This article draws on complexity theory and political will analysis to examine business support for political parties in South Africa between 2021 and 2023. Using a systems dynamics approach adapted to qualitative documentary research, the study analyses budget documents, regulatory texts, disclosure reports, parliamentary records, and media reports. The aim is to establish how corporate political finance operates as a complex adaptive system, one that is characterised by emergent patterns, non-linear responses, and evolutionary dynamics. The analysis employs complexity concepts and political will indicators to identify three system attractors, namely, compliant minimalism, creative circumvention, and defiant opacity. These factors govern corporate political behaviour. The findings also indicate feedback loops between regulatory frameworks and adaptive corporate responses, including a diminishing oversight capacity loop driven by declining Independent Electoral Commission resources. Overall, the study shows how minor regulatory changes can trigger cascading effects, and how weak political will effectively enables phase transitions toward opacity. The documentary analysis methodology demonstrates that complexity theory and political will frameworks can be applied to archival materials to map human agency and the overall system’s dynamics.