At what point will educational actors recognize the limitations and utilize the possibilities of policy implementation processes to actualize long overdue reform measures for students--particularly those from historically marginalized backgrounds? Previous literature has attended to ways schooling processes replicate persistent historical, social, economic, cultural, and political inequities that can hinder student opportunity (Bowles & Gintis, 2002; Bowles et al., 2005; Carlone et al., 2015; Morales-Doyle & Gutstein, 2019). Recent calls for equity- and social justice policies focus on reducing opportunity disparities that envision schools as safe places of learning and social safety nets that offer such social services as meals beyond the school day, technology such as laptops and mobile hotspots for virtual learning (de Royston et al., 2020; Greenberg et al., 2020; Ladson-Billings, 2021). Actualizing these visions of schooling requires moving beyond theoretical discussions to actualization processes through policy implementation. This qualitative investigation is a case study of an equity-oriented reform centered around Science, Technology, Engineering, Arts, and Mathematics (STEAM) learning at the school district level in a historically segregated Southern community. The first permanently appointed Black superintendent in this school district envisioned STEAM equity-minded reform as one critical component of a larger school system reconfiguration plan to bring about institutional change while addressing one of the widest opportunity gaps in the state (Darling-Hammond, 2015; Lee, 1999; Mejias et al., 2021; Secada, 1989, 1994). Navigating the social and political dynamics in this Southern school district required grappling with deep-rooted educational inequities familiar across the nation alongside resistant forces pushing against institutional change (Kendi, 2016). Implementing such change depends upon individuals equipped with leadership skills who can effectively mobilize technical and political factors of reform to actualize ambitious policy initiatives like equity-minded school reform (Darling-Hammond & Wise, 1985; Turner & Spain, 2020). Technical factors focus on changing daily operations that occur within organizations while political factors refer to persuasive strategies like changing mindsets. Sustainable institutional reform depends on both factors in order to change individuals' mindsets and practices in school systems. Through the analytical lens of sensemaking, this inquiry captured participants' real-time interpretations as the reforms unfolded to make sense of their beliefs and actions in service of institutional change (Bridwell-Mitchell, 2020; Scott, 2005; Weick, 1995). Findings from this study suggest while equity-minded leaders should attend to technical factors of reform that alter the day-to-day work of educators, they cannot overlook political factors of reform to gain lasting support--indeed, neglecting the political factors of reform can imperil the policymaking to reform process, rendering the effort invested on the technical side moot. Recognizing this dilemma, the superintendent in this study positioned oft-overlooked actors such as curriculum specialists to assist him in navigating the multilayered school district, build community support and gather much-needed resources for the policy initiatives. The new school district leader determined that such organizational shifts would attend to technical elements of reform expected by political actors within the school district and larger community. Yet this case study highlights that political factors can often outweigh technical factors when stakeholders mobilize in response to threats to existing institutional norms. This discussion contributes to literatures concerned with policy implementation, organizational and institutional ideas, with the added layer of equity-minded changes to school reform and policy and politics with Science, Technology, Engineering, Arts, and Mathematics (STEAM) education. The complex nature of this discussion coupled with multiple successes that began to alter the institutional status quo in this Southern school district is perhaps why this superintendent was seemingly forced to resign in a contentious policy environment after two years of service. In light of complex national, state, and local policymaking and implementation processes, actualizing education reform in United States educational institutions can often present difficulties (Cohen & Spillane, 1992; Smith & O'Day, 1990). These complex processes often reduce to educational decisions residing with school boards and superintendents attuned to the pulse of community stakeholders who hold the most political influence. This can dramatically affect decision-making processes when topics seen as "politically charged" arise around equity, race, and opportunity gaps (Fuhrman & Elmore, 1990; Spillane, 1996; Turner & Spain, 2020). This examination attends to that topic space and continuous calls for critical scholarship that produce accessible insights for educational audiences on how to actualize much-needed equity-oriented reforms (Dumas & Anderson, 2014; Dumas & Anyon, 2006). Ultimately, this work examines the need to mobilize sensemaking, technical, and political skills to actualize equity-minded policies into sustainable reforms when contending with institutionally resistant forces.