Literally this second, I understood something about Booster Gold. During the 52 Pickup arc, Rip Hunter allows Booster to go back again and again to attempt to save Barbara Gordon from being paralysed even though he's completely aware it's impossible - until now, I interpreted that as Hunter simply being a complete dick in getting his point across, which I detested, but that's the point. He knows Booster well enough that sitting him down and explaining "Dude, it's going to happen, you can't stop it. It HAS to happen so Babs can become Oracle. If she doesn't become Oracle, shit goes down in the future. Same reason you can't save Ted" won't stop him, because he thinks he can do it. Only by letting Booster go back again and again and experience it for himself will get the point across, and so that's what he has to do.
It also, I recently realized, could be considered the reason Bruce originally put up with Booster’s antics and why Booster has such a high level of access to the Batcave. It has also led to Booster revealing his “true nature” to the current Batman, allowing him both to have someone outside his very insular group that he can be himself with, and to potentially have an ally that has far more respect within the hero community then he can allow himself to have.