Backgrounds - The Grifter

Backgrounds - The Grifter

I was going to do the next pack in the Equipment Packs series, but I kept coming back around to this throughout the week. I decided it wasn’t worth fighting it and started on the Grifter. It was a fun background to write, and I hope you enjoy it as much I do.

The Grifter

The grifter background is not meant to be just a rehash of the charlatan, but the continuation of that background. The charlatan always struck me like a snake oil salesman. They were someone who ran small cons and made little profit, doing whatever was necessary to get by. Just look at the favorite schemes for the charlatan - games of chance, street corner hustling, and shaving coins are low-level cons. These short cons work on both the noble and commoner alike, but you going to work hard every day, and sure as hell aren’t going to get rich doing it.

The grifter, on the other hand, is the con artist who has bigger dreams and aspirations. You are smooth and confident, not slick and shady looking. You fit in with the nobility and wealthy. You can dress, speak and act the part so naturally that no one is the wiser.

You were never satisfied with rolling (loaded) dice in the alley or convincing some poor slob that the amulet you found in the trash has magical properties. Realizing this, you practiced that art of the long con. A scheme that targeted a wealthy and or powerful individual known as the mark, you learned how to develop a relationship over days or weeks to gain their confidence and trust. Once achieved, you were able to put the con into play.

The long con could take any number of forms. Maybe you were going to be the go-between for stolen art that never actually existed. How about convincing the mark to invest a foolproof opportunity that ends in them being separated from their riches. Whatever the con, a detailed plan had to put into place, executed and then completed without the mark being any the wiser. Anyone can steal, but to do it where the victim doesn’t realize it until you are long gone is the trademark of a true grifter.

Let’s take a look at the Grifter and see what con you can dream up to run with this background.

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Feature: Confident Chameleon

Whether you need to be a roguish charmer so you can seduce the daughter of a noble, or a buttoned-down businessperson with knowledge of accounting, you can assume the role quickly and easily. Even if your knowledge of a specific item is limited, you speak with such confidence and wit that even a seasoned merchant can’t help but agree with you. You can dress and act the part, even being able to learn the mark’s native language.

Personality Trait

Like all the backgrounds, some people’s personality is of high moral standards while others are just in it for themselves.

  1. I have infinite patience so that I can complete my goals - Patience is a virtue, and you are virtuous.

  2. I can talk to anyone on any topic - I have all the good words.

  3. My appearance is just a skin that I can shed at a moment's notice - I’m a snake in more ways than one.

  4. The devil is in the details - Without a good plan, you are destined for failure.

  5. I use humor to defuse tense situations - Laughter is always the cure.

  6. When danger is close, I will look to save myself as quickly as possible - I love you all, but I’m getting the fuck out of here.

  7. I am loyal to a fault when it comes to my crew - I changed my mind…you’re my peeps!

  8. Gambling is for the amateur, as I never bet unless I am confident in the outcome - If that means I have to fix the game, so be it.


I wrote about ideals in the Academic background.

  1. Avarice - The grifter’s favorite of the 7 deadly sins.

  2. Simplicity - Keep it simple stupid.

  3. Loyalty - I mean this in a good, positive way. Not in a Donald Trump, blindly follow me way.

  4. Noble - Ok, so you’re not Robin Hood, but that doesn’t mean you are going to steal from the poor.

  5. Honor - With grifters, there really is honor amongst thieves.

  6. Freedom - You’re not the boss of me!


Bonds always struck me a funny part of one’s background. Sure, I understand why it’s there. Whether to be used as a plot point for part of the campaign, or as a way to explain to the other members of your party why you act the way you do, bonds are a piece of how your character became who they are. I like to think as the character goes through the campaign, their bonds will shift from that of their past to include and be influenced by the rest of the party. Don’t let your past always determine your future.

  1. I am forever searching for the whale of all whales to take down - A Whale is an extremely rich mark, one that can set you up for life. It is not Moby Dick.

  2. I lost a member of my old crew and have never forgiven myself - Guilt is something that you’ll need to work out or it will eat you alive.

  3. My mentor abandoned me and I am forever searching for them - The question is what are you going to do when you find them?

  4. I conned the wrong person in my youth and are being hunted - That first long con may not have gone as well as you had hoped.

  5. I search out other great grifters to learn from their cons - I’ll steal anything, even other people’s ideas.

  6. I conned people indiscriminately in my youth and have been making amends ever since - Ok, so now maybe you really are Robin Hood.


  1. Once I put a con in action, I will see it through to the end, no matter the cost - You have some serious control issues.

  2. My greed knows no bounds - I like gold, silver, platinum, electrum and yes, even copper.

  3. I abhor violence and will fight only if cornered - People need to remember to be careful of the person backed in a corner.

  4. I get so caught up in the details, I sometimes lose sight of the end goal - Sometimes, you just have to look up from the paperwork and take action.

  5. I have a tendency to fall for people I am attracted to - Whether it be a man, woman or even a kobold.

  6. I have played so many different people in my life, I have forgotten who I am - You’re one of those people that when you break up with someone, you tell the jilted lover that you just need time to find yourself.

So there it is, the Grifter background. The long con isn’t for everyone. It takes patience, knowing how to read people, and keeping your calm under pressure. But when you take down that obscenely rich mark, it’s the best feeling in the world.

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Header Art Credit: Billy Christian

The Druid Equipment Pack

The Druid Equipment Pack

Backgrounds - The Academic

Backgrounds - The Academic