Student understanding and retention can be enhanced and improved by providing alternative learning activities and environments. Education theory recognizes the value of incorporating alternative activities (games, exercises and simulations) to stimulate student interest in the educational environment, enhance transfer of knowledge and improve learned retention with meaningful repetition. In this case study, we investigate using an online version of the television game show, ‘Deal or No Deal’, to enhance student understanding and retention by playing the game to learn expected value in an introductory statistics course, and to foster development of critical thinking skills necessary to succeed in the modern business environment. Enhancing the thinking process of problem solving using repetitive games should also improve a student's ability to follow non-mathematical problem-solving processes, which should improve the overall ability to process information and make logical decisions. Learning and retention are measured to evaluate the success of the students’ performance.