Driven by neo-liberal principles, globalization attempts to position education as the source of prosperity and a great social equalizer. As globalization intensifies, Jamaica is actively reforming its educational policies in order to reap the benefits of the new "knowledge economy." However, significant policy approaches, which accompany the emerging policy changes—referred to as policy discourses—have the unintended consequence of perpetuating disempowerment of low income Jamaicans. I identify and critically analyze education as (private) investment as one of Jamaica's dominant policies. I note that the neo-liberal ideology that influences this discourse is fundamentally inconsistent with the post-war/post-independence social welfare approaches that Jamaica used to address social asymmetries of colonialism. The result is that education as (private) investment predicates educational opportunity on the capacity to pay, thus limiting the likelihood of education to be the great socio-economic equalizer.