For many years Batman has been presented as infallible. Both other characters and readers see him as the man who has all the angles covered. As his greatest enemy, the Joker, once quipped, "Every single time I try to think outside his toybox, he builds a new box around me.". This attitude makes the time's Batman does fail all the more shocking and, usually, devastating.
Sometimes it's through the machinations of one of his enemies, but the greatest threat to the Dark Knight has always been Batman himself. Bruce Wayne is a broken and haunted man who cannot always outrun his demons. Writers often present Batman as a man with an iron will who completely controls his emotions. Still, the truth is he suppresses them most of the time—treating them as a common criminal and bending them to his will through intimidation and overwhelming intellect.
Perhaps the greatest of all Batman's opponents is his hubris, the one thing that has seen him bested time and again.
9. Batman's Hubris Causes A Crime War
Stephanie Brown has one of the most storied histories of any DC character. From her humble roots as Spoiler - the daughter of two-bit loser, the Clue Master - all the way up to taking on the mantle of Batgirl. She has been "dead", pregnant and a Bird of Prey, but perhaps her most memorable moment came when she was, briefly, Robin.
When Tim Drake's father finds out about his son being Robin, he forces Tim to choose between him and Batman. Tim sides with his father and Bruce does not take the news well, and he swings into full "spoiled little rich boy" mode. Batman turns around and offers the mantle of Robin to Tim’s on-again/off-again girlfriend Stephanie Brown; someone who Batman had refused to sanction up until then.
The whole thing goes badly and, almost as quickly as Stephanie becomes Robin, Bruce fires her. A hurt and confused Spoiler then steals Batman’s plan to destabilize organized crime in Gotham and attempts to execute it. Stephanie’s ignorance of Bruce's alter-ego Matches Malone, a key component to the scheme success, results in an all-out gang war that tears Gotham apart.