Sentence 1: Don't let the fact that he's an overseer fool you.

Sentence 2: The overseer's decisions were questionable to the characters.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: No; it is not possible you should love the enemy of France, but, in loving me, you should love the friend of France; for I love France so well that I will not part with a village of it; I will have it all and, Kate, when France is mine and I am yours, then yours is France and you are mine.

Sentence 2: I am an enemy of France, willing to part with it.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: She remembered that this was one of the men Tommy was shadowing when she had last seen him.

Sentence 2: Tommy was tailing this man when she last saw him.
Is this second sentence entailed by the first?

Answer:
yes