Considering Cohen, March and Olsen’s (1972) “garbage can model,” this paper seeks to examine how educational reforms, adopted by Israel from pre-statehood to contemporarily times, have impacted the role of principals and whether these reforms have prepared them to address challenges of the system. Using second-order historical sources, the paper employs a socio-historical based data analysis to examine the complex relationship between policies, structures, and values and their impact on the role of the principal. For each historical period in the Israeli education system the paper discusses the immediate societal challenges, the origins of the adopted reforms, and the influence of these reforms on the role of the school principal and his/her ability to respond to the challenges placed before him/her. This analysis demonstrates how imported policies and international trends, that are loosely connected to local social, cultural, political and educational contexts and the first fundamental layer of centralized reform adopted in Israel, have impact policy-making and limited the principal’s response to contemporary socioeducational challenges. It is consequently argued that because the system is consistently delayed in adopting educational reform, principals have been forced to respond to the challenges of yesterday instead of focusing on future, and even current challenges. Few studies have employed both the “garbage can model” and a sociohistorical perspective for studying policy-making in education and its influence on the evolution of the role of the principal. The present novel study has the potential to fill this gap in our knowledge by analyzing long-term processes and turning points that have simultaneously shaped the principals’ ability to face societal challenges.