A brilliant jockey throughout the First World War and the years immediately following, Steve was champion jockey ten years in succession between 1914 and 1923. On top of this he won fourteen classics, including six Derbys. His Derby wins came on Pommern (1915), Gay Crusader (1917), Humorist (1921), Captain Cuttle (1922), Papyrus (1923) and Manna (1925).

On top of this Steve was also associated with two great horses. Firstly The Tetrarch in 1913. The Tetrarch only ran as a two year old, but in that one season his feats were such that he was the fastest horse who has ever raced in England. Secondly Steve rode Brown Jack to six consecutive victories in the Queen Alexandra Stakes at Royal Ascot. These victories took place between 1929 and 1934.