Sentence 1: Instead, it is run as though every year is the same as every other year and is therefore static in its outlook.

Sentence 2: They act like every year is the same, but things have changed greatly.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: Grassmarket has a memorial to the Covenanters (Scottish Protestant clergymen) martyred by Catholic Stuart kings in the 17th century.

Sentence 2: There is no connection between the Catholic Stuart kings and the Scottish Protestant clergymen.
Is this second sentence entailed by the first?

Answer: no

Sentence 1: 'The bastard sounds like you.'

Sentence 2: It is not good that he sounds like you.
Is this second sentence entailed by the first?

Answer:
it is not possible to tell