O'Bryan was extremely active during the administration of the former governor, Charles Turnbull. He headed the Turnbull administration's Office of Public Relations, and was Turnbull's spokesperson during his first term. He also chaired a Turnbull-created task force which worked to remove abandoned vehicles and other garbage from Saint Thomas. In April 2003, the Turnbull administration appointed O'Bryan as head of the committee charged with rebuilding the Sanderilla Thomas Bungalow at Rothschild Francis "Market" Square on the island of Saint Thomas.[1]
He was also the president of Virgin Islanders for Responsive Government.[1]
On April 29, 2003, Governor Turnbull appointed O'Bryan as the administrator of St. Thomas and Water Island, succeeding Louis Hill who had resigned in January 2003 to take office as a senator in the legislature. O'Bryan was working as the assistant to the governor for public affairs and policy initiatives at the time of his appointment.[1]
In 2010, O'Bryan left his morning slot on WDHP (1620 AM), a local radio station, to pursue a gubernatorial campaign.[2]
O'Bryan and Richards Samuel lost the Democratic gubernatorial primary election in 2010, placing fourth behind De Jongh, Donastorg and James.[4] O'Bryan received 432 votes in the election, approximately 3% of the total vote.[4][5] OHe told supporters and the media following the election, "The people have spoken, I respect their wishes, and I will go forward with this episode from now on."[4] He would not say if he would endorse Governor John de Jongh, the winner of the primary, for a second term, explaining, "I’m going to listen to the rain tonight and think on it."[4]