Jolly Jack (Halfling Treasure-Taker)

Halflings are known for their cheerful ways, but you’ve found your joy in turning the tables on the greedy and the cruel. You seek treasure not just for wealth, but to prove that wit and daring can outmatch tyranny and hoarding. You’re no common cutpurse—you’re a thief with principles, a rogue who believes that fortune ought to be shared, not locked away.

Ability Scores: +2 Dexterity, +1 Charisma (Quick, charming, and principled.)

Feat:

Nimble Climber

Prerequisite: Dexterity 13+
You scale walls, trees, and ruins as though gravity is optional.

• You gain a climbing speed equal to your walking speed.

• You can attempt to climb in difficult circumstances without a check once per short rest.

• When making Acrobatics checks to move through tricky terrain (narrow ledges, hanging vines, steep slopes), you roll twice and take the higher result.

Skill Proficiencies:  

• Stealth (for slipping in where you shouldn’t be)

• Insight (to judge who deserves to be stolen from—and who doesn’t)

 

Tool Proficiencies: Thieves’ Tools

Languages:

• One of your choice (you picked it up while bargaining with smugglers, mercenaries, or treasure dealers)

Equipment:  

• A small token from someone you helped with your “redistributed wealth” (a wooden bead bracelet, a patchwork coin, or a thank-you letter)

• A set of dark common clothes with a hood

• A deck of cards marked for luck

• A belt pouch containing 15 gp

 

Suggested Characteristics

Personality Traits

1. I laugh in the face of danger—it’s more fun that way.

2. I don’t mind being underestimated. It makes the reveal that much sweeter.

Ideals

• Justice. “The rich don’t need all that gold—others do.”

• Freedom. “Nobody should be chained down by greed or tyranny.”

Bonds

• I once stole from a cruel lord and gave it all to his victims. Their gratitude fuels me still.

• I protect my crew above all else—we’re in this together.

Flaws

• I can’t resist taunting authority, even when it’s unwise.

• My code makes me predictable to enemies who know me well.

d2	Personality Trait
1	I laugh in the face of danger—it’s more fun that way.
2	I don’t mind being underestimated. It makes the reveal that much sweeter.

d2	Ideal
1	Justice. “The rich don’t need all that gold—others do.”
2	Freedom. “Nobody should be chained down by greed or tyranny.”

d2	Bond
1	I once stole from a cruel lord and gave it all to his victims. Their gratitude fuels me still.
2	I protect my crew above all else—we’re in this together.

d2	Flaw
1	I can’t resist taunting authority, even when it’s unwise.
2	My code makes me predictable to enemies who know me well.