I am surprised that you thought it would be a joke even after Theymos and Mage made their bets. I thought it was our lesson, but somehow it became your lesson.
They placed their bets relatively early. Looking back at Matt's posts I am convinced he created an honest bet to begin with. The "technicality" he escpaed payment from (in his mind only) is so lame it can only be an afterthought. He made an honest wager, was sure Pirate would pay and when it became clear he wouldn't rather than face the music he raised the cap racked up another 70K BTC in bets, and came up with his exist strategy.
If you look at his early posts he was selected in who he took bets from, requires some younger members to escrow their portion (why have someone escrow a bet you know you will lose). That changed roughly 14 days ago when he raised the cap, and started accepted 1,000 BTC bets from Jr members.