Sentence 1: "Sounds as if it might be important,"Drew commented.

Sentence 2: Drew said that it could be important.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: A small, furry, ultra-observant Dutchman in a big black hat is funny if he's not Peter Stuyvesant, who, were he alive today, would probably stick with the Republican Party, but could perhaps become funny if a Jewish squirrel bit him on the ass.

Sentence 2: Peter Stuyvesant is no longer alive.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: They occupied Edinburgh (but not the castle) and defeated a government army at the Battle of Prestonpans.

Sentence 2: They did not spare anything during the battle at Edinburgh. They destroyed everything and every place.
Is this second sentence entailed by the first?

Answer:
no