[10] Rowley entered politics in 1981, where he unsuccessfully contested the Tobago West seat in the general election of that year.

To date he has the distinction of being the only People's National Movement candidate to have contested a seat in a General Election in both Tobago and Trinidad.

Following the People's National Movement's defeat in the 2010 general election, Rowley was appointed as Leader of the Opposition on the 1st June.

In 2004, he chaired the Joint Select Committee of Parliament which examined and made recommendations for the live broadcasting of parliamentary debates.

Rowley again led the People's National Movement to victory in the 2020 Trinidad and Tobago general election for a second term in government under his premiership.

[16] During his tenure, on 5 February 2022, the Trinidad and Tobago coast guard fired upon a vessel with Venezuelan migrants while attempting to stop it, killing a nine-month-old baby and injuring his mother.