The re-raise show's that he has strength and it is meant to intimidate you. No matter what the flop is he will more then likely either bet or raise. You will probably fold. However, if you bet first it looks like you hit the flop and he will likely call or fold if he didn't hit. If he did hit or has a hand such as aces you will get reraised no matter what your bet is. He also has position on you which makes it difficult which means sometimes folding is the correct play depending on the size of his reraise and what type of a player he is (loose/tight)
If you check the flop it means one of two things:
A) You're Weak

You've hit and slow playing
Obviously that's overly simplified and obvious but it makes sense. If you don't bet on the flop and he has anything at all, sometimes nothing he will bet. Depending on your style you can throw a reraise back at him if you think he's bluffing or just call.
Remember, position is everything, and when you don't have it it makes it alot harder to beat a reraise. If you get reraised preflop you won't have position, so folding in a situation, especially when you're near the chip lead is a good move.