Faced with the mandate to achieve adequate yearly progress (AYP) with every student and meet benchmarks at every grade level, teachers have also had to deal with adolescent disengagement from the learning process. This case study explored a relatively new approach to adolescent education, developed from the work of Kieran Egan, who proposed that children developed cognitive tools which were extensions of the oral devices used for teaching and learning in pre-literate civilizations. Egan theorized that the most powerful of these cognitive tools had inherent affective aspects, which could be used to establish context and content meaning for students. Using a case study approach, I examined content acquisition and retention associated with affective scaffolding in a middle school Social Studies unit on ecology and the consequences of choice. I spent 21 days in the spring of 2010 observing the class. I used four instruments for data gathering: 1) Pre-unit and post-unit surveys, 2) Teacher and student interviews, 3) Teacher and student journals, and 4) Direct observation documented in field notes and field journal. The post knowledge score (M = 14.42, SD = 2.317) was significantly greater than that for the pre knowledge (M = 12.74, SD = 1.69), t (18) = 3.318, p< .01. The standardized effect index, d = .7612, indicated a large effect size. The results of this case study fit within Egan's conceptual framework. Based on this study, I developed a grounded theory that using play as a teaching tool (by combining all three learning domains into one teaching strategy) was an important cognitive tool. Further detailed ethnographic studies are needed to explore fully the area and its ramifications for learning instruction.