[jcm4ccc]

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Two things make this hand so difficult for me: the history between you and villain and the coordinated board. He could literally have any two cards.

I think check/fold is the worst option. But also the smallish bet on the flop just smells like weakness, and I don't think is a much better option, especially if every other hand you've been in you've bet strongly. The sudden small bet from a TAG on a coordinated flop is a definite sign of weakness. I wouldn't believe a TAG was trying to trap on a coordinated board. If you had AJ or something like that, you'd be giving odds for straight and flush draws. So my read on you would be that you are hoping to take it down with a whiff or a weak draw.

If I were in Villain's position, I would read it as weak and make a raise, no matter what my holding. So, to me, the small bet is asking for a raise, and the raise can mean anything.

So, all that considered, I'd make a bet of no less than 800 on the flop. I think headsup, with a call from a guy you've been pushing around a bit doesn't mean much, and your second pair is good most of the time.

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I agree that the Hero lost this hand with his weak bet on the flop. The villian sensed it and outplayed him, IMO.

This is a hard hand to play, without a doubt. If you are going to bet this flop, you need to bet at least 50% of the pot--usually I bet about 60%, just to make it look strong. In other words, I would bet about 600 to 650 on this flop. I don't think you have to go up to 800.

Another way to play this is to check the flop and see what happens. If the villian bets strongly, you can let it go. If you sense weakness in the villian's bet, you can push all-in. The danger, of course, is in giving a free card or in folding the best hand.

If you had more chips to play with, I would go ahead and lead out and try to take down the pot. But given the amount of chips you have and the size of the pot, I think I'd rather check the flop and see what unfolds. I'm okay with giving this hand up if I have to. I don't want to lose half my chips on middle pair.