Character development has become an important component of physical education that contributes directly to the affective learning domain. However, teaching character development can be challenging. The purpose of this article is to suggest that character development be promoted through the teaching of wrestling, due to the unique moral development experiences offered through participation in the sport. The article describes the ancient history and current popularity of wrestling among boys and girls, as well as the many benefits of participation, while providing solutions to the common challenges of implementing a wrestling unit in physical education. The article also suggests that physical educators use the teaching personal and social responsibility (TPSR) model through a "Pin it to Win it!" leveling system. The goals and levels of the TPSR model are discussed and specific examples are provided, including a lesson plan for use in a wrestling unit.