[JustPlayingSmart]

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A raise pre-flop to 550 would have clarified this.

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Since no one has really commented on this statement yet, I would like to. I think a preflop reraise is terrible. If villain has an overpair, he almost certainly pushes. If he has AK he probably pushes also. Are we calling this push? Probably not. What if he just calls, which I also think is a possibility since the reraise is small, and the flop comes QTx or AJx. Now we're out of position with a vulnerable hand who could easily be behind, an inflated pot, and too many chips to just push (not like pushing would be that great anyway, since most better hands would call and most worse hands would fold).

This is a concept Sklansky talks about in TPFAP. By raising here, you are effectively turning 99 into 72 (although with this small a raise this is slightly incorrect, since villain will actually call with many hands he would fold to a healthy raise to around 850). Calling preflop is great. We're getting pretty good odds to flop a set and with implied odds the call is a no brainer.

As for the flop, betting out and getting raised is definitely a tough spot because a lot of players will interpret the flop donk as weakness and autoraise with whatever they have. Given that this is a freeroll (even if it cost points or whatever to enter), I would have difficulty letting go of an overpair with 25xBB stacks. I would love to know what this guy's standard raises were though. This is definitely a small raise. If I had seen him make this raise before, I would almost certainly just check/raise all in (or call his push if I bet out on the flop). If this was out of the ordinary for him, I would probably bet out and fold to a push. If I had no read, I would say "bah" and call cuz I don't like to lay down overpairs.