"Pineapple OFC wouldn't be so popular if it were more appropriately named

You either know what you're doing, or you don't.

What that means in Pineapple is knowing your odds. Sure, Pineapple is fun, it's sick, swingy and crazy, you get lots of cards, big hands are always around the corner, gambles often pay off, and Fantasyland is always in play. All of that is true, and that's part of what makes the game exciting. But behind the curtain, it's draw poker, and that means math. Knowing your numbers is going to give you an edge, not only for your hand's trajectory, but it also gives you an understanding of how much risk your opponent is putting themselves in.

I recently played a hand online that perfectly illustrates how knowing one's exact odds can be helpful, and also how NOT knowing (or caring about) them can quickly make you a loser. Out of position on the second pull, I am dealt AQ3, and I've got a decision to make. I'd like to pair Aces in front for a 9 point royalty and a trip to Fantasyland. With 10's already set in the middle with a few unders to a QQ8 back row, I feel I can make this work. However, I'd like to know my exact odds to unfoul before I take that route. Here is the situation before setting:

I don't have a fancy odds calculator to plug in the scenario, nor do I have time to do so. But I have done my math homework, and I know my basic probabilities here.

If I set the Ace in front with Q in back, I will have a 4-outer (QQ88) and a 5-outer (44222) to improve each row. I am excluding the 10's from the outs scenario as that will make trips in middle and would require a 2-out Queen in back to unfoul, which is only 33% likely to occur. However, the 4- and 5-outer are 56% and 65%, respectively, to hit with 6 cards to come. With each row's draw comfortably above the 50% mark, the AA royalty equity of 9 pts, Fantasyland expected value (6-10 points, depending on your opponent), and the fact that my opponent is more likely to flush the back row than I am, I have all the justification I need to gamble.

Curiously, on the next pull, my opponent set KK in front, even with the knowledge that I had already set two Aces, leaving them only one out to unfoul. And herein lies the difference between a good gamble, and a bad one - or 'knowing what you're doing' or not. The probability of their hitting an Ace in the last two pulls was only 19% at that point in the hand. That is approximately the statistical equivalent of getting it in preflop with 22 against AA. Did my opponent know how low their odds were when they set that way? I'd say they probably knew it was a longshot, but I'd also guess they assumed I'd foul with my setup. Either way, I'd take my 50%+ probabilities all day against their >20%. Based on the math, my gamble was perfectly reasonable, but theirs was very unreasonable. When you look at their setup, you might posit that they were hoping for the case Ace or perhaps a wheel straight. But there is a difference between hopeful and probable.

The final runout:

My opponent fouls. It's possible that my aggressive line forced them to respond in kind, but as the numbers and results show, it was not an optimal response to set the KK in front. The fact that my opponent decided to take a swim upstream against the flow of probability extended their points loss; if they had taken a more conservative line they would have made a flush in the back and limited my win to 6 points, rather than giving me the scoop/foul bonus as well as giving up the flush equity they had accrued.

Catching the pair of 7's on the third pull took care of my back row problem; I haven't done hard numbers yet for that scenario (probability to catch a random pair in any pull of 3 cards), but based on game play I estimate the odds in the 15%-25% range depending on board contour. And if the 7's hadn't come it's reasonable to assume a Q or 10 could have appeared in their place, so the possibility of a 77 pull only added % points to my play that I hadn't even factored into my decision. It turns out I could have caught the flush as well, so there were several options, as there nearly always are in Pineapple. I chose a path that was the most straightforward and made sense mathematically with an eye towards overall hand E.V. As far as I can tell the 'luckiest' part of the hand was when the villain decided to gamble poorly.