Penguin
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Real Identity: Oswald Chesterfield Cobblepot
Appearances (BTAS): I've Got Batman in my Basement, The Strange Secret of Bruce Wayne, Dreams in Darkness, Almost Got 'Im, The Mechanic, Birds of a Feather, Blind as a Bat, Second Chance, Batgirl Returns, Joker's Millions, The Ultimate Thrill, Girls' Nite Out, Judgement Day and Mystery of the Batwoman
Appearances (STAS): Knight Time
Skills: Business, Underworld Activity and Umbrella Weaponry
Voiced By: Paul Williams/ David Ogden Stiers
Oswald Chesterfield Cobblepot is a dwarfed gangster in Gotham City. Because of his short stature and bizarre appearance (matched with formal clothing), he soon took on the name of the Penguin. The Penguin often commited crimes based on the motif of birds. He stole items based on birds such as priceless antiques, art or weapons and hires henchmen whose names are associated with that of birds.
While his henchmen stole Von Ulster's fabled Faberge Egg, the Penguin sent his specially trained South American vulture, Scrap to intercept Batman. The vulture was followed by two inquisitive children, Sherman Grant and his friend Roberta, to a condemned bird seed plant. Batman arrived and saved the children. He was doused with a toxin sprayed via Penguin's trick umbrella. The Penguin tracked the children to the Grant household, in the suburbs of Gotham. The children managed to stall the Penguin long enough to allow Batman to recover with an anti-toxin. Penguin was arrested and Scrap was donated to the Gotham Zoo.
Though a social outcast, Penguin still desired acceptance. He became an unwitting patsy for Veronica Vreeland as part of a joke at one of her upcoming parties. Penguin took his relationship with Vreeland seriously and went on a series of dates. Despite displaying some odd habits, Penguin saved Veronica from two muggers. He came to close to proposing marriage to Vreeland until her overheard her friend Pierce gloating. Vreeland was kidnapped and held for ransom. After Batman saved her, she admitted to becoming fond of Penguin, as he was hauled away to jail.
After his henchmen narrowly escaped Batman in a high speed chase, Penguin became privy to Batman's secret relationship with ex-Global Motors engineer, Earl Cooper. The Penguin infiltrated Cooper's compund and held his daughter hostage for collateral. He then forced Cooper to rebuild the Batmobile with death traps. However, Cooper snuck in a fail safe to save Batman and Robin.
When Wayne Tech was showing off its stealthy fighter plane, the Raven XII to the military, the Penguin made an appearance. The Raven's stealth mode allowed for recon, cloaking and cutting edge radar thanks to its Zero Visibility Flight (ZVF) system. Penguin hijacked it and ransomed all of Gotham City for $100 million. In the daring theft, Bruce Wayne's retinas were flash burned. Wayne was temporarily blind. Despite recommendations from Dr. Thompkins, Wayne donned the Batman suit to confront the Penguin with a virtual reality aid, adapted from the ZVF.
Frustrated with constant defeat at the hands of Batman, Penguin devised a more indirect approach at crime. Penguin displayed himself as a reformed individual and became the proprietor of the Iceberg Lounge, Gotham's newest and hottest night club. Behind closed doors, Penguin continued his underworld dealings. He was involved in smuggling, fencing and information rackets. Penguin trafficked stolen goods from the likes of Roxy Rocket, Killer Croc and Two-Face. He also kept himself informed of movement in the underworld such as Livewire's escape while being transferred to GothCorp Labs. At Batgirl and Supergirl's request, Penguin revealed the location of Harley Quinn and Poison Ivy's hideout.
Penguin's largest known smuggling contract involved secret weapons plants used to manufacture and smuggle arms to the East European country, Kasnia. Funded through an alliance with other gang leaders, Rupert Thorne and Carlton Duquesne, Penguin hid the plants behind fronts such as Beak's Bric-a-Brac, a figurine warehouse. Half a billion dollars was paid upfront for weapons such as plasma rifles, laser guns and missile launchers. As lucrative as the deal was, the three incurred the wrath of Batwoman. To make matters worse, Batman and Robin began to investigate. Penguin hired Bane and ceded control to him. The remaining arms were stocked on a luxury cruise liner, S.S. Naiad. Bane ambushed Batwoman, but the remaining Batwomen, Batman and Robin intervened.