Sentence 1: yeah yeah that's pretty bad

Sentence 2: That's not good.
Is this second sentence entailed by the first?

Answer: yes

Sentence 1: John D. Rockefeller Jr. provided th e money to build this wonderful Art Deco/Neo-Byzantine edifice in 1927.

Sentence 2: John D. Rockefeller Jr. was an admirer of the Art Deco style.
Is this second sentence entailed by the first?

Answer: it is not possible to tell

Sentence 1: Hannah was recently spotted in New York wearing a hat with a star on it, while Kennedy was photographed elsewhere in the Big Apple wearing a T-shirt with--are you sitting down?

Sentence 2: Hannah was recently spotted wearing a hat with a star on it, Kennedy was spotted wearing a T-Shirt with stripes on it.
Is this second sentence entailed by the first?

Answer:
it is not possible to tell