So the deadline for, uh, something passed last night at 5 PM CST.

Wait a second, "CST"? This is a clue that Pirate is posting from the Central time zone... From the FUTURE, when CST applies. I've figured out how he does it! Pirate is engaging in temporal arbitrage by sending his coins to the future when they are more valuable and sending fiat back in time. He finally slipped up!