The national security and intelligence advisor to the prime minister (NSIA) is one of the most important officials in the Canadian government. The NSIA counsels the prime minister on critical matters of national interest while coordinating a complex security and intelligence community and engaging relevant actors worldwide. The significance of the office has ebbed and flowed over the decades, depending on the individual in the job, the interest of the prime minister and the state of the world. As the definition of national security has expanded and the world has become more unsettled, the position has become increasingly complex and demanding. This paper examines the evolution of the office over the years, the officials who have held the job and the ways in which they collaborated with their colleagues across government to address emerging threats, while also touching upon many of the security-related events that grabbed the headlines during these years. At a time when threats to Canada are more serious than ever and our closest allies are no longer inherently trustworthy, a complacent attitude toward national security cannot be tolerated. Exploring the history of the NSIA and identifying ways to improve the office in the future may help Canada chart a path forward in a dangerous world.