Across the United States, we have witnessed a lack of school preparedness for learning and engagement, as well as an abysmal divide between the haves and the have-nots. With the onset of COVID-19, school shutdowns are causing disproportionate learning losses, leading to long-term effects on children’s long-term economic well-being and on the U.S. economy as a whole. This qualitative comparative case study of two elementary and two middle schools located in districts in Southern California and Southern Texas examines ways in which leaders of high-performing elementary and middle schools understand essential components of the Partnership for 21st Century Framework and infuse those components across the curriculum. Findings revealed that although each of the four researched high-performing schools espoused four of the 5C’s (Critical Thinking, Communication, Creativity, and Collaboration) of the Framework, the most imperative C—cultural competency—was overlooked. Skills such as functional skills, media literacy, and essential career skills were minimal, but were more present in high- socioeconomic, high-performing schools. Findings further revealed that administrators were not universally familiar with all characteristics of the Partnership for 21st Century Framework and were not ensuring the entire framework was being implemented across their campuses. Administrators were also limited in providing professional development opportunities to staff. The implications for practice indicate the need for Partnership for 21st Century Framework training for school leaders and teachers. Other implications suggest a need for policymakers and leaders to find more innovative ways to connect students to their community and the world.