<p>This study examines whether retrospectively reconstructed trajectories of employment formality and perceived employment-related stress are associated with cardiovascular health among older adults. We use a cross-sectional life-history survey of adults aged 65–75 in Santiago, Chile (<i>N</i> = 768) and apply exploratory, descriptive multichannel sequence analysis to summarize concurrent trajectories of (i) employment formality (formal, informal, out of the labor market) and (ii) perceived work stress (stressful, non-stressful, out of the labor market). Hierarchical clustering of multichannel optimal matching distances yielded six representative trajectory types, including prolonged inactivity and sustained combinations of informality and stress. Weighted logistic regressions adjusted for established cardiovascular risk factors indicate that, relative to continuous formal and non-stressful employment, trajectories characterized by persistent informality and trajectories characterized by prolonged labor-market absence exhibit higher odds of hypertension, whereas for heart disease the most adverse profile is concentrated among trajectories combining persistent informality with prolonged perceived stress and among prolonged inactivity. When models are additionally adjusted for summative work-history indicators, associations with hypertension remain primarily aligned with long-term informality and labor-market absence, while summative indicators provide limited differentiation for heart disease. These findings suggest that long-run employment disadvantage, operationalized as the joint timing and duration of informality, stress, and labor-market absence, is associated with cardiovascular outcomes in later life in this setting.</p>