This study examines the historical trajectory of sugarcane farming at Nzoia Sugar Company (NSC) in Bungoma County, Kenya, from its establishment in 1975 to 2020. Using the Cumulative and Cyclical Interdependence Theory by Karl Gunnar Myrdal as a theoretical framework, the research traces how initial development cycles transformed into negative spirals affecting both the company and the surrounding community. Through qualitative research methods including interviews, focus group discussions, and document analysis, the study reveals how NSC progressed from initial success to eventual decline, identifying critical factors that contributed to this trajectory. The findings demonstrate how institutional, community, and individual factors interact to create cycles of growth or decline in agricultural economic activities, offering valuable insights for agricultural policy and management of agro-industrial enterprises in developing contexts.