Without a doubt the most common time a player is stealing is when they are first to act from late middle position, cutoff, button, or small blind and raise in an attempt to pick up the blinds and antes.
Thus it is only appropriate that the best time to attempt a resteal is when someone has done just that.
However, just because someone has raised first to act doesn’t mean they are stealing, nor does it mean that a resteal is appropriate.
There are several factors you should evaluate before deciding to resteal.
The most important factor of course is the likelihood that the player in question is stealing. If the initial raiser is a guy who has played three hands in the last hour, it’s best to save that move for a later time. If the initial raiser though is someone who has played three hands in the last orbit, this might be the time to make a resteal.
The question then becomes, how much do you re-raise when you are making a resteal? This is a tough question to answer because your opponent has one thing on you that will factor into his decision whether to call, re-raise, or fold. They have position.
Thus you need to know how much to raise in order to compel them to fold. If you make a small raise, they could very well call you to take advantage of their advantage post-flop.
On the other hand, you don’t want to raise so much that if they move all in or call, that you will be crippled. Ideally, you should make a raise of about 2-3 times their original total bet. For example, let’s say the blinds are 100/200 and you and the button each have about 7,000 in chips.
The button raises to 600. You should re-raise to somewhere around 1,800-2,400 total or a raise of 1,200-1,800. This is a big enough raise to discourage an easy call but it’s also small enough to give you some options should they choose to play with you.
Another factor that players often ignore is the stack size of the initial raiser. If they have only 8-15 big blinds and have opened the action, they are much less likely to be stealing than someone that has a bigger stack. They also might be getting the correct price to call.
For example, let’s say they have 10 big blinds and opened the action for three big blinds. Yes, they probably should just open shove but there are a surprising number of players that will do just this. If you raise enough to set them in there will typically be about 15 big blinds in the pot and they will have to call 7 big blinds, or over 2:1 on their money. They’d have to have a really bad hand to justify folding in this spot. Adjust your resteals accordingly against shorter stacks.
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