Background/Context: This study focuses on the educational disenfranchisement of Diego, a disabled bilingual Latino youth. Less is known about how youth experience these inequities and what they can contribute to better understanding these educational conditions. Purpose/Objective/Research Question/Focus of Study: We combine CHAT and speculative education to offer a future-oriented approach grounded in ethical relationality to understand how Diego made sense of the social conditions of his educational experiences and how he used testimonio to reimagine educational systems. Research Design: The original youth program was implemented as a social design–based experiment, from which we used a case study design to highlight the sensemaking and testimoniando process of Diego, a disabled bilingual Latino participant. Conclusions/Recommendations: The case study documented that Diego demonstrated a critical consciousness about the multiple and intersecting systemic inequities and social conditions that shaped his educational experience. Diego used testimonio as a future-making tool to call for collective action and laid out a vision for a system more responsive to his identities.