This article investigates why there appears to be an under-representation of males in comparison to their female colleagues in the Early Years (EY) sector, and the perception of male teachers progressing more quickly to leadership positions when they do enter this context. Using case studies of final year male students on an Initial Teacher Training (ITT) undergraduate degree course at one university, we attempt to analyse data on male under-representation in Early Years against contemporary theories of identity, power and leadership. Questionnaires and interviews were conducted with the male sample group and male senior leaders in primary schools to gain an overview as to the leadership support they needed and provided. Our tentative findings suggested that male trainees are happy to work in an Early Years context and take leadership positions, but the challenge for leaders is that male trainees require strong leadership mentoring processes to help overcome perceived contextual barriers.