Oswald Cobblepot

== Biography ==
=== Early Life ===
Oswald Cobblepot was born on July 26th, 1970 to Esther and Tucker Cobblepot, two poor steelworkers at the Sionis Steel Mill. Ozzie was used to growing up just outside the door of mobster meetings, and the life was illustrious to him. At just the age of twelve, his father died, and so Ozzie took his job as a janitor. The fumes made his asthma flare up but he had no choice but to continue working to support his widowed mother. One winter he fell dangerously ill with a fever that left him with a limp. This made him a social outcast.
He was once working when the beautiful right-hand-woman of Carmine Falcone made an appearance, the seductive Fish Mooney. Ozzie became obsessed with her and offered himself at her feet, begging her to let him do any assignment. Fish Mooney was in need of someone to take down a couple Sionis guys for her, so she put little Ozzie on the job.
He passed with flying colors, he did so well that Falcone wanted to hire him, but the Sionis family now wanted him dead. They put rookie cop Harvey Bullock on the job, but Harvey took pity on the boy and pretended to kill him, allowing Cobblepot to be secretly picked up by the Falcone Family.
=== Early Mob Career ===
Their first move was getting him the hell out of America, the Falcones took him to one of their estates in Sicily. There, he was trained in the family ways of money laundering and bad business. After a few years there, he returned to Gotham, excited to reunite with his mother, only to find that she was in a medically induced coma after losing her home and being forced to sleep on the street.
Cobblepot set about to make a name for himself as Fish Mooney’s right hand man. When he and Fish heard whispers that the Falcones were going down, one name accompanied those whispers: Batman. Fish and Ozzie were given several chances to bail Falcone out, but they didn’t take any of them, with Fish planning to take his empire for herself through the crowning jewel of her work with the family: the Iceberg Lounge. It was at once a successful casino and nightclub and a front for prostitution, drugs, and arms trafficking.
When they made the move to push Falcone out, Ozzie seized the opportunity and cut her car’s brake line - removing Fish from the board, and putting Oswald on top of one of the most major crime enterprises in Gotham. He also began an affair with one of the prostitutes, Ann Ogilvy. When she was pregnant, he framed her for drug possession and landed her in Blackgate. 
=== The Penguin ===
Oswald began to make the powerful acquaintance of several big-bads in Gotham including the Riddler, the Tally Man, and Scarecrow. Although, they often did not remain friends, as is the case of the Riddler, who upon hearing of Ozzie’s mayoral bid, attempted an assassination. His bid for Mayor was usurped by the mysterious Black Canary, working in conjunction with Batman to take down his arms dealing ring.
With his corruption busted, Oz landed himself in Blackgate Penitentiary. He didn’t stay there for long, working with a strong legal team to find some loopholes and get himself out from behind bars. He was back on the streets in mere months, but Black Canary wasn’t gonna let that slide. She broke her way into his office and left him with a crooked nose, a new scar, and a burning hatred for masked vigilantes.
Now known by his street name of the Penguin, Oswald made moves to become one of the most powerful criminal figures in the Gotham Underworld. He brokered deals to keep street gangs in conflict and with the newest arms, acting as a facade for the GCPD, so they wouldn’t notice his slow but effective infiltration of the Gotham City Municipal Government.
A former enemy - Harvey Dent - became a quick ally. After Harvey’s descent into madness, they forged an uneasy partnership. Neither forgot their storied past, but both were willing to work towards the common goal of eliminating the Batman. Neither were ever able to reach their goal, but Ozzie always managed to slip through the fingers of the criminal justice system - until a new DA rolled into town.
Kate Spencer took the stage and launched an anti-mob campaign. Oswald faced a real threat for the first time in his criminal career. As he feared time behind bars, he looked for someone to elect as his underboss. That’s when Ann Ogilvy wandered back into his life, clean, and with a teenage boy with a lot of pent up rage. He’d been kicked out of every school and she had nowhere else to turn. She stowed the boy with Ozzie, they shared a night together, and then she skipped town.
Ozzie took little Ignatius under his wing and trained him with his top lieutenants to make the kid a great killer and a mobster that rivaled his own father. Ignatius was a brutal young boy. When the FBI and ARGUS launched a joint investigation to take down Cobblepot, he went into the handcuffs willingly, knowing his empire was safe with his boy.
In Blackgate, Oswald was a model prisoner, and planned to serve out his sentence with a smile on his face. His status gained him much favor and some luxuries other prisoners could only dream of having. That is until the League of Assassins came to town, and Blackgate was busted wide open. Oswald returned to his place as emperor of the streets, with Ignatius serving as his underboss. The Iceberg Lounge became a haven where the illustrious dealer Bone auctioned off basic goods that Gotham’s citizens, criminal-and-not-alike, needed to survive after the League’s ground invasion.
When the dust settled in Gotham, Oswald was still on top, and he remained out of the next explosive conflict between the Anarchists, False Face Society, and Laugh Pack. As their territories fell apart, Oswald assembled his monopoly. That is until a bullet from Floyd Lawton caught him in the neck, and Ozzie resorted to being a hermit in a secret underground bunker in Metropolis. Ignatius took over the day-to-day operations, while Ozzie called the shots without ever having to step foot in the city. He knows that he’s made himself a target of every conceivable enemy, but he’ll be damned if that stops him.