The main purpose of this chapter is to examine how young children aged between 4-5 years old enact leadership during preschool play. Studies that use a case study methodology are reviewed to illustrate the enactment of child leadership in a preschool setting. Thses case studies reflect on how the individual characteristics of a child (such as cognitive and social intelligence) and peer group characteristics (including power dynamics and the play environment) may predict the emergence of leadership during early childhood. The implications for early childhood practice, including strategies to develop leadership potential and manage children's play, will be discussed.16 page(s