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 over a century. Today, however, WAHS evokes a different image. Between 1960 and 2020, WAHS evolved from a predominately White and high-achieving institution, to one synonymous with failing academics and a majority-minority student body. The current study utilized Dan 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. These events worked both individually, and collectively, to create impacts which challenged the academic performance of the WAHS. Through the use of organizational history, critical incidents were tracked between 1960 and 2020, along with the response, or lack thereof, by the school to these external pressures. Document analysis revealed that WAHS's internal responses to each critical incident were inadequate, contributing to the decline of the school's academics over a 60-year period. Urban renewal, while not directly impacting the internal structure of WAHS, relocated Allentonians of color into the downtown district and laid the foundation for a city segregated by race and socioeconomic status. As the city experienced a rapidly growing Puerto Rican population beginning in the 1970s, it also faced the simultaneous decline of Allentown industries. Each event, while external to WAHS, required the school to respond to a changing demographic and economic base within the city. As the population within the school continued to evolve throughout the 21st century, WAHS was unable to provide the instructional programs and supports necessary for its increasing number of high-needs students. The funding formula defined and implemented by Pennsylvania's public schools forced WAHS to rely heavily on a local tax base that remained unable to generate adequate revenue to support the instructional needs of the school. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]