Oswald Cobblepot

"I'm the new King of Gotham!!!"

- Oswald Cobblepot

Oswald Chesterfield Cobblepot is the former umbrella-man of Fish Mooney, one-time underling of Salvatore Maroni and spy for Carmine 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.

Beginnings
Oswald Cobblepot entered the criminal underworld through Fish Mooney and her gang, where he received the nickname "Penguin", which he despises.

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 Nikoai are secret lovers with plans to overthrow Falcone. 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. 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.

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 fiance 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.

Saving Gordon
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.

Personality
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.

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. 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.

Physical Appearance
Cobblepot is a rather skinny young man of average height, pale skin and noticeably bright blue eyes. His nose is slightly crooked and pointy, like a beak and he is usually grinning. His black hair looks like always wet and messily plastered on his head, with some spiky ends pointing erratically at the top of his head. His attire consists of a white shirt with a black, Continental Cross tie with its ends tucked inside a silk, purple checkered vest and a black coat with dark green lapels, black pants and matching shoes, and mostly carrying a black umbrella. Due the torture he suffered for betraying Fish Mooney, one of his knees was probably permanently damaged or never healed right, forcing him to walk almost waddling "like a penguin".

Appearances
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Trivia

 * The character 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 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.