Sentence 1: Perhaps the story worth telling about Bush's military service is not whether it was cushy or patriotic, but how it was both.

Sentence 2: How Bush's military service was cushy and patriotic, is a story that should be told.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: I want to see you, Rennie! The officer stamped forward a step or so, to stand in the full light of the first lantern.

Sentence 2: The officer wanted to see Reese.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: Jon could smell the rider's horse and see the red light on his boiled leather armor and deeply worn boots.

Sentence 2: The rider was Jon's enemy.
Is this second sentence entailed by the first?

Answer:
it is not possible to tell