Sentence 1: Very sad.

Sentence 2: The thing that happened is sad.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: Mrs. Cavendish, however, was a lady who liked to make her own plans, and expected other people to fall in with them, and in this case she certainly had the whip hand, namely: the purse strings.

Sentence 2: Mrs. Cavendish always goes with the flow.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: And Visual surprise is natural in the Caribbean; it comes with the landscape, and faced with its beauty, the sigh of History dissolves.

Sentence 2: The Caribbean is also a setting for a certain bunch of pirates.
Is this second sentence entailed by the first?

Answer:
it is not possible to tell