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My boss told me this one:
A friend of his, who also happened to have a very senior role working in a large international company, liked to score free food at the markets.
He would dress very scruffily, creating an unkempt look. He waited until the markets were nearly closing, then went to browse.
The shopkeepers, seeing this shuffling, ruffled man, would give him free fruit and vegetables, thinking he was homeless.
Apparently, he never actually said he was homeless, but was simply taking advantage of the human tendency to judge things based on physical appearances.
I think he was just an asshole who liked to take advantage of other people's kindness.