[JrJordan]

Some nice thoughts, let's evaluate them.

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I think raising the flop is in definite order. While I normally would cap preflop, given the button you described, I think calling is okay.
The fact that the button cold calls lightly should make the flop raise easier, not harder. If he does manage to catch his 3 or 6 outs, then oh well, you still will make more in the long run. (And when the button cold calls, you can give a lot more credibility to a SB 3bet).

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An argument could be made for raising this flop, however I'm against it for a few reasons. First, we have a very vulnerable hand that even if it's ahead right now probably doesn't have much equity due to the variety of draws, overcards, and paired K's possibilities. Since I'm confident Button is cold calling with a large range of hands, this puts me in quite the predicament down the road. Any diamond or overcard to my 8's is going to be very tough to play when I have initiative. I'd likely have to bet the turn again with very little folding equity and reevaluate on the river once more to whether I can even see a showdown. The problem with raising this flop is that we're almost always obligated to follow up on the turn when again our equity is negligable. We'd like to get to showdown as cheaply and safely as possible in this hand, not pump the pot.


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Also, I think you missed a bit of value from this hand and perhaps by raising the flop and then firing the turn and river (depending on what hits, assuming SB shows no more aggression) is probably the way to go.

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Again, all we have is a pair of 8's. We don't have a lot of value in here, we're simply trying to efficiently take a semi-bloated pot when there's a decent chance we're ahead. FWIW, there's almost no range of hands that SB can call a bet on the river and I still beat. Button, however would call down with A-high UI.

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The way you played it makes the button play his hand perfectly.

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That's ok, especially because there's 2 people in the pot. The question is did I play my hand perfectly, not the button. Raising the flop (and forcing button to possibly make a mistake by cold calling) will most likely lead to me making a bigger mistake than him when I have to make very tough turn and river decisions.