Question

What is the multiple meaning of this sentence. "We watched Willy over the counter, enter the bank , and take the money."

Answer 1

It could mean that the speaker and their company watched Willy from over the counter, (they were behind the counter) and they watched him enter the bank and take the money.
Or it could mean they watched Willy go over the counter, enter the bank and take the money.
Or, take the money could mean that Willy went to a teller and asked for money
Or that Willy robbed the bank.