[1] O'Bryan was a Democratic Party candidate for governor of the United States Virgin Islands in the 2010 gubernatorial election.
[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.
[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 announced his candidacy for governor of the United States Virgin Islands as a member of the Democratic Party in the 2010 gubernatorial election.
[3] O'Bryan and Richards Samuel lost the Democratic gubernatorial primary election in 2010, placing fourth behind De Jongh, Donastorg and James.
"[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.