As you can see from the image at his island, he has these signs that says there is a chance to win diamond from one of these chests and its just a chance of picking the correct one. I used it and it turns out he was lying none of the chests contain any diamond they are all cobble. He uses chest shop signs that you can not see and 2 of them charged me $102 and the middle charged me $100.

 

Problem resolved he paid me back.

 

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