With their increased popularity, games open up possibilities for simultaneous learning on multiple levels; players may learn from contextual information embedded in the narrative of the game and through the risks, benefits, costs, outcomes, and rewards of the alternative strategies that result from fast-paced decision making. Such dynamics also contribute to building relationships and sharing/delegating authority with others, in other words, acquiring leadership skills. Games and simulations have long histories as tools to facilitate learning and training, especially in formats such as board games, role-playing games, and real-life simulations. However, multiplayer online games are rarely used outside military training for leadership development. With its emphasis on transformational leadership skills in distributed teams (DTs), this study presents several findings on leadership in multiplayer online environments, such as INFINITEAMS and EVE ONLINE. To cope with globalization, technological change, and highly competitive environments, leaders of DTs must have a better understanding of the contextual variables in online environments, and massively multiplayer online video games provide robust platforms to test their skills.