1. The Court of Owls (Batman: The New 52)
Background: At the top of the list sits a group rather than a single person, but they deserve the spot more than anyone else. The Court of Owls didn’t just go undetected to the greatest detective in the world but it moved its members into every building in Gotham City created under the Alan Wayne Trust (Bruce’s Great-Great-Grandfather) while simultaneously being good enough at what they do to convince Bruce that there is absolutely no way in hell that “The Court of Owls” could exist.
The Court of Owls dates back as early as the 1600s, and is a super-secretive coterie of some of Gotham City’s original and wealthiest families, who have no problem using their money and trained assassins to influence Gotham’s political movements for their own interests and gains.
Present day: After Bruce Wayne publicly announces his plans to renovate Gotham City and prepare it for the future, he is sentenced to death by The Court of Owls. This results in a fight between Batman and the Talon (William Cobb) at the top of Wayne Tower and both men falling from the top floor of the building. While Bruce manages to save himself by landing on a stone guardian built into Wayne Tower, the Talon falls the entire way to the bottom, landing on the roof of a nearby car. He is pronounced dead, but later wakes up in an ambulance and escapes after killing the EMTs.
As a boy, Bruce’s first case as a “detective” was trying to find The Court of Owls, as he was entirely sure that they were responsible for the death of his parents. Unfortunately, at the climax of his investigation, once he was convinced that he had uncovered the secret lair of The Court of Owls, he entered a secret room of a large house and was trapped in there for over a week. In his words, “When Alfred finally found me I was already comatose”. Although this wasn’t the last time that Bruce looked into The Court’s existence, he had never managed to find anything out about them and finally came to the conclusion that they did not exist. They convinced the greatest detective in the world that they were nothing but a kids’ nursery rhyme.
So there it is, five times Batman has been thoroughly outsmarted. As I prefaced, of course Batman eventually pulled it together and like only Batman can, and took down each and every one of these opponents. However, for that brief moment, that little slice of time disparate to its parallels, they had the upper hand; they pulled the rug from under the ever-prepared Batman’s feet.
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