Sentence 1: I don't see why he wished to be arrested?"

Sentence 2: I cannot understand why he would have had a desire to be arrested?
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: uh it's a social programs without the corresponding responsibility i guess is

Sentence 2: Social programs have nothing to do with this.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: well see i don't really see the need of it you know how many elementary school teachers do you think are going to be on drugs

Sentence 2: I think most elementary school teacher get away with using drugs during work.
Is this second sentence entailed by the first?

Answer:
no