A South Sydney junior,[3] Why began his first-grade NSWRFL Premiership career during the 1926 season.[4] At the end of the 1928 NSWRFL season he played at centre in South Sydney's grand final victory against Eastern Suburbs, and in 1929 at lock forward in their grand final win over Newtown.
He was chosen as a reserve for the 3rd Test against Great Britain at the SCG on 16 July 1932, but did not take the field. Having also already played representative football for the Sydney and New South Wales sides, at the end of the 1933 season Why was chosen to go on the 1933-34 Kangaroo tour of Great Britain, becoming Kangaroo No. 189.[5] He played in two test matches against England as well as 15 other matches on tour.[6] The 1934 NSWRFL season was Why's last in first grade.[7]
Why died in 1944 while rabbiting with his son and friends in the Victorian township of Bacchus Marsh, west of Melbourne.[8]