"Like, you know what? I'm gay and if you have a problem with that, I really could care less," Cooperman said.
Couldn’t. You mean “couldn’t care less.”
When you say that you "could care less", you are implying that you currently care to a certain degree, which allows room for you to care less.
A lot of people say things like that - sometimes it makes me laugh. One of my favorites is when somebody says "nip it in the butt" instead of "nip it in the bud." If you think about it, the former can mean the opposite of the latter.