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Answer:
HEELED
Possible Questions:
Followed orders
Well-to-do
Listed
In the money
Did some cobbling
Followed closely
Was an obedient dog, perhaps
Well-__ (affluent)
Well-___ (rich)
Like shoes
Well-_____ (rich)
Well-___ (in the money)
Well-__ (rich)
Well- -- (wealthy)
Was an obedient dog, in a way
Walked alongside one's master
Tilted, at sea
Obeyed on a leash
Obeyed a canine command
Followed, as a dog its master
Followed, as a dog
Followed obediently
Followed closely, like a dog
Followed closely, dog-style
Followed closely, as a dog