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William Allen High School (WAHS) was once a pillar of success. From a growing student body to a successful vocational wing, the high school was the epicenter of the district and the city for decades. However, between 1960 and 2020 WAHS evolved from a high-achieving institution, to one synonymous with failing academics. The current study utilized Duke’s (1995) proposed steps for writing an organizational history. Analysis of primary and secondary sources identified four critical incidents- urban renewal, the migration of Puerto Rican residents, the collapse of industry, and the funding formula defined and implemented by Pennsylvania’s public schools. The analysis examines how these incidents worked both individually, and collectively, to create impacts which challenged the academic performance of the WAHS.