In all of comics, no one is better prepared for the horrors that come with being a superhero than Batman. When he isn't punching out Riddler or Penguin, the Dark Knight Detective spends his free time coming up with highly unlikely scenarios and then creating plans on how to handle those scenarios. A whale is dropped directly into the center of Gotham City? You can be sure Batman has a plan for it.
But even having a plan for every possibility doesn't mean Batman and his team of crimefighters will win every fight. Sometimes, the Caped Crusader and his extended family find themselves licking their wounds and trying to figure out how to fix that which went so wrong. Many times, these defeats have left scars, both physical and psychological, on Batman and his crew for years.
10 The Cataclysm
For all his planning and plotting, one thing Batman didn't expect was a massive earthquake demolishing almost all of Gotham City. The city's old buildings weren't made to deal with earthquakes, and in a matter of moments, the whole of Gotham collapsed into itself.
Knowing there wasn't much Batman could do in this time, Bruce Wayne went before the US government asking for funds to help rebuild Gotham. Instead, the government decided to cut Gotham off from all of the United States, turning it into a No Man's Land. Batman had failed to save his city.
9 Lex Luthor Saves Gotham
After the federal government cut off Gotham City, the people who were trapped there found themselves caught in the middle of a war as the various escapees from Arkham Asylum took over parts of the city. As Batman and what remained of the Gotham police worked to take the city back block by block, Lex Luthor created his own plan to save Gotham.
Lex came in and did what the US government refused to do, he covered the costs of rebuilding Gotham. Suddenly, Batman's city was being saved by one of the evilest men in the world, and Batman wasn't in a position to stop him.
8 The Court Of Owls Goes Unnoticed
Batman prides himself on his skills of deduction and attention to detail, which makes it all the more shocking that the Court of Owls was able to work in the shadows of Gotham for so long. How the Bat-Family could have missed an entire organization of criminals secretly running their city is something that they have never fully come back from. No matter how smart or prepared Batman and his crew think they are, they have to live knowing that they missed the massive evil hiding right below their noses.
7 Flashpoint Batman Takes Gotham
It didn't happen overnight. It was a series of small moments, building to bigger and bigger moments until finally, Batman found himself losing his city to an alternate reality version of his father. In Tom King's 85-issue run on Batman, readers saw as Batman believed that he had prepared for this exact moment, only to realize that he underestimated his enemy and failed to stop the Flashpoint Batman and Bane from taking Gotham.
Making matters worse, Gotham City under the control of Bane, was safer than it had been under Batman. Of course, that safety came with the penalty of death being used for pretty much every crime, from actual murder to littering, so safe is a subjective term here.
6 Death of Stephanie Brown
One of the many plans Batman created but never put into motion was found by Stephanie Brown. Stephanie had started her crimefighting career as Spoiler but became Robin after Tim Drake quit, and she wanted to prove herself to everyone. She believed this plan that was designed to take out all the mobs of Gotham would be her ticket. What it ended up being was the path to her death at the hands of Black Mask. Stephanie failed to pull off the plan, and instead of crushing the mobs of Gotham, she got herself killed and started a gang war.
5 The Shooting Of Nightwing
A recent injury to the Bat-Family, Nightwing was shot in the head by KGBeast as ordered by Flashpoint Batman. Nightwing survived the shooting, but lost his memory and became "Ric Grayson". At the same time, Batman hunted KGBeast back to Siberia where the two men fought. Filled with rage, Batman broke KGBeast's neck and left him paralyzed in the snow.
Much to the chagrin of many fans, Nightwing is still going through his Ric Grayson period, although with the upcoming Joker War event, there is some hope that he'll be back to normal sooner rather than later.
4 The Shooting Of Barbara Gordon
The Joker has always been a danger to the Bat-Family, but usually, that danger only came when they were in costume. That wasn't the case on the day that the Clown Prince of Crime showed up at the home of Commissioner Gordon and shot his daughter Barbara in the stomach. The bullet shattered Barbara's spine and left her paralyzed. What her father didn't know was that Barbara was secretly Batgirl.
For the better part of twenty years, Barbara Gordon worked as Oracle, a constant contact point for the Bat-Family and someone they all knew they could turn to when they needed computer help. When DC relaunched there books in the New 52 universe, Barbara was back to being Batgirl, but she has still spent three years paralyzed by the Joker.
3 Death Of Jason Todd
When Jason Todd, the second Robin, found his biological mother, he believed that his life was about to get a lot better. What he didn't know was that his mother was being blackmailed by Joker. Jason's mom tricked the Boy Wonder into going with her to a warehouse where the Joker waited for him. At the warehouse, Joker beat Robin to within an inch of his life. The Clown Prince of Crime then set a bomb with a timer and left the beaten Robin behind. Batman arrived just as the bomb went off. Jason Todd died.
Years later, Jason would return from the dead and, filled with anger for his former mentor, became the Red Hood. While Jason has reformed since then, he is still wary of the Bat-Family, and they are wary of him.
2 Bane Breaks The Bat
As far as new villains go, Bane arrived in the scene with a big splash. After freeing everyone from Arkham, Bane let Batman tire himself out hunting down his rogues before making his presence known. Bane confronted an exhausted Batman in the Batcave and beat the Dark Knight nearly to death, going so far as to break Batman's back. In a moment that shocked the Bat-Family and the readers, Batman didn't choose Nightwing to take over the mantle. Instead, he handed the keys to the Batmobile over to Azrael, a decision he would come to regret.
1 Death of Alfred
The freshest of all the wounds, the death of Alfred Pennyworth was felt by every member of the Bat-Family. There is no one person responsible for Alfred's death. Bane killed him, but it was at the order of Flashpoint Batman, who had set a strict rule for the Bat-Family to follow, with all of them knowing that Alfred's death would be the price for breaking the rule. That rule, don't try to leave Gotham, was broken by Damian Wayne, the fourth Robin, who was ordered to break it by Batman himself.
There is now a permanent hole in the Bat-Family, as the man who was there for every member of the crew is now gone. This is one defeat that Batman and his squad may never even come close to recovering from.