Oswald Cobblepot was the mayoral competition for Dr. Thomas Wayne. Dr. Wayne wanted to change Gotham for the better by becoming mayor but Oswald refused to let another Wayne disgrace the Cobblepot legacy. When the Waynes went to the Monarch Theatre on that fateful night, Oswald paid a corrupt cop named Jacob Weaver to cut the power to cinema. The Waynes decide to leave but not the way Cobblepot intended. Weaver had his men stationed at key points to kidnap Waynes but when they heard the gunfire, Weaver and his men fell back. Cobblepot was still pleased that Dr. Wayne was dead because things worked out better by having some unknown vagrant (Joe Chill) do the Waynes in and no alibi required.
Years later, Bruce Wayne became Batman in order to fight his way to the truth. Oswald feared that this Batman may get too close to the truth of what happened that night the Waynes were murdered. Oswald has a mentally disturbed assassin named the Birthday Boy kill Weaver to keep him from talking but that doesn't stop Batman. The Birthday Boy left clues as to where he was hiding out. Batman interrogates the Birthday Boy and finds out that Cobblepot hired him to kill Weaver. Batman confronts Penguin at his Iceberg Lounge but he underestimates the Feathered Felon. Cobblepot sticks Batman with a trick stiletto from his umbrella then he removes Batman cowl. Cobblepot is shocked but at the same time amused that Batman is Bruce Wayne. Fortunately, Penguin would never get the chance to exploit Bruce's secret because Alfred arrives on the scene and empties two barrels into Cobblepot's chest. The blast sent Cobblepot's body out of the window where he landed into the street below. He was later replaced as Mayor by Jessica Dent after his death.