The Cobblepot crime family was a criminal organization in Gotham City founded by Oswald Chesterfield Cobblepot popularly known as the Penguin after his overtaking of Gotham's criminal empire with the downfall of Carmine Falcone and the murder or both Sal Maroni and Fish Mooney solidifying his claim as kingpin.
After a coup at the hands of Barbara Kean and Edward Nygma Oswald Cobblepot was outed as the kingpin of Gotham's criminal underworld and presumed deceased, being revealed to have actually survived he has reorganized his syndicate with the help of former Indian Hill inmates.
After the retirement of Don Carmine Falcone,Oswald Cobblepot took control of Gotham's Criminal Underworld and began running the city alongside former associates of both Falcone and Maroni officially dubbing himself the King of Gotham.
Penguin along with Tommy Bones (who formerly worked for Sal Maroni), Butch Gilzean (who formerly worked for Fish Mooney), and Victor Zsasz (who formerly worked for Carmine Falcone) went over debts of the then retired Falcone, as, having taken over his organization, the debts were now owed to him. Selina Kyle was in his presence where Cobblepot stated to Jim Gordon that he has her around like a person has a pet cat around.
Cobblepot later spoke to the crime family, as due to Jerome Valeska and The Maniax's recent exploits, business was down. As such, Oswald ordered that all violent acts from then on would need his go ahead, to "restore faith" in their brand. Oswald and his group were later dragged into Theo Galavan's scheme when it is revealed that he has Gertrud Kapelput in his clutches.
The Penguin committed the murders of the mayoral candidates that opposed Theo's and had Butch hire the arsonists The Pike Brothers former Fish Mooney loyalists to carry out an arson based robbery on a Wayne Enterprises building thus discovering the knife which would play a role in the temporary fall of his empire.
After Tabitha Galavan "reprogrammed" Butch Gilzean and stabbed Gertrud in front of Oswald, this leads to Oswald retaliating by orchestrating an attack on Theo's post-election party where he used look-a-likes of him to fool the police.
Oswald later rallied his gang and Selina Kyle when they help Jim Gordon, Harvey Bullock, and Alfred Pennyworth when it came to rescuing Bruce Wayne from the Order of St. Dumas after he was captured by Theo Galavan. The group found themselves in a gunfight which resulted in the members of the Order ending up dead.
Oswald and his gang went into hiding and Oswald planned for them to use a disused meat packing plant as their hideout. However while there they are attacked by Victor Fries, who began to freeze his underlings and chase him down. Oswald managed to escape with the help of Selina Kyle and a surviving underling, who drove Oswald away to safety. But when Oswald went to Gordon and Bullock for help, he was taken outside of Gotham and told to leave town for good as Captain Nathaniel Barnes was after him. Despite this warning, Oswald returned to Gotham.
Oswald's empire fell in his absence and he was a wanted man for the murder of Theo. After spending about a month living on the streets of Gotham, he was eventually arrested and brought to the precinct by Barnes and later sent to Arkham Asylum after pleading insanity. Butch succeeded Oswald as the new crime lord of the Gotham underworld. 
Three months later Oswald formed an alliance to kill a resurrected Theo Galavan. Afterwards Oswald appeared to be back in control and Butch took orders for him, such as attacking a prison bus seemingly containing Hugo Strange - a chief psychiatrist from Arkham Asylum who had tortured Oswald during his time in there.
Six months after the escape of the Indian Hill prisoners, Oswald appears to have taken control of the Gotham Underworld with Butch as his willing right hand man. Offering Barbara to run protection for her nightclub as it is built on his land to which she refuses his offer preferring to run things herself along Tabitha. After being elected as Mayor of Gotham Penguin effectively rules Gotham as kingpin of it's criminal underworld and as the legally elected Mayor of the City. Whilst continuing the rule Gotham out of jealousy for the affection and relationship one of his underlings Edward Nygma had her car sabotaged causing her death. Eventually Nygma discovered the truth and along with Barbara Kean orchestrated the fall of Penguin's criminal empire as well as his reputation as Mayor as revenge finally destroying everything Oswald had built he shot him and dumped him into the Gotham river.
Oswald having survived the attempted murder was nursed back to health by Ivy Pepper and subsequently began to reorganize his syndicate with her help in order to take control of Gotham once more, with the aid of former Indian Hill inmates Victor Fries and Bridgit Pike he began planning his re-ascension by exacting revenge on Edward Nygma.
- Oswald Cobblepot (Boss)
- Butch Gilzean (Underboss,defected)
- Edward Nygma (Chief of Staff,defected)
- Victor Zsasz (hitman,enforcer)
- Gabe (bodyguard,defected, deceased)
- Tommy Bones (hitman,deceased)
- Ivy Pepper
- Victor Fries
- Bridgit Pike
- Selina Kyle
- Barbara Kean (betrayed)
- Tabitha Galavan (betrayed)
- Jim Gordon (unwillingly, formerly)
- "Rise of the Villains: Damned If You Do..."
- "Rise of the Villains: The Last Laugh"
- "Rise of the Villains: Strike Force"
- "Rise of the Villains: Mommy's Little Monster"
- "Rise of the Villains: Worse Than A Crime"