10 Times The Joker Won
4. Killed Sarah Essen - No Man's Land
War, disease, earthquakes, and a complete collapse of society, are all the disasters that hit Gotham seemingly at once. These compounding disasters caused the entire city of Gotham to fall into disrepair and be labeled by the US government as a no-man's-land and abandoned.
With no protection, the innocents of Gotham were completely held at the mercy of the many supervillains that inhabit Gotham.
This was especially true of the Joker, who was the last to be arrested when the No-Man's Land ended, because he decided to time his strike where it would be most effective: on the people closest to the Dark Knight and his allies.
The Joker felt targeting Commissioner Gordon's second wife would be a fitting end to his time in No-Man's-Land, trapping her by kidnapping dozens of innocent babies and then luring Essen into his trap.
Held at gunpoint, the Joker tricked Sarah into dropping her gun to save a baby, which he used as a perfect opening to shoot her in the head.
The Joker barely escapes Gordon's wrath, laughing after being shot in the leg since it was similar to what the Joker did to Barbara in The Killing Joke. This incident proved to the Joker that no matter what he does, he can always win because killing him would only give him yet other victory.