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|As a result of the New 52 in 2011, the entire line of DC characters was relaunched, incorporating properties belonging to the company's imprints: Wildstorm, Milestone, and Vertigo. As such, elements of this character's history have been altered in some way from the previous incarnation's. For a complete list of all versions of this character, see our disambiguation page.|
- Do these men have families? Not anymore they don't.
- -- Penguin src
Oswald Cobblepot is the Penguin, a ruthless Gotham City mobster who frequently finds himself an enemy of Batman.
Before Batman's first official appearance in Gotham, Cobblepot was a rising crime lord, one of his fortes being weapon deals, which he did on his personal blimp. Becoming a good business partner with Luca Falcone, Cobblepot became a weapons smuggler. When Red Hood One, leader of the Red Hood Gang, infiltrated the blimp, intending to steal a collection of WayneTech weapons, the vigilante that would eventually become Batman sprung into action. Unable to get the weapon from the Red Hood, the hero parachuted from the blimp, carrying Cobblepot in his arms. 
Other Early Crimes
During the second year of Batman's career, Penguin was still not the master of Gotham's underworld he would one day become. A lieutenant in Carmine Falcone's operation, Penguin was contacted by the actor Basil Karlo for a less-than-legal edge he could use to make him stand out in the acting world. Cobblepot made him an offer of a magical piece of clay he had gotten his hands on in exchange for Karlo acting as one of his henchmen. Karlo agreed, and the piece of clay transformed him into the Gotham criminal Clayface.
Later that year, Penguin became entangled in what would be called "the War of Jokes and Riddles" between the Joker and the Riddler for the right to kill Batman. The Joker, seeing an opportunity to commandeer Carmine Falcone's operations to bolster his own army, kicked Gotham's strongest crime lord out of Gotham and sent him into retirement. With Falcone's henchman now all Joker's, Penguin became a member of the clown's army against Riddler. For weeks the fighting raged on between the two sides all throughout Gotham until Batman himself was forced to focus his efforts on one army in particular. The Bat chose to set his sights on the Joker and forced Penguin out of the fight. With Falcone gone and many of his lieutenants killed by the Joker, the Penguin filled the power vacuum and became Gotham's new strongest crime lord. Building up his own successful crew, Ignatius Ogilvy soon came into the care of Oswald. During this time he also took up the bodyguard Lark. Cobblepot continued his criminal attitudes, even when the Batman debuted.
Not long after the grand reopening of the Iceberg Casino, Cobblepot took Mr. Toxic, Mr. Combustible, the Imperceptible Man and Hypnotic and had the three invest their money in him. He planned to have Jill Hampton kill the three, giving their money to him and then in turn have Snakeskin kill Hampton, erasing traces of the crime. He had decided to use the money to fund Hady's campaign and bribe other officials into backing out. Although he succeeded in getting Snakeskin to kill Hampton, he failed to take the money of the three criminals as Batman showed up in time. This ended up cementing Cobblepot's fall as the criminal emperor of Gotham city. He was later involved in a nuclear bomb conspiracy, selling the explosive to an unknown party.
Cobblepot tries to regain his influence and power in Gotham by "replacing" Bruce Wayne. During this time Cobblepot would hire Lady Shiva and allow Rose Wilson into his employ. However, for the hit on Bruce Wayne, Oswald hired the Ghost Dragons. However, after humiliating Wayne, Oswald attempted to call off the hit, only to find he was unable to do so. Therefore, he kills an assassin and make it appear that he saved Wayne himself.
His joy was short lived as Poison Ivy began wrecking his factories and he was approached by the Joker. To stay out of harms way, Oswald followed the Joker into Arkham to watch his plans unfold, all while leaving his empire in the care of Ignatius Ogilvy. Upon the Joker's defeat the Batman locked Oswald up in Blackgate Penitentiary only to let him go free a while later.
Ogilvy, however, uses the Penguin's absence to declare him dead, taking over his gang and killing those loyal to him. Under the alias of Emperor Penguin, Ogilvy takes over the Penguin's operations. Upon the Joker's defeat, Batman unsuccessfully attempts to imprison the Penguin in Blackgate Penitentiary only to be forced to release him later. Upon learning of Ogilvy's betrayal, the Penguin attacks his former henchman's new empire, but Batman intervenes and arrests him. The Penguin is found not guilty, however, thanks to the machinations of his ally Mr. Combustible. Meanwhile, Ogilvy releases Kirk Langstrom's Man-Bat serum on Gotham City, turning many of the citizens into the creatures. Langstrom discovers a cure, returning the citizens to normal. Ogilvy then takes the serum himself, along with additions made by Poison Ivy. Emperor Penguin then challenges Batman openly to a fight, defeating the masked vigilante with his newfound prowess, and leaving him to be rescued by the Penguin. The pair forge a temporary alliance, and defeat Ogilvy.
The War in Badlands
It did not take Oswald long to resume his criminal activities, though. Almost immediately afterwards he began a gang war in which he hoped to eradicate Catwoman and the new rising gang the Rat-Tails. Oswald easily began the war and soon after decided on a new way to eliminate his enemies. He decided on manipulating Clayface and the Mad Hatter though the Batman quickly put an end to this plot. Clayface then proceeded to end his relations with Oswald, forcing the Penguin to resort to human trafficking. However, the Batman quickly put an end to the Penguin's new business.
When the Crime Syndicate arrived on Earth and seemingly killed the Justice League, Gotham City was sent into a wave of panic without Batman to defend them. Cobblepot, undaunted by the hysteria, ran the Iceberg Casino as usual. As the city began to break down, a group of card sharks known as "the Illusionists" attempted to cheat the system at Penguin's casino, which resulted in the order to have both them and their families killed. So, business as usual.
Later, Governor Carter Winston, an old friend of Cobblepot's from grade school, attempted to bring justice to Gotham in Batman's absence by first targeting the Penguin and his operations. Having a tense dinner together, Winston swore that he would bring his old pal down for the crimes the Penguin committed. Penguin, disappointed that he was being underestimated, drugged Winston with Venom and blackmailed the governor when the man woke up the next morning with his assistant's blood on his hands. Governor Winston, distraught, has no choice but to back down abd, the next day, committed suicide by shooting himself on live television. 
With matters continually getting worse and worse in Gotham without a hero to save it, the Penguin usurped the current position holder and declared himself the new mayor of the city. During Cobblepot's "term", the super villains from Arkham Asylum and the prisoners from Blackgate Penitentiary began to battle for territory in what was later named the "Arkham War". Playing for both sides, Mayor Cobblepot made deals with the leaders of both sides - Scarecrow representing the Arkhamites and Bane representing the Blackgate prisoners. Penguin traded Bane information in order to have one of Blackgate's prisoners - Emperor Penguin - who Penguin believed hadn't suffered enough for his betrayal.
After many bloody battles throughout the streets of Gotham, Bane and his army were victorious in the war. Mayor Penguin, congratulating him on his victory, awarded the victor food, weapons, and free range of the city  until he was kicked out of office when Batman returned.
After the Joker sent the city into chaos, the Penguin, now armed himself to teeth with assault rifles and modified weapon umbrellas, was among the villains summoned by Batman to help him fight along the Joker's army. He was later seen taking down many Joker-venom infected with his trick umbrella.
- Business Management: Oswald has a keen business sense. He has kept his casino business on the right side of the law to set up a front to launder money from his illegal businesses.
- Hand-to-Hand Combat (Basic): Oswald, despite his appearance, is trained in the usage of his personal weaponry. A few thugs or a tussle with Batman is nothing for the Penguin.
- Leadership: The Penguin runs one of the most elusive and strongest gangs in all of Gotham.
- Tactical Analysis: Oswald never forgets an injustice done to him. He may not exact his revenge in the same moment or even the same year but at some point, in some place, he will have his vengeance.His tactical skill ensures the stability and prosperity of his crime empire, which has always remained as the most powerful crime empire in Gotham and claimed victory in gang wars.
- Penguin (Oswald Cobblepot) was created by Bill Finger and Bob Kane, first appearing in Detective Comics #58. However, in the Prime Earth continuity Penguin (Oswald Cobblepot) first appeared as part of the New 52 DC Universe in Penguin: Pain and Prejudice #1 by Gregg Hurwitz and Szymon Kudranski.
- In Batman (Volume 3) #58, it was said that Oswald Cobblepot was born in 1970. While that date can't be taken literally (as time will pass but the character will not age), it does show that Cobblepot was 48 in that story.
- Penguin murdered his three brothers; Jason, William and Robert. They all attacked him and his birds one night, and he retaliated in time. Jason died due to poisoning, William in a hit-and-run, and Robert in a freak accident which left him at the bottom of a frozen lake. 
- During his high school years, Cobblepot considered fellow student Veronica Vreeland the love of his life, even though he had never even asked her on a date. He killed one of his few friends because he thought the friend was romancing Vreeland behind his back (the friend was actually visiting Vreeland to ask her to consider dating Cobblepot). 
- Penguin's prepared tombstone reads "So they lov'd, as love in twain had the essence but in one;" with his beloved penguin Penny's reading "two districts, divisions none; number there in love was slain."
- 168 Appearances of Oswald Cobblepot (Prime Earth)
- 52 Images featuring Oswald Cobblepot (Prime Earth)
- 20 Quotations by or about Oswald Cobblepot (Prime Earth)
- Character Gallery: Oswald Cobblepot (Prime Earth)
Secret Society of Super-Villains member