I recently posted something on X that I felt was harmless. I thought it would be fun to write about a hand with a play that many people don’t do enough. Over five minutes or so, I wrote this:
'You're playing a loose $2/$5 game. It's folded to you in the lojack. You have $860. You look down at 
.
You raise to $25. Hijack and cutoff fold. The button calls. He has $775 behind. Small blind folds. Big blind calls. He has $575 back.
The board comes 
. The big blind checks. What do you do here?
Let's say you bet $35. The button calls you quickly. The big blind folds. There is now $147 in the pot. You have $800 behind. Button has $740 behind.
The turn is the 
. The action is on you. What do you want to do?
You should overbet here. You should bet something like $162.
You're risking $162 to win $309. Your bet as a total bluff only needs to work 52.5% of the time.
However, it's likely to work way more than that. Why? Your opponent just flatted you on the button. In a loose game, that could be an extremely wide range because these players like to see too many flops. That is why we are not checking range here. This opponent is wildly exploitable.
Your opponent just flatted you on a board with flush draws and straight draws. He likely would have three-bet pre-flop with QQ, KK, and AA. On this board, it is likely he would have raised some of his best jacks, sets, and weird two pairs.
His most likely hand is a mediocre pair, something akin to A-3, A-5, 44, 66, 77, 88, 99, TT, J-8s, J-9s, J-Ts, J-To. None of those hands want to see you overbet this turn.
And if he calls? The hand is not over. There is a great chance you will still win if you hit the river. After your opponent gets this committed, he is likely to pay off any reasonable bet on the river.'
Post goes viral, polls are conducted
I didn’t think anything of it until I checked my phone later and saw the post had gotten 100,000+ views. And people were making polls and other threads about it.
I reread the post. What had I said?
I knew people would have problems with the overbet. I have an 80%+ success rate with my overbets, which is great because the average overbet needs to work 51% to 66% of the time in order to be immediately profitable.
However, whenever I teach the play, I get into this debate with players:
“I can’t overbet! These idiots never fold to me! I will be spewing all my chips!”
“Okay,” I say. “Then overbet the next time you flop a set.”
“I can’t do that! They’ll fold!”
As you can imagine, this makes blood shoot out of my nose. The contradiction never seems to stare people in the face. It takes time to help people get out of their risk-averse style of play that doesn’t get them results.
Interestingly, that’s not what caused all the polls and spinoff threads. It was my wording of one particular line. Allen Kessler seemed to have the most problems with what I said.
Allen would later rephrase his question and post these two polls:
And this one:
The line he had an issue with had to do with my overbet math. The bet we discussed was $162 into the $147 pot. I wrote this about that play:
'You're risking $162 to win $309. Your bet as a total bluff only needs to work 52.5% of the time.'
Why did I say that? Let’s think about this logically.
How do we figure out how often our bet needs to be successful? How would we do that math?
Let’s start with a simple situation
You and a friend are flipping a coin. You are wagering $50 on every flip. How would you mathematically express how often you need to win to break even?
You’re risking $50 to win $50 in this situation, but if you divide 50 by 50, that obviously can’t be right. You don’t need to win a coinflip 100% of the time in order to break even.
What you do instead is take the $50 and imagine the pot you’re committing it to. You and your friend take $50 out of your wallets and commit it to the pot. The pot is now $100. Your $50 doesn’t belong to you anymore.
Now, you’re risking $50 to win $100, which is everything that’s in the pot. Your $50 doesn’t belong to you anymore, but you do get that $50 back should you win the coinflip.
So, let’s do this math: $50/$100 = 0.50. That is exactly correct. You need to win a coinflip 50% of the time in order to break even. You have now expressed this with simple division.
The fun part about poker is that this kind of math applies as well. In this hand, when we overbet, it looks like a massive bet to most casual fans of the game. Recreational players assume overbets need to work 70% or 80% of the time due to how big of a play overbetting is. However, that’s not true.
Let’s express the math for this overbet. We bet $162 into a $147 pot. Because of what we have just learned, we know that we don’t divide $162 by $147. Our bet does not need to succeed more than 100% of the time to break even. Instead, what we do is divide $162 by the entire pot we stand to win. This is just like the example we used of flipping coins. We put the $162 in there and it no longer belongs to us. It belongs to the pot, which is now $309. If our bet succeeds, we’ll get that $309.
So, the correct math for this is $162/$309 which equals 0.5242. I rounded up and called this 52.5%. Hence, this line:
'You're risking $162 to win $309. Your bet as a total bluff only needs to work 52.5% of the time.'
If our bet succeeds, say, 70% of the time in this situation, then we are printing money. We are winning so often it makes up for all the times we get caught. If our opponent chooses to just call us, we get another chance at winning the pot on the river when all of our outs could come in. This is an amazing place to be.
The Kessler conundrum
What Allen Kessler had a problem with was my saying we are winning $309. He pointed out that we are not gaining the $162 we are wagering but instead are only gaining the $147 that is in the pot.
I can see why he makes this point, but it doesn’t help us with the shorthand of analyzing a hand. You can also extend this back to the previous streets. Should we not count the amounts we wagered pre-flop and on the flop because those chips came from our stack?
The way to see this spot and other situations without confusion is to always remember what is in the pot doesn’t belong to us anymore. It belongs to no one until someone claims it. That’s why we divide what we are wagering by the size of the total pot we win. Once our chips cross that line, they are up for grabs if someone wants to go after them.
I can see the semantic reason people have a problem with my language, but it’s largely just a figure of speech that expresses the correct percentage of the time we need to win a pot. What most people care about is the answer to the question, 'How often does my bet need to succeed?' That is why I use this language.
That’s pretty much the whole story for what should not have been that big of a thread on X, but hey, I appreciate the traffic. Special shout out to Allen Kessler. I know many people have this question, and I appreciate him starting a healthy debate in a public forum. This is what’s fun about the game. It’s fascinating to see all the different perspectives people have around the world.
If you enjoyed the strategic insights I provided in this article and in my thread, be sure to sign up for my free daily strategic newsletter. You get three free training packages just for signing up. You can learn how to play ace-king when it misses the flop, how to triple barrel bluff, and how to three-bet. Also, get in touch if you're looking for private coaching.
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