I wouldn’t have bet on it. That’s what many analysts said in the hours after news broke that Gotham Mayor Oswald Cobb was being indicted for his involvement in an underground casino ring. They said something similar about the controversial mayor’s upset election win in 2022.
It’s not that anyone—anyone—is astonished the former chair of the State Senate Racing, Gaming, and Wagering Committee with a checkered past has received illegal campaign funds, but that for most of his life, the police officer-turned-restauranteur and nightclub owner turned politician has been untouchable.
The Joker
The grandson of Italian immigrants—fleeing Italy after the fall of Mussolini, Antimo Cobblepot truncated the surname to Cobb—Oswald Cobb has associated with Italians, Turks, and Polish immigrant communities and mobs. Oz’s ties to any illicit activity, however, have always been tenuous at best.
Take the arrest of Harvey Dent, in 2008, for instance. The high-flying, charismatic prosecutor seeming destined for the very seat Cobb now stands to lose was arrested in İyi Içki Içebileceğiniz Bir Yer, a Turkish smoking lounge which Cobb owned a forty-percent share in at the time. Yet the once squeaky-clean Dent found himself mired in back-door deals, dark alleys with shady characters, and on clandestine recordings saying things of questionable legality.
Cobb outright owned the Iceberg Lounge and was present on April 14, 2014, the night waitress Annika Koslov was butchered in the women’s room. The crime remains unsolved a decade later. Cobb sold the property, a known hangout for mafioso Salvatore Falconi, to a development group in 2015. The lot stands vacant to this day.
During his tour as chair of the State Senate Racing, Gaming, and Wagering Committee, Cobb came under scrutiny for accepting campaign donations from video-lottery machine companies seeking contracts with the state.
Clayface
Before his time as a property owner and politician, the adaptable Oswald Cobb was a police officer. Four investigations were opened against him in his twenty-two year career with the Gotham PD. Mayor Cobb has said that all were opened as retaliation for his criticism of department leadership.
“You do an analysis of my Internal Affairs Bureau investigations, you’ll see they all come out with the same thing,” Mr. Adams said in a 2021 interview with The Gotham Times. “Oz did nothing wrong.”
Lately, he has been critical of the department’s tacit endorsement of masked vigilantes. His campaign was founded on getting rid of the so-called “Bat-man.” Many voters agreed with Cobb’s spin on the “lawless streets of Gotham.”
He also promised to lower taxes by increasing the efficiency of the city government. “We’re too bureaucratic, too expensive and too difficult to do business in,” he said during his campaign. Critics worried he meant he wanted to slash vital government initiatives, which is exactly what has happened under his leadership.
The Penguin
Mayor Oswald Cobb has embraced his shady past, spinning himself as a roguish nighthawk, hardworking and hard-playing.
“Gotham is the city of night life and I must test the product,” Mayor Oswald Cobb said recently in an interview. Known among confederates as “Oz” and publicly often nicknamed “the Penguin” on account of his penchant for high-end tuxedos and black suits, Cobb has come under criticism for his behavior while in office.
“I frequent all sorts of establishments, but I have never engaged in any illicit activity.”
Earlier this week, the Mayor was spotted at Oh No, an exclusive nightclub with a one-thousand dollar minimum. Last Tuesday, it was Ese Lugar, a dancehall famed for its sweaty, jam-packed attendance—and, like the Iceberg under Cobb’s ownership, the occasional knife fight.
While Cobb may consider testing bottle service at İyi Içki Içebileceğiniz Bir Yer, or smoking in a gambling club which notorious prosecutor Harvey Dent once frequented, Non Sono Ammessi Pipistrelli, part of his civic obligation, his critics disagree.
“They try to tell you it’s because I’m a kid from the projects. That what they think is so shady about me,” Cobb said when asked why the federal government was investigating his campaign finances not long after he assumed office. “They think someone like me can’t be successful.”
Mr Freeze
This isn’t the first time the Italian-American—his grandfather shortened the family’s surname from Cobblepot to Cobb upon immigrating in the 1940s—has spoken to how his ethnic roots have been used against him. He has often portrayed himself as a “pulled myself up by my bootstraps,” self-made man, but the multi-millionaire’s father owned and operated Gotham’s most successful casino, which the ATF raided in the nineties not long after Guzman Cobb sold it.
“We love having Mayor Cobb in our establishment,” said Portino Oberon, owner of Tutaj Zawierane Są Nielegalne Interesy, a Polish cafe open late into the night which Cobb began frequenting in the beginning days of his campaign. “Business has picked up significantly since he started coming here.”
Speaking of his campaign, no one expected Cobb to win. Not even Cobb. “He was entirely silent when I told him,” his campaign manager said in an interview after the race—a surprising, razor-thin victory for Cobb. “He didn’t say a damn word for a certain three minutes. When he finally did, it was: ‘get me my lawyer.’ He wanted to get started on his work right away. An incredible man.”