42.5kBTC now.
It's funny that this is getting up to be a significant percentage of the estimated Pirate debt at the time of collapse. Pirate being Matthew's backer would be quite a funny twist; if Pirate has enough BTC left and could afford to buy back enough of his debt at a really distressed rate, he could still make out handsomely on this without being as open to getting in trouble with the law.
I don't think so. I'm not sure, but I don't think so. Here's why:
For Matthew to win his bet, Pirate has to settle with everyone. For people who insist on 100% payout, the only way Pirate can settle is to pay 100%. Because some people think Matthew knows something they don't, they're much less likely to take a low settlement. This is especially true for people who took Matthew's bet to hedge. If they take a partial payment, they may lose their bet with Matthew. If they refuse, they are guaranteed either 100% payment or they'll win their bet.
So Matthew's bet almost certainly made it much more expensive for Pirate to settle. I suspect by at least 40,000 BTC. (Weirdly, this means that if Matthew loses, most of that money may wind up indirectly going to Pirate since Pirate benefits from the higher value of his debt because he can sell it for more.)
Oh, I don't think that's what Matthew is doing either, it was more just a commentary on how massive the size of this bet has become. As the date comes closer and closer, it's possibly people will continue to toss bets that they think are sure things. It could easily double in size towards the end.
That being said, apart from the fact that it could make it more expensive for Pirate to buy back his debt it would become almost an impossible logistical nightmare to contact all his debtors in a couple day span and negotiate a lower settlement. Those he can't contact he'd have to pay out in full plus interest in order to win the bet. It would only be feasible if Pirate was running an incredibly profitable business that just spiraled out of control, still has a significant percentage of what he owes and wants to walk away with cash in the bank without getting sued or arrested.
There's no reason to think that Matthew is colluding with Pirate though, other than how insane it seems to continue taking bets at this point if that's not the case.