The practice of the twentieth-century teacher has been entrenched within a rigorous concern for the manner in which her/his practice is being reshaped and imprisoned by neoliberal initiatives of accountability, governance and programmed performances. This article continues and extends this current debate by highlighting the historical antecedents of a teaching practice which simultaneously operates within the Trinbagonian educational context as a practice of oppression and a practice of intellectual subversion. In doing so, it introduces the notion of plantation pedagogy as an inherited educational practice which, in the practice of the teacher, can be manifested as a practice of hopelessness (oppression) and hope (subversion). Within the scope of this article teaching as an action of hopelessness, and teaching as an action of hope, can be constructed as practices of teacher anti-agency and agency. Data collected within an extended focus group session with 10 primary school teachers revealed that the practice of the teacher in the primary school can be constituted within and by two levels of agency. These agencies can be characterised as opposing views of plantation pedagogy, both of which emerge out of a process in which teaching is constructed as labour in service to a plantation society.