I was reading some old posts about gambling and figured this might be a good question to ask here, especially for the old-timers, those who were already around during the early days.
I hope when you share your story, it won’t be something you regret too much.

We're not talking about your biggest wins here, but your biggest single bet, and maybe include a little background too, like how much that amount was worth at the time and why you were willing (or able) to risk it.
I’ll start with mine. Back in 2016, I remember placing a max bet of 0.1 BTC. I don’t recall the exact price of Bitcoin at that time, but looking at today’s price, that’s around $12,000. No way I’d ever do a single bet that size now.

But it was one of those moments I’d probably tell my kids about someday… especially if Bitcoin ever hits $1 million per coin.
I've not actually spent any BTC gambling before. It's kind of something I don't really think I would do. Every bitcoin I own and buy is very special to me because they are more like an investment for me. I one time won on a casino and got the bitcoin deposited directly there.. I transferred them out and left just little fractions of satoshi.. but eventually I lost them to crash game lol.. the fact is we don't want to be spending our bitcoin on gambling. I mostly gamble using my local faith currency since it's much easier to deposit through my local bank..