Batman may be well known for his “prep time,” but the Dark Knight’s plots and plans almost destroyed Gotham City. It’s become something of a running joke that Batman has a contingency plan for anyone and everything. In truth, his contingencies are more a demonstration of his character flaws than anything else; a desperation for control, exerted over a world of gods and monsters, aliens and metahumans. Batman’s contingencies are his greatest strength, but they’re also his greatest weakness.
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There have been so many occasions where Batman’s enemies have taken advantage of his contingencies to attack the Justice League. Some of the most fearsome Batman villains have even orginated in his preparedness; think Brother Eye, an AI surveillance system that was taken over by Maxwell Lord and, later, Lex Luthor. But Batman’s greatest failed contingency came when his plans were found not by an enemy, but by an ally.
Batman’s Contingencies Led to a Gang War in Gotham

Running from 2004 to 2005, the “Batman: War Games” event kicked off when all Gotham’s gang leaders were called to an unexpected meeting. Nobody knew who had brought them all together, and the various gang leaders all feared a double-cross, meaning it didn’t take long for the meeting to descend into a firefight. Enough major gang leaders were killed to trigger a full-blown gang war, one that soon consumed Gotham City. Batman found himself disturbed by the fact that the conflict seemed almost familiar to him, following patterns that he recognized.
It took Batman far too long to recognize this as one of his own contingencies. The so-called War Game had a simple goal; to trigger a gang war that would allow Batman to position one of his own people in charge of all crime in Gotham City, a “control freak” solution of highly questionable morality. Even Batman had decided to shelves the contingency, but he had kept the files on record. His plans had been taken by Stephanie Brown during her time as Robin, and she triggered the gang war hoping to earn Batman’s respect.
There was just one problem; Batman’s plans involved the presence of one crime lord who didn’t make the meeting: “Matches” Malone. Always secretive, Batman had never told Stephanie the truth; Malone was one of Batman’s own aliases. Without Matches Malone’s presence, the gang war spiralled out of control. Worse still, the Black Mask learned the truth about the War Game, and saw the opportunity; he managed to maneuver himself into place as Gotham’s new kingpin of crime, killing Batman’s own agent.
Stephanie Brown’s Death Sealed Batman’s Defeated

The War Game cost the Batman family on a personal level in the end. Stephanie Brown – currently going by the alias of “Spoiler” – was captured by the Black Mask, and brutally beaten. She was taken to one of Batman’s closest allies, a medic named Dr. Leslie Tompkins who came to resent Batman as she realized how much his presence had harmed Gotham. Horrifically, she allowed Spoiler to die of her wounds, a way of trying to teach Batman a twisted lesson.
This wasn’t the only cost, either. The Black Mask successfully located Oracle’s main base of operations, and attempted to hold Barbara Gordon hostage because he believed he’d found the Batcave. In the aftermath of “Batman: War Games,” the Dark Knight lost the edge that Oracle had given him. It left him seriously weakened during a time when his enemies had organized themselves under Black Mask’s leadership.
Gotham City itself was left badly battered, with the citizens beginning to lose confidence in Batman. The disturbing truth, of course, is that the people of Gotham were right to doubt Batman. They had no idea that everything they’d gone through was a result of his being a control freak, putting together the most absurd contingencies and refusing to disclose his secrets to others.
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