The Tokyo 2020 Olympics will see a record number of 110,000 volunteers. The image of volunteering in Japan has undergone significant changes over time. Olympic volunteering is to be fun, be a “once-in-a-lifetime” experience and aid in creating a “Volunteer legacy” for decades to come. This chapter explains how this positive view is juxtaposed with voices criticizing the organization, recruitment, payment, and working conditions of the volunteers for the Olympics.