In December 1941, as de Valera announced in the Dáil the opening of Ireland's first diplomatic representation in Lisbon, Fine Gail leader James Dillon declared: “Let us at least dismiss the implication that Salazar's policies are de Valera's and that when we praise Salazar what we are really doing is patting De Valera on the back, because if there are two men in Europe further apart...”. At the time, Salazar' dictatorial regime was still enjoying widespread praises from some parts of Ireland's society, including the Taoiseach himself who was sometimes accused of trying to benefit from Salazar's alleged achievements and popularity. Indeed, beside their exceptional duration at the head of their respective countries, approximately at the same period, a closer look at both leaders' biographies reveals many chronological coincidences as well as common characteristics about their origin, education, personality, influences... The objective of this paper is to analyze how both Salazar and de Valera were represented in Ireland's main daily newspapers of the period (the Irish Independent, Irish Press and Irish Times), with special emphasis on how this representation of both leaders stems from each newspaper's position within the Irish political debate.