Australian Dictionary of Biography

Chris Webb (1866-1948), boatman, was born on 17 October 1866 at Blues Point, North Sydney, and named Henry Christopher, seventh child of William Webb Wagg, a boatman from Farnmouth, England, and his Sydney-born wife Sarah, née Turner. He began working for his father (a yachtsman who was known as 'Old Billy Webb') on lighters carrying stone for St Patrick's College, Manly. Starting his racing as for'ard hand for his brother Charlie, Chris first won as helmsman with the 14-foot canvas dinghy, Latona, in 1884 when he took the J. W. Durning trophy. In later seasons he skippered the 'fourteen', Violet, to twelve wins, and in 1891-93 the 24-footer, Mantura, to eleven. On 3 September 1892 at Redfern he married Nellie Eliza Rogers with Wesleyan forms.

By 1903 Webb had won 100 races and been placed 118 times in 23 yachts of various classes, but his reputation as 'the best-known, the most successful, and perhaps the most popular skipper of open sailing boats on the waters of Port Jackson' was gained in 18-footer races. Pioneered by Mark Foy, these handicap events over a triangular course on Sydney Harbour, featuring craft with coloured sail identifiers, became a popular sport from 1891. Crews included working watermen, and owners were often boat-builders. Spectators watched from Clark Island and from ferries; illegal betting enhanced the excitement. Webb came to dominate local events, probably receiving some of the owners' prize-money. He also contested intercolonial and Australian 'eighteen' championships, winning with Sam Williams's Australian in Brisbane in 1897, with W. M. 'Watty' Ford's Australian (formerly Arline) in Perth Flying Squadron Challenge Cup races in 1908 (in Perth), 1909 (Sydney) and 1910 (Perth), with Golding in the 1912 Interstate Championship (Sydney) and with Australian in the 1914 Mark Foy Challenge Cup (Perth).

Employed until the 1930s by Sydney Ferries Ltd as a night-watchman who also dampened engine fires and hosed decks, Webb lived at North Sydney; about 1924 he moved to a boatshed and refreshment kiosk which he ran at The Spit, Middle Harbour. Returning to competition in 1922, with George Press's H. C. Press II he won the Mark Foy Challenge Cup in 1924 (Sydney), 1925 (Perth) and 1927 (Sydney). He last contested an Australian championship in 1937.

This incomparable record and his longevity as a helmsman were due to his knowledge of rigging and trimming, and to acquaintance with 'every swirl of a Harbour eddy': one journalist quipped that Webb could get 'the most for his boat out of a fishtail swish'. Short, quiet (nicknamed 'Rowdy'), moustached and pipe-smoking, he was 'cool, skilful and reliable'; his face 'tanned by many an exposure to strong winds and hot suns, wears a rather thoughtful expression. His dark brown eyes, deep set, show an undaunted nature'. Predeceased by his wife and survived by their three daughters, he died on 9 June 1948 at Beauty Point, Mosman, and was buried with Anglican rites in Northern Suburbs cemetery. In March 1942, aged 75, Webb had won his last 'eighteen' race in Sydney; it was for the title, 'Cock o' the Harbour'.