A Newtown junior, Kessey made his debut for the club in Round 15 of the 1926 season against St George.
In 1928, Kessey was a member of the Newtown side which finished last on the table with only one win for the entire season.
In 1929, Newtown's fortunes changed and the club went from wooden spooners to grand finalists as they faced South Sydney in the 1929 decider.
Kessey captained the team as they were soundly beaten by Souths 30–10 at the Sydney Sports Ground.
Kessey played a further three seasons for Newtown and retired at the end of 1932, a year before the club was to claim their second premiership in 1933.