Old School Rebellion, Part I

— Howard Pyle, early 20th century


In “Picaro and the ‘Story’ of D&D,” James Maliszewski of GROGNARDIA draws parallels between picaresque literature and pulp fantasy—and thus between the picaresque and old-school Dungeons & Dragons. (Note that throughout this text “old-school D&D” functions as a shorthand, referring not only to early editions of Dungeons & Dragons, but also to retroclones and other derivations within the OSR and NSR, particularly those that hew closely to the core gameplay loop of early D&D and retain experience-points-for-gold.) He outlines a series of assumptions that old-school D&D adopts from pulp fantasy. Of particular relevance are the following:

  • The protagonists are “rogues” […] of low station […] who live on the margins of society.
  • Said society is generally corrupt, or at least venal.
  • Consequently, the protagonists generally pursue personal betterment […] rather than more “noble” goals.
– Maliszewski, GROGNARDIA

While I agree with Maliszewski’s characterization of low-level play in old-school D&D as picaresque, I’d argue that high-level play involves something else entirely. Here’s an excerpt from page X3 of Expert D&D:

As player characters grow in wealth and power, they may build castles or strongholds to keep themselves and their retainers safe. They may encourage settlements around their fortresses in order to support them, eventually becoming the rulers of their own territories. From their wilderness bases, they can settle and rule larger areas, bringing civilization to the wilderness. Through the rules of the D&D Expert Set, the campaign area can be extended to cover an entire world.

Dungeons & Dragons by Gygax & Arneson, edited by Cook & Marsh, 1981

Player characters seize wealth through violence—or at least thievery and trickery—and the more wealth they seize, the more capable they become. Once they have amassed sufficient wealth and power, player characters can muster armies, conquer swathes of land, and rule over subjects. Zedeck Siew of A THOUSAND THOUSAND ISLANDS couches these activities in more trenchant terms:

Going forth into the “wild hinterlands” (as if this weren’t somebody’s homeland) to “seek treasure” (as if this didn’t belong to anybody) and “slay monsters” (monsters to whom?)… Yeah. Problematic stuff here. And definitely these aspects should make people uncomfortable.

Siew, via Twitter

(I initially came across this thread as quoted in “Apolitical RPGs Do Not Exist,” an excellent piece by W.F. Smith of Prismatic Wasteland. And in turn, my introduction to that piece was through episode 130 of Nick L.S. Whelan’s Blogs on Tape. I love this conversational, intertextual aspect of the blogosphere; it makes it easier for a newcomer like myself to find influential texts and expand their horizons.)

The point that should be apparent here is that the core gameplay loop of old-school D&D involves land-grabbing, relic-looting colonialist invasion. But I’m not here to condemn the fun D&D provides as inherently bad or wrong—and neither, it seems, is Siew:

“It’s an error to ‘decolonise D&D‘ by scrubbing such content from the game. […] I think it more truthful and more useful, to not avert one’s eyes from D&D‘s colonialism. The fact that going forth into the hinterland to seek treasure and slay monsters is a thing and fucking fun tells us valuable things about the shape and psychology of colonialism.

— from the same thread as above

I’m reminded of the value in approaching art with a critical eye and in creating art with intention. I’m also reminded how violence in games too often becomes divorced from any semblance of its real life context or consequences—how it becomes sport. While the kind of fun Siew identifies clearly has value, it surely isn’t the only kind of fun D&D has to offer. This series aims to explore how D&D might offer a different kind of fun without being cleansed of its original themes.

James Maliszewski acknowledges that picaresque rogues “sometimes achieve noble, or at least broadly beneficial, goals in the course of their pursuit of personal betterment” (again, from “Picaro and the ‘Story’ of D&D“). He seems to characterize the achievement of such goals as incidental, but as a GM and player of old-school D&D, I’ve witnessed another phenomenon.

Time and time again, I’ve seen characters engage in noble acts, often at the expense of some authority or tyrant—even when doing so interrupts or inconveniences the characters’ pursuit of wealth and power. Many of the people I’ve played with harbor a nigh irrepressible anti-authoritarian streak.

There’s inherent fun to be found in anti-authoritarian transgression, even, as W.F. Smith observes, in a game as simple as Don’t Wake Daddy. Couldn’t a game as complex and immersive as D&D be a powerful conduit for that kind of fun? How might one accomplish this without utterly sanitizing the game, without turning a blind eye to the fact that few revolutions end happily? Perhaps old-school D&D—with its fragile characters and lack of regard for balanced combat—will prove weirdly suitable for such an endeavor.


I am, of course, neither the first to think about this nor write about this. In “Marx & Monsters: A Radical Leftist Fantasy Sandbox,” TheLoneAmigo proposes that the radical might easily replace the rogue as the protagonist of a sandbox campaign. I’m leery of their summary of the rogue’s role in a sandbox game. Killing monsters in order to save people seems more the purview of the modern D&D “hero” than of the old-school sandbox’s roguish protagonist.

However, Allandaros of Legacy of the Bieth recognizes that TheLoneAmigo is onto something. In “Towards a Leftist OSR,” Allandaros brings James Maliszewski’s “Picaro and the Story of D&D” into the conversation, observing that the environment suitable for a roguish protagonist—”the margins” of a “generally corrupt” society—also suits a radical one.

Both Allandaros and TheLoneAmigo recognize that XP-for-gold wouldn’t function well within an anti-authoritarian framework. But instead of fully abandoning XP-for-gold, both writers see the potential of wealth to improve player characters’ communities. TheLoneAmigo proposes awarding experience points for wealth redistributed to the community or for capitalist wealth destroyed. Allandaros builds upon this premise by developing a system via which characters can expend wealth to improve aspects of their community.


Expanding upon these ideas, I’ve drafted a system intended to ground experience points and levels within the diegetic fiction of the game and reinforce the framework of rebellion:

Present among the rebels are expert warriors, sorcerers, and thieves. However, they are stretched too thin to provide training to every eager young recruit. When the player characters engage in activities that benefit the rebellion and their community, they earn repute. Once a character has earned enough repute to gain a level, rebel veterans will train them.

Player characters may earn repute by:

  • Plundering treasure from the empire and redistributing it within their community
  • Liberating occupied territory
  • Freeing prisoners
  • Destroying apparatuses of the empire
  • Thwarting the empire’s plots
  • Converting agents of the empire to the rebellion’s cause

The Core Gameplay Loop

The core gameplay loop of old-school D&D remains roughly unchanged. Dungeons, of course, still feature heavily; after all, the empire needs someplace to keep their prisoners and ill-gotten treasure. The wilderness is still out there, and the player characters will know little of their country beyond their hometown and immediate surroundings. The roads, patrolled by agents of the empire, will be more dangerous than in a conventional game. The player characters still advance by accumulating treasure, though additional avenues of advancement create space for more varied adventures.

To Be Continued…

That’s all for now. This post is the first of a series of three. Part two explores session zero procedures and several player-facing mechanics. Thanks for reading. I welcome your thoughts and criticisms.

Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

Comments (



  1. Tom H

    This is a great re-framing of that core D&D loop and one I think my players would definitely enjoy. Thanks and looking forward to the rest.


  2. A History of the World in Lies – Too Many Swords

    […] world so harsh and cruel. For many of these ideas, I must give credit to the excellent blog posts Old School Rebellion and Marx & Monsters: A Radical Leftist Fantasy Sandbox for inspiring me to create this world of […]


  3. Diego Bassinello

    I loved! Xp for money has aged badly and reinforces a lot of problems of capitalism.
    Looking forward to reading the next part!

    Liked by 1 person

Create a website or blog at WordPress.com

%d bloggers like this: