Taking the gun he shoots the man and turns it on Gabe, having him carry the bodies he attempts to once again swear his allegiance to Penguin but under the influence of Ivy's perfume is shown to once again be lying stating that they had only followed him out of pure fear not respect referring to when he used to carry around an umbrella and being a freak himself causing Oswald to lose his temper and hack him into pieces with a gardening tool much to Ivy's amusement.
Oswald feeling dejected at the fact that without any loyal follows his plans of revenge will be short lived, to which Ivy offers to ally herself with him and help him retake Gotham with the help of the remaining "freaks" from Indian Hill causing himself to smile.
Their first stop was Victor Fries, who was living far off in an ice chamber in the snow to stay alive. At first he was mad at Oswald and threatened his life because he drove the other freaks out of Gotham, but Penguin convinced him that he only said that stuff because that's what the people wanted to hear, he would give him all the supplies he needed to free himself from his ice chamber once he had his power back, and he had his suit, Fries smiled implying that he accepted the offer.
Next, they tried to recruit Bridgit Pike, who was currently working at a blacksmith shop and was constantly being picked on by her boss and co-workers for being a freak. She turned the offer down as she thought that this place was bad but Gotham's worse, although Ivy convinces her that there's nothing wrong with being a freak. Penguin offers to kill her boss but she says,"nah", and kills him herself and tells him she quits.
They return to the mansion, where Bridgit and Victor meet again and are not happy about it so they point their guns at each other until Ivy reminds them that their like a family. Penguin finds out on the news that Nygma is now going by The Riddler, and tells the rest to rest up for tomorrow.
Oswald visits Jim, with the information that Nygma was demanding information about The Court of Owls on television until Jim had arrested him but he escaped, but Oswald doesn't believe that Nygma escaped Jim's custody. Jim tells Oswald to let it go but Oswald still gives him his phone number and tells him to call him later. Jim calls him later and tells him where the location of a Talon and an Alice Tetch bomb are so he could talk with the Court about Ed, Oswald shows up and has Bridgit kill the Talon with her flamethrower but the bomb is about to go off so Jim leaves. Since they killed a Talon The Court had another Talon kidnap Oswald at his mansion and lock him up.
Imprisoned by The Court of Owls
Oswald demanded to speak to the person in charge until Edward, who was in the cell next to him, asked, "Oswald?", which caused Oswald to try and grab him through the bars. Edward wasn't sure if Oswald was real so he knocked his forehead, which really frustrated him. Oswald attempted to make a sharp blade to try and stab Nygma but Nygma says that he was making it too thin and it would snap off when he tried to stab him. Oswald calls him Edward which gets Nygma mad and he tells Oswald to not call him that and to call him The Riddler but Oswald repeatedly says Edward to frustrate him until Edward says enough and calls him pathetic.
Edward had stolen a dart from one of the guards and was planning on using it on them but decided to use it on Oswald instead, wow'll Oswald was passing out Edward used a lock pick to escape but Oswald made a loud banging noise with his food tray so the guards could come in and ruin Nygma's plan, and sure enough they did, they beat him with a bat as Oswald passed out.
When Oswald woke up he sarcastically asked if they clubbed him and Edward gives the response that he knows they did. Oswald comes to the realization that they both want to kill each other but being locked up in cages does neither of them any good so they have to help each other escape so they can resume trying to kill each other on the outside and Nygma agrees but says there have to be rules, and one of them is that they have to have a six hour window to kill each other.
Edward fakes Oswald's death with red jello as blood, one of the guards realizes it wasn't real but Oswald grabs his neck and kills him with a knife wow'll Edward shoots a dart gun at the other and they escape. On the outside they see a bunch of homeless men and Oswald scares them off, they drop their weapons as their agreement still holds for five hours. Edward says that Oswald doesn't stand a chance because him and Barbara have all the gangs and Oswald has nobody but Oswald reveals that he has an army of Hugo Strange's freaks in his command and the two walk off.
At War with Nygma
Oswald met up with Ivy again who was with Selina Kyle, Ivy explained that when Oswald disappeared Victor and Bridgit assumed he was wasn't coming back so they split up which really frustrated Oswald and made him throw a bunch of breakables. Edward had figured out where they were and him and Butch came in and Selina ditched them. However, Oswald had an escape route through a bookcase and him and Ivy escaped but Tabitha knocked out Selina and brought her back to Sirens club.
In exchange for money to get out of town Selina called Ivy, who was at the last safe house with Penguin, and asked her where they were. Ivy told her where they were and Penguin called her an idiot because he knows it's a setup. Soon, they found them but Nygma wouldn't kill Penguin until he calls him Riddler. Eventually, Fish Mooney returns and takes Penguin for herself.
Forming an alliance together Fish and Penguin combined their forces with the ultimate goal to seize the antidote to the Tetch Virus in order to create a Gotham City for people like Penguin and all the freaks, via Hugo Strange whom Fish had captured once again, Penguin with the help of Mr. Freeze and Firefly tortured Hugo using the same device used on himself during his stay at Arkham Asylum causing him to reveal the location of the antidote he had hidden away. Arriving at the location and retrieving the antidotes they noticed Fish's men had been killed and were attacked by masked warriors causing a fire fight between them, Mr. Freeze and Firefly. Interrupted by Jim Gordon and Harvey Bullock Jim being infected with the Tetch Virus took out most of the masked men single handedly and killed Fish in the heat of the moment causing Penguin to lash out at him.
Jim almost chocked Oswald to death until Harvey knocked Gordon out with his shotgun and took Penguin into his custody. Jim and Harvey had decided to hand Oswald over to Nygma in exchange for Jarvis until Barbara, Tabitha and Butch came to get back Jarvis which caused Nygma to throw a grenade at them and run away. As Nygma tried to leave the scene Oswald knocked him out and handcuffed him, using a police car to flee the scene. When Nygma came to and realized he was handcuffed, Oswald told him he was not as smart as him and Nygma responded that Oswald's tendency to gloat was always one of his least attractive qualities and that he could never love someone like him as he behaved like a spoiled child who threw a tantrum whenever he did not get his own way. This led to Oswald drawing his gun and preparing to deal with Nygma, until the latter kicked the door open, having broken free of his handcuffs, and knocked Oswald to the ground. He grabbed the gun and pointed it at Oswald, leading the latter to rant that he was supposed to kill him this time and that when Nygma shot him that was the day he was reborn as the Riddler and that his entire persona was based on a lie, adding that there was nothing he could do about it but Nygma disagreed.
Nygma took him to the pier where he shot him and pointed his gun at him, asking if he had any last words but Oswald said that he was fine for now. Nygma said there would not be a later since he was going to kill him, which Oswald understood. However, when he tried to shoot him, no bullet came out which led Oswald to reveal that he removed them when he knocked Nygma out before summoning Ivy and Mr. Freeze. A shocked Nygma realized that Oswald had been playing him since he knew that Nygma would take him to that spot. Oswald revealed that Nygma had used his tie pin to remove his handcuffs as he wanted it to be personal and further added that he was predictable since he was driven by a desperate, compulsive need to complete what he started. When Nygma asked why he did not kill him, Oswald said that Nygma was the one time he let love weaken him and that he would be keeping him around as a constant reminder not to make the same mistake again, leading Mr. Freeze to turn him into an ice sculpture which Oswald later planned to use as the centerpiece of his newly founded club The Iceberg Lounge.
At first glance Cobblepot appears to be milquetoast, subservient, and somewhat of a sycophant. In reality he is an ambitious and cunning sociopath who is willing to do whatever it takes to obtain power. Despite this hunger, Cobblepot is patient and uses his high intellect to concoct plans in order to reach his goals. Virtually every move he makes is premeditated to a certain degree.
Even when things don't go exactly as planned, Cobblepot is highly adept at playing the hand he is dealt for the best. Among the more darker parts of Cobblepot's personality is his tendency for violence. He is more than willing to kill someone when he feels it's necessary and does so without pity or remorse. He speaks with a constant smile, often talking fast and shaky, with variant levels of flattery to whom he speaks to, often sarcastically.
Despite his malice and ruthlessness, he has a softer side and a degree of humanity when it comes to his mother whom he loves deeply and devotedly and his father whom he also loved but knew for a little amount of time. When his mother got killed, it devastated him deeply and when Edward said that his mother was Oswald weakness, Oswald almost slit Edward's throat saying how his mother was the only person who truly cares and loves him. His father's murder shocked him out of his mental conditioning by Hugo Strange and prompted him to kill his stepfamily for killing Elijah. He also started to care about Edward Nygma and became a close friend. When Edward was unconscious after Butch nearly strangled to death, Oswald was scared and worried about Edward being dead but was relief that he woke up. He even took care of him when Edward had a sore and bruised throat after the strangling. When Edward didn't come home for 12 hours, Oswald tried to file a missing person report when he thought Edward was kidnapped and hugged Ed when he came home. Oswald even comforts Edward after Isabella's death and helps him move on.
At first, calling him Penguin made him very infuriated, to the point of murderous intents, but later, he decided to accept and adopt the epithet, admitting that it "grew on him". With the current outfit, name and mannerism, he is becoming closer to his original concept in the comic books.
The rapidity and precision of his Biblical references when he was picked up outside Gotham by the church group suggest that Christianity played a role in his upbringing. His facial expressions declare that, like the spoiled only child he seems to be, Oswald is always picked on by others and the universe, rather than ever being at fault himself.
Oswald Cobblepot is a skinny young man of about average height, with pale skin and noticeably bright blue eyes. His nose is slightly pointed and beak-like. His black hair styled and messily plastered on his head, with some spiky ends pointing erratically at the top of his head. His attire consists of expensive custom made suits of many variations with an assortment of different neck wear as well and is mostly carrying a black umbrella. Due to the beating he suffered for betraying Fish Mooney, one of his legs was permanently damaged having never healed properly, forcing him to walk with a noticeable limp with many comparing it to a "penguin". Later on he started utilizing a Penguin themed cane to aid him while walking.
- High-level intellect/Expert tactician/Leader: Oswald is methodical in creating plans that are meant to benefit him. He managed to orchestrate a gang war between Maroni and Falcone that he hoped would result in their deaths and allow him to control Gotham's criminal underground. He is also capable of running a criminal organization without getting caught by the GCPD. He was also able to convince the citizens of Gotham that Fish Mooney and her gang of "monsters" were a serious threat to the city, despite his status as a criminal.
- High pain tolerance/Indomitable will: Oswald has a high tolerance for pain. After being picked up by the college guys following Jim sparing his life, he says that he has been walking for hours. He showed no reaction after being stabbed in the hand with a pin by Fish Mooney and has been non-fatally electrocuted twice. He was also able to kill Mooney and escape from the GCPD, despite being shot both times. He has shown to almost never give up on getting revenge towards those who have wronged him. He was also willing to let himself be killed to protect Nygma due to his love for him.
- Intimidation: While most people do not take him to be a serious threat, he is able to intimidate several people with threats of violence, such as Liza.
- Master of Deception: Oswald is able to manipulating others and use them in his plans. He managed to convince Irish hitmen to kill Maroni by telling one of them it would make them Falcone's top hitmen instead of Zsasz, when in reality he planned to have them killed by Maroni and his men. While working as a double agent in Maroni's organization for Falcone, he was able to prove his usefulness to Maroni, with the latter not realizing it was all a ruse.
- Network: As a crime lord, Oswald has connections to multiple crime families and hitmen.
- Singing: Oswald is skilled at singing as shown he performed duets with Nygma in the latter's apartment.
- Skilled marksman: Oswald is proficient in the use of firearms.
- Torturer: Oswald is able to inflict brutal torture on several of his victims without restraint, such as when he beat Theo Galavan with a bat multiple times.
- Toxicology: Oswald has some knowledge of poisons as he laced the cannolis he served to the bank robbers he hired with a unknown poison that killed them.
- While most versions of Penguin tend to accept and like the name 'Penguin', this version has a great dislike for the name, even going so far as to kill someone, if he can get away with it. However, as time goes on he doesn't seem to be bothered by it anymore, possibly tending to accept and like it like most versions.
- Jim Gordon, Harvey Bullock and Oswald are the only characters in Season 1 and season 3, along with Leslie Thompkins, who appear in all the episodes of that season.
- In the episode "Mad Grey Dawn" Oswald mentions that he is 31 years old.
- His surname appears to be an Anglicized form of his mother's 'Kapelput', probably due to the fact that she used to refer to him herself as "My little Cobblepot".
- This is the first version of Penguin to be presented as LGBT, due to his attraction to Edward Nygma.
- In DC Comics, Oswald Cobblepot was created by artist Bob Kane and writer Bill Finger and he was introduced in Detective Comics #58 (December 1941). According to Kane the character was inspired from the then advertising mascot of Kool cigarettes – a penguin with a top hat and cane. Finger thought the image of high-society gentlemen in tuxedos was reminiscent of emperor penguins.
- While Bruce Wayne has come into contact with Penguin numerous times during Season 2 it wasn't until Mad City: Anything for You when Penguin interacts with Bruce for the first time directly.
- Gotham marks the second live-action television appearance of the Penguin, with the first being in 1960s television show Batman in which he was portrayed by Burgess Meredith
Oswald has killed 26+ people and a dog
- Unnamed Fisherman - Stabbed in throat with knife
- Two unnamed college kids - One stabbed in neck with knife, another unknown
- Unnamed Enforcer of Fish Mooney - Stabbed to death
- Unnamed dishwasher - Unknown
- Unnamed Gunmen working for him - Killed with poisoned cannoli
- Frankie Carbone - Stabbed multiple times
- Timothy - Gave his henchmen the order to kill him
- Marge - Shot with a shotgun
- Unnamed Delivery man for Sal Maroni - Stabbed in throat with shard of glass
- Multiple unnamed gang members - Gunned down
- Fish Mooney - Pushed from ledge into the water (Revived)
- Janice Caulfield - Stabbed multiple times
- Leonard - Killed together with Edward Nygma
- Theo Galavan - Bludgeoned with a bat and then shot in the head by Jim Gordon (Revived)
- Pet dog - Poisoned it to test what caused his father's death
- Charles and Sasha Van Dahl - Killed, cooked and served up to their unknowing mother Grace as revenge for them poisoning Oswald's father Elijah Van Dahl and mistreating him
- Grace Van Dahl - Stabbed
- Theo Galavan - Gave Butch the Order to blow him up with a bazooka
- Boris (Butch's lead mobster) - Shot in the head
- Isabella - sabotaged her car, causing her to crash into a train.
- Tarquin - Smashed his head with a golf trophy.
- Auctioneer - Shot in the head
- Gabe - Stabbed repeatedly out of anger
- Court of Owls Guard - Throat slit