In hindsight, mine didn’t age very well… in 2015 my best freind and I were on opposite ends of an MMA bet. I was convinced Connor McGregor had the power to beat José Aldo and avoid the grappling. At the time, I thought McGregor was the best striker and best talker the UFC had seen (he objectively was at the time). He won, my buddy was inconsolable and I put 300 bucks in my pocket. For YEARS it was a fat feather in my cap.
Edit for clarification, it was a 100 dollar bet he gave me 3 to 1 odds on because McGregor really should have lost based on everything. So phenomenal win and the fact it was over in seconds was peak excitement. It aged poorly because McGregor turned out to be a rapist.
2 cousins and me participanted in a Formula 1 Fantasy league over the whole season (24 races, all year long). We bet some money on it.
I created a program that would run simulations, scenarios and see tendencies that helped me make informed choices before the next race. Aditionally, one of my cousins was very annoying about it, he would use every small victory of his team to agressively mock us in our faces, and this made impossible to talk with him about actual F1, because all he could see was this fantasy league.
Each of us had right to manage 3 teams, and we agreed that winner takes 75% of bet pool, and second team takes 25%. In the end, I won it all :)
It was satisfying to 1. win thanks to a program I created; 2. win to my annoying cousin, 3. win both first and seconds place.