I agree 1 is terrible unless he's super weak. He limp-calls so he probably has a pair. That flop is garbage, your re-raise says "I HAVE KK".

Which means, either he has no respect for your re-raise, or has AA/44/ or a 9. I think stack sizes worked against you here... once he raises and you re-raise, the pot is too big for him to fold 88, becuase of the high probability that you are on overcards trying to buy it.

Alos, he check raised... so I bet he has an overpair and will not lay it down. Given the open limp, probably TT.