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Was there any damage to the box the speaker was shipped in? You should ask him to send you a picture of the speaker and the box.
Enough time has passed that it is really borderline whether you should take responsibility for the speaker issue. He had the speakers for almost two weeks and anything could have happened in that time. Perhaps do the paperwork with the shipper for the $100 automatic insurance.
Another thing you should always do is make a note of the serial number of any gear you are selling, before shipping it. Then include that in the auction description, or email correspondence with the winner after the auction ends. It might discourage people that like to do the switcheroo.
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