[7] Aregbesola's interest and involvement in politics dates back to his undergraduate days when he was Speaker of the Students' Parliament (1977–1978) at The Polytechnic, Ibadan, and the President of the Black Nationalist Movement (1978–1980).

Upon the return of the country to democratic rule in 1999,[8] he was a ranking member of the Alliance for Democracy, led by Senator Bola Tinubu,[9] who would go on to become governor of Lagos State in the same year.

[19] After incumbent Olagunsoye Oyinlola was declared the winner of the 14 April 2007 elections,[20] Aregbesola immediately proceeded to the courts to overturn this outcome.

[28][29] Oyinlola alleged that there was telephone contact between Justice Ayo Salami, head of the Nigerian Court of Appeal, and the Action Congress of Nigeria (ACN) chieftains prior to the decision and urged the Attorney General of the Federation "to exercise his power of public prosecution entrenched in Section 174 (1) and (2) of the 1999 Constitution by initiating legal action against MTN Nigeria Limited after he petitioned the National Judicial Council.

[41] National forces were therefore deployed in a plot to intimidate voters and reduce votes,[42] but despite several arrests of his key associates, Aregbesola defeated the PDP's candidate, Senator Iyiola Omisore.

[51] In 2016, The National Judicial Council recommended Justice Oloyede for compulsory retirement after it found that the petition written by the judge "contained political statements, unsubstantiated allegations and accusations aimed at deriding, demeaning and undermining the State Government of Osun, the person and character of the Governor, his deputy and aides".

The summit, chaired by Wole Soyinka, centered around the primary and secondary levels based on the belief that basic education is of paramount importance.

Opon Imo received a UN-World Summit Award for innovation[58] as well as endorsement by UNESCO, the West Africa Examination Council and several others.

[59][60] Aregbesola's government also paid the external examination fees for all public senior secondary schools, in an effort to reduce the burden on parents.

[65][66][67] Also, the United States Ambassador paid a visit to Osun in June 2017, where he praised Aregbesola for his implementation of social investment programmes.

[71] The state government also oversaw the standardisation of the school uniforms to create a unique identity for its students, promote its culture and stimulate the local economy.

[72] The implementation of the O-Uniform scheme led to the building of the largest garment factory in West Africa in Osogbo, Osun, where the uniforms are made and shared to students around the state.

The investments in education have started yielding results, as private proprietors have begun to comment on the loss of students to the public schools, which are now of increased capacity.

In 2009, International Breweries plc, Ilesa, known for its Trophy brand, doubled its production capacity to cater for the boost in the local economy.

[96] In Osogbo, there was a renovation of the Nigeria Railway Station terminus and urban renewal of the city center towards Olaiya junction and the building and repair of roads.

Aregbesola has always received press attention for his approaches toward human capital development, education, and infrastructure, which have often landed him in the center of public discussion.

He supports Fiscal federalism for Nigeria and Regional Integration as a means of attaining sustainable economic development and national competitiveness.

[97] Aregbesola has supported the development of human values through extracurricular programmes, such as calisthenics, the Omoluabi Boys and Girls Club,[98] and other schemes for youths to channel their energies towards a society that promotes the common good.

Simply put; Omoluabi is the word in the Yoruba language that describes an individual, male or female, young or old that possesses the following qualities: hard work, honesty, integrity, fairness, egalitarianism, respect for elders and constituted authority; and fear of God among other virtues.

His contributions were recognized when, in 2016, the Alaafin of Oyo, Oba Lamidi Adeyemi III, a revered Yoruba traditional leader, named Aregbesola as the 'Omoluabi of Yorubaland' for being at the forefront of projecting the Omoluabi ethos.

[102] Aregbesola has remained within the same political group even as it went through several mergers, first changing to the AC, then the ACN and the APC, which would later become the federal ruling party in the country.

When Aregbesola decided in 2005 to run for governor, a political support movement was instituted named Oranmiyan, after the son of Oduduwa, regarded as the founder of the Yoruba race.