This article examines the roles of former National Security Advisors H. R. McMaster and John Bolton in the Trump administration. The article discusses four general roles performed by the Assistant to the President for National Security Affairs—administrator, coordinator, counselor, agent—and asserts that while McMaster served as a coordinator and Bolton served as a counselor, both failed to achieve a close relationship with the president. Probing the role and performance of President Trump’s second and third APNSA underscores both the significance of two partly influential APNSAs and apparent constraints in relation to what a president with an unconventional management style allowed them to do.