Rogue Gambler Archetype | New Player Option for Dungeons & Dragons Fifth Edition

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Playtest Content

The material here is presented for playtesting and to spark your imagination. These game mechanics are in draft form, usable in your campaign but not refined by final game design and editing. They aren’t officially part of the game.

Constructive feedback is welcome and appreciated in either comments or social media. If you can give me a valid reason with examples why something is off, 9/10 I’m likely to make changes to the content and credit you for doing so. Otherwise, feedback without anything to back it up gets ignored (or at most a smile emoji like this 🙂 ) Thanks!

Design Notes

Here are my notes for this build.

Before the Build

This one was a pain in the butt to create. Not because I didn’t enjoy the concept! The concept is cool. But I couldn’t figure out a mechanic that just “made sense” for the flavor. Finally, after a few days of deliberation, I decided on a pretty cool mechanic.

Here’s how I see this subclass working:

  • For the gambler rogue’s 3rd level action-economy-booster, it can “place bets” on the outcome of certain events, pretty much anything that requires a die roll. These have to be purely yes or no outcomes. IE, making an attack and having it hit. Or picking a lock and opening a door. Anything that’s a “gray” area–like doing a knowledge check or making a persuasion–doesn’t really count. It’ll take a bunch of rules fixing, but this will be how it powers its sneak attacks. “I bet you don’t hit the monster”… and if you’re right, you get instant inspiration. Because Sneak Attacks are fueled by advantages to attack rolls, you’ve just created a Sneak Attack engine for your rogue.
  • The 9th level feature will probably be something that works outside of combat. Probably a way to earn extra income during downtime.
  • At 13th, probably a defensive power that ties into the theme somehow. Or a different use for inspiration other than giving a bonus on a roll.
  • Finally, at 17th level, another use for the gambler’s inspiration, probably to inflict some serious damage. Maybe something along the lines you can bid your inspiration on an attack, and if it hits, you get to deal X amount of damage. That’d be cool.

After the Build

Once I got the idea to “weaponize” inspiration, the rest of the subclass came together pretty quickly.

The Place Your Bets power is the engine that drives the whole thing and comes chock full of flavor. Some might complain that a class that ties in inspiration like that kills the idea behind inspiration. My argument is that it’s a gambler. It’s gambling. Therefore, it’s doing what it’s supposed to do. Boom. Inspiration. The only cap I decided to put on it was that it wasn’t “inspiration” but a “gambler die.” It works similar to inspiration, but it can only be used to fuel the gambler’s powers and attack rolls and it can’t give it away.

From there, the rest of the subclass uses gambler’s die for various things. The secondary 3rd level power is more of a “roleplaying” power, kinda like mini-downtime that helps fill the petty cash box for the party. At the tiers listed, the gp amounts shouldn’t be too broken since they’re waaay less than what you’re supposed to get at those levels while adventuring.

At 9th, you can read bluffs. Again, this one is a little outside of combat, but it’s a pretty useful power. Plus, it ties in another use for the gambler’s die, effectively giving you lie detection powers.

13th level’s power flipped the way inspirations work. Instead of betting the gambler’s die before the die roll is made, you can use it after in one of two ways. First, to completely reroll. Second, to add +5. That way, if you roll like shite, you can totally reroll the die and increase your chances of success. And second, if you feel like you’re damn close to a success and need the extra bump, you can add a late-in-the-game +5 to the roll.

Finally, the 17th level power sort of duplicates what inquisitive rogues do as their capstone, except it lets the gambler use the gambler’s die to get the bonus to attack rolls. Because you have to use your place your bets ability (which should, in theory, succeed 60% of the time) to get this extra damage, and that requires a reaction, and you have to find a different way to get the advantage on the attack, I bumped it up from the 3d6 to 5d6 to account for the use of extra action economy.


Roguish Archetype

At 3rd level, a rogue gains the Roguish Archetype feature. The following Gambler option is available to a rogue, in addition to those normally offered.


Believe it or not, even the Gods of Luck and Fortune have chosen ones that they imbue with certain powers. Of course, being a god of luck doesn’t mean just handing it over to the chosen one willy nilly. No, the chosen one must prove that they are worthy of such a mantle by demonstrating their natural affinity to bending the curve of probability. These roguish archetypes are known as gamblers, and they live life on the edge. Betting on (and against!) allies, foes, and events all around them.

Place Your Bets

When you select this roguish archetype at 3rd level, before you or any of your allies make an attack roll, you can use your reaction to place a bet. You must tell the GM before the roll is made whether or not the roll will succeed or fail. After the attack roll is made, if your guess was correct you are automatically rewarded a gambler’s die, which acts like inspiration. If your guess was incorrect nothing happens. You can only have one gambler’s die at a time–you can’t stockpile multiple “gambler’s dice” for later use.

Using your gambler’s die. If you have the gambler’s die, you can expend it when you make an attack roll. Spending your gambler’s die gives you advantage on that roll. Additionally, if you have the gambler’s die, you can expend it to use more of the gambler roguish archetype’s features, as detailed below.

Easy Money

At 3rd level, you are excellent at making money while traveling. As long as you are in a somewhat civilized area that’s predominantly populated by humanoids with an average Intelligence scores of 8 or greater, you are carrying at least 10 gp, and have a gambler’s die available, you can gamble to earn extra income. To do so, you must spend eight hours of downtime gambling, at the end of which you expend your gambler’s die. You earn 10 gp from your efforts. This amount increases to 100gp at 5th level, then 1,000 gp at 11th level.

Once you use this feature, you can’t use it again until you complete a long rest.

Call Your Bluff

Starting at 9th level, you have an incredible sense for when people are lying to you. You have advantage on all Wisdom (Insight) checks to detect lies. In addition, you can expend your gambler’s die when you wish to detect a lie. If you do, you automatically know what you’re hearing is a lie or not.

One-in-a-Million Chance

At 13th level, you possess supernatural luck. After you make an attack roll, ability check, or saving throw, you can expend your gambler’s die to do one of the following:

  • Reroll the die. You must use the new roll.
  • Add +5 to the die roll.

You must choose to use your gambler’s die in this way after you make the roll, but before the GM tells you whether or not you succeeded.

Full House

At 17th level, your natural luck assists you in combat. Whenever you hit a creature with your Sneak Attack, you can expend your gambler’s die to increase your Sneak Attack damage for that attack against that creature by 5d6.

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1 thought on “Rogue Gambler Archetype | New Player Option for Dungeons & Dragons Fifth Edition

  1. Love this! Only thing that may need tweaking is either the coin yield of downtime gambling or the duration before you can do so again.

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