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Bearing Off Answer

It's often right to take as many checkers off as you can, not only because you win more gammons, but also, it helps your winning chances.  You might leave a shot later no matter which play you make, but with 2 more checkers off, you're going to win more often even if you get hit.

If you look at the numbers on the ExtremeGammon XG+ Rollout, you will see that the aggressive play gets you 6 percent more gammons and your wins stay about the same.