The historic boundaries of downtown St. John's is usually thought to start at the harbour extend north to Duckworth Street and is bounded by Springdale Street in the west and Empire Avenue in the east. In recent years the boundaries of downtown have extended further north and usually take in Military Road or sometimes even as far as Empire Avenue, this may also be referred to as the greater downtown area.
O'Keefe was elected to municipal politics in 1997 as a councilor at large and was subsequently re-elected to the position in 2001. In 2005 he was elected Deputy Mayor of the city and held that position till the resignation of Mayor Andy Wells in 2008. He served as acting mayor from March to April 2008 before resigning to run in the June by-election to replace Wells. He won the race beating former deputy mayor Marie White by a 5,000 vote margin. In the 2009 municipal election O'Keefe was re-elected Mayor, taking 57 per cent of the votes.