Background/Context Research has shown teachers’ expectations of students to be a powerful predictor of the racial opportunity gap. Yet, many teachers continue to profile White students and Students of Color very differently in schools when it comes to intellectual capacity and motivation to learn. One of the major ethical challenges of teachers’ expectations is how sympathy is constructed in the classroom. Too often, teachers exhibit sympathy through feeling pity for the life challenges facing low-income Students of Color, a dynamic that can result in the lowering of expectations via anticipation of school failure. Purpose/Objective Inspired by W. E. B. Du Bois's (1935) concept of sympathetic touch, the purpose of this article is to introduce asset-based instructional practices rooted in sympathy as a method for confronting systemic problems of pity and deficit thinking which perpetuate low teachers’ expectations. There is a pressing need for an antiracist framework within which teachers can communicate sympathy in an appropriate manner that still hold students to high expectations for learning. This study intends to fill the gaps in the literatures of teachers’ expectations of students, social context of education, urban education, and teacher education by reenvisioning a way to effectively meet the needs of America's diverse school populations. Participants The study was conducted with a sample of nine teachers from low-income, racially segregated neighborhoods in a large urban school district. These teachers were selected for the study based on the following criteria: (1) minimum of three years of teaching experience; (2) working with a majority of Students of Color; and (3) perceived by either their principals and/or counselors to have a positive impact in the classroom and positive relationships with their students. The participants were screened based on these criteria before their participation in the study. We then drew on the literature to inform the final selection of the teachers. Research Design This case study was conducted over the span of one year and included semistructured interviews, three rounds of teacher reflection prompts, informal observations, and a collection of archival data such as course syllabi, lesson plans, lists of ongoing activities related to content instruction, flyers or other materials related to these activities, examples of students’ assignments, and photographs of classroom activities. Data Collection and Analysis All the data from the interviews, journal responses, and documents were prepared, analyzed, and categorized into codes that were in alignment with the research questions. The coding process was done through both hand-coding techniques and the use of the NVivo qualitative data analysis software program. The codes were then analyzed for patterns and themes across the data to document the ways in which the teachers defined and fostered sympathy with students. In addition to using multiple sources of data for triangulation, we validated our findings by engaging teachers in continuous member-checking during the academic year and a debriefing session to enable them to provide feedback regarding the accuracy of the themes found in the data, as well as additional comments regarding their ethics of classroom expectations. Findings/Results Teachers reported that their expectations and awareness of Students of Color's racialized contexts, as well as their position and responsibilities within those contexts, were important factors in their perceived effectiveness. The study discovered that the ethics and practices of sympathetic touch manifested in the forms of equitable student-teacher relationships, empowering curriculum, and the centrality of students’ voices in the construction of knowledge. Specifically, teachers’ sympathetic touch was found to be an important mediating factor in how their expectations were communicated to students in the classroom. In the context of this school district, these teachers reportedly fostered sympathetic practices through high expectations focused on equity, community, and students’ cultural wealth as the basis to generate knowledge in the classroom. Conclusions The results of the present study underscore the importance of asset-based conceptions of sympathy as a mediator of teachers’ expectations in the classroom. Teachers and school administrators’ ability to reframe and redefine sympathetic practices with students is a key factor in improving the educational experiences of diverse populations.