Woolsey's Law

To double or not to double, that is the question. What should our thought process be?

First of all, we (mentally) move to the other side of the table and ask ourselves the following question: If we were doubled in this position, would we take? There are three (not two) possible answers to this question:

1) Yes, I'm absolutely sure it is a take.
2) No, I'm absolutely sure it is a pass.
3) I'm not 100% sure.

If the answer is (1 - Take), then it still might be correct to double. This would be the case if there were a significant chance that on the next exchange (we roll, he rolls) he will now have a big pass. If the position is that volatile, it is proper to double even if the take is easy. Otherwise it is correct to wait.

If the answer is (2 - Drop), then it still might be correct to double. This would be the case if either the gammon chances were small or if there were a significant chance that after the next exchange (we roll, he rolls) he will now have a big take. Otherwise it is correct to wait and play for the gammon.

If the answer is (3 - Hmmmm), then it is always correct to double. I have written this elsewhere calling it Woolsey's Law. It is valid in virtually all situations. The only possible exception may occur when you are well ahead in the match and the double would put you out or nearly out. In this situation it may pay to be conservative. Otherwise, follow Woolsey's Law. You won't go far wrong.

Source: Backgammon Galore