A slightly built (173 cm, 68 kg) and very quick rover with brilliant skills, Leonard played in Subiaco Football Club's 1924 premiership side.

With the Great Depression limiting employment options, Leonard moved to Victoria in 1931, coaching Maryborough in the Ballarat Football League, then in 1932 being appointed as Captain-Coach of South Melbourne.

He is credited with laying the groundwork for the "foreign legion" team which won the 1933 VFL premiership, recruiting leading WANFL players such as his Subiaco teammates Brighton Diggins and Bill Faul.

After World War II, Leonard was again appointed as Claremont coach for the 1946 season after no one else could be found, but business commitments meant he had to leave most of the work to deputy Jack Reeves and the Tigers won only three matches.

[2] Seven years later, Leonard was asked at the age of fifty to re-take the coaching reins at South Melbourne, but his business in a football-making factory took up all of his time and he could not accept.