In the context of the Cayman Islands and their people, this article examines the dynamic relationship between history, traditionalism, subjectivity, and memory. First, the author contends that expressed traditionalist memories are automatically accompanied by vibrant mental images that work to capture, perpetuate, and immortalize any perceived underlying past spirit in Caymanianness-affirming terms. Second, the attempt is made to explain how the subjective nature of expressed traditionalist Caymanian memories can be understood from the uncomplicated standpoint that people are keen to remember and talk about their lived past. The author also applies the concept of subjectivity to those more complex strains of expressed traditionalist memories that lament the loss of certain Caymanian traditions in a diluted, globalized present. Finally, the author demonstrates how younger Caymanians keen to cherish their ancestral past necessarily depend on expressed traditionalist memories, and in so doing, refashion such expressions in highly personalized, idealistic, and oftentimes problematic ways.