2) He's trying to cover the fact that he's actually *selling* Pirate debt.
I don't understand what you mean by selling his debt.
I can understand how he could buy it at a discount, which would equate to a partial discount. But selling it? Selling what?
Buying it would involve giving someone money.
Selling it would involve getting more money.
He's been selling Pirate IOUs all along. Maybe he's still selling them, I dunno. But he's not buying them, lol.