When considering whether or not to squeeze, table dynamics are the most crucial factor. In fact, the player types, their stack sizes, and their positions at the table might be the only factors you need to consider. To make things simple, I have a formula that I use to help me decide if squeezing is a good idea. It depends on the order of the players involved.
If the preflop raiser is a fish and the caller (or callers) are regs, this is not a good time to squeeze lightly. The fishier player is likely to call my squeeze with a wide range. Then, the preflop callers will be getting excellent pot odds to call in position. In short, when the players are in this order, I’m extremely likely to see a multiway pot. So, squeezing with a weak hand in this position is generally burning money. If I had a value hand, though, I’d feel comfortable squeezing it to value-bet it against the fish. It’s important to be careful of the regulars calling in position when playing postflop, though. These players will usually be calling to make a big hand. So, let’s say a fish raises in the CO and a regular calls on the button. I’m in the big blind with KJo, so I squeeze (again, I wouldn’t bluff in this spot). Both players call. The flop is JT4r. I c-bet for value, and the fish calls. At this point, the regular moves all-in. This is a good time to fold—the regular is almost always calling preflop with the intent to make a big hand, and his action post-flop is consistent with that. Let’s say the flop was T93, though. I’d still c-bet this for a few reaons; the fish is unlikely to raise me off my equity and the regular is likely to fold anything that didn’t smash the flop. So, I have the proper combination of pot equity and fold equity.
If the order of raiser and caller is reversed, though, I have an ideal squeeze spot. It looks like this: a regular raises in the CO and a fish calls on the button. We’re in the big blind holding two random cards. If we reraise, we expect the regular to fold often—he has a wide range, he’s not guaranteed position, he’s not closing the action, and he’s not getting great pot-odds. The fish, though, will call lightly with a lot of hands and generally play fit-or-fold postflop. Additionally, most fish will reraise their premium hands preflop (AA, KK, etc.). So, we’re extremely likely to isolate the fish (or collect dead money when everyone folds). Then, when we end up heads-up, we find ourselves in a +EV situation even when we miss the flop. And finally, our skill advantage will lead us towards efficiently value-betting the fish postflop when we make a hand.
Of course, the regular could decide not to fold and begin 4-betting us. In this case, we have two options—squeeze less or shove over his 4-bet more. Whichever you choose to do will depend on stack sizes and the level to which your opponent is aggressive. However, I wouldn’t be intimidated away from squeezing in this spot—In fact, it’s so important to me that I’ll go to war with another reg over the right to squeeze given these conditions (regular raising and fish calling). If I think he’s 4-betting with a wide range, I’ll start shoving lightly. This spot is too just too profitable to give up without a fight.
In short, if the order is regular-then-fish, squeezing is a fantastic play with basically any two cards. If the order is fish-then-regular, you’re limited to value-betting and should avoid squeezing lightly. These types of “rules” are rare in poker, but table dynamics makes the squeeze formula incredibly simple. Take note of the order in which your opponents act and you’ll capitalize on table dynamics easily.