Magriel's NYT Columns 
 Black to play 42. 
In the diagrammed position, Black, with all 15 men in his home board, is ready to begin bearing off. Black has a 42 to play which gives him two options:
 He can play 4/off, 2/off, bearing two men off.
 He can play 6/off, using the whole roll to bear a single man off the 6point.
The novice may choose option 1, simply to remove his men as quickly as possible. This approach is superficial. Black’s objective is to bear off all his men as safely as possible, not necessarily as quickly as possible. As long as he avoids being hit, both the game and the gammon as assured.
The problem confronting Black is to find the safest procedure. Because White holds the 5point, the danger lies in clearing the 6point. Thus the only relevant difference between the two options is the number of men that would remain on the 6point after each play. A more experienced player will attempt to assess the options by using his knowledge of the odds. He computes how many ways, in each case, Black would be forced to leave a man exposed on the 6point on the following roll:


Option 2. This leaves two men on the 6point and forces Black to leave a shot next time with either 61 or 51 (four ways out of 36).
Based on this comparison an experienced player, like the novice, would also choose option 1, for its apparent safety value. However, the expert sees a flaw in option 1. In backgammon, sometimes a little knowledge of the odds can be misleading.
The safety of option 1 is illusory. This play is safer only on the very next roll. Black must instead consider the overall problem of removing all his men from the 6point. Option 1 is ultimately more dangerous because Black only delays clearing the 6point. Unless Black is lucky enough to roll a double, he will eventually reach the option 2 result anyway — two men on the 6 point. He is merely postponing the same danger he was trying to avoid. Thus option 1 places Black in double jeopardy; that is he exposes himself both to the risk of rolling a 65 in the threeman position immediately and later to the risk of rolling a 61 or a 51 in the twoman position.
The correct play, 6/off, immediately prepares Black to clear the 6point, without first incurring an additional risk. This play, even though twice as dangerous on the next roll, is safer overall. In fact, a refined mathematical analysis shows that Black is actually 30 percent more likely to be hit sometime during the bearoff by exposing himself to double jeopardy with the incorrect play.
Rollout
Tom Keith 2013 

Money play White owns 2cube Black rolls 42 1296 games with VR Checker play: 2ply Cube play: 3ply Red 
42:  Game  G  BG  Equity  
1  6/off 
W L 
.9714 .0286 
.9537 .0000 
.0003 .0000  +1.8814  Option 2  
2  4/off, 2/off 
W L 
.9660 .0340 
.9481 .0000 
.0005 .0000  +1.8640  (0.0174)  Option 1 

