Who do you think Batman's greatest enemy is? I know most people would say the Joker or even Ra's but I think the one person who almost completely destroyed not only Batman but Bruce Wayne too would have to be Dr. Hurt. In R.I.P. he comes THIS close to destroying everything but was defeated because Bruce had created the "Batman of Zur En Arrh" almost on a whim. Not to mention Hurt releases all the doctored photos and news articles to try and destroy the Wayne family name. And then in Batman and Robin Must Die! he returns as Bruce's father (not literally) and again tries to destroy the Wayne name.
I guess one could argue that the Black Glove is his greatest enemy since that is the organization that Hurt belongs to, but the group targets and destroys "Good" people with their yearly(?) game of "Good vs Evil" while Hurt is the one who has a hard on for destroying Bruce Wayne/ Batman personally.
What do you think?