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.
This is just unbelievable and this is a huge bet at the moment and as a person who has seen Bitcoin at $100 I can fully understand you, because at one time a friend also threw me a tenth of a Bitcoin, and I used this money to pay for housing and communal services. Lol.
No, I've never placed such huge bets in gambling. The only big bet I've ever made was $50 for a spin on the slots.