- It was my own fault. Foolish arrogance led me astray. But I learned my lessons. I'll be back, stronger and smarter than ever.
- — The Penguin src
Oswald Chesterfield Cobblepot - nicknamed the Penguin, to his initial dismay, but later proudly embracing the name as a badge of honor - is a greedy, emotional, and lonely Gotham City underworld figure who slowly worked his way to the top of the city's crime organizations. He is the longtime nemesis of Jim Gordon, the on-and-off friend of the Riddler, and an enemy of the Dark Knight.
At the time of the murder of Thomas and Martha Wayne, Oswald Cobblepot was a young man working as an umbrella boy for nightclub owner and crime boss Fish Mooney. He is also completely devoted to his mother and has aspirations of making a name for himself in the city. However, under the surface, he is cold and calculating, notifying the MCU that Fish Mooney has in her possession the pearl necklace belonging to Martha Wayne, who was murdered alongside her husband Thomas by a mugger while on a night out with their son Bruce. When Fish discovers his betrayal, she breaks his leg, leaving him with a limp. Detectives Harvey Bullock and Jim Gordon later bring him to the docks but the latter ultimately spares his life. When Oswald swims to safety he kills a fisherman in a bid to protect the fact that he is still alive.
After hitchhiking for several hours, he is picked up by two college frat boys who tell him he stinks and offer him a beer. Oswald is grateful for their kindness and comments on his arrogance before one of the frat boys tells him he walks like a penguin, triggering him to smash the beer bottle and stab the boy in the neck, killing him. He takes the other boy hostage and rents a mobile home, keeping the boy hostage and bribing his mother for a ransom. However, the boy's mother does not believe him. Oswald later returns to Gotham wearing the boy's clothes.
No Man's Land
Once the main bridges were destroyed and Gotham was plunged into chaos, the Penguin and his gang started establishing their own territory and took control of the abandoned Gotham City Hall, which Cobblepot would use as his power base for the whole No Man's Land year. Later that night, Penguin's thugs found the bodies of Nygma and Lee Thompkins in the Gotham Narrows and took them to Sofia Falcone's mansion so that Hugo Strange could revive them. However, Professor Strange was secretly contacted by Nyssa al Ghul, who ordered him to put a mind control chip into the brains of Lee and Nygma. She planned to use them in her scheme to avenge the death of her father.
When Jeremiah Valeska's chemicals poisoned the river, Oswald and Nygma both agreed that Gotham was no longer a city but a prison. Penguin suggested that they should escape, whereon Riddler comes up with the idea to built a submarine. The next day, Oswald and Nygma arrived back at Gotham City Hall, where Barbara was waiting at the mayor's office in order to murder Penguin in retribution for killing Tabitha. She explained that she had a look through the secret treasure room, revealing that Selina told her about it. However, Ed then realized she is pregnant, noting that she is glowing. When Barbara raised her gun to shoot Oswald, he decided to offer her to escape from the city alongside him and Ed, so she wouldn't have to raise her child in a toxic waste war zone. Ed and Cobblepot revealed the blueprints of a submarine that can track mines in the river using sonar. Barbara agreed that she will not murder Penguin for the sake of her child and told them to call her once construction on the submarine has finished.
The War for Gotham
After the end of the No Man's Land year, Penguin and Nygma were invited to the reunification ceremony at City Hall, where Mayor Chang promoted Jim Gordon to the rank of Commissioner.
The Dark Knight
Six months after the war for Gotham, Riddler and Penguin were apprehended by Commissioner Gordon and taken into custody. Cobblepot was then imprisoned at Blackgate Penitentiary, where he would stay for the next ten years.
When the Penguin was finally released from Blackgate after a decade, he was welcomed by a group of reporters who tried to interview him. When asked about the first thing he will do as a free man, he said that he will lay flowers on the grave of his beloved mother Gertrud. He also revealed that the best revenge against the Commissioner will be a life spent serving Gotham, indicating that Cobblepot will be the villain known as the Penguin for the rest of his days and prevent Gordon from ever finding peace.
- Cheating Death: No matter the odds, Penguin always manages to find ways to escape lethal situations that seem impossible to survive. He was fatally shot in the chest by Nygma and sank to the bottom of the cold Gotham River, but was later pulled out of the river alive under mysterious circumstances. During No Man's Land, he was almost shot in the heart by Tabitha and only survived because of a misfire. When Oswald later battled Bane's army to protect Gotham, a grenade exploded right in front of him, yet for some reason only damaged his right eye.
- Tactical Analysis: Known to everyone as a "sneaky little bastard", Oswald is capable to planning several moves ahead of his enemies. However, when he is emotional, he is less observant and less tactful.
- Deception: Cobblepot has succeeded in fooling both Fish Mooney and Sal Maroni, acting as an undercover informant for Falcone. Adding to this is he will always talk with a smile to others, unless they've incurred his rage.
- Business Management
- Political Science
- Gadgetry: After Magpie stole the Russifer Diamond from his treasure chamber, the Penguin used booby traps to secure his valuable belongings.
- Limp: After being punished for betraying Fish Mooney, Cobblepot's leg never healed right, leaving him with a visible limp. He later had an ankle brace which restored his ability to walk right. However, Gordon shot his knee, restoring his limp.
- Damaged Eyesight: During the final days of the No Man's Land year, Penguin participated in a dangerous battle to defend Gotham from Nyssa al Ghul and Bane. Cobblepot's right eye was heavily damaged when a grenade thrown by the enemy exploded right in front of him and shot shrapnel into his face. The injury caused Oswald's eyesight to become weaker and from now on required him to wear a monocle for the rest of his life.
- This version of the character is exclusive to the continuity of the television series Gotham and its tie-in webseries and shorts, Gotham Stories and Gotham: A City Gone Mad. It is an adaptation of Penguin. The original character was created by Bob Kane and Bill Finger and first appeared in Detective Comics #58.
- The Penguin was portrayed by Robin Lord Taylor.
- As of the episode Mad Grey Dawn, Oswald is 31 years old.
- Given how much time passes over the course of the show, this makes him about 33 when the final season begins, and 43 in the finale.
- The Penguin appeared in ninety-four episodes of Gotham, making him the most commonly-appearing villain on the show.
- 103 Appearances of Oswald Cobblepot (Gotham)
- 9 Images featuring Oswald Cobblepot (Gotham)
- 10 Quotations by or about Oswald Cobblepot (Gotham)
- Character Gallery: Oswald Cobblepot (Gotham)
- Gotham (TV Series) Episode: Wrath of the Villains: Prisoners
- Gotham (TV Series) Episode: Arkham
- Gotham (TV Series) Episode: A Dark Knight: No Man's Land
- Gotham (TV Series) Episode: Pena Dura
- Gotham (TV Series) Episode: Ace Chemicals
- Gotham (TV Series) Episode: They Did What?
- Gotham (TV Series) Episode: The Beginning...