You’ve lived your life by the turn of a card, the roll of a die, or the spin of a wheel. Luck has been both your ally and your enemy, and you’ve learned that fortune favors the bold—or at least, those who know how to cheat fate. Whether in the smoke-filled dens of bustling cities or the back rooms of roadside taverns, you’ve read more faces than books and learned that every risk carries a lesson. The thrill of uncertainty still calls to you, and perhaps adventuring is simply the biggest game of all.
- Ability Scores: Dexterity, Constitution, Charisma.
- Feat: Lucky (see chapter 5)
- Skill Proficiencies: Sleight of Hand and Persuasion
- Tool Proficiencies: Choose one kind of Gaming Set (see chapter 6)
- Equipment: Choose A or B: (A) 2 daggers, Gaming Set (same as above), 2 pouches, Costume, 2 Rations, 25 GP, or (B) 60 GP
You can convince nearly anyone to put up something that they aren't willing to part with (coin, property, or information) in a game of chance, but you must put something up, as your wager, of equal value (your DM determines if what you offer can be considered 'equal value') to what you are trying to win. When using this feature, you roll persuasion with advantage. This feature can only be used once per Rest without penalty. Any attempt to use this feature more than once per Rest, for each attempt after the first time, you roll persuasion with disadvantage.
Suggested Characteristics
| d8 | Personality Trait |
|---|---|
| 1 | I treat every challenge like a game—and I never play for free. |
| 2 | I can’t resist a good wager, no matter the odds. |
| 3 | I keep a calm face and a steady hand, even when my heart is racing. |
| 4 | Luck isn’t real—it’s all about knowing when to bluff and when to fold. |
| 5 | I talk my way out of trouble better than I fight my way out. |
| 6 | I believe every problem has an angle; you just need to find the right bet. |
| 7 | I hate cheaters—unless I’m the one doing the cheating. |
| 8 | I keep souvenirs from my biggest wins and worst losses as lucky charms. |
| d6 | Ideal |
|---|---|
| 1 | Fortune. The gods of luck favor the daring—so I make sure to give them a show. (Chaotic) |
| 2 | Fair Play. Everyone deserves an honest game… until they prove they don’t. (Lawful) |
| 3 | Freedom. I gamble because I refuse to be chained by anyone or anything. (Chaotic) |
| 4 | Ambition. Wealth and fame are just the stakes of the ultimate game: life. (Neutral) |
| 5 | Redemption. I’ve lost everything once—I won’t waste my second chance. (Good) |
| 6 | Control. Chance is an illusion. The clever make their own luck. (Any) |
| d6 | Bond |
|---|---|
| 1 | I owe a dangerous person—or organization—a massive debt I can’t easily repay. |
| 2 | I carry a lucky token from someone who believed in me when no one else would. |
| 3 | My old gambling partner double-crossed me, and I’ll see them pay for it. |
| 4 | The thrill of the game is nothing compared to the one person I truly care for. |
| 5 | I once ruined someone’s life with a bad bet. I owe it to them—or their family—to make it right. |
| 6 | I’m still chasing the one win that will make me a legend. |
| d6 | Flaw |
|---|---|
| 1 | I’ll bet on anything, even when I can’t afford to lose. |
| 2 | I can’t walk away from a challenge—or an insult. |
| 3 | I lie as easily as I breathe, even when I don’t need to. |
| 4 | I always believe my luck is about to turn, no matter how bad it gets. |
| 5 | I hold grudges far longer than I should, especially over money. |
| 6 | I value the game more than the people playing it. |
Previous Versions
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11/6/2025 2:00:41 AM
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3
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1
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Coming Soon
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11/6/2025 2:16:25 AM
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5
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Coming Soon
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