Re-stealing is one of the best methods of chipping up when you are a short stack. The key is to make sure that you’re not so short that calling is automatic for the initial raiser. Ideally you want to have enough chips that calling would hurt their stack and they’re not getting a ridiculous price to call like 2-to-1 or better. Usually somewhere in the range of 12-15 big blinds is the right number of chips to pull off a successful short stack re-steal.
Let’s look at an example to see why. Say your opponent has 30 big blinds and has opened the action for three big blinds. If the blinds are 500/1,000 with a 100 ante at a ten-handed table this means there is 5,500 in the pot. If you have 9,000 left after posting your big blind and move all-in there will be 14,500 in the pot. Your opponent would have to call 7,000 to win 14,400 or over 2-to-1 on his money. What if you had 14,000 instead of 9,000? Now your opponent would have to call 12,000 to win 19,500 or 1.6-to-1 on his money. The price change is significant but more importantly 9,000 is a much smaller percentage of his remaining stack than 14,000. He can make the 9,000 call and still have 18,000 if he loses. If you hold 14,000, however, he'd only have 13,000 left if he lost.
All the correct conditions
As is the case with any type of re-steal, and perhaps even more so when you are a short stack, you need two conditions to be in place before attempting the move. One, your opponent must be willing to fold. If he isn't, the move will never work. Second, your opponent needs to be the kind of player who is raising light. Re-stealing against a rock has about the same probability of success as re-stealing against someone who never folds: little to none.
Re-stealing should not be something you use as an excuse for bad play. Shoving and crossing your fingers is pure gambling, but analysing a situation and exploiting your opponents’ playing habits, albeit with some degree of risk, is another matter entirely.