This study develops a moderated mediation model that explores the relationship between principals’ transformational leadership and older teachers’ intention to delay retirement. We tested the model using a two-wave survey of data collected from a sample of 204 older teachers in primary and secondary schools in China. Our results indicate that principals’ transformational leadership is positively related to older teachers’ intention to delay retirement, where the relationship is mediated by organization-based self-esteem. We also found that life expectancy moderates the indirect relationship between transformational leadership, organization-based self-esteem, and older teachers’ intention to delay retirement. Such an indirect relationship was stronger among old teachers with low life expectancy rather than high life expectancy. Findings enrich the literature on transformational leadership and retirement decision-making, and provide practical implications.