D&D 2024 Backgrounds - Grifter
The grifter is a background I have done previously. I’ve updated it for use with D&D 2024. A grifter is often one part bard, one part thief, with a dash of arrogance and a sprinkle of narcissism. Whether the hustler on the street corner luring you into a game of three card monty or a crew working a long con, they all have one thing in common - separating you from your money without realizing you’ve been conned.
Grifter
Ability Scores: Charisma, Wisdom, Intelligence
Feat: Unchecked Confidence
Skill Proficiencies: Deception and Persuasion
Tool Proficiencies: Gaming Set (Three-dragon Ante Set)
Equipment: Choose A or B: (A) Costume, fine clothes, three-dragon ante set, traveler’s clothes, waterskin, 27gp or (B) 50 gp
Your charming smile and self-assurance have allowed you to separate many a victim, known as the mark, from their coin. You are a natural in the art of the con. You learned at an early age that acting with complete confidence and seducing people with the lure of riches is, for you, a much easier and less violent way to steal money.
You started by learning the art of the short con. Using words and sleight of hand, you found a quick and easy way to get cash in your pocket regularly. It was a grind, however, as the small scams you ran never seemed enough. Every day was a struggle, and you had to hustle every day just to make ends meet. As you grew older, you discovered and learned the art of the long con. Through careful planning and manipulating your victims, you plotted over a series of days, weeks, or even months for a much bigger score than when you ran short cons. Targeting nobles and wealthy merchants, you were to turn the higher risk of the long con into a much larger bounty. Some grifters work solo, while others work with a crew. No matter what style fits your personality, there has never been a mark you haven’t been able to swindle.
Background Story Ideas
You conned the wrong person early in your career. Since then, they have spared no expense to hunt you down.
Your proficiency in running the short con caught the eye of the local thieves guild, who took you in. You completed an ‘impossible con’ to gain freedom and left in good graces.
You were the frontman in your crew when you were young. After a con went wrong, everyone in your crew was captured or killed. You’ve tried to leave that life behind, but it is all you know how to do.
Origin Feat
Unchecked Confidence
Some say it’s overconfidence, but you’re comfortable saying it’s an undeniable abundance of Charisma.
You gain the following benefits.
Gaming Set. You gain proficiency with two gaming sets of your choice.
Confidence Points. You have a number of Confidence Points equal to your Proficiency Bonus and can spend the points on the benefits below. You regain your expended Luck Points when you finish a Long Rest.
Advantage. When you roll a d20 for Charisma check or to impose the Charmed condition, you can spend 1 Confidence Point to give yourself Advantage on the roll.
Disadvantage. When a creature rolls a d20 for a Charisma check or to impose the Charmed condition against you or an ally within 30 feet, you can spend 1 Luck Point to impose Disadvantage on that roll.
