This study investigates the Jewish history engagement for middle school students "playing" in the Jewish Court of All Time (JCAT), an online simulation of a current events court case with historical roots (http://jcat.icsmich.org). Through an online platform across several schools, students research and play historical and current personalities invited to debate and eventually decide a complex issue. In following the experience of four focus characters through the simulation process, we demonstrate a variety of types and levels of engagement with Jewish history: with Jewish history content through character background and the historical roots of the case, with historical big ideas, such as freedom of expression and continuity and change, and with historical skills, such as perspective taking and critiquing research sources. We articulate some benefits and constraints of simulation role playing, particularly in an online context, for exploring Jewish history.