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Amidst political attacks against public education, defunding, and historical whitewashing efforts, this study amplifies the wisdom of experienced middle school educators. Part of a larger dissertation study focusing on six 8th-grade Gilder Lehrman History Teacher of the Year winners and their pedagogical content knowledge (PCK) (Jay, 2023, 2025; Shulman, 1986, 2004), this paper specifically investigates how these teachers consider students' developmental and contextual needs in their classrooms. Using a qualitative case study approach with portfolio analysis, interviews, and focus groups, preliminary findings reveal that these teachers prioritize creating safe, relationship-rich environments. They also employ clear classroom structures and daily habits, often with humor, to meet diverse student needs. This research offers an optimistic counter-narrative, showcasing effective practices in challenging times.