This article describes the adaptation and use of the Monopoly® board game as a simple simulator to help introduce the principles of probability and risk. It focusses on teaching experiences in an undergraduate business program and offers a new approach to teaching probability and risk with dice to produce a collaborative simulated gaming environment. It allows students to be actively involved in developing the probability of throwing dice numbers and the analysis of risk and decision making in a competitive environment. Concluding with a probability analysis technique, it allows students to reflect on formal and informal approaches to decision making in risk environments and helps build communication for discussion, collaborative learning, and self-analysis among students.