Through his paternal grandfather, Swan is a 6th-generation descendant of Charles Roach Ratteray (1799–1872), a renowned ship builder, entrepreneur and pioneer of the AME Church in Bermuda.. Swan attended Southampton Glebe, Berkeley Institute and Warwick Secondary Schools in Bermuda before receiving his tertiary education at Palm Beach Junior College (now Palm Beach State College) in Lake Worth, Florida.
He partnered with fellow Bermudian Keith Smith to qualify for the 1984, and for three Bermuda Open Golf Championships.
Initially, Swan contested four general elections over 25 years before winning a seat in the House of Assembly of Bermuda in December 2007.
On 10 May 2011, Swan, three other former party chairmen and others successfully filed a court injunction preventing UBP from disbanding.
He finished third, receiving 23% of the vote behind 39% for the new One Bermuda Alliance, only narrowly besting 38% for the Progressive Labour Party candidate.
In 2014, Swan accepted an invitation from Leader of the Opposition Marc Bean to join the Progressive Labour Party.