Position 460

 How should White play 53 here:

You first wonder if just making your 5 point is correct here. Consider 10/5 8/5:

It is often said “if in doubt make your 5 point”. But here you should have a lot of doubt. You are trying to prime a single black checker and that checker is at the edge of your 4 prime. With any 6 or 5 Black can jump your 4 prime and escape.

You do not want to get into a prime versus prime battle where Black has only one checker back but you have 3 checkers back, as that is not a winning strategy.

If you want to go ahead in the race you can hit 23/15*:

Although this sends black back the most pips, Black can hit you from the bar with 55, 33, 11, 62, 53, 52, 51, 32, 31 and 21 – 17 rolls or 47% of the time. This is way too many return shots for Black.

Consider 8/3* 6/3:

Now you are only hit from the bar with one roll 55. Rounded up that is 3% of the time, a difference of 44% of the time you will be hit. Getting ahead in the race would be nice, but you are sacrificing too much to achieve that goal.

You will also have 3 builders aimed at your open 5 point.