Orlando Smith originally qualified as a physician, specialising in obstetrics, and was the territory's chief medical officer for many years both before and after entering politics.

[3][4] He entered politics at a relatively late stage of his career, being first elected to the Legislative Council of the British Virgin Islands (now called the House of Assembly) in the 1999 general election, as the head of the newly formed National Democratic Party (NDP).

In 2003, Smith led the NDP to victory, defeating the ruling Virgin Islands Party for the first time since 1983 in the 2003 general election.

Smith barely retained his seat as the at-large candidate, receiving the fourth largest number of votes.

[5] He passed Willard Wheatley as the third longest serving head of Government in British Virgin Islands history on 14 February 2016.