He was seeking easy money, not to improve society. Nor was he joking. Didn't look like a joke, didn't sound like a joke. Looks like a scam, was a scam. Not a joke.
Matt's "bet" was obviously a 100% trollish prank. Only those with a compulsive gambling problem would want to believe it was somehow (herr durp, maybe pirate is seekretly backing him???!!!1?) legitimate.
Just as with pirate, people were warned, repeatedly and loudly, not to take him seriously. But they didn't listen.
The bet started at a limit of 10k BTC or $110,000. That was a bit extravagant but modest enough for Bitcoins that could of been acquired months ago at a cheaper price. The bet was somewhat reasonable in the beginning. Trust in his gentleman's agreement was reasonable. It was only when he went beyond this limit that the bet came into question.
I will say that the larger betters should of insisted on escrow.