2010-07-10 Money Play/Answer

You simply must hit and take your chances.  Yes, you can lose immediately, and White picks up all three of your blots you can even get gammoned, but your odds of winning the game are so much higher when you hit that you have to take the risk.  "Sometimes the greatest risk is to take no risk at all."  

There is no general rule that tells you when to hit and when to just try to win the race, as distribution, the pip count, odds of getting back in and still winning after you get hit, and gammon odds (both ways) come in to play, but generally speaking, if the race is within 10 percent, from a pure hit vs. race standpoint, it's generally better to hit.