You dont know that, and its very unlikely. But if indeed Pirate doesnt have most of the coins he owes, he and his investors are in deep trouble. Good luck trying to buy 10s or 100s of 1000s of coins without BTC exchange rate shooting through the roof.

Moreover, whatever pirate is doing, and assuming its not a ponzi/scam, if he needs to trade btc for $ or vice versa, it would be in his interest not to say if he is long or short on coins and in fact give the opposite impression. Just saying he needs to buy 100K BTC would cause a huge price increase. Likewise, if he plans to sell out, he would most likely say or imply the opposite to ensure a better price for his coins.

To think Pirate is just showing you his cards is naive, or assuming Pirate is naive.