If this is true, then he was probably trying to manipulate the market by making negative comments to drive the price down. It could have been his desperate attempt to get in on Bitcoin if he hadn't gotten in earlier. With the price over $4000 when he made negative statements, he probably regretted not buying when the price was much lower.

This is probably true of a lot of people that didn't believe in Bitcoin and thought it would fail. They waited until the price was too high to make a fortune. Now they have to settle for buying in the thousands and still making a profit but one that isn't as big.