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 can't remember but it was just around $100 = x amount of Bitcoin in around 2018. So I think it's a big amount as we are in the bear market that time. Yes, we really don't know back then that Bitcoin will be this huge and if we could just go back in time and hold.
In any case, no regrets though, I mean for gamblers it's just money and we wanted to enjoy and just have some fun. It was a sports bet, it was in NBA games and I remember the team, it was Portland and Dame was still playing with them it was one of those game winning shot, so it's all good and for fun.