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One of the Penguin's early plots was to get the Vonalster Fabergé Egg. He sent his two henchmen, Jay and Raven, to retrieve the egg, but Batman intervened. The two managed to escape and met the Penguin at a condemned birdseed factory. The Penguin scolded the two on how his pet, Scrap, was the only thing that kept them from getting caught. To their surprise, Batman tracked them down and Scrap found two kids, Roberta and Sherman, spying on the meeting. After Batman buried the trio under birdseed, the Penguin dug his way out and pelted Batman with a gas bomb that would "keep him nice and void for a good week". As the kids helped Batman's motionless body into the Batmobile, the Penguin and his men vainly attempted to open the Batmobile's driver compartment, but the kids started the Batmobile's engines and it caused the Penguin's two men to fly off into a window and dumpster. The car stopped for a dramatic pause as the Penguin sat dazed and confused and the car quickly restarted and as it was going to run into a ladder, the Penguin retreated via umbrella.
Scrap tracked the kids down eventually at Sherman's house with the Penguin and his crew right behind. The Penguin and his men bolted through the house, destroying everything near. The Kid's petty booby traps were mere annoyances and they tracked the kids to the basement where Batman lay. As the Penguin reunited with the egg, he attempted to shred Batman with the propellers from his umbrella, but Batman took the capsules Sherman gave him shortly before the Penguin's arrival and scuffled with the Penguin's bodyguards. The Penguin and Batman had a final duel, but Batman sent the Penguin flying into a nearby basement shelf and knocked him unconscious. His pet, Scrap, was donated to the Gotham Zoo while the Penguin himself was sent to Stonegate.
The Penguin was soon called after by Dr. Hugo Strange to attend a mysterious auction. The Penguin, along with Two-Face and the Joker, arrived by plane to find a limo awaiting them to take them to Yucca Springs. When the auction finally took place, it was revealed that the item was proof of Batman's secret identity. The Penguin's initial bid was a million dollars, but after seeing Two-Face and the Joker bickering, he had the idea to not fight but share the bidding. So the three of them decided to split the payment.
As Batman had switched the tapes, the Penguin and the other two angrily watched a recording of Strange trying to cheat them out of money by making a fake tape. Batman had used Strange's machine to imagine Strange admitting to the scam and recorded it on tape and intercepted the signal to broadcast that instead of the Bruce Wayne tape. The Penguin's own umbrella pistol destroyed the tape and the trio went after Strange in a high speed chase, but caught up with him at Gotham International Airport and took Strange off in his own plane to dispose of him. Batman tampered with the engine and the plane crashed. A police blimp was at the ready overhead and the Penguin, the Joker, Two-Face, and Strange were taken into custody.
The Penguin later attempted to steal a pair of breeding condors from the Gotham Zoo. As he was about to break in, Batman showed up and knocked him to the ground. The Penguin sprayed pollen on Batman which attracted his hummingbirds. Batman had to fight the hummingbirds, who had their beaks tipped in poison. Batman escaped them, and Penguin sent his cassowary to rend him apart. Unfortunately, Batman took one of the Penguin's poison-tipped hummingbirds and poisoned the cassowary. The Penguin was traumatized and flew away on his umbrella to escape the Dark Knight.
He soon retreated to a night club and played cards with the Joker, Two-Face, Poison Ivy and Killer Croc. After the group told stories of how they almost killed Batman (the Penguin told about his most recent encounter), they were infuriated to learn Croc was a disguised Batman all along. Before they could do anything they were ambushed by police.
Out of prison again, Penguin attempted to steal a priceless Audubon painting from a museum, but was foiled by Batman. He spent some time in jail, but upon his release, he found he was not quite welcomed in the manner he had hoped. He had to take a trashy bus back to Gotham. Though he tried to convince Batman he was reformed, the Dark Knight did not buy it. Soon after, Gotham's favourite socialite Veronica Vreeland called him for a date. On their first date, they were mugged, but as the Penguin fended them off, Batman came and trashed the muggers while thinking the Penguin was behind it. Veronica defended the Penguin and they left as Batman stood in optimism.
The Penguin and Veronica went to the opera and afterwards a party. He overheard her and her friend Pierce Chapman talking about how they planned to use him to attract publicity for their party. Enraged, he knocked both unconscious with sleeping gas. He kidnapped Veronica and flew away right as Bruce Wayne entered the balcony, vainly trying to rescue her. Penguin demanded Pierce deliver the ransom. Pierce went to the delivery point in a condemned part of the city. The Penguin called him by phone booth and instructed him to take one step out and start walking left. Pierce did as commanded and fell into the sewers via a trap door. He was caught by the Penguin's duck mobile and the Penguin led Pierce to his headquarters above his sewer lair: the opera hall. Batman came in as the Penguin was about to dispose of both Veronica and Pierce, and the Penguin retreated to a higher stage platform. He came back out in a Viking helmet and rode a giant metallic dragon. The Penguin and Batman had a prevailing fight as the chandelier that held Veronica was loosening. Batman saved them in the nick of time; he stopped the Penguin by slicing the dragon's wires with a batarang. Penguin crashed into the stage curtains. The Penguin was taken by police soon after.
Some time later, the Penguin had his new henchmen Eagleton, Falcone and Sheldrake, steal the reversed audubon stamps. Unbeknownst to him, they were chased by Batman. After they managed to get back to the sewer lair, the Penguin was furious to discover that the stamps they stole weren't the reversed versions. After the failure he was about to have his new pet, Percival, poke out Eagleton's eyes if he couldn't come up with a good reason not to have that done. In this instance, Falcone got his friend Arnold Rundle. Rundle, who worked for an auto parts store, had isolated several purchases which coincided with times the Batmobile was damaged. It led him—and now the Penguin—to Earl Cooper's shop. They tampered with the Batmobile and abducted Earl's daughter Marva. After Batman retrieved his car from a very suspicious Cooper, the Penguin took control of the Batmobile on an interstate highway. He controlled it from his newly fixed limo. He drove the Batmobile off the top of a parking garage, but he was horrified to find the Batman and Robin right behind his limo on gliders.
Eagleton drove into the airport flying dock, only to crash into a moving loading truck. As his limo lay in ruins and Eagleton and Sheldrake were unconscious, the Penguin came out with his hostage at gun point. She stepped on his feet and with that he was about to shoot her when Robin came down and kicked him to the ground. Helpless, he was taken to Stonegate once more. Later as he was polishing the license plates at the prison he grabbed one that said "1BAT4U". He broke it in half out of anger.
Out of prison once again, he was reunited with Eagleton, Falcone and Sheldrake. He stole Wayne Tech's prototype helicopter, the Raven X1-11, blinding Bruce Wayne in the process. He kept it for ransom; he destroyed a bridge to demonstrate his seriousness. Mayor Hill broadcast a message saying he would comply with the demands. It was a trap, and Batman threw a net around the Penguin and Falcone as they retrieved their payment. They got out via the Penguin's umbrella, got back into the Raven and went after the Batwing. The Batwing ran the Raven down with spiked round casings.
The Raven brought the Batwing down as well using its sonic lasers even while handicapped with flight. Batman ran helplessly into a nearby building as Penguin and Falcone watched in amusement. After Batman beat Falcone, the charge that kept the mask he was using to see died leaving him helplessly blind. It didn't take long for the Penguin to realize Batman was blind and he started to toy with him. Batman almost fell into a vat of liquid metal, but was able to hang onto some pipes. He managed to even the playing field by fogging up the room. Penguin was then easily defeated, and left for police.
Still an avid lover of birds, he ordered a stuffed extinct penguin that the Ventriloquist & Scarface had available. They tried to get him interested in other stuffed creatures they stole from the Vreeland exhibit. He never got his penguin because Batman and Catwoman interfered with the Ventriloquist's plans.
The Penguin and Two-Face had an apparent fight as Two-Face had stole a rare Avis from him. Batman interrogated him at Stonegate after Two-Face was kidnapped, but Penguin had no part in the plot.
The Penguin also stole plutonium from Wayne Tech's lab and threatened to blow up Gotham City.
According to Batman, the Penguin once tried to kidnap a famous singer named Ricky. Batman was on stakeout for a month, apparently watching to see when Penguin made his move.
The Penguin later opened Gotham's hottest nightclub, The Iceberg Lounge. He presented himself as reformed and a businessman, but after hours he did smuggling and other ruthless professions.
He soon became overwhelmed about the Joker's new found fortune. So the Penguin threw him a party at his club, only for it to be overpowered by gunfire by King Barlowe 's right-hand bodyguard. Though Nightwing and Batgirl came in and stopped the gun noise, the Penguin lay in panic.
The Penguin soon found use for Roxy Rocket and had her steal some valuables. After she was putting his operations at risk, he attempted to do away with her. She prevailed and escaped, leading him to order his henchwomen to "clip her wings" before she told someone about his empire. As the Penguin was set for bed at his skyscraper suite, Batman came in and asked about the location of Roxy. The Penguin didn't come quietly and shot at Batman with a machine gun. Batman overwhelmed the Penguin and hung him off over his balcony before he gave in.
When he saw three ladies fighting (Harley Quinn, Poison Ivy and Livewire) at a table in his lounge, he tried to cease the commotion. When Livewire backtalked him and called him "Lard Butt" he ordered them out. They rebelled and left his lounge smothered in vines and thornes. Soon after, Supergirl and Batgirl interrogated him on were the trio of ladies were and the Penguin was at first reluctant, but then gave in and told them he had a hunch they were at the old Gotham Zoo.
The Penguin was later interrogated by Superman (Disguised as Batman) on the whereabouts of the Mad Hatter (for Bruce Wayne went missing after mind control probes were found on his office phone). Only after "Batman" kicked a desk at the Penguin did he comply.
After he had a small dealing with Killer Croc and Two-Face, the Penguin was encountered by The Judge. The Penguin was horrified and was chased through his design studio. As his henchladies were tied up, he was alone. He was crushed by a giant penguin prop that the Judge set loose. He survived, but was enlisted in critical condition at the Hospital.
The Penguin soon allied himself with Rupert Thorne to smuggle illegal weapons to Kaznia. As Batwoman interfered with one road shipment and his factory went up in a blaze, the Penguin knew that their muscle, Carlton Duquesne, was out of his league. As the Penguin and Thorne were discussing whom their new muscle would be, Batwoman sneaked into the Penguin's file cabinet. The two caught her, but a fight was unleashed and Thorne agreed with the Penguin they needed to bring someone better in as Batwoman escaped.
While at his lounge, the Penguin called up his new enforcer. Bane agreed to meet him in the Penguin's frequently used back entrance. As soon as the Penguin got off the phone, Batwoman appeared and wrapped a metallic alloy around him. She squeezed and squeezed him until the Penguin gave in and said "Bane" very mildly. It didn't take long for the Penguin's henchladies and Batwoman to fight. Their fight got taken out into the lounge and the Penguin shot motion-seeking missiles. As the Penguin aimed the missile launching umbrella at Batwoman, Batman came in and the Penguin was pushed to the ground. As Batwoman escaped, Batman was pushed into the lounges' center arctic pool. As the Penguin shot homing missiles into the water, Batman set and detonated a bomb from inside the pool. It caused the lounge to flood and the Penguin was whipped in the face by one of his seals.
The Penguin, Thorne, and Duquesne met with Bane at an isolated warehouse, because the mercenary couldn't come to the lounge due to the previous incident. The Penguin allowed him full control of the operation and showed him the ship and plans he was to be using. Later that night, as the Penguin and Thorne played cards, they got a call to come to the ship. To their surprise, Bane found out who Batwoman was, Kathy Duquesne, Carlton Duquesne's daughter. Batman soon came in and another fight was unleashed. After Batman and Kathy escaped, the two crime bosses ran to the Penguin's boat to retreat for the bomb Kathy had was missing. They ran into the other two Batwomen. As the ship exploded, Sonia was injured and Rocky went after the fleeing felons. She latched onto the boat and the sudden stop made the Penguin and Thorne fly into the water. They were caught and the Penguin, after years of being "reformed", was finally punished for his crimes and sent back to Stonegate with Thorne.
Years later, Batman kept one of the Penguin's outfits in the Batcave.
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