Sure, he could _buy_ passthrough shares at distressed rates. If he had an intention of paying up, this could save him a lot of money in the long haul. Bu that is not the topic of this sub-discussion.
ETA: "...sell them at a discount...". What motivation would he have to do that?
When it compounds to, say, 13,000 BTC, he can turn around and sells it for 6,000 bitcoins or so, he just made 6,000 bitcoins for nothing. Plus, while that 10,000-13,000 bitcoin PPT was outstanding, it makes him look bigger and helps build a market for PPTs.
So before the 'close' he may have bought a lot of PPT debt. OK. But that does not equate to newly-minted debt (debt issued after the close), which is the entire scope of discussion.
I explicitly qualified my scenario as being one in which he has a desire to redeem his debt. In this scenario, it most certainly makes sense for him to buy heavily discounted Pirate debt. If he can absolve 1BTC of obligation by buying it on the open market for 0.5BTC, then that is 0.5BTC less he needs to pony up to settle. If he leaves it on the market, he would need to spend the full 1BTC to settle the debt.
But this is obvious, and I can tell you are a smart guy. Are you just not reading what I am writing, or are you trolling me?
Lastly, I disavow any knowledge of the last paragraph you quoted, as it was not a quote of my writings.
He did not buy any of his own debt. That makes no sense if you have no intention of paying. Some have speculated that he SOLD debt after the 17'th through sockpuppet accounts but I doubt that really happened.