This collective case study was an exploration of the connection between preservice teacher preparation regarding reading in the content areas and the role of the high school reading specialist as a result of that preparation experience. The case study involved high school reading specialists working in suburban school districts in the Midwest. Interviews and a modified Experience Sampling Method (ESM) were conducted as well as a collection of various artifacts. These artifacts included job descriptions, reading specialist work logs, and actual lessons created for content area teachers by the reading specialists to illustrate the work they did with teachers. Throughout the data collection process, specialists shared that although they were hired as reading specialists, their jobs had evolved into literacy coaching positions without a change in their job title or job descriptions in some cases. Participants walked through the evolution of their positions and the new and changing role of the high school reading specialist. Ultimately, participants agreed that a better preparation experience would be advantageous for future content area teachers, but moreover, they agreed that the best way to ensure reading was successfully being taught in the content areas would be to provide teachers with on-going professional development by an onsite reading specialist(s). Participants agreed that this would be the most effective method to improve the teaching of reading across the content areas regardless of a teacher‘s preparation experience.