A corrupt society always punishes those that seek to improve it.
Hope you are not imply his most reaction action was an act seeking to improve "our" society?
Pretty sure he did it for his own entertainment and maybe even profit.
More recent logs of him talking about it prove at least the first part.
The second part is pretty much the nature of gambling, bets, hedging what ever you want to call it.
Anyone who sets out to point out that the vague and interpretive nature of language, laws, agreements, rules and any other arbitrary/false authority is exactly that, arbitrary and false, is doing so in order to prove that we need to operate on a reality based society. Why invest so much time, effort, emotion and attention to frivolous things like money, games, politics, religion etc., when it ultimately hinders and cripples us rather than makes things better for everyone. We are so caught up in these myriad fantasies that we do not even notice when the very important and real systems and structures that support life are crumbling to ruin and are enduring irreparable harm.
Matt most likely feels bad because he has spent his life in a society that promotes and rewards adherence to arbitrary rules and false authority because that's all many of us have ever known. But for those that have learned that we can't rely on fantasies, meaningless words and empty promises then they have learned that it is time to pay attention to reality instead. And that is an improvement to our society that I wish was happening sooner and faster for everyone.
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