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Here are some rough EV calculations, assuming villan has c/r'ed a smaller pair or is bluffing half the time(hands you beat), and has a set/ straight the other half(hand that have you beat). I think $100 is definitely on the low end of the raising spectrum, so i don't think we are raising too much to get our information about villan's hand.
You raise to $100. Villan folds.
Result: +53 Probability: ~50%
You raise to $100. Villan calls, and you fold to a turn bet.
Result: -$87 Probability: ~23%.
You raise to $100. Villan shoves, and you fold.
Result: -$87. Probability: ~25%
You raise to $100. Villan calls, and the turn comes a Q. Villan goes allin, you call and win the hand.
Result: $178. Probability: ~2%
($53 x .5) + (-$87 x .48) + ($178 x .02) = -EV
$26.5 + (-$43.75) + (~$3.6) = -$13.65
Raising looks ugly, but if you call the flop he almost certainly is going to bet the turn again. Now you don't know if he has you beat or not. You will have to invest nearly your whole stack in to get to showdown. This just seems to magnify the -EV of raising. We need to factor in the scenarios where he won't continue to bet with a smaller pair and will continue to bet to the river on a bluff, but they don't account for a majority of the scenarios so it certainly wouldn't tip the balance to +EV. Therefore, calling seems to be worse than raising.
Folding may be the best play after all, since you lose just $13.
Those are my thoughts. This is a really difficult spot.
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