This case study explores the experiences of student/players (n=2), coaches (n=2), faculty/staff advisors (n=2), and Lone Wolves' (n=6) experiences in eSports environments relevant to American Indian education and cultures. Specifically, this study explored the intersection of eSports, 21st century skills, and Indigenous futurisms and was guided by theoretical frameworks of Tribal Critical Race Theory (Brayboy, 2005), Indigenous futurisms (Dillon, 2012), and P21 Framework (Partnership for 21st Century Skills, 2019). This case study analyzed data from six individuals who are affiliated with higher education sponsored eSports programs, with added interviews of six players unaffiliated with sponsored eSports programs but still heavily engaged in eSports (i.e., Lone Wolves). Semi-structured interviews were used to explore individuals' perceptions associated with eSports programs at Southern Plains Tribal College, State University, and Lone Wolves operating in the unstructured "Wild West" of eSports. Findings showed that participants were experiencing growth in various specific 21st century skills, such as technological, global awareness, health literacy, and business. Indigenous values were also found to be part of structured eSports programs, as well as foundational ideas related to Indigenous futures and leadership. Findings also show that Indigenous ways of knowing are present in eSports through humor and re-imagining eSports futures, which privilege Indigenous voices, yet also revealed complex tensions of using Indian humor in unstructured environments. This humor shows up as a unique cultural layer of student/player experiences, but also presents a need for important conversations among educational leaders about ethics, racism, structure, and expectations when thinking about the differences between unstructured "Wild West" eSports environments, and programs sponsored by institutions of education. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]