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A particular voice in Caribbean women’s short-fiction writing stands out, not only because of the talent and skill displayed by the author and by the numerous awards bestowed upon her, but also because Barbara Jenkins is a septuagenarian who in 2013 published her debut collection Sic Transit Wagon and Other Stories. Her age makes her distinctive among her younger peers who are contributing to a literary renaissance in Trinidad and Tobago. This article explores Jenkins’ positioning as a successful older writer as well as two of her short narratives on marriage, family and health as they relate to older characters. Theories on intelligence, creativity and achievement regarding age and ageing, and the socio-political situation related to the aged in Trinidad and Tobago, are discussed to contextualize Jenkins’ success and the foci of the narratives. This article examines particular discourse strategies used in the two selected stories, as well as themes of marital infidelity, and the impact of age-related disease on spousal and filial relationships.