Exploring the legacy of Tipu Sultan, this essay delves into the dichotomy of his reign, celebrated for his defiance against British colonialism and critiqued for controversial governance tactics. Born on November 20, 1750, Tipu Sultan’s rule is a subject of historical scrutiny, with historians like Sandeep Balakrishna, Arun Shourie, and Sankunni Menon offering divergent perspectives. Balakrishna labels him a tyrant for his religious intolerance and brutality, while Menon discusses the severe impact of his campaigns in Malabar. Despite these criticisms, Tipu’s strategic military innovations and efforts to modernize Mysore highlight his complex legacy as a leader navigating the tumultuous political landscapes of 18th-century India. This nuanced discussion aims to illuminate the multifaceted nature of Tipu Sultan’s legacy, inviting readers to ponder the complexities of historical narratives.