The Penguin (Batman: Arkham Knight)

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.

After the events of Joker's death in Arkham City, the Penguin, alongside Batma

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, Oswald soon became known to the criminal underworld as the Penguin.

Batman: Arkham Knight
After being released from Arkham City, Penguin and his gang spent time recovering from their time there, including doing gunrunning to and from Blüdhaven via a front company known as North Refrigeration, which eventually got Nightwing involved. Eventually, he met up with the recently escaped Harley Quinn. Despite their animosity in the past (mostly due to her boyfriend), they nonetheless managed to form a partnership, being kissed by her to seal the deal. Months later, he proceeded to enter a meeting arranged by Scarecrow, alongside Quinn and Two-Face. While waiting for his arrival, Penguin proceeded to smoke one of cigars in front of Two-Face, resulting in him telling him not to do that, and Penguin taunting him regarding whether it gave him bad memories of his disfigurement, as well as being insulted alongside Two-Face by Harley Quinn by her calling them "bozos". After Scarecrow alongside the mysterious mercenary known only as the Arkham Knight arrived and explained why they were there, Penguin then confirmed they knew they were afraid of Batman, and told him to tell them something they didn't know. Some time later, although they agreed to the truce, Penguin nonetheless continued to bicker with Two-Face, largely because of the latter's smart remark about Penguin's height after he commented that when making a deal, he preferred to "look them straight in the eye," as well as vocally voicing distrust of the Arkham Knight. He also mentioned that, his cut aside, he won't have anything to do with Two-Face's bank heists, before Two-Face reminded him that he needs to keep them armed and their guns loaded via their gun smuggling operation, at least until the truce ends with Batman's death. At some point later, Penguin had a group of his thugs go over to the docks for what is presumably a business deal. However, only one of his men returned with a broken arm. Penguin then proceeded to interrogate him, threatening to "give him a matching pair" if he doesn't have a good reason for why their operation failed. He then explained that his forces ended up ambushed and taken out by unanticipated methods, causing Penguin to deduce that the person who ambushed them was none other than the Arkham Knight. He then proceeded to break the man's arm anyway, in response to the saying "don't shoot the messenger."

Some time later, Penguin gave radio support to Harley Quinn when she raided the Blüdhaven to retrieve Poison Ivy and recruit her into Scarecrow's cause, although throughout the mission it was clear their alliance was uneasy as he and Harley constantly gave biting remarks to each other.

Eventually, on Halloween night, Penguin proceeded to conduct gunrunning businesses in Gotham, which eventually drew Nightwing in to put a halt to it. Batman, after learning of North Refrigeration and Penguin's ties to Scarecrow from brutally interrogating a Militia member regarding the Arkham Knight and the then-recently abducted Oracle's destination, also proceeded to meet up with Nightwing and reluctantly accepted his aid in stopping Penguin (as he wasn't willing to risk losing any other allies after Oracle ended up abducted). Penguin then had the place put under heavy guard in case Batman was nearby and ordered his men not to lead Batman to them, although Batman nonetheless managed to trace them via one of the rounds of a firearms disabling device placed on one of their delivery trucks. Penguin then proceeded to give a speech telling his men that they're now "bloody rich" with the proceeds from their weapons racket during the night, as well as implying that once Batman's dead, he will take out Scarecrow and the others to be the top kingpin. However, Batman was lurking in one of the grates below, and proceeded to interrogate him on Oracle and the Arkham Knight's location. He then told him that they and Scarecrow had departed to meet up with Simon Stagg on one of Stagg Enterprise's Airships, although he managed to escape after some of Penguin's men managed to restrain Batman. However, it wouldn't be without a cost, as Nightwing proceeded to save Batman and their proceeding to blow up the weapons' cache. Around the time Batman was tracking the second weapons' cache in Gotham, Nightwing snooped around and uncovered the final weapons' cache, although he ended up captured by Penguin and held hostage, with Penguin transmitting a video message revealing Nightwing's current status with the threat that he will kill Nightwing if Batman doesn't back off. After being traced and freeing Nightwing from his bonds and eliminating the men in the room, Penguin managed to subdue Nightwing just as Batman was about to detonate the bombs. While threatening Batman (as well as Nightwing alluding to his past as being a part of the Flying Graysons), Nightwing managed to break free and have Batman pin him down. Despite demanding Batman to not blow up the cache, Batman proceeded to do so in front of him, causing Penguin to angrily threaten to kill him if Batman doesn't break his one rule of no killing. He is then transferred over to the GCPD Lockup, also angrily lamenting the destruction of his weapons cache, with Batman suggesting that, if he ever gets out of jail, he can always sell them for scrap. While being led to the holding cell, he was cheered on by Penguin's troops in their cells, with Penguin remarking to Batman that this is what true loyalty is like.

Trivia

 * Depending on when the player beats the Gunrunning mission, Penguin's dialogue while in transit to the GCPD will vary. If it was before confronting Scarecrow, he will taunt Batman with nearly killing Nightwing, causing Batman to subtly threaten Penguin with killing him by telling him that he can choose GCPD or the morgue as his next destination, with Penguin attempting to call his bluff by reminding him of his one rule, with Batman admitting he's not himself that night (alluding to Joker's toxin slowly taking him over and turning him into the next Joker). If it was after Scarecrow is defeated, Penguin will instead reveal that he now knows that it was a Wayne who was underneath the cowl, and scolds him two-fold for ruining his family and for ruining his operations as Bruce Wayne and Batman, respectively, with Batman informing him that the Cobblepots were corrupt, and Penguin shooting back that the Waynes are dead before asking tauntingly if he touched a nerve. He also proceeded to imply that he'll get the drop on him soon, although Batman tells him that he may change identities, with Penguin mockingly suggesting he become a squirrel.
 * In addition, his dialogue will also vary depending on whether he was placed in the cell first or Two-Face. If the latter, Penguin will voice a complaint about working with Two-Face in the first place and stating that he told Scarecrow that it was a bad idea to get him involved, with Two-Face proceeding to subtly threaten him to watch his tongue due to being behind the same set of bars now.