Oswald Cobblepot

Oswald Cobblepot is The "Penguin", a ruthless Gotham City mobster who frequently finds himself an enemy of Batman.

Early life
Oswald Chesterfield Cobblepot was born to Tucker and Esther Cobblepot. Oswald was born with a birth defect that gave him a uniquely beak-like nose that horrified his father so much the man dropped him on the ground moments after birth. Tucker Cobblepot would go on to hate his son for his appearance for the rest of his life, despite Esther showing unconditional love.

Growing up, Oswald was heavily bullied by his peers, who mocked him for his appearance and were the first to compare him to a penguin. Because of their teasing, Oswald developed a fascination with birds, which he felt more kinship with than people.

The only human he cared about was his mother - who was the only person to ever show him compassion. Oswald would craft mechanical birds for his mother as presents, which she always appreciated. Oswald would have an unhealthy obsession with his mother - going so far as to develop a complex of wanting to be strong and powerful through violence due to the way his father did so to get her attention.

Adulthood in Gotham
In his adulthood, Cobblepot opened a new building called the "Iceberg Lounge" in Gotham City. It was a lounge and casino in one. Not many of Gotham's residents could enter, and it was considered one of the wealthiest places in the city. Cobblepot had the building look "flashy" or "neon" to boast how wealthy he was.

After opening it, Oswald was a rising crime lord, one of his fortes being weapon deals, which he did in his lounge and casino, the Iceberg Lounge.

In 1999, shortly before the coming of Batman, Cobblepot had become a renowned figure in Gotham, and a feared one at that. However, that put him on Gotham City Police Department (GCPD) Most Wanted list. Despite the GCPD conducting a present investigation, there was no concrete evidence they could pull him on, so they kept a keen eye on him.

Corruption
This didn't stop Oswald, instead, he continued his weapon trafficking and crime, knowing how to stay off the radar. This caught the attention of many of Gotham's elite, in turn, a meeting was hosted at Oswald's casino to discuss territory-dealing. Oswald had the casino cleared out, and the meeting began.

In this meeting was another renowned figure of Gotham City, Carmine "The Roman" Falcone. Falcone had many of Gotham's workers and residents under his thumb, however, Penguin was not one of them. This, and his arrogant attitude, lead Penguin to disrespecting and talking above Falcone.

Being offered low numbers of territory, Penguin stood for himself. Falcone assured him he would not receive anything he wants, but rather whatever Falcone decided for him. Penguin immediately laughed and commented he was not scared of Falcone, and assured Falcone he was not one of his cogs in his organization. Falcone told Penguin to show a little respect, as they're mutual benefactors, however before Penguin could respond, the lights shut off, and a loud bang was heard. The lights turned back on, and Batman made his first public appearance in the building, interrupting the meeting.

Everyone was surprised and confused about how he entered. Batman spoke, giving them a direct warning to either give it up now or suffer the fate of a collapsing empire. Batman directed a statement towards Falcone and Commissioner Loeb, stating they've demoralized the GCPD. Falcone and Penguin told their men to shoot rather than be distracted. The mobsters were about to shoot him, but Batman then drops a smoke pellet and vanished from the area. This immediately changed the ongoing topic of the meeting, instead, it was on everyone deciding to deal with Batman. The then-commissioner Loeb eventually assures everyone the GCPD will take care of him. The meeting is then adjourned.

Assault
Batman later located a weapons cache hidden near the docks of Gotham belonging to Penguin. Batman had arrived on the property and began taking out the thugs guarding it, he planned to foil the shipping and deliver the goods to the GCPD.

However, during his assault on the cache, one thug managed to flee from Batman and activate a fire alarm, this alerted the GCPD and they arrived with numerous squads and a SWAT team. As the thug made his escape to the front exit, Batman followed, only to find the GCPD waiting for him outside. The GCPD rushed to the door and apprehended the thug, then planning to go after Batman.

Afterwards, Penguin was informed of what happened, and he was led to believe Falcone had informed Batman of the weapons cache. Penguin, infuriated, began plans to have a gang-war with Falcone's side, starting with manufacturing stronger and better weapons.

Abilities

 * Business Management: Oswald has a keen business sense. He has kept his casino business on the right side of the law to set up a front to launder money from his illegal businesses.
 * Hand-to-Hand Combat (Basic): Oswald, despite his appearance, is trained in the usage of his personal weaponry. A few thugs or a tussle with Batman is nothing for the Penguin.
 * Leadership: The Penguin runs one of the most elusive and strongest gangs in all of Gotham.
 * Tactical Analysis: Oswald never forgets an injustice done to him. He may not exact his revenge in the same moment or even the same year but at some point, in some place, he will have his vengeance. His tactical skill ensures the stability and prosperity of his crime empire, which has always remained as the most powerful crime empire in Gotham and claimed victory in gang wars.
 * Firearms: Penguin is good at using his umbrella shotgun to defend himself against opponents and has been seen taking down armed opponents with firearms on multiple occasions.
 * Swordsmanship: Penguin is capable of taking down multiple armed opponents with his umbrella sword.