U.S. National Professional Development (NPD) grants can afford a longitudinal understanding of how teachers learn to support English learners. When NPD projects are completed successively and successfully, they can provide an even greater longitudinal arc of understanding. This article chronicles the designs and lessons learned across five NPD grants between 2002 and 2023. Each grant represents a snapshot in time, presenting a set of assumptions from the field, programmatic innovations, and insights from research outcomes. From highlighting the difference between incremental and radical pedagogical change and what it takes to move beyond individual teacher change to systemic change benefiting multilingual learners, the article outlines the succession of aspirations (capacity building, sustainability, and scalability), experiences, changing conditions, and data points framing lessons learned and new cycles of praxis. This article offers implications for theory, practice, and research. It stands as an argument for adapting, innovating, and moving beyond the status quo to inspire more innovation in teacher preparation for multilingual learners.