Has worked as an assistant to former Environment Minister Jean Charest in Ottawa and to former Justice Minister Edward Roberts in St. John's, and was policy advisor and speechwriter to the Premier of Newfoundland and Labrador, Brian V. Tobin.
His Father was a judge of the Supreme Court of Newfoundland and Labrador.
Most notably known as a former co-host of Canada A.M. (1972) [2001-2011].
He received his Master of Philosophy degree from the University of Cambridge, England.
In 2007, O'Regan became the first journalist to be named to Canada's Top 40 Under 40 list.
In 1999, he was named to Maclean's magazine's "100 Young Canadians to Watch".
Elected to the Canadian House of Commons for the electoral district of St. John's South-Mount Pearl on October 19. 2015.
Sworn in as a member of The Queen's Privy Council for Canada and appointed Minister of Veterans Affairs and Associate Minister of National Defence in the Canadian government of Justin Trudeau on August 28, 2017.