Studies on older adults’ civic engagement have been dominated by a win-win narrative, which assumes that the activity is beneficial both for the individuals involved and for communities. However, civic engagement may also be a source of negative experiences. The aim of this study was to understand these experiences in greater depth through an analysis of older Spanish activists’ narratives of negative episodes of political participation. We also aimed to contribute to the methodological literature on narrative research by highlighting the strengths of analysing not just the content but also the structure of older people’s stories. Life story interviews were carried out with 40 members of Spanish political organisations aged between 65 and 86 years old. As part of the interview, they were invited to narrate a negative event related to their stories of political participation. Answers were analysed both for their content (using thematic analysis) and for their structure (using Christopher Booker’s plot typology). Participants recounted many negative experiences of political participation, which challenged the win-win master cultural narrative around civic engagement. These stories, which often reflected Booker’s plots of ‘tragedy’, ‘overcoming the monster’, ‘the quest’, and ‘redemption’, recorded political defeats, conflicts with other members in the organisation, feelings of loneliness associated with engagement, and undesired consequences for relatives and friends. The results highlight the importance of providing a more nuanced understanding of what it means to be politically engaged in later life. This understanding would integrate the positive aspects assumed by the master win-win narrative with others that clearly challenge its assumptions.