For the next 200 years, Oracabessa functioned as a tiny agricultural community with its main crop, bananas, controlled by a small group of British landowners. The arrival of Reverend James Phillippo in 1834 changed the course of Oracabessa's history. Phillippo built the first church in Oracabessa and led a defiant protest against the local landowner's refusal to sell land to former slaves. The parish of St. Mary, where Oracabessa is located, had a large population of freedom fighters, known as Jamaican Maroons, who worked closely with Phillippo in his quest for justice. With this show of force, combined with a decree from the British Government, the landowner's relented and sold Phillippo enough land to build houses, schools, churches and businesses for the hundreds of residents in the area.