Penguin

A brutal and sadistic crime lord, Oswald Chesterfield Cobblepot is known in the Gotham City Underworld as the Penguin and funds much of its criminal operations as one of its biggest black market manufactures. Directing his affairs from the Iceberg Lounge, Oswald was seen as a reputable business man to the people of Gotham, but was a sadistic, mass murdering gang leader in reality.

Childhood and Arrival in Gotham
Throughout the history of the Cobblepot's family, many of his family members were in a constant rivalry with the Wayne family for control of Gotham City. However, in the case of the Waynes, they were simply conducting their businesses to make a living and were not aware of the direct competition the Cobblepots saw in them. Regardless, the unhealthy fixation to outdo the Wayne family and their business cost many of the Cobblepots their health and their business empires, including Oswald's father, Stanley Cobblepot, who began to neglect his son as a result and sent him overseas to England to spend his educational years. While overseas however, Cobblepot was often bullied for his small stature and spent many days outside of school and on the violent streets instead, associating with the various criminals and thugs.

Feeling appreciated and seen as somebody worth while by the criminal element, Cobblepot began to learn and educate himself about the criminal lifestyle that so appealed to him and how to accumulate massive amounts of wealth and numbers. In the meantime, Cobblepot's father died after nearly bankrupting his own businesses while trying to outdo the Wayne family, the final straw for Oswald, who saw the Wayne family as nothing more than spoiled individuals who ruined his family.

Arriving back in Gotham, Copplepot used his inheritance money to purchase the Cyrus Pinkney's Institute for Natural History, which was in the process of being shutdown due to its position in a dilapidating part of Gotham City. Cobblepot saw the museum as the perfect base operations and converted both the museum and the attached restaurant, the Ice Burg Lounge, into his main criminal quarters. Reestablishing the Ice Burg Lounge into one of the finest restaurants in Gotham, Cobblepot gained the attention of the wealthy and criminal citizens of Gotham with a den of booze, drugs, gambling, and beautiful women.

On the outside, Oswald was a legitimate business typhoon, but truly made a living off of the black market in Gotham, having shipments of drugs and firearms arrive in Gotham each week, which he then sold to Gotham's criminals, while also performing his own scores and heists with his gang.

Oswald soon became known to the criminal underworld as the Penguin and gained a reputation for sadistic torture and mass murder, particularly on those he caught cheating in his casino. Within the museum, Penguin created a gladiator pit where he would select various criminals from Gotham's streets to partake in illegal fights to the death. The winners would become part of Penguin's growing gang while those that died would be put on display in various cases or fed to his shark, Tiny, originally part of the museum's underwater attractions.

Penguin also added a torture chamber to punish those who stood against him or were caught cheating in his gambling activities and additionally added a war room to plan his criminal operations, and a weapons cache to store his own personal shipments of weapons for his gang's use or to be sold to the black market. Gambling ran rampant through the Lounge and those who couldn't pay were either put into a private torture room or were killed.

Arkham City's Construction
When Arkham City was developed, Penguin ended up trapped within the city because of his refusal to abandon the Iceberg Lounge (as he didn't wish to let it be caught at the hands of some of the thugs), to which he also hated Dr. Hugo Strange for forcing his place in Arkham City. After Joker escaped Arkham Asylum and arrived at Arkham City, Cobblepot briefly met with the clown prince attempting to make peace with Oswald, to which he reminded Joker that he hadn't forgiven him for ruining the Iceberg's Lounge's opening, thus beginning the war between the two anew during the events of the game.

In order to survive Arkham City's violent environment, Mr. Penguin starts his own gang, hoping to seize complete control over the rest of the facility for his own ends. He ends up meeting Lester Kurtz, who wished to join the gang after fleeing the Joker's. Unlike Joker, Penguin didn't want to put Kurtz through any initiation and just told him to follow orders and he'll be paid. He then turns to another thug named Grisby, revealing a picture showing him double-crossing Penguin by giving information to Harley Quinn. He then sends a panicked Grisby to "tell the man downstairs" and sends him down a trapdoor.

Kurtz asks him what's down there and Penguin simply replies "Pray you never have to find out." Since Grisby told the Joker about the raid on the Security Armory planned by the Penguin, he tells his thugs they will have to get the weapons before they get to the armory. Due to the unexpected appearance of the Joker's goons, Kurtz had to destroy the guns infuriating Penguin, but Kurtz was able to talk his way out of being sent "downstairs" and instead cuts his pay in half and makes him lead a strike on the weakened Joker's hideout the next day.

To be sure he doesn't escape, Penguin tells his men to lock Kurtz up for the night, but he escapes anyway by knocking out the goons, a little later. Penguin never realized that Kurtz was a new alias of his mortal enemy, Batman. Presumably because of Kurtz' earlier actions, the Penguin instigated an initiation process where he would handpick any "horrible psychopaths" who wished to join who proved themselves to be the best, the exact initiation process being different each day.

Hugo Strange's Plans
Eventually, Penguin was taken to Hugo Strange by TYGER operatives to begin taped interview sessions, as much of the rest of the super-criminals had to do as well. There, Strange began to diagnose Penguin, much to the villain's annoyance, and even struck an alliance with the gang lord as part of his own plans for power. At the Penguin's request, Strange purchased and delivered a wide variety of military grade weaponry, ammunition, and technology to his base of operations, telling Penguin that Arkham City is merely an experiment to observe the actions of the criminal populace it houses when Penguin questioned his motives for the alliance.

With Penguin's new and incredible artillery in conjunction with all the resources he had at his disposal to begin with at his museum, Penguin took the compound by storm, killing all who opposed him and recruited hundreds of individuals to build up a massive gang. Throughout the months, Penguin's men would go on recruitment missions, assembling large groups of potential gang members and other inmates to be locked up in the gladiator arena within the Iceberg Lounge to eventually undergo duels to the death to determine who is worthy of joining Penguin's gang.

Penguin would remain in contact with Strange, who would continue to supply him with weapons and even hand over victims of his inhumane experiments to be used as target practice. Strange eventually informed Penguin that his rival, the Joker, was indeed sick and dying, but has blackmailed Mr. Freeze into developing a potential cure for his Titan illness. Strange reveals that Freeze has already been captured and locked up in one of his holding cells and offers to hand him and his various freeze equipment over to Penguin in order impede Joker's progress on a cure and cement his fate.

Penguin agreed and has several of his men take Freeze away to be locked up in one his display cases in his museum, cruelly choosing the one that it ventilated with extreme heat. As one last string to pull, Strange revealed to Cobblepot that ten inmates that work within his gang are actually inside agents for the Gotham City Police Department for Commissioner Gordon, trusting Penguin to dispose of them. Penguin wasted no time when he returned to his museum and has all ten of the undercover cops abducted, beaten, and locked away in his torture chamber for eventual death.

Batman: Arkham City
When Bruce Wayne is imprisoned within Arkham City for leading a protest against the city, the Penguin and his gang are among the first of the criminals to greet him. Desiring revenge against Wayne for his family, the Cobblepots, being ruined, he takes out some brass knuckles to beat him up. Although he managed to land a blow on Wayne, Wayne managed to grab his hand while he was preparing a second blow and bend it around, breaking it. Penguin then has his gang kill Wayne, but he defeats them with ease, also breaking his handcuffs in the process.

Later the during the night, Penguin had his men rig the bridges and streets that lead to Joker's base of operations, the Sionis Steel Mill, with explosives to cut off the Clown Prince of Crime's forces. When all the explosives were put in place, Penguin detonated them, killing many of Joker's followers and his own men in the process and stranding any who were left on the other side. Eventually, Batman, trying to locate Mr. Freeze so he could gain a cure for the Titan poison that he and thousands of Gotham citizens were infected with by the Joker, managed to encounter Penguin, who mercilessly executed one of the cops, Officer Best. After a failed attempt at getting Batman to surrender and become a part of his collection, he then has some inmates attempt to kill Batman as their initiation.

Batman defeated all of them with ease, enticing the Penguin to unveil his big guns: more specifically, a henchman he injected with some the Titan formula he acquired from shipments Joker previously sent off from Arkham Island. After Batman managed to defeat the minion, Penguin escaped from the chaos and back to the Iceberg Lounge. One of the cops he held hostage, Forrester, also managed to escape Penguin, but wasn't able to get to the exit before Penguin froze him with Mr. Freeze's Ice Gun. Penguin then revealed that he had a shark in the frozen pool of water known as Tiny, which he regularly used to dispose of bodies and even devour living victims.

Penguin ordered the rest of his gang to guard the other cops in the armory, with the threat of killing them should they fail to do so. Eventually, Batman, after saving most of the cops, debating legions of Penguin's gang, and even Tiny, proceeded to the Iceberg Lounge. Once there, Penguin taunted Batman with the intention of torturing another undercover cop by the name of Dennis by freezing one of his hands as well as declaring his intention of shattering the frozen hand with a hammer.

Batman managed to arrive in time, but Penguin forced him to retreat due to his use of the Ice Gun. Batman eventually returned and, thanks to the override code for the Ice Gun from Freeze, the gun failed to fire on Batman, resulting in the Dark Knight decking Penguin off the iceberg monument. Penguin tried to talk his way out of his predicament, but when Batman implied that he wasn't simply going to let him go after all the destruction and death he caused, Penguin destroyed the iceberg monument with a remote-controlled detonator, dropping Batman to a room below the lounge, with Penguin declaring that Batman brought it upon himself.

He activated an entity that he discovered under the lounge presumably before Arkham City was even established, Solomon Grundy, and forces Batman to fight him. After Batman manages to completely destroy the mechanism that continuously revived Grundy and putting the beast down for good, Penguin is eventually forced to fight Batman himself with a grenade launcher, but is easily defeated. Batman then delivers Penguin to Mr. Freeze. who step on Penguin's already broken hand. Batman ordered Freeze to stop hurting Penguin and focus on the cure, enticing him to place Penguin within one of his own display cases, the one he had reserved for Bruce Wayne.

Catwoman can speak to Penguin inside the display case. She asks him what he's supposed to be in the exhibit. Penguin rudely tells her to "piss off". Offended, Catwoman warns him against talking like that to her again before leaving and Penguin immediately apologized out of cowardice.

When Protocol 10 began, Penguin's museum was targeted for destruction, but it withstood the missile attack with Penguin still safe inside. When Two-Face and his gang took control of the museum, Penguin hid behind the display in the display case to avoid being spotted by Dent. If Batman returns to speak with him, Penguin denies his cowardice.