passive Insight is a nice and easy way to represent that, or Sleight of Hand vs. For example, in poker a big part of the skill comes from hiding your reactions and bluffing your opponents, so Deception vs. Otherwise with simplicity in mind you usually want to boil it down into some relevant skill check(s), which will depend a lot on the game.

Though if you want to play an actual dice game that can work well enough with the tools at hand (Plaguescarred's example is a really good one). Gambling is a tricky one, for me the key is to keep it as simple as possible D&D is firstly a roleplaying game, not a gambling simulator, and the more rolling you have the players do, the more you'd be better off just actually playing poker or dice or whatever. Don't fall in the middle, that's my opinion.

This is nice because statistically speaking a PC is going to win more often than they lose if they're proficient. Xanathar's Guide has a table of things that might happen if a player keeps gambling for a while. A bluff would be Deception against Insight, pure skill would be the chosen ability plus proficiency with the game, and cheating would usually be Sleight of Hand against Perception.

Or whatever feels appropriate to you for them. I would suggest dice are Charisma (maybe?), chess is Intelligence, cards are Wisdom, and I don't know what three dragon ante even is, so let's call it Strength for laughs. There's a bunch of gaming sets a character can be proficient with. So the gambling system you use only needs to fill a pretty small range of play. Or they can, but it doesn't matter to you who wins anymore. Phandelver and Below: The Shattered ObeliskĪfter, like, level 3, you're getting enough money that nobody can afford to gamble with you anymore. Mordenkainen Presents: Monsters of the Multiverse

Good gambling games