DECISION POINT: In a Tournament it folds to you on the Button with 3♥3♠ and 17 big blinds, what is your strategy?

PRO ANSWER: First-in late position play with an awkward stack can be tricky. Our awkward stack size makes it more likely for either the Small Blind or Big Blind to play back against us.

In general, you should tighten up your late position open-raising range with awkward effective stacks (10-20 big blinds), since failed steal attempts deplete significant portions of your remaining stack. In addition, if you open with a high frequency, a reshove strategy from the SB or BB becomes extremely profitable against you.

There are two main strategies to use when holding hands in our tighter late position opening range. We can either move all-in (using an awkward stack push/fold strategy) or we can open-raise to a smaller amount. When open-raising to a smaller amount, we will call off our stack versus a reraise with our better hands and fold our worse hands.

Against most opponents, who are predictable and relatively tight 3-bettors, choosing to open-raise a smaller amount is by far the better play. This allows you to fold certain hands to reraises and avoid confrontations when you are behind. Because these opponents rarely 3-bet with weak hands, we can avoid getting stacks in against their premium hands by simply folding if they reraise all-in.

With 33 on the Button, open-raising to between 2 and 2.5 big blinds with the intention of folding to an all-in reraise is the better play against the vast majority of more passive opponents you will face. Against opponents with very high 3-bet frequencies, simply moving all-in from the button will be more profitable.

However, raising with the intention of folding to an all-in is best against most opponents you will face is the best play.