Physical education teachers with a strong sense of purpose are more resilient and maintain high-level performance over time. Therefore, this longitudinal, mixed-methods exploratory case study describes how two teachers' (Gary and Wayne) sense of purpose in life and well-being has influenced their intent to remain teaching in high-poverty schools. This inquiry followed the two participants over four consecutive school years (2015-2019) and included eight formal interviews with Gary and Wayne, two administrations of the Ryff's Psychological Well-Being Scale questionnaire, and one administration of the Teaching Sustainability Questionnaire over the four-year project. Gary's and Wayne's strong purpose in life contained central values that led to their intention to remain teaching in their high-poverty school context. This strong sense of purpose stemmed from their perceived internalized and externalized support associated with life experiences, familial influence, and the school environments where they worked. Gary's and Wayne's sense of purpose appeared to have a direct effect on their intention to remain teaching in the high-poverty schools where they were employed. Identifying a teacher's sense of purpose and the extent to which it aligns with a specific school district's mission/vision may be an important factor in recruiting and retaining teachers in high-poverty environments.