What's the most degen bet/gamble/trade you've ever made?

I'll start:

60% of my NW is in crypto and/or COIN

Crypto @ Coinbase, foreign policy, political theory. yugacohler.twitter

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I didn’t pull profits on clucoin, resulting in my initial $80 investment, turning into what it is today. 5 billion CLU > at its peak, almost $800.00. Now?  Maybe a wooden nickel since its founder admitted to robbing the project to fuel his gambling addiction. It gamified early so I made money other ways from them.