We’ve got a new member of our hand discussion group, and he brought us a doozy of a hand right out of the gate. I’m going to call this fellow “Doyle,” but he’s not that Doyle. Doyle is taking a shot at a slightly bigger online game—in this case, a 2/4 Unlimited Hold-them table.

Nine players are dealt in, and the lo-jack (LJ) player limps in for 4. The hi-jack (HJ) player makes it 16, the cutoff (CO) calls the 16, and now it’s on Doyle, sitting on the button with 99. Doyle describes all the players involved so far as, “Bad aggressive regs with high VPIPs.” VPIP, again, is “Voluntarily Put [chips] In Pot”—it’s how often you chose to put chips in the pot when you weren’t forced to by the blinds.

Anyway, Doyle calls the 16, and…

Wait a minute—somebody press the pause button. When you read that, did you think, “Hmmm. What about a 3-bet?” Cause that’s what I thought. If the original raiser (HJ) is, “aggressive with a high VPIP,” then his hand doesn’t need to be anywhere near as good as 99. And certainly the CO flat calling doesn’t suggest a hand better than 99.

Of course, simply calling the 16 and “set-mining” is a reasonable approach, and nobody could fault you for doing it. Sitting on the button with a set of 9s in a four-way raised pot would be the nice start to a, “I won this massive pot…” narrative. However, that third nine appearing on the flop happens far too infrequently—only one out of eight times. Wouldn’t it be cool to win a pot half as big, but 4–5 times more frequently?

Think of all the good that can happen from a 3-bet:

Everybody folds. What a glorious result. He picks up 10 big blinds without a flop. Notably, there’s usually no rake if there’s no flop (“No flop, no drop”) so he gets every last chip from the pot. And he doesn’t need to mess about with the 88.5% of the time he doesn’t flop the set. This latter bit is important, because as strong as 99 is (and it’s up there), it rarely looks spectacular after the flop unless it does indeed flop a set.

Everybody but the original raiser folds. This is the second-best outcome. The chances of Doyle winning the pot with an unimproved 99 against three opponents is pretty low. But against one opponent, and with the button, he can frequently navigate his way to a showdown, where 99 has a reasonable chance of being best. Furthermore, by bloating the pot early, he wins a relatively big one, compared to the single raised pot.

If I were to 3-bet, I’d make it a chunky one. There are three people in front of me who have already VPIPped (yes, it’s a verb now). Normally, I’d make my 3-bet 3–3.5x the original raise. But with all that company, I’m thinking 5–6x. Like 85. Yeah, 85 seems right. Give myself a chance to win the pot right now, and if not, almost definitely get it down to heads-up.

Finally, if Doyle were in the HJ or CO, rather than on the button, I’d consider a 3-bet obligatory. By calling in the HJ or CO, especially after a gaggle of VPIPpers, Doyle would make it all the more attractive for the Button to come along, or worse, squeeze the whole field with a 3-bet themselves. I rant about this probably more than any single subject, but I cannot overstate the value and importance of acting last. If it’s a close decision between 3-betting and calling, and you’re near, but not at, the button, then that is enough reason to choose the 3-bet.

But that’s not what happened. Press play, please.

Doyle calls the 16, and we’re off to a flop with 70 in the pot. It’s about as good we can hope for, short of a set: 3c–8s–7d. The LJ started with 300, the HJ started with 400, and Doyle covers them both.

There’s a check, HJ (the original raiser) bets 42. The CO folds. That’s good news for Doyle, because CO could have had some hands like 88 and 77. Nice to see him out of the way. Doyle calls, which seems completely standard. Now the original limper (LJ) calls too, which is at least a little worrisome. But let’s see a turn card.

The turn, with 196 in the pot, makes the board 3c–8s–7d–7c. And the skies turn bright—both players check to Doyle.

Press pause again.

Do you bet or do you check?

If you said, “Bet,” give yourself three points.

It could be tempting to check here. The HJ bet, and after you called, the LJ decided to call again. But the LJ didn’t check-raise the flop and he didn’t lead the turn. The HJ decided to stop betting too. Do you think he’d stop betting QQ here? I sure wouldn’t stop betting QQ, especially if I wanted to keep my reputation as “aggressive.”

It’s really starting to look like Doyle has the best hand, but no doubt he has to fade a fair number of outs between the two remaining hands. It’s a good time to bet, and (press play)…

That’s just what Doyle does—he bets 98 (half pot).

I think this bet should be bigger. I know it’s scary that there are two of them, and we just have this measly pair of 9s, but we don’t want all those scary outs to see a cheap river card. It’s almost monsters-under-the-bed, but one of those guys could have Ac8c, which has 13 outs against us. We need to be sizing up here, and I would have liked to see Doyle bet more like 65–70% pot—130–140. This is also theoretically correct—as you progress down streets of the hand, your bets should become larger and more “polarized.”

We’ll get to the last street of this hand next week. As you can see, there’s plenty to chew on just through the turn betting. I sure appreciate you sticking with me this far, and I look forward to spinning the rest of this yarn in the next installment.

Lee Jones has been in the poker industry for over 30 years. He writes at the Global Poker blog, plays poker every chance he gets, and coaches poker. You can contact him at www.leejones.com.