Kennedy previously served as a Member of the Legislative Assembly (MLA) for Newry and Armagh from 1998 to 2017.

[1] He ran unsuccessfully for the UUP in the Westminster election in 1997, in which he polled over 18,000 votes against Seamus Mallon.

His performance in this office garnered him the award for "Best Committee Chair" from the Slugger O'Toole blogsite in 2008.

[3] He contested the constituency of Newry and Armagh for the UUP in the 2005, 2010, and 2015 general elections, finishing fourth, third and second with 13.9%, 19.1% and 32.7% of the vote respectively.

[4][5] Kennedy lost his seat as an MLA in the 2017 Northern Ireland Assembly election, which was held on 2 March 2017.