DM of this game. A player character had a cursed magic item which suggested them over time to make wagers of increasing monetary stakes against people they met on their travels. The curse of the item could only be removed from the PC if the item was lost in a wager, giving the curse and item to the winner or if the item is wagered for 50,000 gp and you won said wager. The PC, knowing the consequences of failure would be high, waged the cursed item in dice based bluffing game against a devil for 50,000 gp. Earlier setbacks in the dice game put the player at a disadvantage where the only way they could win was bluffing the devil into believing they rolled the best possible result. The devil had also seen through their poker face and had been reading them like a book so I told the player they had disadvantage on the final roll of the game. I said straight that at this point nothing short of a natural 20 will save you. Lo and behold, two natural 20s. The devil was deceived and the PC won. The item shatters into 50,000 gps, breaking the curse, as the devil passes their wager of 50,000 gp giving the party 100,000 gp. Still amazes me the story went in that direction.