The Penguin

The Penguin is a major antagonist in Batman: Shadow War, Batman: Red War and Batman: New War. He is a brutal and sadistic crime lord and an old enemy of Batman.
==Biography==
===Early Life===
Oswald Chesterfield Cobblepot is the son of Theodore and Esther Cobblepot. He was born into one of Gotham City's wealthiest and most powerful families, a dynasty of generals, mayors and industrialists. The Cobblepots were among the founding fathers of the city, building a park for the city's public. However, a long-standing rivalry with the Wayne family led to them encountering financial difficults, and had them neglect their successful newspaper business in favor of a hotel chain. As a result of those difficulties, Theodore neglected his son and packed him off to boarding school in London. Feeling abandoned, and ostracized by his fellow students for his grotesque appearance, Oswald skipped more and more classes, and preferred to associate with the criminal elements and other unsavory types outside of school. 
Eventually, the family businesses, and the Cobblepots along with them, went bankrupt, due to events set in motion by Thomas Wayne, Hamilton Hill and Carmine Falcone. This gave Oswald a lifelong grudge against the Wayne family, in particular the last member, Bruce Wayne, who Oswald saw as nothing more than a spoiled little rich boy. By that stage, Oswald had abandoned his education altogether, and preferred to educate himself into a criminal lifestyle in order to rebuild his family fortune.
While in the United Kingdom, Oswald set up a number of illegitimate enterprises, including illegal boxing matches and arms dealing. Oswald was also arrested many times, once by the Essex Police Department, and served a number of prison sentences.
As an adult, Oswald established himself as an international criminal and arms dealer who was known as the Penguin, and returned to Gotham with plans to build a criminal empire within the city. Having purchased an aging cruise liner named the Olivia B. Meredith from a group of Somali Pirates, Penguin renamed it "The Final Offer", and exploited a legal loophole by selling weapons on-board, sales which would be illegal on US soil, but were perfectly legal on-board. He also used the casino on-board as an additional source of revenue, and cheated people out of their money. Penguin had, by that stage, developed something of a sadistic streak, and brutally killed anyone who had done something to wrong him, whether it would be to fail their duties as a henchman, or an attempt to cheat at gambling. The bodies of those who had wronged him were displayed in the theater of his ship as a grim warning to others.
The Penguin would also inadvertently help create the serial killer Victor Zsasz. Zsasz was playing poker in the Iceburg Lounge and started doing very well. He eventually worked his way up to the Penguin's personal table in the back. Throughout the night, Zsasz was winning hand after hand. Then, Zsasz went all in, thinking he would win with his four 6's. The Penguin taught him that the only person who wins in "his house" is the owner. Penguin cheated, pulling out a 6 he had hidden. This gave him a straight flush and he took all of Zsasz's money and kicked him out. This led to Zsasz's first murder, killing a man in anger because he demanded Zsasz's money. 
===Fighting The Vigilante Before Batman===
Before Batman's official appearance in Gotham, Cobblepot was still a rising crime lord and he operated out of his personal blimp at one point to sell weapons to Carmine Falcone's lieutenant, Jimmy Saviano. However, 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 weapons from the Red Hood Gang, the hero parachuted from the blimp, carrying Cobblepot in his arms.
==="First" Encounter with the Bat===
At some point, one of the Penguin's former henchmen, Lark, had went behind the Penguin's back for a deal acquiring stolen rare diamonds worth millions and made the Penguin believe the deal failed. The Penguin, realizing that Lark had tricked him, sent a group of armed henchmen led by one of his lieutenants, Tracey Buxton, to take Lark's wife Rose hostage and ransom her for the diamonds. In order to show he is being serious, the Penguin orders for Rose's tongue to be cut out and she is then trapped in a cage bound and gagged with duct tape. In reality, the diamonds were inside Rose and Lark told the Penguin he did not possess them anymore, not wanting for Penguin to kill his wife to get to the diamonds, so he bought time by saying he will get them back and goes to the police about the ransom for help. Captain Jim Gordon gave Lark fake diamonds from evidence to bait the kidnappers into a sting operation, which was going successful until Buxton realized it was a trap and tried to flee but Batman managed to stop and capture her.
Batman interrogated Buxton before handing her over to the police, then he heads off to find Rose. Batman frees Rose but the Penguin arrives with his henchmen onto the scene. The Caped Crusader proceeds to fight the Penguin and his men when the Penguin intended to kill Rose in retaliation for Lark going to the authorities, but Batman manages to defeat the Penguin and Gordon and his officers arrive. Gordon tries to arrest Batman alive and stops his cops from firing, though Batman escapes and leaves a tied up Penguin and his henchmen for them. The Penguin is arrested but manages to use any legal loopholes he could use to prevent a conviction, instead having one of his henchmen take the fall. Lark and Rose skip town before the Penguin can get his revenge however, but the Penguin simply decides to return to his normal business however a newfound hatred fills up inside him for Batman. When he returns to his office, the Penguin discovers a Batarang placed in his desk which confuses him until it explodes and creates a smokescreen, panicking the crime lord and pulls out a machine gun but Batman confronts him, disarming him of his weapon and grabbing him. Batman warns the Penguin to not get too comfortable in his freedom; the Dark Knight will always be following and watching him.
===Investigation of Zsasz===
The Penguin has Alberto Falcone kidnapped and taken to the Final Offer in order to make his family get out of the weapon's trafficking business. Due to leaving his fingerprints at a scene where a murder took place, the Penguin was suspected of murder however bribed the cops to avoid pressing charges but did not expect Batman to come after him. He hosted an annual fighting tournament in his ship's Boiler Deck and dispatched one of his arms dealers, Ricky "Loose Lips" Leblanc, to supply weapons to a gang of criminals. Penguin began torturing Alberto, but was interrupted by Batman, who began to interrogate him as he smashed him into a mirror in his office.
Penguin started to give Batman information on the murder but Penguin's lieutenant, Mr. Sickle, suddenly attacks Batman. Penguin watches the fight between Batman and Sickle, but when Batman won, Penguin tries to kill the Dark Knight with one of his weaponized umbrellas that fires explosive grenades. Batman though defeats the Penguin, brutally beating him down and incapacitating him. Afterward, Batman called Gordon to seize the Penguin's illegal weapons however Penguin's actions to Alberto succeeded in forcing his father out of the weapons racket, which also increased his popularity among the criminal underworld. Thanks to the Penguin's information, Batman managed to discover the murder was committed by a serial killer named Victor Zsasz.
===Working for the Phantasm===
At some point, the Penguin was approached by the Phantasm to join her cause in order to get revenge on Bruce Wayne, revealing that it was his father who murdered Oswald's father and set in motion the events that led to the downfall of the Cobblepots. Penguin later contacted Mayor Hill and blackmailed him into compiling information about Falcone and Thomas's illegal activites. The Penguin also hired famed cat-burglar Catwoman to assist them.
The Penguin is seen by Bruce at a fundraiser event at Wayne Manor and was seen drinking at a table with some of his goons, though did not converse with any of the guests. As he left he met with Bruce's Alfred Pennyworth, leaving arrangement to meet at Cobblepot Park the next morning. A short time before he arrived, Bruce encountered two thugs who attempted to mug him however the Penguin's presence when the crime lord finally arrived scared them off. Afterward, he and Bruce discuss about their family histories and the Penguin showed disdain for the park and how badly his family's legacy had fallen. Penguin also made threats to Bruce about something big coming and left.
The next morning, the Penguin and his men arrived at the Skyline Club to look around for evidence linking either Thomas or Hill to Falcone's organization. However, he was confronted by Batman who pressed the Penguin of knowledge of Falcone's murder, and the Penguin admitted to having been involved. The Penguin then arranged for Catwoman to be murdered, to whom Batman leaves to rescue while the Penguin leaves himself with his men.
Later, the Penguin provides Phantasm with his henchmen for the Phantasm's next stage of her plan to terrorize the debate and publicly revealed Thomas's misdeeds through evidence that the Penguin had salvaged from the Skyline Club. Despite Batman and Harvey Dent's efforts to save Hill, Phantasm had abducted the mayor and brought him to the Penguin as promised to exact his revenge on the remaining man responsible for his family's downfall. The Penguin proceeded to sadistically torture Hill and finally ended his life by impaling him with his bladed umbrella, then stuffed an umbrella down his throat as "something to remember him by". Bruce was framed by Phantasm and the Penguin for Hill's murder, as well as Falcone's, damaging his reputation and part of their revenge against the Waynes.
Penguin managed to infiltrate Wayne Enterprises, being hired into the board through his influence. Penguin managed to manipulate the board to effectively put on the facade of a successful and legitimate businessman with no criminal record. This managed to impress the Wayne Enterprises board, who considered hiring him as a replacement CEO, as they were considering a replacement for Bruce. Penguin managed to learn about Wayne Enterprises' use of telecommunications and managed to find a backdoor, to monitor the entire city's communications. Once implemented, the Phantasm was able to expect and were able to prepare for oncoming threats. 
After a meeting discussing Bruce's future at the company, the board decided to replace him with the Penguin, though this role would only be a temporary CEO. Following the meeting, Penguin visited Bruce in his office, subtly mocking him to avoid suspicion. As Bruce prepared to leave, he pick up an audient given to Bruce as a graduation present. Pretending to hand it back, Penguin dropped it on the floor as a way of aggravating Bruce. Bruce though manages to refrain himself, the Penguin gathers up the pieces of the present and gives them back to Bruce. As Bruce departs, the Penguin listens to his final words with glee.
The next day, the Penguin appeared at the press conference held to announce Bruce's resignation as CEO. However, Bruce is injected with a drug by Andrea Beaumont (Phantasm) which causes him to brutally attack the Penguin. After Bruce was arrested and committed to Arkham Asylum, the Penguin took full control of Wayne Enterprises on Phantasm's behalf, but let their connection remain a secret. He used Bruce's money to arm his men better and invest it into his criminal empire, something which was promised as a reward by the Phantasm as well as revenge on Bruce. Penguin also discovered Batman's computer network was connected to Wayne Enterprises, along with all of his gadgets and technology. Finding the connection point, he had a Black Box break in to take control of the Batcomputer and disrupt the vigilante's equipment, along with learn all the information about Batman.
Phantasm then incited a riot at Blackgate Penitentiary with the intentions to kill Joe Chill and Batman, forcing Batman to give up on stopping the Penguin and instead focus on defeating the Phantasm. While Batman drove to the prison, the Penguin managed to take control of the Batmobile which forced Batman to eject from and abandon the vehicle. Batman found the majority of his gadgets useless during the Blackgate riot, forcing him to defeat the Phantasm and her soldiers the old-fashioned way. After Batman made the tough call to save his parents' killer and emotionally defeat the Phantasm, once believing the woman behind the mask would have been his path to happiness though let go of these feelings. Phantasm disappeared into the fire despite Batman's pleas to not go. Afterwards, the Dark Knight confronts the Penguin at Wayne Enterprises.
The Penguin gloated over the apparent success of his revenge scheme against Bruce, claiming he had taken everything from him and that he and his family's reputation have been tarnished, something which the Penguin believed is poetic justice. Batman defeats the Penguin's guards and the vigilante fights the Penguin, who uses drones in an attempt to kill him as well as arming himself with prototype technology in an attempt to keep up with Batman. Nevertheless, Batman disarms the Penguin and even breaks his leg, defeating him, and this leads to his limp which makes him walk like a penguin.
The Penguin watches in vain as Batman shuts down the Black Box to save his tech and his attack on the Batcomputer, making sure the Penguin knew he has lost despite being close to victory. Batman mocks Penguin, saying that Phantasm is gone and that all he was to her was a pawn. The Penguin becomes enraged and states that he better kill him otherwise he will not stop until both Batman and Bruce are dead, so Batman then proceeds to knock him out. Penguin is then strung up in one of the stairwells and handed over to the GCPD. Due to the evidence provided by Batman, the Penguin is convicted for his crimes and sent to Blackgate Penitentiary.
===Apparent Reform===
The Penguin was expected to serve forty years in Blackgate after his arrest, having plead guilty during his trial, but, due to the combination of his lawyers' immense efforts (the Penguin agreed to testify in court against the remaining criminals he worked with and act like he was being forced to serve the Phantasm) and the Penguin being a model prisoner who was respectful to both inmates and staff, he received an early release from prison and is apparently reformed, something which Batman does not believe and closely keeps an eye on him.
Despite appearing to be a reformed criminal, in reality, Penguin decided to collude with Randall Holmes, a childhood rival who has grown into one of Gotham's most powerful financiers to manipulate Wall Street computers; though Holmes still detests his heavy-handed partner, his greed spurs him to honor the partnership until he can secure the Penguin's methods for himself. Aside from the arms selling business, the Penguin became a criminal broker, and bought much of the Bowery after sweeping record profits from the stock market, even beginning to enter Bruce's social circles. His most notable purchase is the Cyrus Pinkney Natural History Museum, and turned it into the trendy Iceburg Lounge.
Posing as an up-market restauranteur, Penguin became convinced that he had finally found the acceptance that he had always craved from Gotham's in-crowd and elite, who saw him as a legitimate businessman. Eventually, the Penguin enters a charity ball at Wayne Manor, where he talks to Bruce and appears "remorseful" over everything he did to him. Hoping to distract and eventually trap the Penguin, Bruce agrees, much to Alfred and everyone else's horror and shock, to sell the Penguin the manor as a sign of "good faith".
Meanwhile, Holmes' own investigation of Penguin encounters Bethany Wilcox, a ruthless social-climber whom the Penguin had humiliated in high school. As part of her own vandetta, Bethany agrees to help Holmes unearth Penguin's methods, unaware that the Penguin has already made arrangements to get rid of Holmes to tie up loose ends and because he believes that he no longer requires his assistance. Holmes makes an attempt himself to have the Penguin killed by hiring a hitman, though the hitman is killed by the Penguin's assassins. Batman, who had been monitoring the Penguin, intervenes and stops the assassins from killing Holmes.
Batman receives a full confession from Holmes regarding his deal and activities with the Penguin, and it is revealed that Bethany is at the Iceburg Lounge because she plans to kill the Penguin. Batman restrains Holmes and has the police pick him up, while he rushes off to save the Penguin from Bethany. Bethany uses a hidden gun to shoot the Penguin in the shoulder and during their fight she smashes a glass bottle and ran the bottom deep into the Penguin's left eye which blinded him and gave him the appearance of always wearing a monocle, but before she can finish the pleading crime boss off, Batman drops in and disarms Bethany. Batman and Bethany briefly fight, but he manages to subdue her though Penguin narrowly escapes down to a chamber which inhabits a giant shark named Tiny. Attempting to apprehend the Penguin, the Penguin shoots at Batman with an umbrella and causes him to fall into the chamber. Batman is nearly killed by Tiny but barely saves his own skin, and proceeds to confront and take the Penguin's umbrella and snaps it in half over his knee angrily. Batman grabs the Penguin by the neck though, instead of hitting him in the face, he cuffs him to the ground and tells him he will receive medical treatment for his gunshot wound. The Penguin is arrested again by the police for insider trading alongside Holmes, and Wayne Manor returns to its proper owner. 
After this incident, the Penguin sought the finest doctors to remove the glass in his eye, only to be told that the attempts to remove it would potentially kill him. Penguin eventually became content with it, and believed that it gave him a unique look.
===The Debut of the Joker===
After the Joker (under the disguise of Black Mask) robbed the Gotham Merchant's Bank and stole laundered money from many mobsters, the Penguin was framed for the robbery by employing one of the Penguin's henchmen to participate in the heist but betrayed and killed him, leaving his body at the scene of the crime, and made it appear that the Penguin ordered his men to hit Black Mask and his allies' bank. This led to a violent gang war between Black Mask's allies and the Penguin in order to distract Batman and the police for his far more twisted and evil plans.
Batman intervened and stopped the shootout between the Penguin's gang and his enemy mobsters. However, the Penguin took a police officer hostage and threatened to kill her until Batman stopped him, gaining the respect of Gordon. Sometime later, his boat was hijacked by Batman who drove it alongside a boat that was owned by the rival mobsters. Batman attacked both gangs at once with assistance from his new device. The Penguin and his rivals argued until the Penguin confessed that he was not the one behind the heist, making Batman realize that someone robbed the bank instead and framed the Penguin for it. When everyone came to this realization, the gang war ceased but one of the mobsters fired at Batman so he fled.
===Holding Grudges ===
To boost the Iceburg Lounge's reputation, Penguin decided to invite the Joker one night. Things seemed to go off without a hitch, but a clumsy waitress accidentally spilled a drink on the Joker, he returned the act by melting the poor girl's face with acid from his flower. Angered by this action, Penguin decided to never allow the Joker back into his club again. At a later date, Joker forced himself back into the club; Penguin invited him to the V.I.P. room, and then right outside the door. Penguin stated "no clowns allowed", slamming the door on the Joker's face.
===The Penguin's Favor===
While being driven in his limousine, the Penguin has an encounter with mild-mannered salaryman Tommy Blackcrow whom cusses out the Penguin after he runs him off the road. The Penguin and two thugs corner Tommy, with Tommy being desperate to save his own life and mentions his family and he promises to do anything the Penguin asks of him. The Penguin accepts after considering what to do about Tommy and takes his license; then tells Tommy that he will keep in touch for that favor.
Seven months later, the Penguin had effortlessly kept tabs on Tommy, even when the latter changed his name and moved to a different city. The Penguin calls him for that favor and drops a thinly-veiled threat to his family when Tommy attempts to refuse, then has him travel back to Gotham. The Penguin has his henchmen abduct Tommy by tasering him and bundling him into the back of a car and they take him to a warehouse where the Penguin is waiting. The Penguin's favor is revealed to murder someone, much to his horror. The Penguin promises that he will apparently dispose of all the information he has gathered on the Blackcrow family once Tommy carries out the hit, to which Tommy tries to back out of but hesitantly agrees to it for the sake of his family. The Penguin gives Tommy instructions and sends him away to carry out the favor.
It is revealed that Tommy's target is Harvey Bullock because he was in business with the Penguin but broke off their association and has become a threat to his criminal operations. One of the Penguin's henchmen provides Tommy with a gun and Tommy proceeds to attack Bullock in his apartment, managing to knock him out because he ambushed him and kidnaps him with a van to take him to the murder spot at the docks. Tommy struggles in his decision to murder Bullock or not, constantly thinking about his family. Bullock tries to convince Tommy to let him go and that they can work out something, however Batman arrives by surprising Tommy and then disarms him. It is revealed the Penguin wanted Tommy to take the fall for the killing of a police officer, however Bullock and Batman understand Tommy's situation and devise a plan against the Penguin.
In order to gather evidence to arrest the Penguin and convict him, Tommy fakes Bullock's murder by using his phone to record shooting him in the shoulder which causes him to fall into the river and seemingly drown. However, Batman managed to save Bullock and give him medical treatment to save his life before having Tommy head into the Penguin's club with a wire to tell him the job is done. Tommy is frightened, but Batman manages to comfort him that he will be right behind him and that this is the only way to ensure his family's safety. The Penguin is seen playing cards at his table and winning by cheating until he is informed by a bodyguard that Tommy has arrived, so a thrilled Penguin tells Tommy to go into his office to discuss the details. In the office, the Penguin asks if Tommy has proof of Bullock's murder, to which Tommy shows him. Apparently satisfied, the Penguin claims he will make good on his promise by handing over all the information he has on Tommy and his family. However, before he does, the Penguin needs one more favor: for Tommy to lift up his shirt, revealing he is aware that Tommy is working with Batman. The Penguin had caught onto the nervous Tommy but he refuses, causing the Penguin to ask someone to point their gun at his head, resulting in all of the crime boss's goons to point all their guns at his head but the Penguin claims that one should do. Tommy reveals the wire underneath his shirt, so the Penguin greets Batman via the wire and warns him that can either chase him or save Tommy's life. Batman pursues the van carrying Tommy in the Batmobile, finding it at an abandoned warehouse where the Penguin had another snitch murdered and chained Tommy to a time-bomb. Batman though managed to rescue Tommy and free him before the bomb went off, narrowly escaping the explosion.
The Penguin and his crew try to make their way out of Gotham to keep their heads down for a while as the heat is on them, but they are suddenly stopped by a convoy of armed cops. The Penguin is shocked to find a vengeful Bullock alive and well, pointing his gun in the Penguin's face and arresting him and his gang. The Penguin says that Tommy's family will pay the price, causing Tommy to take a cop's a gun and hold the Penguin at gunpoint. Batman tries to stop an enraged Tommy from murdering a visibly frightened Penguin and warns him it will determine the rest of his life and to think about his family, but Tommy argues he is and that as long as the Penguin lives they can never be safe. The Penguin, desperate to save his own skin, surrenders all the information he had on his family much to Tommy's satisfaction of saving his family and scaring the Penguin. The Penguin is then hauled off to the GCPD Station, ending his feud with Tommy.
===Birth of Clayface===
The Penguin managed to steal the Renuyu cream, an untested cream that allowed the wearer to reconfigure his or her face to whatever he or she wanted by loosening the facial cells of the user, and then sold it to disfigured actor Basil Karlo in exchange for a favor that Basil would pay at a later time. He employed the talents of Basil and used his addiction of the cream to make him always remain at his side for more of the drug. The Penguin had Basil target Wayne Enterprises in several attacks, eventually leading up to ordering Lucius Fox to be eliminated by impersonating Bruce Wayne. The job failed when Batman intervened. 
In retaliation, the Penguin had the highly addicted Basil's cream supply cut and this enraged Basil to the point he took out his temper on a director who berated him physically. Basil then broke into the Iceburg Lounge in an attempt to find and steal the cream however the Penguin's henchmen caught him and hyper-satured the former actor in the formula by drowning him with a canister of Renuyu. Instead of killing Basil like they thought it would, it instead transformed him into a humanoid mass of living clay re-christened as "Clayface", retaining his shapeshifting powers as well as other superpowers. The Penguin was unaware of Basil's survival and continued his business as usual, meeting with gangster Sal Maroni for a deal. However, one of Sal's henchmen turned out to be Clayface, who had already subdued Buxton and Candy as well as throws Maroni and the other gangsters out of the window. The Penguin is horrified of Clayface, especially that he has come to take his revenge and kill him but the Penguin tries to reason with the monster. The Penguin though uses a fire extinguisher to fend off Clayface and survived long enough for Batman to arrive, who had saved Maroni and his surviving men from their near-fatal fall. Batman tries to reason with Clayface that the Penguin will face justice and that he will help him, but Clayface has already embraced that he is nothing more than a mold of rage and violence. Batman defeats Clayface and saves the Penguin's life, though Clayface manages to escape. 
===War Between the Joker and the Riddler===
The Penguin became entangled in the war between the Joker and the Riddler for the right to kill Batman. The Penguin became a member of the Riddler's army against the clown. 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 the Penguin willingly helped, begging Batman to stop the bloody and destructive war. After the war, the Penguin filled the power vacuum and became Gotham's new strongest crime lord after the Joker had the Falcone crime family wiped out when he took over their manor as his base of operations.
Joker's Wild
The Penguin met with a real estate tycoon named Cameron Kaiser who was working on a casino called Camelot, however the casino was on the brink of bankruptcy. The Penguin took advantage of the situation and purchased it for a low price which Kaiser willingly agreed to out of desperation, then he changed the theme and name to that of the Joker with the intention to lure the mad clown into a trap to finally kill him, leaving him with no rivals to climb to the top of Gotham's criminal underworld as the "rightful king". 
As a result, the Joker saw the news story about the opening of the casino and he broke out of Arkham Asylum, and made his way to the casino, where he blended in as all the card dealers were dressed like him. Bruce found the Joker while investigating the casino. Meanwhile, Joker's cheating was detected by the Penguin's guards, but Penguin overruled their recommendation to stop him. The Penguin meets with the Joker and offers a game of poker, to which the eager Ace of Knaves just could not turn down. The game of poker slowly becomes hostile as the Penguin passively mocks the Joker and constantly provokes him, but the Joker reveals to the Penguin he had already rigged the basement with explosives. Penguin tries to have his men kill the Joker, but Joker's goons, disguised as some of the casino staff, ambush and execute the Penguin's men. Batman arrives at the casino and fights off both criminal leaders' minions, so the Joker captures the Penguin and takes him down to the basement where a pleading Penguin is strapped to a giant roulette wheel, which the Joker had rigged to detonate the bombs. Penguin makes an attempt to talk his way out of being killed, though the Joker doesn't fall for his trick and spins the wheel, but Batman enters the basement and stops the wheel, rescuing the Penguin and preventing the destruction of the casino. 
Penguin later arrives at the helipad and witnesses the Joker and Batman's brawl in a helicopter, to which the Penguin takes advantage of his distracted enemies and uses a specialized umbrella to fire an explosive at the helicopter, shooting it down and killing the pilot but Batman and Joker survive. After Batman stops the falling helicopter from killing the crowd of civilians below, the Penguin turns up on the rooftop with a large number of his henchmen and gives the order to kill them both. Batman disarms the Penguin when he utilizes a bladed umbrella and the Joker then moves to murder the Penguin with his flower lapel, but Batman stops him and saves the Penguin yet again, who passes out from shock. The Penguin is then arrested alongside the Joker, taken to prison for his crimes.
===Imprisonment of Commissioner Gordon===
After Commissioner Gordon had been framed by a new criminal called Prometheus for the murder of three dirty cops, Gordon is taken to Blackgate Penitentiary while awaiting trial and so Gordon's allies including Batman and DA Harvey Dent as well as police officers Renee Montoya and Harvey Bullock are determined to prove Gordon's innocence and that he is being wrongly accused. While in Blackgate, Gordon is taken to a wing ran by the Penguin who is in rivalry with the other big-time criminals who run the other wings Black Mask and Bane. While Gordon tries to keep to himself in prison despite being targeted by his fellow inmates for being the arresting officer in many of their cases and is the police commissioner, a young inmate named Peter Davies tried to befriend Gordon as he was grateful as Gordon was responsible for rescuing his sister, revealed to be one of the children kidnapped by the Dollmaker. 
In the courtyard, the Penguin and his gang aggressively observed Gordon and Peter. The Penguin confronted Gordon and threatened him as he was on "his" turf now and that he has no power or authority anymore, but Peter defends Gordon despite Gordon trying to stop him from getting involved which causes the Penguin to get his inmates to restrain Peter while he beats him up ruthlessly. Gordon attempts to intervene, but is stopped by one of the Penguin's thugs. Gordon fights back and manages to stop the Penguin before he goes too far, saving Peter. Gordon continues to protect Peter from the Penguin, which results in the Penguin having a corrupt guard take Gordon to the janitors closet where the Penguin and two thugs are waiting for him. The Penguin orders Gordon to murder Black Mask with a shiv or he will instead kill Peter. Gordon in the end though refuses and instead fakes Black Mask's death in the theater to buy himself time. When Gordon is seen as innocent and is released from prison, Gordon taunts the Penguin that Black Mask is still alive and states he will have his prison sentence increased, humiliating him in front of the other inmates. Gordon then arranges for Peter to be transferred to another prison for his own safety, leaving the Penguin enraged and humiliated.
===War with the Joker ===
After the Joker's supposed death, the Penguin became the most dominant and powerful kingpin within Gotham's underworld and his empire took control of several of the Joker's businesses, territories and numerous members of his gang, however the Penguin considered the possibility of the Joker's narrow survival and return to Gotham and would seek to take back his empire and be determined more than ever to kill the Penguin for his actions. Amongst what he took from the Clown Prince of Crime was his "Grin and Bare It" strip bar and had one of his lieutenants, Monty, run the place on his behalf. The Penguin relied on one trusted henchman, Johnny Frost, in the plan to assassinate the Joker by infiltrating his criminal organization and luring him into a trap. The Penguin also had Monty hire Harley Quinn, the Joker's moll, to work in his strip bar as a pole dancer in an attempt to infuriate the Joker.
However, the Joker in reality knew of the Penguin's plan and countered it with his own to kill the Penguin by first instructing Harley to work in the bar despite her protestations, and purchased information from the Riddler regarding almost everything about Frost. When the Joker and Frost first met, the Joker played along to build up to his revenge on both the Penguin and Frost. The Joker, with the assistance of Frost and Harley, murders Monty and embark on a killing spree of the Penguin's lieutenants and henchmen who stole his money, turf and bizarre sense of reputation. After the Joker murdered his former right-hand man in a "fit of rage" to further manipulate Frost and then he promoted Frost to his new number one henchman, an increasingly nervous Frost meets with the Penguin for a new instructions.
The Penguin hires corrupt cops to ambush and kill the Joker and his crew, however, due to Frost accidentally saving the Joker's life, the operation failed and as a result the Penguin made a second, more desperate attempt on the Joker's life by agreeing to meet at Gotham Zoo. The Penguin orders his men to fire at the Joker when he is attacked by the maniacal clown with shards of broken glass glued to his fingertips, however a disguised Harley instead turns the tables on the Penguin and kills his henchmen. The Joker and the Penguin briefly fight, resulting in the Penguin being left with a limp due to the Joker crippling one of his legs with the broken glass. The Penguin somehow survives and escapes, despite being cornered and at the mercy of the Joker, and abandons Frost to the grisly fate the Joker planned for him as punishment for his actions. After this incident, the Penguin fires Frost for botching the assassination attempt on the Joker that took months of planning.
===Hiring Roxy Rocket===
The Penguin came into contact with thrill-seeking criminal Roxy Rocket and hired her to steal illegal weapons. 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 kill her before she told someone about his operations. The Penguin's attempts to have Roxy killed had failed, then he was later interrogated in his penthouse by Batman on Roxy's location.
===Feud with Harley and Ivy===
When the Penguin witnessed Poison Ivy and Harley Quinn fighting and arguing in his Iceburg Lounge, he tried to cease the commotion. He realized one of the ladies was Harley and tried to attack her in retaliation for everything she and her boyfriend had done to him and his interests, though Ivy steps in the Penguin's way in Harley's defense. They attacked the Penguin and left his lounge smothered in tree-sized vines and thorns. Soon after, Batgirl and Robin interrogated the Penguin on where the ladies were while he was overseeing a team of hired arborists cutting through the growth. The Penguin was at first reluctant, but then gave in and told them he had a hunch of where they were.
===Plot to Assassinate Harvey Dent===
After District Attorney Harvey Dent's effective crackdown on several of Gotham City's crime lords' operations, the Penguin himself was arrested for arms trafficking though he spent a short time in jail because the Penguin's lawyers found a loophole in Dent's investigation which is something that greatly frustrated Dent and he even yelled at and threatened the Penguin when they two were alone because the Penguin bragged about being free once again. This is something the Penguin though did not take lightly and he formed a truce with his rival crime lord, Black Mask, in order to formulate a plan to eliminate Dent.
The Penguin and Black Mask collectively hired six assassins (Killer Croc, Deathstroke, Clayface, Deadshot, Bane and Firefly) to deal with Batman while the two made their move to kill Dent. While Batman was busy with the assassins, Robin and Batgirl had to stop the Penguin and Black Mask's plans after discovering they were the ones who hired the assassins. Robin disguised himself as "Matches Malone" to infiltrate the Penguin's crew as a new recruit and was present for a meeting in the Iceburg Lounge that the Penguin ordered, while Batgirl closely monitored. The Penguin addressed his new recruits and then he had a former henchman brought out and stuffed him in a box much to Robin and Batgirl's horror. The Penguin proceeded to burn the man alive, claiming it is what happens to those who cross him. The Penguin then adjourns the meeting with his new henchmen. 
Robin continued to work undercover in the Penguin's organization and at one point due to the unexpected appearance of Black Mask's goons (who were used to bait out the suspected mole), Robin had to destroy the Penguin's guns, and infuriated Penguin, but Robin was able to talk his way out of getting executed and instead had his pay cut in half, and also made him lead a strike on Black Mask's base the next day. To be sure he did not escape, the Penguin had his men lock Robin up for the night, to which Robin was forced to comply. The next day, Robin and the Penguin's men attack Black Mask's hideout which turns out to be abandoned and a bomb was left to be triggered though he managed to survive with only one henchman being killed in the explosion.
Robin finally discovered what he was up to, he was plotting to murder Dent and betray and kill his current partner, Black Mask. However, the Penguin had Batgirl captured and came to the conclusion that there was a mole within his organization and threatened Batgirl with a bladed umbrella unless the mole revealed themselves. Robin reveals himself and demands he release Batgirl, though the Penguin orders his henchmen to kill Robin before Batgirl manages to cut her bonds and she fights off Penguin. The brawl ends up with Penguin shooting Batgirl in the stomach and wounding her, however Robin saves her life and takes down the Penguin. Before Robin leaves with the injured Batgirl, the Penguin smiles despite being restrained and left for the police, because he played a role in the attempt on Dent's life by distracting Robin and Batgirl long enough for Black Mask to ambush the mayoral campaign speech where Dent is located with his own gang and that the Penguin tricked Robin and Batgirl with a different, fake plan to allow the true one to commence. However, despite Black Mask failing to kill Dent, he instead inadvertently, with the Riddler's help, transformed Dent into one of Gotham's biggest and most tragic criminal, Two-Face, who eventually became one of the Penguin's most hated ganglord rivals.
===War with Two-Face===
While in Blackgate for conspiring to kill Dent and being one of the men responsible for his transformation into the schizoid criminal Two-Face, the Penguin met with Deadshot. The two inmates came up with a breakout plan and it all started with the Penguin's sudden "death". The Penguin was buried after this, but his henchmen dug him out and once he was revived, he helped Deadshot escape prison and hired him to help kill Two-Face.
The Penguin engaged in a bloody gang war with his most recent and greatest gang rival, attacking each other's turfs and businesses and killing each other's gang members. When Two-Face was arrested by Batman, the Dark Knight used him as bait after he discovered Deadshot was involved. Batman's plan was successful and he managed to defeat Deadshot though the Penguin's goons kidnapped Two-Face during the ordeal. Brought into his office, the Penguin mockingly took his scarred coin and decided to flip on what he will do to Two-Face: on the good side he will die a quick and painless death but the scarred side Two-Face will receive a long, painful one. Two-Face though claimed he already flipped the coin to decide the Penguin's fate a long time ago and that it is his time to die, then Two-Face's goons break into the building and both gangs shot each other in a rage-fueled gunfight. The Penguin tried to quickly kill Two-Face, though Two-Face broke his bonds and fought the Penguin in hand-to-hand combat. Batman and Robin intervened to put an end to the fight, but this resulted in both villains managing to escape and thinking of another plan to kill each other.
===Poker Game with Fellow Freaks===
The Penguin later hired the best assassin he knew of, Deadshot, to be involved in a plan to finally kill Batman so he can run his empire with little interference. The Penguin lured Batman into a trap by staging a bank robbery, where Deadshot was waiting for the Dark Knight. Batman and Deadshot fought, though the Penguin used a trick umbrella which doused Batman with a red gas to which apparently was the wrong umbrella. However, suddenly vultures the Penguin had kept nearby in a cage were released and were attracted to the chemical that Batman was covered in. The vultures' beaks were tipped with poison and Batman struggled to fend off both the vultures and Deadshot. However, Batman managed to turn the tables and the vultures attacked Deadshot, weakening him with the poison and causing him to fall off the catwalk which knocked him unconscious. Batman then easily defeated the vultures and was forced to allow the Penguin to get away in order to get Deadshot to a hospital immediately. The Penguin took the opportunity and fled with his umbrella copter.
The Penguin soon retreated to The Stacked Deck and played poker with the Joker, Two-Face, Poison Ivy and the Riddler. After the group told stories of how they almost killed Batman, in which the Penguin told about his most recent encounter, they were stunned to learn the bartender was a disguised Batman all along who listened in to their conversation. Before they could do anything, they were ambushed by police who were disguised as patrons.
===Suicide Squad Incident ===
The Penguin was hired by Amanda Waller to supply arms to the Suicide Squad, and help them get into terrorist KGBeast and his faction's headquarters. However, he once caught the sight of Harley Quinn and reacted with rage; she and the Joker had recently stolen a truckload of drugs from him and had crashed into the river just for a laugh. However Deadshot pointed it out that it would be bad for business if it was known that the Penguin double-crossed his clients. Fearing damage to his reputation, Penguin let the Suicide Squad go with the warning not to show up on his turf again. He gave them a one-night stay in the upper floor rooms, and supplied them with whatever they needed before demanding them to get out of his sight.
After Batman faked his death in a fight with the Suicide Squad, the Joker attempts to destroy all of Gotham City. In an attempt to save themselves and not wanting the Joker to destroy "their" city, the Penguin collaborated with the Ventriloquist, Two-Face and Killer Croc to confront the Clown Prince of Crime at his hideout. The Penguin makes an attempt to negotiate with the Joker, though the Ace of Knaves responds with firing a rocket launcher at them. A shootout ensues between the Penguin and his allies and the Joker's gang, allowing the Joker to get away. 
===Laughing Stock of the Underworld===
Due to the routine basis of his operations being shut down by Batman and Gotham's Finest, the Penguin went bankrupt. As a result, the Penguin attempted a robbery though was thwarted by Batman and Robin and left behind his henchwomen to be arrested while he escaped. Penguin retreats to his Iceburg Lounge and gets a sudden burst of glee when he reads a letter that one of his greatest enemies, the Joker, had left a staggering fortune of $250 million to him after he "died". The first thing the Penguin does with his money is assemble a team of shady lawyers that are able to erase the Penguin's criminal records. The Penguin completely rennovates the Iceburg Lounge and hosts a party to celebrate with Barbara Gordon and Tim Drake attending to keep an eye on the Penguin. However, Harley Quinn and a group of henchmen crash the party with the intention to kill the Penguin because Harley was angered that her boyfriend would leave him everything despite hating him, while she received nothing despite doing nothing but love and dedicate her life to the Joker. Tim returns as Robin and manages to stop Harley from killing the Penguin and the other guests. The Penguin mockingly gave Robin a hundred dollar bill for his good work, but Robin refused his money stubbornly and stated that he will be watching him much to his amusement. Laughing at the thought of Batman and his "family" no longer being able to touch him, the Penguin continues to enjoy his new wealth.
Problems soon arise for the Penguin when he learns that he owes the IRS a large inheritance tax. When he opens his vault to gain his necessary cash, he finds all of his remaining money is counterfeit by seeing that every pack of bills has the Joker's picture on them. He also finds a videotape, on which the Joker left behind, explaining that the inheritance was a ruse to get the Penguin exactly the fix in which he now finds himself having to choose between going to prison for tax evasion, or else admitting that the Joker pranked him, thus becoming a laughing stock of the criminal underworld. The Joker finishes by laughing himself to tears, resulting in an blood-boiled Penguin to shoot the television before walking off and taking out his anger on a henchman by punching him hard in the groin.
The Penguin laments over the situation he's in now since he knows if he doesn't pay his taxes, he will be in jail. But if he admits the Joker duped him, he will look like a fool and would not be taken seriously. He decides to return to crime to rebuild his fortune and ensure that no one suspects he is behind it and have his name protected. He plans to steal a load of money from a boat. So that no one will notice his absence, the Penguin instructs his accountant Arthur Penn to make sure everyone knows he will be taking a vacation outside of Gotham but Batman sees through this lie and interrogates him.
Batman, Nightwing and Robin are able to successfully stop the heist and capture the Penguin and his goons, even though at one point the Penguin tries to commit suicide as an alternative to losing his money. Back behind bars again, the Penguin is seen sobbing in his cell over his defeat and loss of his fortune. 
===Encounter with the Judge===
When Two-Face develops a personality christened as "The Judge" which operated as a ruthless vigilante that aimed to brutally attack and execute Gotham's criminals as the consequences of their actions, the Penguin became one of his targets. He had a small dealing with Two-Face's henchmen and the Riddler but they were dissatisfied by their profits at the end of their deal. The Judge then confronted the Penguin who chased him through his design studio. As his henchwomen were tied up, he was alone. The Penguin tried to use a trick umbrella to fight off the vigilante, though ended up being crushed by his late father's statue headstone which critically injured him. The Judge pulled out his sword and prepared to finish the Penguin off, but a cop who was passing by heard the commotion and entered the studio to find the Penguin alone and wounded. The Penguin was later hospitalized and managed to survive, he was later interrogated by the police over the incident but found no answers.
===Mayor of Gotham===
After his release from Blackgate, the Penguin visited his parents' grave at the Cobblepot Park to pay his respects until he is met by Ra's al Ghul. Ra's managed to easily persuade the Penguin to join his plan in exchange for controlling Gotham, to which the Penguin could not turn down such an opportunity after being presented with a demonstration of Ra's' power and talents when he used Lazarus Pit chemicals to heal the Penguin's injuries in his leg and hand. Impressed and grateful, the Penguin assisted Professor Hugo Strange release the monsters onto Gotham City and framing Mayor Quincy Sharp for it. Following the incident, he arrived at the police precinct during a press conference, accusing Commissioner Gordon of lying to the people of Gotham. The Penguin then told the reporters that he was present when the monsters escaped into the town, and urged them to find the main instigator, Quincy Sharp. Under Ra's' instructions, the Penguin continued to gain public support by using his tragedies for sympathy which is something that Batman and Gordon see through and is aware that the Penguin is up to no good. During a fundraiser hosted by the Penguin at the Iceburg Lounge, Strange's monsters attack however the Penguin manages to fend them off and save a child from one of them as a plan to increase his public support by looking like a reformed criminal and now a hero. 
The Penguin ordered for the other mayoral candidates to be killed and have the hitmen attempt to "kill" him too publicly, but miss the shot. On a speech, the Penguin declined candidacy, but after the hitmen attacked him in front of everyone but missed every single shot. He said if the villains want him down, he will run for mayor. Ra's then had the Penguin abduct Sid Bunderslaw, and then he had one of his eyes cut out for identification purposes. The Penguin later had another meeting with Ra's in his penthouse, as they discussed the terms about their plan.
The Penguin continued his reign as Mayor of Gotham, and had a few run-ins with Batman. The Penguin taunted Batman that he was now untouchable, but Batman threatened the Penguin and told him that he will find out what he is up to in the mayor office before leaving as security arrived. The Penguin managed to surprisingly drastically decrease Gotham's crime rate with his ruthless methods which were disapproved by the likes of Bruce Wayne, Gordon and many others. After the Penguin and his allies set up a criminal's murder as if Batman crossed the line and killed him, the Penguin used this to his advantage by turning the city and police against Batman which results in a large-scale manhunt for the vigilante. The Penguin had Sharp kidnapped and broke his mind with torture and forcing him to take drugs in order to control him like a puppet and have him willingly take the fall for the monsters' attack on Gotham. However, Batman discovered this truth as well as that Ra's and Strange are involved, managing to clear his name of the murder accusation and arrest the Penguin for kidnapping Sharp.
While awaiting trial, the Penguin was incarcerated at Blackgate. After the Penguin attempted to make arrangements while behind bars in a desperate attempt to gain freedom, he was confronted in the darkness of the prison by Talia al Ghul, Ra's' daughter, who threatened to kill him if he tried anything stupid again and provided him with new instructions. A day later, the Penguin was a trial sitting and listening to Sharp telling everyone who actually kidnapped him. Sharp claims the Penguin did not kidnap him but rather Batman. Gordon yelled that Sharp was lying though the judge declares the Penguin to be released. When the Penguin addresses Gordon, saying he bears no ill will towards him and the GCPD. Gordon then hooks the Penguin in the face, causing him to be restrained by two officers who then tased Gordon afterwards. Later at a hideout, Gordon wakes up to find himself restrained. The Penguin is present when Strange appeared and taunted Gordon. When Gordon revealed his knowledge of the nine random murders, Strange reveals that they are all not random, causing Gordon to realize that he plans on murdering Bruce Wayne. Strange then frees Gordon and taunts him to attack him. When Gordon does, a League of Assassins member easily beats him. He then leaves Gordon to be executed by the pair of dirty cops, but Gordon is saved by the Penguin unexpectedly who kills the cops.
Penguin reveals he discovered Ra's and Strange's true intentions for Gotham and that the Penguin will be one of their victims in the destruction. As the Penguin works with Batman and other allies (including Nyssa Raatko, Ra's' other daughter who has turned against her father) to try to save Gotham, they confront Ra's, Strange, Talia and a group of League of Assassins members at the building used to oversee the "cleansing" of Gotham. A furious and deadly battle broke out in which Batman tried to reduce the casualties as best as he could while also trying to defeat the opposition, and the Penguin was crippled once again in the leg when Ra's sadistically crushed it. The battle ended with the deaths of Ra's and Nyssa as the two killed each other, however this did not stop their plans as Strange gave the order for the bombs to be detonated before he was knocked out by Batman. A horrified Penguin and the others witnessed Gotham's main bridges collapsing into the river after their connections to the mainland gave in. Afterwards, the Penguin realized the battle was already over and took his leave in disappointment that he failed to prevent "his" city's downfall. 
===No Man's Land===
While Gotham becomes an abandoned No Man's Land, all the villains claim their territory and take over certain sectors. At night, the Penguin and his henchmen enter Gotham City's noble city hall in order to make it property of the Cobblepot crime family. Some gangsters have already claimed the building and was not pleased about the Penguin's presence. With a simple hand gesture, Penguin orders his thugs to eliminate the gang before finishing off the remaining injured criminal by impaling him with his umbrella. Satisifed, Penguin then looks around in the abandoned hall, stating that this building will do nicely.
At some point afterward, Penguin, alongside Two-Face, Harley Quinn, Scarecrow, Riddler and other super-criminals for a meeting. Confused, they wondered who set up the meeting, with Penguin accusing Two-Face and proceeded to smoke one of his cigars in front of him though Two-Face denied it and threatened him to keep out of his face. Penguin then decided to make a tasteless reference to Two-Face's origin, while both he and Two-Face were insulted by Harley before being ordered to stop by a mysterious figure calling himself the Red Hood. Penguin questioned who he was and after Red Hood explained that they were present because they feared Batman, Penguin arrogantly told him that they knew that and asked him to tell them something they don't know. Red Hood offered the villains an opportunity to eliminate the Dark Knight. Penguin disliked Red Hood and insulted him, claiming that he isn't the first Bat-fanatic to muscle in on his turf, and expressed he had no intention of trusting him. The Penguin and Two-Face then verbally fought after Two-Face decided to agree to work with Red Hood because the coin chose to. 
After the meeting, Red Hood attacked his territory single-handedly and mercilessly wiped out the gang of henchmen Penguin sent to kill him. Before Red Hood broke a thug's arm and could finish him off, the Penguin agreed to his plan out of fear and Red Hood, satisifed, left the Penguin alive and gave him instructions. When Red Hood left, the Penguin, out of anger, screamed at his henchmen for failing to protect him and broke the henchman's other arm in a fit of rage. During the Penguin's reign of control over his territory, he had a choir that sang an anthem in his honor, and he underfed his men while he kept most of the food for himself. He also a runs a factory that manufactures weapons for Red Hood's army and is in charge of providing the arms to the militia and the other villains' crews as well. Penguin sends Harley Quinn on a mission in Bludhaven to rescue Poison Ivy, who was wanted by Red Hood as part of his plans. During an arms deal with Two-Face, the Penguin plotted a double-cross with Two-Face's men however this failed due to Red Hood's intervention, leaving one survivor alive from Penguin's men to tell his boss of the incident. 
Penguin was smuggling guns from Gotham City to Bludhaven, the home of Nightwing. The Penguin was also ordered by the Red Hood to capture Nora Fries, Mr. Freeze's wife, in an attempt to force Mr. Freeze into joining their cause. Batman then tracked Penguin down and interrogated him on the location of Barbara Gordon, who was kidnapped by Scarecrow, and the Red Hood. Overwhelmed due to the fear of Barbara's fate and anger of allowing it to happen, Batman choked out the Penguin aggressively and then Deathstroke shot a pellet into the Penguin's neck, poisoning him and putting him into a coma with the poison in his veins slowly killing him in an attempt to silence him and prevent him from answering Batman's questions. Out of options, Batman was forced to strike a deal with Mr. Freeze to help save the Penguin's life in exchange for rescuing his wife. Batman was successful and used the antidote on the Penguin, saving him before he died and waking him up for interrogation.
Penguin woke up, only to find himself tied to a chair in a dark location (which is revealed to secretly be a part of the Batcave) by Batman. Penguin refused to tell Batman anything, so Batman proceeded to brutally beat up the crime boss and then threw him, still restrained, under a wheel of the Batmobile threatened to crush his head if he did not talk. The Penguin finally cracked into talking and revealed that they were meeting with someone, which is later revealed to be Talia al Ghul for a deal.
Batman then took the Penguin to the GCPD Station and muttered that he was going to castrate the henchmen responsible for leading Batman right onto his doorstep. When the Red Hood disappeared, Deathstroke led his remaining forces to assault the GCPD Station for a final battle with Batman which in turn led to the Penguin and several other villains breaking out. Penguin discovered his arms smuggling operation was ended by Nightwing and as a result, the Penguin managed to capture Nightwing and take him to the Iceburg Lounge, with the intention to kill him in retaliation for Nightwing ending his weapons trafficking and destroying his factory. Batman arrives soon and rescues Nightwing from the Penguin's men, though the Penguin shows up and detonates an ice pillar which leads into an underground section where the Penguin has been secretly housing Solomon Grundy chained to a wall. 
The Penguin sets Grundy on the Dynamic Duo but they manage to defeat him, much to the Penguin's anger. Penguin then surprise attacks Batman and Nightwing with a grenade launcher though he was easily apprehended, then the Penguin dared Batman to kill him otherwise he will kill him and Nightwing for costing him a lot of money. Penguin is taken back to the GCPD Station as a prisoner and Aaron Cash told Penguin it hadn't been the same without him as he took him back to his cell. Two-Face is amongst the Penguin's new cellmates and Penguin said he should have told Red Hood it was a bad idea to involve him, only to be vaguely threatened by the latter.
===The Joker's Last Laugh===
After the events of No Man's Land, the Penguin tries to regain his influence and power in Gotham by "replacing" Bruce. During this time the Penguin would hire Lady Shiva however, for the hit on Bruce, Penguin hired the Ghost Dragons. However, after humiliating Bruce, Penguin attempted to call off the hit, only to find he was unable to do so. Therefore, he kills an assassin and makes it look like he saved Bruce himself.
His joy was short-lived when he was approached by the Joker. To stay out of harms way, Penguin followed the Joker into Arkham Asylum to watch his plans unfold. Upon the Joker's defeat the Batman locked Penguin in Blackgate only for him to go free a while earlier.
===Red Hood Incident===
==Personality==
The Penguin was known for his extravagance and brutality, and his brilliant and unorthodox mind naturally led him to positions of power and respect. He demanded things done his way, and had an intense love for money. In his own words, he only takes the best: that went for weapons, equipment, assassins and the like. He felt that he needed to overcompensate for his shortcomings and comical stature through material wealth and violent outbursts. Penguin also takes pride in his aristocratic status and the influence and power on his family name in Gotham City, speaking about it as if it were still happening despite the Cobblepots having lost their influence. This also shows why he enjoys the best; having lived a life of privilege, luxury and entitlement, it was simply a thing he got used in his childhood and seeks to regain the power and wealth he lost through his crime empire. Though he is slightly sophisticated it does not hide who he is; a person who enjoys the suffering of others. His hedonistic desire for self-pleasure was displayed by how he makes sexual advances on many females.
The one thing Penguin craves above all else was the subjugation of everyone and power over everything, something which he could only achieve through fear and total control as to overcompensate his insecurities regarding his stature. This can be attributed due to his megalomania and the Napoleon Complex and, being helpless for most of his life towards abuse and only desire to dominate over others, forcing them to be helpless so he can feel powerful. This can cause him to act extremely aggressive, over dominative and ruthless towards everyone which leads him to flippantly shout out or even kill his own men over betrayal or irritations. He controlled his empire and men with fear, often intimidating them and using brutal torture. Though he appears menacing and powerful, when faced with a truly powerful opponent, Penguin reveals that which he is; a grovelling coward, despite being defiant at times. 
Behind his intimidating demeanor, Penguin is actually terrified of the dark. He is also very coerce, often using various curse words of British origin and he is also misogynistic and potentially homophobic, being overall offense to various groups. He also demonstrates a somewhat sarcastic demeanor.
==Abilities==
*Genius-Level Intellect: From an early age, Penguin was not very physically strong or appealing and this forced him to apply his naturally keen intellect. He is methodical in creating plans that are meant to benefit him.
**​Master Businessman: Penguin's criminal operations would succeed without a hitch if not for the actions of Batman. He has existed both above and below the law with his businesses; running a legitimate nightclub as well as selling contraband from within it.
**Expert Leader: Penguin always travels with his henchmen or any criminal mission. He controls bodyguards, gang members, servants, criminals, chefs and so on with masterful talent. He had both legal and illegal operations within Gotham City; under any conditions.
**Master of Deception: Penguin is able to manipulate others and use them in his plans.
**Expert Networker: As a crime lord, Penguin has connections to multiple criminal organizations and hitmen.
**Expert Toxicologist: The Penguin has some knowledge of poisons.
*Advanced Combatant: Penguin dedicated part of his life to martial arts, mastering judo and boxing.
*Intimidation: The Penguin is able to intimidate people with several threats of violence and built up an initmidating and feared reputation.
*Skilled Marksman: Penguin is capable in the use of firearms.
===Equipment===
*Trick Umbrellas: The Penguin employs an assortment of trick umbrellas, many of which can be used as weapons as well. Penguin's numerous trick umbrellas included built-in flamethrowers, firearms, swords, spinning blades to be used as a helicopter or a weapon, poison tip, a black and white swirl umbrella that had a hypnotizing pattern when spun and fired blanks, lockpick, poison gas, acidic smoke compounds, electric charges, lasers and missiles.
*Various Firearms: The Penguin has used a variety of firearms including pistols, shotguns, assault rifles and machine guns.
*Various Knives: The Penguin has used a knife multiple times.
==Killed Victims==
==Appearance==
When the Penguin was younger in his criminal career, he had a half-full head of black hair and was short in stature and hefty in weight. He wore a custom brown coat with a collar that was lined with white fur over a silk button up shirt, along with black gloves, pants and shoes.
When he got older, his hairline had receded significantly and had bottom half of a broken glass bottle that had been shoved into his eye. As a result of heavy smoking, Penguin also had a speaker in his throat and wore a dark fur-lined black jacket over a button up shirt with a white cravat around his neck. In the future, Penguin's hair was all gone and wore less elegant clothing; wearing a simple white button shirt with a loosened black necktie, as well as black pants with suspenders and wore fingerless gloves on his hands. He also wore a watch on his wrist and a gold chain around his neck. 
==Relationships==
==Quotes==
*"The Penguin never flies alone!"
*"Why can't you two just get a day job?"
*"Look at me. No woman in the world ever gets drunk enough, and believe me, I've tried."
*"A perfect crime is a work of art, a thing of beuty and a joy forever."
*"Ah...the Batman. While I have an affection for most flying creatures, the winged rat is not among them."
*"I believe the word your looking for is AAAAAAAAAAAAAAAHHHHHHH!"
*"Tragic irony or poetic justice? You tell me."
*"Like you, I want some respect. A recognition of my basic humanity."
*"My babies...did you miss me?"
*"Sorry about the intrusion, but at least you were ransacked by a man of impecable taste."
*"Your aim appears to be a little off today, Batman."
*"A revolution is knockin' on Gotham's door."
*"The Waynes caused the ruin of my entire family!"
*"This is Gotham City, there will always be crime."
*"My name is Oswald Cobblepot. Many of you with no doubt will have heard of me. So...you clearly have not...for those poor, ignorant souls I offer illumination. I am not a man to be trifled with, no...I'm powerful! I'm vicious! I am the King of Gotham!"
*"Memories. They're like daggers in my heart."
*"There will be chaos, rivers of blood in the street."
*"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 GCPD is not Gotham. Gotham listens to me!"
*"You wanted a war, ya bloody got one!"
*"Anything for an old friend."
*"Yes...this will do nicely."
*"The Bat Man? You expect me to believe that? Listen, I happen to know that the Batman's got way more important things to do tonight than mess with our shipment, and that's saving his own ass. So next time you wanna make up a story, you'd better hope the person you're tellin' it to ain't dumber than you are! Oh wait. That's right...there ain't no one dumber than you!"
*"I don't care what you think you saw. If you're not back 'ere with my money in the next ten minutes, I'll cut your damn eyeballs out. And then you won't have to worry about seeing nothin' ever again. Is that clear!?"
*"I always get a laugh outta you first round lot. That's why I keep you boys 'round. Well that 'an I need someone to clean out the pisser!"
*"Oh, come on ladies! Stop trying ta keep yer dresses clean an' fight."
*"Come on, now. I've seen schoolgirls with more grit!"
*"That the best you can do? You hit like a ponce!"
*"Kick his arse you numpty prats!"
*"Miserable. You're all miserable ain't ya?"
*"C'mon, son! At least make a show of it."
*"Ooh! You are a wanker, aren't ya?"
*"Kick 'im in the ampsteads!"
*"Crack on, now."
*"I see you're lips flappin', but they ain't makin' the sound I want to hear."
*"You idiots better kill him cos if not, you better 'ope he kills you!"
*"Kill 'em you bloody wankers!"
*"Now hold on, hold on a bloody minute!"
*"Remind me why I pay you ponces!"
*"I seen your act. I ain't done nothing you'd not a done."
*"Nice seein' ya, Batman. Feel free to let yourself out."
*"Ah, yes. Catch anything interesting?"
*"You don't think I'm gonna forget this, do you Batman?"
*"Alright, son. Now is your chance to shine. So wipe away those tears and do your bloody job!"
*"I had no idea you were a lot of cream-puff, poncey wakers!"
*"It's like a bad joke."
*"Bloody 'ell. You're supposed to be a genius, aren't cha? And you think you can outmuscle me? Ave a look around!"
*"Oh. So, you came back to gloat, 'ave ya? I'll 'ang you with that bloody cape. You 'ear me!?"
*"Are you completely and utterly dense?"
*"You're a cold-hearted bastard, you know that."
*"It's play or die!"
*"Enough gabbin! To the death!"
*"Hurry, you fools! At this rate, I'll finish my entire sentence waiting for you!"
*"You messed with the wrong Cobblepot!"
*"Wrong, Batman...I've claimed this turf, and you're the one who's trespassing!"
*"As long as I'm paying you, I'll speak to you however I please, fool."
*"Aww, you flatter me, Batman."
*"Nobody steals from me and walks away. It's bad business, luv."
*"Now get the hell out of here!"
*"Welcome to hell, Brucey-boy."
*"Oh, what's up? Do you need me to call your butler?"
*"Let's call this good, old-fashioned revenge."
*"I think he's broken my bloody hand!"
*"When this lot is done with you, I'll personally break every both in your body with both of my hands!"
*"Good. Oh yeah, I hear Batman's coming your way. Good luck."
*"I'll have that tongue cut out of your head, boy. I don't like people tellin' tales on me."
*"Try and get me if you like."
*"Try and take some of them down before you die, son."
*"I hope Batman broke every bone in your stupid bodies. I hope you're lying there, desperately trying to breathe through fractured ribs and punctured lungs. If you're not, you'd better summon up whatever strength you've got left and run, 'cause I'm after done with the Bat, you're all next!"
*"I wouldn't do that if I was you."
*"If someone wants, I like to think...I got it. And if I don't have it, I'll get it."
*"Are you going to be a good boy and give up nicely?"
*"This horrible bunch of psychopaths are all begging to join up with me, but unfortunately for them, I only take the best. And today, best means whoever can kill you."
*"You weren't supposed to do that, Batman."
*"You're forcing me to bring out the big guns."
*"This little piggy's got some life in 'im. Good. Let's hear him squeal."
*"Batman's on the way and last time I saw him, he didn't look very happy."
*"I tried to help you, Batman. I gave you an opportunity to end this and walk away, but oh no. You had to be the big man."
*"Just you and me left! The Bat vs. the Bird!"
*"I'm a patient man. I can wait!"
*"My family used to own Gotham. It will again."
*"I'll take this all back. Just wait and see."
*"Piss off!"
*"Oswald Cobblepot doesn't hide from anyone, understand?"
*"The joke is definitely on these losers! Tell me, what do I need to do to stop you sending these goons into my home, Joker? Kill you?"
*"When I get my hands on that spoiled little rich kid, I'll make him regret what his family did to mine."
*"This is all that's left of a man who spent too long in the shark tank."
*"Can you smell that? That's the smell of someone who tried to steal from me and spent four hours in a hot oven as punishment."
*"This is what happens when you try and get clever with me. Look closer! Do you want this to happen to you?"
*"She'll be good for minutes of entertainment before I cut her head off!"
*"To be honest, I really don't find him funny."
*"Who doesn't like machine guns? These little beuties fire over 100 rounds a minute and even better, are so inaccurate, you don't even need to try. Just pulling the trigger means somebody in the room will be lying in a pool of blood in seconds."
*"Look at all these lovely shotguns. I remember this was all you needed to rob a Gotham bank or two."
*"These sniper rifles can blow a single hair of a man at a thousand yards. Aim a little lower, and there won't even be a head left."
*"Use these grenades to flush out all the dirty little vermin that likes to hide in dark corners."
*"How good is this stuff!? Stops a millimeter at close range and keeps you warm in the cold."
*"Take a look at this lovely bit of kit. Pull the trigger and smile as three and a half pounds of explosives hurtle towards the sneaky little runt who thought he could get away from me."
*"Now when you really want to surprise the sneaky little bitch who's hunting you down, use these! Nothing yields surprise like a pound of C4 blowing your legs off when you least suspect it."
*"Are you scared? Good. Fear makes you better. Fear makes you win."
*"Pull it together, or I'll put you apart."
*"You useless harlot!"
*"Stupid mug."
*"Why you little...!"
*"Gotham's finest."
*"Batman!? Don't worry about Batman. He's about to become extinct."
*"This truly breaks my heart, lads, we've been working with the other freaks to take down the Bat together. I know. I know. It's been hard. But, look on the bright side...we're bloody rich!"
*"Look at this! Lovely, lovely, lovely money! And it's all mine."
*"Now that's not very nice, is it?"
*"Give that man a cigar! Course we're gonna kill that ugly, twisted son of a bitch! We're gonna kill 'em all, lads!"
*"It won't you do any good!"
*"Well, ain't this cozy!"
*"Cocky little bastard."
*"You've been takin' from me all night Batman. It's time I did a little takin' of my own."
*"You're about to suck down your last breath, boy. I'd make sure you say your goodbyes."
*"Shut up, ya fairy!"
*"Nobody takes from Penguin, nobody!"
*"You've ripped me off one too many times!"
*"You bastard! I swear to God, you better kill me Batman, otherwise I'm gonna kill you!"
*"Empty threats, Batman. We all know you don't kill."
*"Good nights kip can do wonders, mate."
*"Keep ya cape on."
*"See that Batman? That's loyalty."
*"Not happy unless ya taking that pointy little nose into my business, are ya?"
*"Only so much the human body can take before it gives up!"
*"I'm not in the mood for your games, Batman, not by a long shot."
*"I want my phone call. My lawyer's gonna have a field day...entrapment, assault, not providing adequate sanitation while in custody. You watch, I'll have this lot banged up by morning!"
*"Piss off, pretty boy!"
*"Get stuffed."
*"Oh, sod off."
*"I hate the dark. Brings back memories. Bad ones."
*"World's greatest assassin? You? Bollocks!"
*"Boys, get 'im out of here, and don't ding up any of that gear. That's worth some money!"
*"And that's why I'm the boss!"
*"Break out the champagne, boys!"
*"Someone rip his mask off for my collection, at least it's not spandex."
*"Someone cut that mask off of his face. No need to be gentle."
*"Having a little lie-down, are you? Enjoy it. It's your last."
*"Anyone want a slightly used Batsuit? I'm sure the blood'll wash off."
*"Not so cocky now, are ya?"
*"Aw, don't be so sad Batman, Gotham's in good hands now. I'll take good care of it."
*"Well, would you look at that? A new stuffed head for my cigar room. Someone get me a hacksaw."
*"Take comfort from the fact that I never got a hold of ya, would've been real messy."
*"Do these men have families? Not anymore they don't."
Category:Penguin Empire
Category:Males
Category:Criminals
Category:Blackgate Inmates
Category:Alive
Category:Characters
Category:Antagonists
Category:Crime Lords