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|First Appearance:||The Road to Arkham|
At some point, the Mayor was holding a city hall meeting. The Joker and his henchmen managed to track down the Mayor and crash the meeting, claiming that the city had a "paucity of parking spots designated for clown cars," and that he "tried to park in the handicapped spot, but people told him that he wasn't sick enough." The Mayor, instantly recognizing the Joker, exclaims in shock that someone had better call the police.
Unfortunately, the Joker, "sensing" that the Mayor looks like he's about to explode, wires him up to an explosive vest pattered after the colors of the American flag. An anonymous person also gave a 9/11 call relating to the Joker's plans seconds before the Joker's assault. Joker then declared his intent to blow up the mayor with various explosive chemicals to give a "big bodacious blast of patriotism." Batman then intervened (ironically right after Joker expressed disappointment that Batman apparently wasn't coming), and unstrapped the Mayor, while the vest was blown up by various henchman trying to shoot at Batman.
The Mayor then declared that he has "had enough of this city" before announcing his resignation. Due to these circumstances, it made it all the more easier for the then-Arkham Asylum Warden Quincy Sharp to win in his campaign for Mayor, a political victory that was eventually solidified when he took falsified credit for stopping Joker's plans in a brutal riot at the Asylum, which occurred that very same night.
As Sharp's victory of becoming Mayor allowed him to implement plans at the behest of his secret collaborator and manipulator, Hugo Strange, which took the shape of Arkham City, Joker's attack on the Mayor and City Hall was an easily overlooked event, but was an extremely pivotal one nonetheless towards the entire series as it served as one of the catalyst for the rest of the events that would unfold over the following years.