This paper describes a partnership between a university and an urban school district, formed with a goal of preparing mathematics teacher leaders to conduct professional development (PD) at their schools. The university and district partners worked together to achieve the district’s mission of providing every student with high-quality instruction and equitable learning opportunities in mathematics by building the district’s capacity to conduct school-based PD for mathematics teachers. Given the power of school-based subject-specific PD for improving instructional quality, we worked with Teacher Leaders from participating schools to prepare and support them to lead PD workshops at their schools. In this paper, we examine how Teacher Leaders learn and adapt key elements of a PD model over three school years through the lenses of Prediger et al.’s Three-Tetrahedron-Model (2019) and the university’s Learning to Lead model. Over 3 years, we see that Teacher Leaders use the key structures of the PD model; make adaptations in response to school goals, interests, and priorities; and gain confidence in their work with colleagues. By viewing the adaptations through the lens of pedagogies of practice as well as the relationships illustrated by the 3-T model, this work offers insights into the complexities of teacher leadership development.