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I would bet the turn.

I think checking is only good if you're sure this guy will always fold a worse hand to a bet, always bluff at the river if you check it through on the turn, and never check-raise with a worse hand. That's a pretty big parlay.

I'd also call it down after he raises. I think you'll see 77-TT or 6x more than 20% of the time. After all, you've probably got AK, right?

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I agree with pretty much everything you say and I'm starting to think that checking behind is pretty much never right at these limits without a super read. Don't know if it was a mistype, but one of the reasons to check the turn is that he would c/r with a worse hand, but at the correct percentage that we are screwed whether we call or fold. If he never c/r a worse hand we can safely fold to a turn c/r.