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AU History for Nolanverse.

A jaded former employee of Wayne Enterprises, Edward Nygma turned to a life of crime when he found his genius unappreciated by Bruce Wayne. One might say it would be completely petty to go off the deep end after someone denies you an audience, but let's face it- Nygma wasn't all there to begin with. A genius and admirer of Bruce since his return to the company, he had hoped that the two would be partners- two geniuses working together to usher in a new era of the company- but those hopes were shattered on the rocks when he realized that Bruce had no desire to take over the company from Lucius Fox and had zero interest in discussing the matter.

It didn't take him long to adopt his own persona in the rogue gallery. Harkening back to a moment in his childhood when his father beat him for believing that he cheated at a contest at school by beating an impossible logic problem. He did cheat, but that wasn't the point. His father believed he was a moron and his ego and paranoia refused to believe disinterest in partnering up had any play in Bruce's decision to refuse his request. He was jealous of Nygma's mind and worse, he was insulting both of their intelligences by sitting around being a pretty boy playboy. As a means of proving this, he sent Bruce a complicated riddle anonymously before leaving the company. It was solved easily, while Nygma spied, and that was the final nail in the coffin. The next day, the Riddler made his official debut in Gotham- a genius criminal who leaves riddles at every crime scene, who traps victims in overly complicated traps to see if they can solve their way out of it- they can't, usually.

Of course, then Batman had to show up, giving him a new person to hate, although in private life, he's taken to likening himself to Bruce- dressing like him, cutting his hair similarly, attending the same parties, and attributing his newfound wealth to an inheritance and not the fact that he's been stealing.