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Jeffrey Winters' conceptualization of oligarchy, “the politics of wealth defense”, provides four ideal-type theorizations of oligarchic modes of rule that are contingent on 1) the degree of direct involvement in the provision of coercion needed to claim property; 2) and the spectrum between individualistic fragmentation and collective institutionalisation of rule. These four modes are: warring, civil, sultanistic, and ruling oligarchy. The Colombian puzzle, democracy with various forms of violence, keeps reproducing actors at the margin of legality who, via territorial control and regulating the illicit economy, also construct political networks. The contention that this paper aims to address is whether oligarchic theory can better explain the persistence of the Colombian conflict, which continues despite peace processes with the most important armed non-state actors (AUC, FARC-EP), as it better incorporates the political context of violence structures than institutional and democratic theory. Colombia is a most suitable case, because politics-cum-violence has been a permanent feature in the various phases of the conflict. In order to test the applicability of Winters’ theory, this paper will test the presence of a warring, civil and ruling oligarchy in Colombia’s Caribbean Coast (sulatinistic oligarchy is outside the scope conditions). The Caribbean is suitable because: as a gateway to overseas markets, it has played a key role in the illicit economy (producing various armed actors) and public politics is competitive but dominated by a select number of powerful political families. Thus, the case can illustrate not only how democracy and oligarchy can coexist, it also can show the sources of instability in the concert of different actors leading to peaks of violence.