[Jack plyr]

First off, this is a great question posed by Acevader. Having said that, I am going to ignore it for the moment to focus on the issue of bluff check raising continuation bets. As Pokerfarian mentioned, a check raise will turn a hand like 88 into a bluff. He also correctly notes that turning it into a bluff might be the best option.

Given the flop texture and villain’s hand range, he likely has no draw and no hand unless he started with a large pocket pair. He might bluff back at you if he views this flop as unlikely to have hit your range, but in the live games I play, most players won’t bluff you back and they don’t draw to 6 questionable outs.

What makes the check raise attractive is that villains are continuation betting flops that are extremely unlikely to hit their hand range. You must make players pay if they consistently c-bet without regard to board texture and can only represent an overpair or a 6 outer. Obviously, the viability of a check raise bluff depends on hand ranges, continuation bet percentage, and images.

Hand Range: Tighter the villain the more likely he will have a big pocket pair which makes it less likely he will fold to your check raise. This is somewhat counteracted because tighter players tend not to play back at you with air. Looser players might end up calling with a draw but are less likely to have a made hand. They are also more likely to play back at you.

Image: I will also check raise with my big hands and I am generally viewed as a tight player. Both these factors make my bluff more believable.

Continuation bet percentage: The higher the continuation bet percentage the less likely villain has a hand on a given continuation bet. If he sometimes checks behind on dry flops, then it might not be profitable to check raise bluff. Usually his preflop raise percentage considered along with his continuation bet percentage can give you a great idea if he is betting with air.

Now back to Acevader’s question. In many situations I do think it is best to turn your 88 into a bluff. Why?
I am unlikely to get paid off by weaker hands anyway so no big loss there.
Villain likely has overcards that I don’t want to draw against me.
Bluffing exploits a current game weakness that some players always c-bet
You can change your bluff into pot management if he checks behind. Then use the showdown value of 88 to your benefit.
It works well with my overall approach. I will check raise my sets sometimes.

It is important for me to reiterate that the check raise depends critically on how often the opponent is continuation betting. The higher that percentage the better the value of the check raise.

I could give you my thoughts on how to play the hand but you can basically rationalize any line based on hand ranges, continuation bet percentages, floating percentage, etc. I would recommend that you develop a simple excel model and play around with the numbers to reflect different player types and bet sizes.

Keith