Researches critical of electoral freedom and fairness, integrity, financing, and security in Nigeria have challenged Nigeria's democratization process. However, not many of them have captured these challenges considering the paradox of the civil society organizations' collaborations (CSOs) in Nigeria. We argued that for civil society to activate the democratization process, a historically structured imbalance through dualism of political and economic collaborations of the civil society should be resolved. The study made use of the Exploratory Research Design, using the Structural-Functional Analysis and the Post-Colonial State theory as frameworks for analyzing the imperativeness of economic collaborations to direct the political collaborations. It made use of mixed method of data collection and analysis, using a sample of 312 respondents drawn from population of 1434 members of civil society organizations. We used the Multilinear Regression model in the Statistical Packages for the Social Sciences IBM (SPSS) version 20 to test the statistical hypothesis that: civil society organizations' uncordial relations with government organizations and their uncordial relations with business organizations are significantly related to their detection of electoral challenges in Enugu State, 1999-2020. It was found that civil society organizations' uncordial relationship with government organizations rather than uncordial relationship with business organizations is significantly related to help in detecting electoral challenges in Enugu State, 1999State, -2020
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