US education is hardly divorced from systemic societal inequalities. Utilizing the cases of the English-speaking Caribbean and post-apartheid South Africa decolonization efforts, we engage the settler coin concept to interrogate the popular notion that we can achieve systemic change in the US without fundamentally transforming the education system. What lessons might the US glean from other decolonization efforts in the Caribbean and South Africa? How have the instrumental ideas and work of Caribbean and South African scholars and educators shaped and advanced a decolonization vision? Answering these questions requires considering the overall goals of the US education system relative to advancing a larger decolonization project.