That may be true, although one interesting way of looking at this is that Matthew was actually peddling an insurance product rather than a gambling wager as classically understood. I don't have all the transcripts of what exactly Matt himself said, but there was certainly a lot of discussion about this being a way to hedge a Pirate default.  Financial insurance products such as credit default swaps and even classic insurance are all "bets" in a way between those exposed to risk and those offering an offset.

So it may be that for many Matthew bets, there was no skin in the game, and it was just a wager on the sideline about whether Pirate will pay, just like whether Liverpool will win.  But for those holding Pirate debt and looking for a hedge, this contract worked more like insurance and, depending on what Matthew said about it, might be more solid in terms of a liability in legal proceedings.  Maybe.