Sentence 1: Yes, the American people have a right to be skeptical.

Sentence 2: The Americans are able to be skeptical.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: This war of attrition ended in 1739, when agreement was reached between the two sides.

Sentence 2: The war was brutal, with hundreds of thousands of casualties.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: Senator, You and Cindy -- Are the greatest -- I had the time of my life

Sentence 2: I had dinner with the Senator and his wife Cindy at this amazing restaurant.
Is this second sentence entailed by the first?

Answer:
it is not possible to tell