This article explores how preservice teachers can develop mentoring capacities (i.e., perspective taking, connection with students, and self - reflective opportunities on their roles as teachers) by participating in a historically - based online simulation game with middle school students. The arena for this exploration, the Jewish Court of All Time (JCAT), is a web - mediated learning platform that utilizes character play to enhance historical and cultural understanding. Through the description of three preservice teachers/mentors in JCAT, we illustrate how the preservice teachers/mentors work to support the learning of the middle school students while developing their teaching skill set. Our research explores the ways in which participation in the dual roles of character and mentor shapes the university students’ development as preservice teachers.