At the opening of the Cobblepot Towers, Henry Cobblepot, print magnate turned hotelier looked at his latest hotel, determined to outclass the also-newly opened Grand Wayne Plaza. Desperate to ruin his rival, Judge Solomon Wayne, Henry laughed at reports that the people of Gotham preferred the restrained splendour of the Wayne Hotel to his own locations. He swore that the Cobblepot Hotels would be the premier destinations of the world. He was wrong and it cost him both his fortune and his health. On his deathbed, Henry left the remains of his fortune to his son, Stanley Cobblepot. Stanley vowed to outdo the Wayne Family and their empire, now headed by Alan Wayne. Stanley Cobblepot instigated a very public feud with the Wayne Family.
As the Wayne business empire extended to include hotels and other public buildings, Stanley was determined to outdo them. Pouring more and more money into his fledging hotel business to the detriment of the newspaper business and his relationship with his son, Oswald. As Stanley’s businesses crumbled around him, he sent Oswald to school in England. Feeling abandoned and picked on by his peers for his homely appearance, Oswald skipped class after class, preferring the company of the thieves and scoundrels he met on the streets. By the time his father’s empire collapsed, Oswald had vanished. When the council decided to shut down the Pinkney Natural Museum, they sold this historic structure to the highest bidder. Located in a deteriorating part of the city, many investors passed up on the opportunity, for Oswald Cobblepot this was exactly what he wanted. He purchased the building and established this as his base of operations, converting the attached theme restaurant, the Iceberg Lounge, into a high profile nightclub. To the public, the Iceberg Lounge was a reputable establishment.
But below the surface was a den of iniquity. A go-to place for illicit and illegal wares. The adjacent museum exhibit halls were repurposed as the Penguin's storage facility, housing everything from his torture room, his weapon cache and a gladiator pit. Illegal fights to the death occurred nightly with the victors earning a job on Penguins Crew. The Penguins operation was run on fear and pain. One night, a guest at the Iceberg Lounge was caught cheating at poker. The Penguin tortured this man in full view of everyone. A friend of the man grabbed a beer bottle, smashed it on a table and attacked, driving the bottle hard into Penguin's face.
As The Penguin screamed, the attacker and his friend were dragged away to a private torture room. Cobblepot was examined by the finest doctors in Gotham City but the prognosis was always the same; removing the bottle could be fatal. When The Penguin received the eminent domain seizure from City Hall ordering him to vacate the Iceberg Lounge, he replied with a letter telling Mayor Sharp that no-one tells Oswald Cobblepot what to do. He bought his property legally and the city could find somewhere else to stick their prison.On the day that the perimeter wall was due to be completed, the GCPD were dispatched with back-up from TYGER guards to forcibly reclaim the building. The Penguin ordered his men to fire at the Police, killing their veteran officers. With the Penguin's criminal nature no longer in dispute, Mayor Sharp ordered the wall closed, trapping the Penguin and his gang in Arkham City.
- Given this information, the present day Arkhamverse likely takes place in the 1980s
- The story is a tad contridictory, given Henry had another son named Theodore, who ran for mayor of Gotham City.