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Money Play. How should Red play 31?

Red’s best hope is to outprime White even if that is relatively unlikely. Therefore, 5/2*/1 is the wrong plan.

The best play is 8/4, hoping to either make the point next time or get hit and stay on the bar long enough to preserve the home board. 5/1 without hitting is the second-best play. The 3-pt anchor will give Red long-term winning chances and he actually wins more than 25% of the time from here, although he loses quite a few gammons.