His first wife upon his rise to the throne was Adeke, he inherited her from his predecessor, Ojijigogun, and they had one son, Ogunlade (grandfather of the current Deji, Odundun II).
This created a vacancy in the office, and several eligible princes sought the throne, including Odundun and his cousins, the three sons of the deceased king: Arosoye, Ifaturoti, and Olofinlade.
It is said that the officers that were sent to enforce control of Akure were oppressive and often raped and killed the people that they met there, so when Oba Odundun heard of this, he refused to pay the tribute anymore.
[citation needed] Oba Odundun was known to be a brutal and ruthless tyrant, and is often compared to King Henry VIII of England, in that he swiftly executed one of his wives for sharing a joke with him in the bathroom.
[6] Another one of his wives, Olori Ifámùgbẹ̀ẹ from the nearby village of Ikota whom he married at the beginning of his reign, fled the palace in 1887 to the town of Ilara-Mokin because of his cruelty due to her childlessness.
In the early 1990s, the Osupa family was recognized as one of the official ruling houses of the Akure Kingdom by the military administration of Ondo State.
Falae was a civil servant and politician who served as secretary to the Government of the Federation during the administration of Ibrahim Badamasi Babangida.
[7] Another one of his descendants include his great-grandson Ogunlade Aladetoyinbo Aladelusi, who later became the Deji of Akure, Oba Odundun II, the current king.