Head Start comprises a substantial share of the early childhood workforce. Given this, changes in Head Start workforce policies impact the broader early childhood ecosystem--and changes in the larger ecosystem in turn affect Head Start. This paper seeks to inform efforts to strengthen the early childhood workforce by documenting the current state of the Head Start workforce and examining the effects of recent efforts to improve the skills of Head Start teachers. The first part traces the evolution of Head Start workforce policy over the last 50 years and identifies how shifts in the broader early childhood landscape, especially state-funded pre-k programs, have influenced these policies. The second part analyzes the impact of the most recent reauthorization of Head Start, which required half of all Head Start teachers to hold bachelor's degrees with training in early childhood education. It reveals that while the bachelor's degree requirement succeeded in raising the credentials of Head Start teachers, it did not alleviate, and may have exacerbated, other challenges related to recruiting, retaining, and compensating a high-quality Head Start workforce. The third part provides case studies of the evolution of the Head Start workforce in four states (Alabama, New Jersey, New York, and Washington, D.C.), which demonstrate the interconnection between Head Start and the larger early childhood workforce and offer lessons for both state and federal policymakers. The fourth part of this paper details how the broader policy and research context has evolved since the last Head Start reauthorization. Finally, the paper offers policy recommendations to strengthen the Head Start workforce.