Hmmmm. I've had a few big ones.
Blackjack letting it ride 6 hands in a row. $25 -> $50 -> $100 -> $200 -> PUSH -> $400 -> BJ (2/1) $1000. This paid for approximately a single dinner for 5 at Momofuku in The Cosmo and it was so worth it. Still the best food I've ever had.
Danny Willett $10 at 150 for the Masters. Brooks Koepka this year $50 at 50-1. Tony Finau this year $50 at 35-1.
My buddy hit same number in roulette (26) 3x in a row. Back to back, walked away, and again when we left. $10, $20, $100. And the table ALL played with him on the last one. I'm pretty sure they thought he cheated, pit bosses stared him down for a good long while. I think on the last hit there was well over $5k on 26. They had to bring in the GM of the casino to verify it all and give payouts. Some rich dude walked away with what had to have been over $18k and bought us drinks the rest of the night lol. He threw $500 on it.
I definitely am missing a few, but cant think of them right now. We've done the BJ let it ride to success a few times, but usually stop after 4 rounds.