After graduating from Northwestern Regional High School, he attended The Citadel, but left after he was beaten by a fellow cadet because of his sexual orientation.

[2] He wound up at American University in Washington, D.C., where he earned a Bachelor of Arts in political science and economics and a Master of Public Administration.

He is also a graduate of the University of Virginia’s Sorensen Institute for Political Leadership, the Harvard Kennedy School for State and Local Leaders, and the Air Command and Staff College.

[3] He was a vice president for government relations of the Healthcare Information and Management Systems Society (HIMSS), an international non-profit, but retired from that position when he was sworn in as county supervisor.

Earlier, he served as a budget analyst for the United States Department of Defense and as a staffer for Senator Lowell Weicker.

[5] He has also served as a federal advisory commission member in the administrations of President George W. Bush and Barack Obama in the United States Department of Health and Human Services.

While on the council he is credited for work on traffic-calming projects, a local coastal plan, business relations, opening new parks, a plastic bag ban, and support for the arts and North Coast Repertory Theatre.

He narrowly defeated Republican Steve Danon, chief of staff to Congressman Brian Bilbray, in the November 2012 runoff election.

[15] On September 15, 2015, The San Diego Union-Tribune and Los Angeles Times newspapers reported that the Board of Supervisors had agreed to settlements totaling $310,000 for three of Roberts' former staffers in relation to various claims that he had created a hostile work environment.

Roberts and his spouse are active members of North San Diego County Adoptive Parents Association and Friends of the Solana Beach Library.