Leo Wescott

Henry "Leo" Wescott’s career was defined by his role as a shrewd defender during the Magpies’ most dominant era, though his quest for coaching opportunities likely cost him a place in history as a four-time premiership player. Born into the Collingwood family—his father Alf had captained the club's juniors in the 1890s—Wescott was initially a wingman who broke into the senior side in 1922 following the departure of Bill Twomey Snr. While he featured in the losing Grand Finals of 1922 and 1925 in the midfield, his true calling was found when he was shifted to the back pocket. Standing just 170cm, he relied on pace, composure, and precise distribution rather than brute strength, with a style built on short dashes followed by driving kicks to clear the danger zone.

A key member of the famous "Machine" team, Wescott claimed premierships in 1927 and 1929 but missed the 1928 and 1930 flags due to lucrative stints as a playing coach in the country—a common path for players seeking financial stability during the Depression. He captain-coached Dimboola to a premiership in 1928 and won a league best-and-fairest with Longford in Tasmania in 1930, proving his quality far exceeded his standing as a role player. He returned to Victoria Park for a final two-season stint in 1931, retiring as a life member and later becoming a founding figure in the club’s Past Players Association.