By the 1840s, Taiwo had become a protege of
Kosoko, Oba Osinlokun's son. Kosoko reigned as
Oba of Lagos from 1845 to 1853 and, as can be expected, Taiwo leveraged his closeness to Kosoko for mercantile gain, establishing partnerships with European and Brazilian merchants. While it is unclear whether Taiwo fled with Kosoko to Epe after the British
Reduction of Lagos in December, 1851, and the subsequent installation of Oba
Akitoye, what is known is that colonial Governor
Freeman invited Kosoko back to Lagos in 1862. Taiwo built a mutually beneficial relationship with both Freeman's administration and successive ones. In 1861,
Kosoko introduced Taiwo to Governor
Glover In an 1865 letter to Colonel Ord, a British colonial official, Taiwo and other Lagosian merchants wrote that they had been "born slaves" and had "risen by [their] energies" to become successful slave owners, planters, canoe owners, and traders. The historian
Kristin Mann notes that the exact dates of Taiwo Olowo's redefinition as a merchant and manumission from slavery are unknown. Taiwo was baptized in the late 1870s at the Holy Trinity Church in Ebute Ero, taking the name Daniel Conrad Taiwo. He also served as an emissary of the British colonial government in Lagos, and was ambassador to the court of the King of Porto Novo. When
Oshodi Tapa, earlier war captain and now chief of business, died in 1868, Taiwo Olowo became Kosoko's business chief. Upon Kosoko's death in 1878, Taiwo became leader of the Kosoko economic faction (versus the smaller numbered Dosunmu faction headed by
Oloye Apena Ajasa) of at least 20,000 followers. Taiwo feuded with the other powerful Baba Isale - Chief Ajasa - over trade routes and in other complex Lagos power plays. Ajasa was originally an ally of Oba
Dosunmu, but the two fell out when Ajasa became too powerful for Dosunmu to handle. In an attempt to counterbalance Ajasa's political strength, Oba Dosunmu sided with Taiwo, contributing to Ajasa's political fall. ==Philanthropy==