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Past research underscores the critical role of principal brokers in facilitating the flow of resources and information to achieve desired educational goals. Navigating through the evolving policy landscape, Hong Kong principals need to employ diverse leadership strategies, including brokering. Yet, little is known about their brokering practices. Grounded in social network and social capital theories, this study investigates how different generations of principals engage in brokerage and their specific roles. Our interview data indicate that principal brokers primarily act as gatekeepers and coordinators. A complex interplay of individual, organizational, and societal factors shape principals’ brokering practices. Across different generations, there is a growing trend that younger principals delegate responsibilities to middle leaders, reflecting a shift towards distributed leadership.