Play to Lose

Animation, Failure, and the Milieu in Trophy Dark

In this paper, I want to take a different approach than I do usually—that is, to overtheorize, to become lost in the thicket of critique—and instead focus on practice. All too frequently in my work, I find myself following bypath after bypath, turned about amidst the woods and ruins, never to make it to the destination I set out to reach.1 There is certainly a place for theory, and much of my research efforts last year were concentrated on theorizing tabletop roleplaying games (specifically, lyric games and Belonging Outside Belonging games).2 But here, I want to dwell on practice, be animated by practice, spending these pages to discuss a semester of play in the university classroom, and in particular, a three-part play session of the “Witchwood” incursion for Jesse Ross’s Trophy Dark (2021).3

Published by Jason Cordova of The Gauntlet, Trophy Dark is a fantasy horror tabletop roleplaying game adapted from Cthulhu Dark (2017) and Blades in the Dark (2017), with a table experience that owes much to the tradition of story games.4 Trophy Dark sets the expectation for narrative collaboration and improvisation early on—players are recognized as “co-storyellers,” with the power to “introduce story elements that no one—not even the GM—was expecting.”5 Every incursion (an adventure module in the Trophy Dark format) is structured around a theme, and as the game master’s principles emphasize, the most “rewarding session is one that brings the theme to life.”6 The best incursions have a way of luring players into the story, just as their characters are lured deeper and deeper into the dark forest. My students’ eyes shone with dread delight as we moved from ring to ring of the incursion, concentric scenarios driving us closer and closer to our doom.

The “Witchwood” incursion,7 written by Ross, plays with images, characters, and plots from The Wonderful Wizard of Oz. Our group of player-characters set off in search of “Dora,” following a crumbling brick road that lead to a rumoured “green fortress.” Along the way, they came upon a pair of magical slippers that drove their wearer to ruin, and found themselves stalked by a monstrous lion that struck cowardice in the hearts of those who witnessed it. I chose the incursion specifically for this layering of literary elements, and my students were thrilled when they recognized the source, and terrified to see what twisted turn the story would take next.

This play experience was the final play experience of the course, an introduction to game design that I teach using tabletop roleplaying games. I had fifteen undergraduate students under my care (twelve of whom participated in all three Trophy Dark sessions), split roughly in half between students with varying levels of experience with Dungeons & Dragons (and solely Dungeons & Dragons) and students with no tabletop roleplaying experience whatsoever. Students came from a variety of majors, including a few from our game development program, as well as from media and communication, English literature, creative writing, and business administration. The class was conducted online via Zoom, with students spread between several countries. We began the semester by playing Ben Robbins’ Kingdom (2021), then proceeded through The Quiet Year by Avery Alder (2013), The Skeletons by Jason Morningstar (2015), and Dialect by Kathryn Hymes and Hakan Seyalioglu (2017).8 Class time we spent focused on play, and then after each play experience, students would use concepts from the course textbook, Colleen Macklin and John Sharp’s Games, Design and Play (2016), to complete exercises reflecting on the games played during class.9 Upon completion of our Trophy Dark incursion, having built up a significant frame of reference for tabletop roleplaying and a critical vocabulary to go with it, we pivoted to a multi-week design intensive wherein students wrote and workshopped their own tabletop roleplaying games.

Throughout the semester, I was incredibly impressed with my students’ openness to play and improvisation, and their willingness to be vulnerable and kind with each other at the virtual table. For my part as both facilitator and instructor, it is important to emphasize that this does not happen by accident, and actively cultivating a safe play culture is vital to successful and healthy play experiences,10 especially when such experiences are taking place in a classroom between peers who did not necessarily choose to be there with each other member of the class, and when the games being played, like Trophy Dark, have the potential to delve into disturbing territory (see the content warnings at the beginning of “Witchwood”: body horror, graphic violence, manipulation).11 As the facilitator, I made sure to set the tone before every session, laying out ground rules for interpersonal interaction during play, as well as lines and veils for the content that would be permitted at the table.12 We adhered to a fairly strict PG-13 content rating for all of our games, including Trophy Dark, which, rather than limiting the students, presented them with a safely bounded field for expressing their creativity on all manner of subjects—conflict and violence, to be sure, but also such fraught domains as community building, familial relationships, and personal identity. I owe so much credit to my students for being willing to play, to take risks, to share space with one another, and to be generous with each other as co-storytellers all semester long.

In the case of our Trophy Dark incursion, I specifically want to focus in on the concept of failure, which Trophy Dark enshrines in its three player principles: embrace tragedy, don’t hold back, and play to lose. By this point in the semester, my students were already well-versed in putting story first, and had become quite adept at playing off of each other’s characters to produce drama. So, when I read these principles from the game book, and proceeded to tell my students that their characters should be desperate, complicated, and morally compromised, and that most of them were certainly going to die, the excitement was palpable. Especially in a university course, where “failure” and “losing” typically have such severe connotations, and even material penalties, the prospect of embracing failure, of participating with the intent of losing, had a radical effect.

Trophy Dark is elegant and precise in the ways it supports drama. My students were surprised and pleased by the playful ambiguity of the random tables for occupations, backgrounds, drives, and rituals.13 Some picked from the lists, and some rolled for random results. Unprompted, students compared character sheets and started weaving bonds, intuiting relationships based on social position and aligning (or opposing) goals based on motivations. In response to the question “what does this mean?” regarding various table entries, I would always respond, you tell me, and the glee in my students’ faces at this answer was wonderful to see.14

The gameplay mechanics of Trophy Dark do an excellent job pushing players toward tragedy and failure. The balance of risk and ruin is a powerful instrument for drama, presenting frequent opportunities for things to go wrong and disaster to befall the player-characters. Using ruin in the place of hit points is a brilliant bit of design, providing the facilitator with numerous handles for storytelling. For instance, at the end of our first session (character creation and ring one), one player, who had managed to reach five ruin (of six maximum) through a rather chaotic series of events, casually picked up the “pair of iridescent shoes” dropped by the witch the party had encountered and decided to put them on. Not realizing that they were already at five ruin, I told the player to automatically mark one ruin, as dictated by the rules. There was a shocked pause, the player staring at me, mouth agape, and then—“I’m already at five… what happens now?” Rather than have them keel over and die on the spot, I was able to reply: “you lose yourself to the wilds that have been growing inside you. You choose whether you become a monster in service to the forces of nature (and the whims of the GM), or whether you simply die.”15 There was another pause as they typed a private message to me in Zoom chat: “can I come back? I have some ideas!” Their character would reappear throughout the remainder of the incursion, becoming a key figure in the plot in a way none of us could have foreseen.

Another mechanic that became the instrument of much drama was the devil’s bargain.16 Every time a risk roll occurs, the facilitator and other players at the table can offer bargains to the one rolling in exchange for an additional die. My students quickly realized that devil’s bargains provided an additional means for shaping the trajectory of the story, outside of direct, in-character action. The bargains offered ranged from silly to sombre, and frequently involved elaborate ploys, devastating betrayals, and tragic losses. Through one devil’s bargain, one player-character ended up with a sentient tree growing inside of them, which eventually sprouted as a second, bark-covered head with the chosen name Brock. At first a means of comedic relief, by the end of the game Brock had become a character in his own right, and served as a fulcrum for a touching moment between two of my students’ characters.

In a group so large, conflict between characters is bound to occur, and occur it did. Unlike previous times that I have run Trophy Dark, this group made regular use of the contest roll, in all manner of contexts. Sometimes player-characters disagreed about a course of action, and a contest roll would help determine which way the rest of the party swayed. Other times, player-characters drives would directly conflict, and a contest roll allowed for tense resolutions of strife and interpersonal violence. Rituals were frequently deployed in creative ways, and always to unpredictable ends, and more than once were the tables turned on an over-confident player-character who thought they could get their way. As the facilitator, one of the best features of the contest roll is the way in which it levels the playing field between players. As mentioned above, about half of my students had experience playing Dungeons & Dragons, and the other half had no experience at all with tabletop roleplaying games. As might be expected, the players with D&D experience tended to be more dominant in their play, centring their characters and making it difficult for quieter players and those with less tabletop experience to participate. In one such situation, early in our second session, one player-character, a disgraced town-guard with a military background, tried to bully another player-character, a mourning widow with some witchcraft up her sleeve, into following his directions. The disgraced guard thought that he had gotten his way, but clearly the widow was not onboard, so I paused the action and invoked the contest roll.

First, we agreed what was at stake: recognition as leader of the group. Then, we gathered dice. Each wanted to win the contest, so each took a few extra dark dice, risking more potential ruin from the roll. And then, we rolled, looking for sixes. The guard looked at his roll in disbelief; the widow had more sixes. And to the guard, with a face of stone, the widow said a single word: doom. And she slapped him. The player pointed to the ritual on their character sheet, “Doom,” and said that since they had rolled extra dark dice, it made sense in the story that the widow had used her ritual to exert her will against the guard, focusing her magic into the open-handed blow. One of the dark dice that guard had rolled showed a one, so he marked one point of ruin, as per the rules. For the rest of the game, players would joke about the “slap of doom” that changed the course of events, a simple mechanical intervention that transformed the order of things.

It is with this sense of transformation that I want to conclude this paper, drawing on the philosopher of science Isabelle Stengers’s theory of animation—just a moment of theory, I promise—to form an understanding of what happens in the practice of playing tabletop roleplaying games, what happened in my class’s collective practice of the rules and mechanics of Trophy Dark.

In her essay “Reclaiming Animism” (2012), Isabelle Stengers writes that reclaiming “means recovering, and, in this case, recovering the capacity to honor experience, any experience we care for, as ‘not ours’ but rather as ‘animating’ us, making us witness to what is not us.”17 To be animated by an experience is to be “lured into feeling,” to be “compromised by magic,” to encounter and be transformed by the “not ours” and “not us.”18 Trophy Dark expertly forces its players into such compromised and metamorphic encounters, short circuiting player agency in order to teach players a different kind of desire, a different kind of play.19 The incursion is an instrument for this teaching, an “assemblage” or “milieu” that beckons players into a new feel, the feel of failure, of tragedy, of disaster, the feel of drama, and of love.20 Rather than progress through skill trees, characters in Trophy Dark connect and contest with each other in rhizomatic networks of touch, subterranean systems that cannot be pinned down with “criteria,” only navigated by “craft.”21 Through our adventure in the Witchwood, we found ourselves caught up in the “flux of participation,” in the work of “realization,” that labour whereby the real is not disclosed, as some philosophers might phrase it, but made.22

“Reclaiming means recovering what we have been separated from,” writes Stengers, and “regenerating what this separation has poisoned.”23 The tabletop roleplaying hobby, indeed the tabletop roleplaying industry, is in many respects a “poisoned milieu,” overdetermined by relations of bigotry and extraction that go back to fantasy gaming’s roots.24 Beyond tabletop games, the students that signed on to Zoom to join my class in January of this year expressed a deep alienation and despair, a feeling that I too share, grappling with an “absent future” realized by violent state apparatuses and predacious corporations.25 But as Stengers argues, the “need to struggle and the need to heal” are “irreducibly allied” if we are to “avoid resembling those we have to struggle against,” if our “poisoned milieu” is to be “reclaimed.”26 Through our time with Trophy Dark, we caught a glimpse of what such reclaiming work might look like in the tabletop roleplaying game community—nothing guaranteed or complete, always an “imperfect realization”—how one might, in a decisive moment, stare power in the face and pronounce doom upon it, become like the Furies, taking back the future from those tyrants who believed it theirs.27

To bring theory back to practice, I will close with a final anecdote. After our story ended, while debriefing as a class, one student, who had participated less than some of the others, remarked how they never knew what to do, because any time they wanted to act, their actions would put their character in danger. They said: it’s like, to do something, to accomplish anything, you have to accept that you might fail, that you might lose. And perhaps it is trite to say, but that is precisely the point.


Stein, Eric. “Play to Lose: Animation, Failure, and the Milieu in Trophy Dark.” Presented at the GENeration Analog: The Tabletop Games and Education Virtual Conference, July 28, 2022. Mirrors: Academia, ResearchGate.


  1. After all this time, Melville is still my teacher: “In this matter of writing, resolve as one may to keep to the main road, some bypaths have an enticement not readily to be withstood.” Herman Melville, Billy Budd, Sailor (an Inside Narrative), ed. Michael J. Everton (Peterborough, ON: Broadview Press, 2016), 66. 

  2. See Eric Stein, “Bodies in Form, 2: Tabletop Roleplaying as Cosmic Poetics” (May 28, 2021), and Eric Stein, “No Dice, No Masters: Procedures for Emancipation in Dream Askew / Dream Apart” (August 5, 2021),

  3. Jesse Ross, Trophy Dark (Hedgemaze Press; The Gauntlet Gaming Community, 2021). 

  4. Graham Walmsley, Kathryn Jenkins, and Helen Gould, Cthulhu Dark (Thieves of Time, 2017); John Harper, Blades in the Dark (Silver Spring, MD: Evil Hat Productions, 2017). On story games, see William J. White, Tabletop RPG Design in Theory and Practice at the Forge, 2001-2012: Designs and Discussions, Palgrave Games in Context (Cham, CH: Palgrave Macmillan, 2020), 69-71, and throughout. 

  5. Ross, Trophy Dark, 22, 24. 

  6. Ross, 24. 

  7. Ross, 120-125. 

  8. Ben Robbins, Kingdom, Second Edition (Lame Mage Productions, 2021); Avery Alder, The Quiet Year (Buried Without Ceremony, 2013); Jason Morningstar, The Skeletons (Bully Pulpit Games, 2015); and Kathryn Hymes and Hakan Seyalioglu, Dialect (Thorny Games, 2017). 

  9. Colleen Macklin and John Sharp, Games, Design and Play: A Detailed Approach to Iterative Game Design (Boston, MA: Addison-Wesley, 2016). 

  10. An excellent resource to this end is Kienna Shaw and Lauren Bryant-Monk, “TTRPG Safety Toolkit V2.5,” 2021,

  11. Ross, Trophy Dark, 120. 

  12. See “Lines and Veils,” in Shaw and Bryant-Monk, “TTRPG Safety Toolkit V2.5.” 

  13. “Player’s Guide,” in Ross, Trophy Dark, 5-20. 

  14. This approach is encouraged by the rules text. See Ross, 9. 

  15. Ross, 19. 

  16. Ross, 17. 

  17. Isabelle Stengers, “Reclaiming Animism,” e-flux, no. 36 (July 2012): 1–10,, 7. 

  18. Stengers, 7, 8. 

  19. On agency and desire in games, see Meghna Jayanth, “White Protagonism and Imperial Pleasures in Game Design,” Medium, November 30, 2021,

  20. Stengers, “Reclaiming Animism,” 7, 3. On love and feel, see “Fantasy in the Hold,” Stefano Harney and Fred Moten, The Undercommons: Fugitive Planning and Black Study (Wivenhoe, UK: Minor Compositions, 2013), 87-99. 

  21. Stengers, “Reclaiming Animism,” 7, 8. 

  22. Stengers, 8, 9. 

  23. Stengers, 4-6. 

  24. See, for instance, Emma Vossen, “There and Back Again: Tolkien, Gamers, and the Remediation of Exclusion Through Fantasy Media,” Feminist Media Histories 6, no. 1 (January 2020): 37–65,

  25. California Student Occupation Movement, “Communiqué from an Absent Future,” We Want Everything, September 24, 2009,

  26. Stengers, “Reclaiming Animism,” 6. 

  27. Stengers, 7. See Stein, “No Dice, No Masters” for my detailed analysis of games and emancipatory possibility. To summarize: what makes a game emancipatory cannot itself guarantee emancipation. 

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