K-12 Education is in crisis in the United States of America. At the center of the crisis looms a severe teacher shortage. To understand the severity of the crisis it is necessary to explore the nexus between structural factors, strategic blunders, and the socio-economic environment. A case study guided by grounded theory, helps elucidate the complex nature of the phenomenon. Official statements released by school districts, the Department of Education of Florida, and professional associations are interpreted through the constant comparative method to reveal the interaction between strategy, structure, and environmental context. A tentative model of the interrelationship between factors considered to be important by the organizations in question was developed to help stakeholders understand the complexity of the crisis and by doing so, engage in more constructive and effective ways in the policymaking process.