"I think it's to review the stuff I learned a long time ago. I guess it's to make sure I can do it really fast without thinking about it... Is that truly sad, or am I just really tired?
I think it's really sad. And truly dangerous. I also think it would be sad to put more on your plate (unless there really is no other choice) or to cut into his tree climbing time.
Have you thought about changing his school environment? Where are you with that process?
If you can find some audio books on history that you can enjoy together in odd moments, such as 'don't know much about history' or those by the Teaching Company, perhaps you can sneak in some fun/challenge as well.
I'm a big fan of afterschooling if there is no other choice - BUT - fixing the problem is my fist reccomendation.