[1] Bailey was an amateur wrestler before taking up professional wrestling,[2] beginning his career by asking to be trained at Fred Porter's gymnasium and impressing with his ability to lift weights.

[7] In 1920 Bailey was one of two wrestlers to be able to throw Australian Olympic prospect Roy Jenkin during his training at the Victorian Railways Institute,[8] although he lost to him in the Ballarat Championship later in the year.

[10] As of 1922 professional wrestling had almost ceased to exist in Australia since the First World War and the company Country Stadiums Ltd. aimed to re-establish it.

[16] In 1927 he announced he was willing to wrestle any heavyweight in Melbourne,[17] and in October 1927 he refereed a match between Ted Thye and Walter Miller in Launceston.

[18] In 1928 a Launceston promoter offered to book him,[19] with Sam Burmeister agreeing to wrestle him in the city in May, although it is not clear if the match ultimately took place.