This chapter analyses the final phase of Cruiskeen Lawn against the backdrop of economic expansion and political transformation in Ireland from the mid-1950s to O’Nolan’s death in 1966. It situates the column within the context of the Second Inter-Party Government, Fianna Fáil’s return to power, and the implementation of the First Programme for Economic Expansion, examining how Myles responded to emerging narratives of modernization and national confidence. Key moments such as the visit of John F. Kennedy in 1963, the general elections of the 1960s, and Ireland’s gradual reorientation towards international engagement are read alongside changes in the tone, frequency, and focus of the column. The chapter argues that while Myles increasingly engages with concrete political realities, his satire also reveals fatigue and repetition. Nonetheless, Cruiskeen Lawn continues to function as a critical lens through which state rhetoric, bureaucratic self-congratulation, and political spectacle are exposed. The chapter contends that this period encapsulates the paradox of late Myles: a commentator simultaneously sceptical of progress and deeply invested in the political life of a rapidly changing Ireland.