instruction: Is the next sentence syntactically and semantically acceptable?

Near everyone Angleton did, Dulles stood.

response: unacceptable

instruction: Is the next sentence syntactically and semantically acceptable?

Darin has eaten more squid than John has octopus.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

John made a fool of himself in front of anyone who was there.

response: acceptable

instruction: Is the next sentence syntactically and semantically acceptable?

The money which I will have a chance to squander amounts to $400,000.

response:
acceptable