Studies of teachers' lives and careers rarely include a precise focus on subject teaching. This appears a limitation given the often strong connections there are between subject teaching and professional identity. With the intention of understanding the connections between the two better, the research adopted a case study methodology to describe the career of "Jack" who taught physical education in a secondary school in a socially deprived area of Scotland for thirty-six years. The paper collected data from a series of six semi-structured interviews with findings referenced against recent theorising on physical education futures. Descriptive analysis used the structural contrasts provided by Dickens opening to "A Tale of Two Cities", (It was the best of times, it was the …) as an interpretive device for framing discussion. Findings showed that Jack's identity and focus in teaching were closely linked with improving performance through sustained practice and that subject purposes were rarely discussed with colleagues. In agreement with recent policy advice in Scotland, the paper considers that subject-based discussions should be a more substantial component of career long professional development.