5/10 draw against a rock

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Jason, to answer your questions: he would never bet with JJ in this spot; he is a real rock. The fact that he bet the flop with so many people in the hand gives away his strength, as he would check behind without top pair or better. He also would just call a raise with two pair or a set and hope to trap later as he realized how aggressive the game was, but I felt pretty confident the look he gave me means he was caught off guard and unhappy to see the raise.

I agree with your advice (especially not going for a check raise if the draw hits), but I still like occasionally check-raising flops like this against tight players. They lay down often enough to make it profitable even as a pure bluff, and you can still win if they call and you get lucky.