A common predicament arises in many backgammon positions called the “Pay Now vs. Pay Later” dilemma. It comes up most frequently in holding games. The idea is this: your opponent is hanging back waiting for a shot, and you are waiting for the opportune moment to clear your last point and secure victory. Suddenly, the dice gives you the chance to safety one of the checkers on your last point, leaving the other exposed. Do you take the risk (pay) now? Or, do you delay the risk, hoping for something better (e.g., a doublet) later? As this dilemma typically arises with the midpoint, it feels like a good moment to cover this lesson in the syllabus — one last lesson needed to truly master the midpoint.
My general sense is that new players vastly underestimate the likelihood of a good roll appearing, and so they tend to take unnecessary risks by Paying Now too often. When the game is in the balance, I think it would be great advice for beginners to avoid Paying Now until the last possible second. Let’s run through a sequence in a holding game to show what I mean.
Below, we have a typical holding game position. We are in the lead by about 20 pips, and if we could only clear the midpoint, we’d find ourselves in a pretty good situation. Suddenly, we roll a 54. Of course, we were hoping for the perfectly safe 53 or a large doublet, but this isn’t so bad since we have a potential landing spot for one of our midpoint checkers. The question is: do we Pay Now and clear the midpoint (13/8, 13/9), leaving a direct shot?
No! We wait for something better. Instead, we clear the 10-pt (10/5, 10/6).
Gary plays his turn, biding his time, and we roll a 54 again. We have 1 fewer landing spot, but we’re still lucky to have rolled a safe 5. We are faced with the same question: do we Pay Now and clear the midpoint (13/8, 13/9), leaving a direct shot?
No! Better to wait. We have many safe plays available to us… How about we unstack our 6-pt (6/1, 6/2)?
Gary plays his turn, strengthening his board. On our next roll, another 54! We’re starting to run out of landing spots and spare checkers. So, then, how about this time: do we Pay Now?
No! We still have safe plays left. Let’s cover two of our blots while we wait (8/3, 5/1).
Gary continues to strengthen his board, and we roll another 54. Once again, we have the opportunity to Pay Now, and play 1 checker to safety while leaving the other exposed. Do we take it?
No! We casually play two checkers from our 6-pt and wait for a doublet.
Meanwhile, Gary is starting to get desperate. He chooses to leave a checker behind on his midpoint to increase contact. We proceed to roll a 65. Now, we have a safe play available to us (8/3, 8/2), but that would eliminate our last landing spot in the outfield. We also have a strong, 5-point board made. Surely this time it must be correct to Pay Now, right?
No! Even now, it is much better to wait for a double. Clearing the 8-pt turns out to be the superior play.
This sequence of events is fairly typical in a holding game. Our situation gradually gets more dire as we lose landing spots and spare checkers, and our opponent’s board gets more threatening. Still, we had plenty of time for a doublet to appear. From the first moment we considered whether or not to Pay Now, we’ve rolled 6 times. You’d expect to roll a double every 6 rolls, so actually we should be expecting to roll a doublet, not merely hoping to.
Now, an astute observer might say, “But Orad, of course, you never wanted to Pay Now, Gary has always had a strong board, making it much too risky.” To this observer, I have a special position to share:
Here, we have a much stronger board than Gary’s, with more purity and no blots, compared to his 2 blots in his homeboard, 4 blots total. This position appeared in the 2013 World Championship Finals match between Vyacheslav “Slava” Pryadkin and Lars Trabolt. In this position, perhaps surprisingly, it is still correct to Pay Later. The eventual champion, Slava, correctly sussed this out, casually playing 8/2 6/1.
To conclude, there are certainly situations where it is worth it to pay now. Otherwise, this wouldn’t be much of a dilemma. That said, it’s a truly studied concept. I think most new players in holding games would benefit by playing maniacally safe, always Paying Later and slowly learning from their exceptions instead of trying to guess what makes a good “Pay Now” situation.
Further reading:
- Pay Me Now or Pay Me Later, an article by Kit Woolsey that I believe coined the term in the backgammon context.
- Pay Now or Later?, a video by Dan Rovira with a great explanation on when it’s actually worth paying now, on the Backgammon is Beautiful YouTube channel.
Next lesson: Playing loose 1: safety
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