[Lloyd]

First of all, I'd only call pre-flop. You don't have a hand good enough to make a value bet. You already said the chip leader likes to gamble so he'll probably call. All you've done is get rid of the blinds. If you're going to raise you have to make it at least 800 to 1000 to get the chip leader to even consider folding.

Given that you raised pre-flop and don't have any draws on the flop, making a continuation bet is standard. You could probably have bet less and he'd still fold if he had nothing and call if he did. But not a huge deal. Once he calls I'm done with the hand unless I improve.

Which you did. But you know have to start considering the possibility that he is slowplaying a real hand. That doesn't mean that I'm going to fold, but I'd prefer to play a smaller game with top pair here. When he checks the turn, I'd check behind. Yeah, it's possible that he has Ax and could make a straight, or 2 clubs and make a flush. But I can get away from top pair pretty easily if the betting gets out of line.

I'd then be prepared to call (not raise) a bet from him on the river. You still might be beaten with a big pair, but he could also bet a missed straight draw or a middle pair like 66 or 77.