Toxic behavior remains a salient challenge for online gaming environments, such as multiplayer online battle arena video games (MOBAs). In this study, we sought to understand player roles and settings in which toxicity occurs using a mixed-methods approach. First, we conducted ethnographic observations and interviews with players of the most popular contemporary MOBA, League of Legends (Study 1). During the qualitative analysis three main themes emerged: (1) the fluidity of roles, (2) the subjectivity of the toxic experience, and (3) cascading effects and changing modalities of toxicity. Based on the themes, we formulated hypotheses regarding players’ experience with toxicity. To test these hypotheses, we gathered cross-sectional data from MOBA players (n = 216), which we analyzed with co-variance-based statistics (Study 2). Our quantitative findings showcase the complexity of toxicity as well as players’ ambivalence toward the topic. We found indicators of substantial influences of personality and a cycle of retaliation toxicity spread as victims retaliated against the perpetrator.