He won the Benson & Hedges National Award for Outstanding Work in Provincial Journalism in 1980, which resulted in him joining The Irish Times as a general reporter a year later.
[4] It was this appointment that began his career as a successful political editor as opposed to a general reporter,[2] and he continued to work from Leinster House until his retirement.
[5] He particularly enjoyed analysing potential electoral outcomes and the motives of decisions of politicians such as Charles Haughey, Dick Spring, and Albert Reynolds.
[2] He made regular appearances on current affairs shows on RTÉ, Newstalk, and TV3, while he had a weekly Call from the Dáil slot on Radio Kerry.
[4] O'Regan's brother, Gerard, was also involved in journalism as editor of three national newspapers, while his younger sister Eilish was the Irish Independent health correspondent.