Derin Ologbenla the founder of Okeigbo was a warrior from Ile-Ife whose trade was to prosecute war on behalf of the poor and the oppressed. It was through one of his efforts to liberate people that he founded what we know today as Oke-Igbo. Although, no official date could be given as when precisely Oke-Igbo was founded but history has it that the period between 1830 and 1840 are most likely to be the period that Okeigbo was founded.
Derin Ologbenla was said to have received an invitation from Ajibike, an Ifa consultant to Ooni Adegunle Abewela between the periods of 1839-1849. Ajibike was also serving Osemawe of Ondo, Oba Arilekolasi who as at that time was having a running battle with his subjects, the Ondo people. Derin being a friend of Ajibike was invited to liberate the Osemawe from the shackles of his subjects who are bent on killing him. Derin Ologbenla who as that time was in Ijesha after he has assisted them to win a war led his army from Isoroge to Ondo. Although, the decision did not go down well with the Ijesha, he went ahead to pursue his purpose of liberating Osemawe.
Initially, he sent three spies to Ondo and bring back the situation report and assess the strength of the Ondos. After, they came back with their report, he was said to have assembled other notable war veterans who included: Ife prince, Are, Sowo from Egba Owu, Adumbu from Origbo, Onileowo from Origbo, Ebi from Ijesha, Esubi from Offa and Jarogungbo from Origbo and Kuole an Oyo man who had settled in Origbo. The journey to Ondo from Ife was through uninhabited jungle traversed by only powerful hunters.
The journey to Ondo began as Derin Assembled 75 soldiers who carried their weapons through the thick forest, hills, rivers and streams on their way to Ondo. It was on their way to Ondo that they arrived at a place where they met one Ife hunter who goes by the name ‘Ojoge’. Derin was said to have persuaded his soldiers to pass the night at that place which later became what we know today as Oke-Igbo. Another thing was said to have happened mid-way in the night was the disappearance of Ojoge, the Ife hunter. The next morning when he appeared, he was said to have been drilled and it was discovered that his disappearance in the night was to inform the Ondo people about an invading army. Upon the discovery of his betrayal, he was executed at a place that is today the current site of Saint Andrew’s Primary School, Okeigbo. Although, Ojoge was executed for his betrayal, a stream he discovered was named after him and today it is known as ‘Odo-Ojoge’ in Oke-Igbo.
As expected, the Ondo people who have been informed about an invading army had assembled at Odosida, a well prepared army ready to rout the Derin’s gendarme. As the war progressed, Derin was said to have invoked charms and incantations which made him automatically invincible for the Ondos and aftermath of this, the Ondo soldiers in their hundreds were murdered by Derin who was said to have used his sword to unleash hell on the Ondos who were subsequently defeated. After the victory of Derin and his soldiers he was said to have told his men that they should go back and to that place ‘Okeigbo’ meaning ‘over the bushes’ at a place where they had earlier settled and that was how ‘Okeigbo’ was born.
History further has it that the Osemawe who Derin and his soldiers came to liberate was killed by his people before Derin could reach him, but he was said to have been given a befitting burial and Derin installed another head for the town before his eventual departure from Ondo.