Spain is considered the world leader in the field of Organ Donation (OD). Italy has adopted the Spanish model in its health system but failed to reach the Spanish primacy. This work investigates the cultural elements influencing the choice to donate in Italy and Spain. We collected from two newspapers of Italy and Spain, all the published articles (2001–2021), containing the respective translation of OD. The two final corpora were analyzed through the Emotional Text Mining methodology. The analysis produced 4 CR for the Italian corpus and 5 CR for the Spanish one. The principal CR for Spain is viewing the OD as a national project, while in Italy, the donation is viewed as a life-saving product. In Italy, the theme of death is viewed as unacceptable. In Spain, the principal context in which donation is discussed is the family. Another difference is related to the developmental process: Italy is rooted in established promotional models, while in Spain, the desire for innovation emerges. Finally, OD is connected to other fields in Spain. In conclusion, this study allowed us to understand deep cultural differences between Spain and Italy in OD. Results ought to be used to improve promotional campaigns to citizens.