Career
O'Brien began his career with the schoolboy club Stella Maris. He began his senior career under Billy Young at Bohemians where he was also a youth international representing his country at the 1983 UEFA European Under-18 Football Championship where Ireland were knocked out despite not losing a game. In April 1983 he played for the League of Ireland XI U21s against their Italian League counterparts who included Roberto Mancini and Gianluca Vialli in their team.
After only five League appearances, he signed for in September 1983. He joined the Reds for an initial fee of £50,000. Alex Ferguson took over from Atkinson as manager in November 1986, and O'Brien made his debut in the 1986–87 season, making nine appearances, including an appearance in January 1987 where he was shown a red card just 85 seconds into a game against Southampton.
The sending-off is the quickest dismissal in club history. The majority of his appearances in the 1987–88 season were as a substitute, and that summer, frustrated by lack of first-team opportunities, he joined in a £275,000 move after 36 appearances (31 in the League) & two goals for Manchester United. His career at St James' Park brought mixed fortunes.
O'Brien suffered relegation from the top flight in the 1988–89 season. O'Brien found himself surplus to requirements as Newcastle rejoined the top flight and subsequently made a £350,000 move to Tranmere Rovers after a successful loan period. He enjoyed some great European nights during this season as Bohs knocked out Aberdeen and beat 1.FC Kaiserslautern.
O'Brien played for the Republic of Ireland national under-19 football team that qualified for the 1983 UEFA European Under-18 Football Championship where despite remaining unbeaten in a group that included eventual winners France they were eliminated. He was also a Republic of Ireland international, winning his first cap while still at. After retiring as a player, O'Brien had spells as assistant manager at Bohemians and.
He was appointed first team coach of Hibernian in November 2011 by Pat Fenlon. O'Brien left Hibernian after the end of the 2012–13 season. Club Individual.