Not that it really matters, but to clarify, it was a female reporter.
And I really didn't find it to be a silly question. Just because she asks him what he's playing for doesn't mean that she's implying that there's nothing to play for.
First what you play for is to get into the playoffs, then when you no longer can get into the playoffs you play for something else -- she was simply asking what that is for Drew.
Don't be so hard on her, she's a sports reporter for goodness sake :)