Roll20 Marketplace Product

A Card-Driven Fantasy Roleplaying Game of Fate, Fools, and Fortune

Jester’s Gambit is a complete fantasy tabletop roleplaying game built for Roll20, where fate is dealt one card at a time. Players create strange heroes through randomized card choices, explore dangerous fantasy encounters, collect odd treasures, survive brutal injuries, and gamble with fortune as the story unfolds.

Built with a whimsical-but-dangerous tone, Jester’s Gambit mixes fantasy adventure, dark humor, strange magic, and unpredictable card-driven play. Characters are made from Race Cards, Trait Cards, Class Cards, items, spells, and optional Flaw Cards, creating heroes who feel different every time they enter the game. The core design focuses on card-based character creation and card-based exploration, with encounter cards that can reveal enemies, events, shops, traps, challenges, or free loot.

This main game includes everything needed to begin playing Jester’s Gambit on Roll20: a full rules system, character options, enemies, allies, and a massive library of cards ready to deal into your campaign.

What’s Included
Full Jester’s Gambit core rules
687 cards
10 unique playable races
15 playable classes
26 enemy stat blocks
11 allies
Race, class, trait, flaw, injury, spell, item, encounter, shop, enemy, and reward cards
Card-driven character creation
Card-driven adventure and encounter play
Fast fantasy combat using Strength, Reflex, Brawn, Mind, and Charm
A dangerous injury system where heroes can stay standing by accepting lasting wounds
Roll20-ready content for quick setup and digital play
Create Heroes by the Deal of Fate

In Jester’s Gambit, players do not simply build characters from a menu. They draw from fate. Choose from strange fantasy races like Goatmen, Calavera Skeletons, Moon Wildlings, Quirrels, Dragnons, and more. Then combine those races with traits, classes, spells, gear, flaws, and cards that can twist the character into something heroic, cursed, ridiculous, or terrifying.

15 Classes Full of Strange Power

Take the battlefield as a Barbarian, Clown, Hex Warrior, Living Weapon, Mage, Minstrel, Rubber Hose, Thief, Zoanthrope, and more. Each class brings its own flavor, abilities, resource style, and role in the party, giving every campaign a different mix of chaos and strategy.

Deal the Adventure

Game Masters can use the card system to quickly create unpredictable sessions. Draw cards to reveal enemies, traps, events, rewards, shops, and strange situations. Every card adds momentum, surprise, and replayability, making Jester’s Gambit ideal for one-shots, campaign arcs, dungeon crawls, weird fantasy adventures, and chaotic table nights.

Whimsical. Dangerous. Unpredictable.

A hero may win glory, draw a cursed flaw, stumble into a deadly encounter, uncover a legendary scroll, or survive a killing blow by accepting a terrible injury. The game is built for players who enjoy fantasy adventure with a sharp edge, a little madness, and a lot of surprises.

Shuffle the deck. Deal the cards. Trust the fool.

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License: Roll20 End User License Agreement
(Personal Use Only, Do Not Distribute)