<p>Rehumanizing mathematics with and for students with disabilities is a critically important, and often overlooked, aspect of mathematics education. This paper describes a professional development project that paired Universal Design for Learning with Design Thinking for mathematics and special educators. We situated disability in a political framework, as a shift from a medical model to a political/relational model. Across data sources, the educators in our study attributed shifts in their beliefs and practices to empathy, both as a value and a practice of empathy interviews. Educators reported shifts away from deficit thinking about disability, towards instruction from the perspective of their disabled students. Educators described UDL as moment-to-moment decision making during instruction based on empathic relationships with students. They also connected the practice of empathy to their emerging critique of oppressive systems impacting their students with disabilities. Engaging in empathy interviews as a practice appeared to be central to these shifts, giving educators a tool for innovation in the emotionally challenging year of 2020–2021 in which many educators taught online. Building from the new uses educators made of empathy, we propose a model that integrates empathy with conceptualizations of teachers’ knowledge as both politically situated and emergent in relationship with marginalized students.</p>