Harry Chesswas

Harry Chesswas was a local Clifton Hill product whose nickname "Bottles" stemmed from a childhood spent collecting glass bottles to support his impoverished family. A gifted all-round athlete, he was a standout schoolboy cricketer who was invited to train with the Collingwood Cricket Club by Test player Jack Ryder. However, Chesswas ultimately spurned the flannelled fools for football, admitting he preferred the winter game to standing in the field during hot weather. After cutting his teeth with the "Collingwood Districts" reserves side—where he featured in back-to-back flags in 1919 and 1920—he graduated to the senior team in 1922, making an immediate impact by kicking a match-winning goal in the dying seconds of the final home-and-away game against Essendon.

Throughout the club's golden era, Chesswas became a vital cog in the famous "Machine" team that secured four consecutive premierships between 1927 and 1930. While often deployed on a wing where his pace and fine judgement could shine, he was the definition of a utility, capable of filling almost any role the coach required. He was not a flashy superstar but a selfless, consistent worker who schemed for position and rarely wasted the ball. His standing at Victoria Park was such that he served as vice-captain, remaining a loyal servant until his retirement in 1931 after more than a decade of service to the Magpies.