Odogbolu is situated southwest of Ijebu-ode and is a part of ijebu kingdom which is quite a large one. It comprises eight Orule (home steads) each of which migrated from separate settlements. There has however been a great difficulty in determining who the original founder of Odogbolu was and this has resulted in the inability to agree on who should be the head of all Odogbolu chiefs. Over the years three contenders to the headship of Odogbolu town have emerged. At various times, the Elesi, the Oremadegn and the Moloda have all made claims which suggests that the headship of the town belongs to them. Due to the rivalry which plagued the political life of the town (as a result of the struggle for supremacy among the three principal Obas) the town could not realize its full potentials. The spirited effort of Brigadier Oladapo Diya (a distinguished son of the town) to solve the problem when he became the Governor of Ogun State came to naught. It was not until recently that some degree of harmony was achieved. This paper therefore examines critically the politics of supremacy among the three Odogbolu obas and concludes that the Odogbolu Chieftiency crisis was the product of the town’s peculiar history.