Monstrous Mondays: Criminals and Bandits

This week, we expand what Monstrous Monday means. See, to this point, I’ve only designed…well, monsters. However, I’m in the process of designing a short 5-level campaign for my group, and it takes place in a city. In the city, it’s not near as likely for you to encounter hunting drakes or mangles. Instead, you’re far more likely to encounter NPCs. Thugs, thieves and crime bosses.

In the spirit of that idea, this week sees my first official NPCs. And this week, I’m taking on Bandits, and specifically city bandits (is there a better word for that?) There are a few that already exist in the D&D Basic Rules, but I wanted to create something a little more unique.

I also wanted to take on an idea that the Angry GM proposed in his Articles on Monster Design. And that’s the idea of “racial traits” for monsters. The way he described it was that goblins all share a trait: Nimble Escape. Similarly, zombies all share the Undead Fortitude trait. I wanted to expand that idea into NPCs. All of the bandits in this article (and all future bandits) share the Banditry trait, which gives them the ability to use the Dash or Disengage actions as a bonus action on their turn.

This is also the most expansive Monstrous Monday that I’ve done. I’m presenting 5 NPCs here, all ranging in style and difficulty, including a “boss” enemy, to use in your low-level city games.

I hope you all enjoy!


Thugs are the most basic of bandits within city walls. Their jobs are simple. They intimidate shop keeps and enemies of their gang, and act as combat fodder when push comes to shove. They carry iron-bound clubs that they tend to call “beat sticks.” While not intelligent, thugs are definitely dangerous to the common folk they confront.   Bandit Thug


Rakes are killers and cutpurses. They are hired as thieves, most often. However, they are also adept in combat, and can be especially deadly when ambushing and ganging up on foes. Most rakes carry daggers and hand crossbows, as they are can be worn under clothes in public without drawing attention.

Bandit Rake


Enforcers are called when violence needs to be done. While thugs might occasionally pick fights with rival gangs and clans, enforcers are used for necessary, deliberate actions taken against an enemy. They are highly trained, unlike thugs or rakes, and only get more dangerous the more damage they take. They wear chain shirts and carry stout and sharp longswords.

Bandit Enforcer


When someone needs to swim with the fishes, or an item in someone else’s possession needs to be…acquired, that’s when the boss calls in a “specialist.” Specialists are skilled at ambush tactics, but are also adept spellcasters. They can fly, turn invisible, and even conjure magical armor to protect themselves in combat. Specialists carry daggers, but also shortbows to slay foes at range.

Bandit Specialist

Crime Boss

Crime bosses are the bosses, both thematically and mechanically. They command the gang and plan the actions that their people take. They are the head of the snake. They are skilled at fighting in the thick of it with their allies, as well as commanding them from a distance. Their greatest power is their ability to spot enemies’ weaknesses and call them out to their allies in order to give them an edge. Crime bosses carry rapiers and hand crossbows.

Bandit Crime Boss

As always, here’s the PDF.

And don’t forget that if you want a comprehensive list of all the monsters I’ve designed (including the boss from Night of Samhain), then check out the new Downloads page at the top!

And that’s that. A slew of new bandits to use in your games. You’ll note that they’re denoted as “humanoids” without any specifics thereafter. This is so that you can apply any relevant factors by changing their race as you desire. A dwarven crime syndicate might operate differently than a wood elf street gang due to their racial features. One thing I would note is that ability scores should not change, as the changes throughout the NPC’s statistics could modify the Challenge (and therefore the XP value) of the NPC.

Good Gaming! And I hope you get some fun out of these masters of crime.

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