Sentence 1: Well, I'm damned!

Sentence 2: That's not surprising.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: Caterpillar believes the risks are too high.

Sentence 2: Caterpillar things that there is no risk in doing that.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: He waited for the group on the nearby 18 th green to finish.

Sentence 2: He was irritated but waited for the group on the 18th hole to finish.
Is this second sentence entailed by the first?

Answer:
it is not possible to tell