1) F. and don't give in on it. hold to it. as long as it takes. let his parents deal with it from there.
2) students that fail - even once - need to be put in separate classes. they should be able to get out of those classes by passing a full year, too. but, it's the way to get out of this pushing-them-through mentality. nobody wants 20-somethings in high school. that does have real consequences; i broke some asshole's arm in the ninth grade by pushing him down the stairs because he kept slamming me into the locker, and he should have been in 12th grade (and he was white, of german descent). so, put them in their own classes. at their own schools, even.
we need to bring back the idea of failing.