This chapter examines the complex and sometimes contradictory role of powerful Irish-American business figures, particularly members of the Irish American Economic Advisory Board, in shaping Ireland’s economic development from the 1980s to the 2000s. Initially celebrated for their investments and diaspora-driven engagement, figures such as Chuck Feeney, Donald Keough, and Tony O’Reilly contributed significantly to Ireland’s economic modernisation. However, their involvement often reflected dual motives—both philanthropic and profit-driven. The chapter details how their influence extended beyond business into politics, notably through lobbying efforts, government access, and media control. Controversies, such as the Eircom privatisation and the awarding of telecommunications licenses, reveal tensions between national interest and private gain. Moreover, Ireland’s diplomatic silence during controversial periods of US foreign policy, such as the Iraq War, is linked to the government’s desire to maintain favourable economic ties with the United States and appease influential Irish-American figures. The chapter raises critical questions about transparency, accountability, and the long-term impact of foreign influence on national policy, highlighting the blurred lines between strategic partnership and economic dependence.