Chris Webb was the most famous 18 footer skipper during the early period of the class.

He was a legend and a major draw card every time he raced for the Sydney Flying Squadron (SFS), won four ‘official’ Australian Championships, 1913-14, 1923-24, 1924-25 and 1926-27, and four interstate events in the years prior to the first official Australian Championship in 1911-12. 

Chris Webb c1890 (John Stanley Collection)

He was born on 17 October 1866 and started his racing career as forward hand for his brother Charlie and won his first as a helmsman with a 14-foot canvas dinghy named Latona, in 1884.  In later seasons he skippered the ‘fourteen’, Violet, to twelve wins, and eleven more in the 24 footer, Mantura between 1891 and 1893.  

By 1903 he 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.   

He owned few racing boats and was a ‘jockey’ who raced everything from 12 footers to 24 footers at many clubs.  His skill and daring in the 18 footer Australian, from 1897 to 1903, made him a crowd favourite as Australian proved more than a match for the bigger boats. 

Among the many victories Chris Webb achieved during his long and distinguished career in the 18s and other classes was victory in the Sydney Flying Squadron’s first major race, sailing the 24 footer Mantura, in October 1891. 

The Sydney Morning Herald of the time summed up the new club and its unique handicapping system.  “When the boats are well handicapped as they proved to be on Saturday last, exciting finishes are the result, and the winner can be picked by any person watching the race.  Taking everything into consideration, the opening race was a success.  The winner on the day was the 24 footer Mantura, sailed off scratch by Chris Webb, who passed Mark Foy’s Kannanook on the line to win by one second.” 

As a result of his successes in Australian, in 1905, W.M. ‘Watty’ Ford bought Arline, a boat built in 1903 by Billy Golding, and renamed her Australian II for Chris Webb. 

Australia, Mele Bilo Mascotte & HC Press at the 1927 Australian Championship (archive)

Australian II was an immediate success and Webb won club championships with both the SFS and Sydney Sailing Club in the 1905-06 season, then dominated the class for the rest of the decade. 

There had been some inter-colonial events before Federation in 1901, but interstate competition lapsed until Western Australia introduced the Perth Flying Squadron Interstate Challenge Cup series which was intended to continue over five years with the races to be held in different States. 

The first championship was sailed on the Swan River in January 1907, and was won by WA’s Aeolus, which defeated Chris Webb’s Australian II by 1m11s. 

When Webb won the next three contests (1908, 1909 and 1910) in Australian II, the fifth race became unnecessary and the boat’s owner, W.M ‘Watty’ Ford, was awarded the Perth Challenge Cup outright. 

Chris Webb skippered Australian II in all but two races of her six year reign from 1905-11 and took six firsts, 33 seconds, 21 thirds and nine fourths.  Webb and Australian II were three times Sydney Sailing Club champion, twice Sydney Flying Squadron champion, NSW champion in 1907, as well as the three times Interstate champion and winner outright of the Perth Flying Squadron Challenge Cup. 

Mark Foy introduced a new interstate trophy, the Mark Foy Challenge Cup, at the start of the 1911-12 season, but three weeks into the season ‘Watty’ Ford stunned everyone when he sold Australian II. 

He then purchased Golding as a replacement for Webb and his crew pending the building of a new boat, Australian III, for the 1912-13 season. 

That season, Billy Dunn’s Kismet defeated Australian III but in the next season Webb took Australian III to Perth and won the Mark Foy Challenge Trophy, which was the last interstate contest held prior to the outbreak of WW1. 

In 1917 it was reported that Australian III had been disqualified for an unspecified breach of rules and Chris Webb banned for three races. 

Australian III’s owner ‘Watty’ Ford vehemently protested and threatened to withdraw the boat.  When the ban was upheld, Ford backed up his threat and both he and Chris Webb withdrew from all 18 footer racing. 

The nature of the dispute wasn’t stated, but it is believed it involved Webb’s refusal to vacate his customary starting position (off scratch) and take a handicap.  Something he was guilty of doing several times during his career. 

George Press built H.C.Press II for the 1921-22 season and sailed her with reasonable success but late in 1922 stunned everyone when he coaxed Chris Webb out of his self-imposed exile for a couple of races. 

Webb improved her performance in each race and by the end of the season was almost unbeatable.  With Webb on the helm, H.C.Press II took out the next two interstate contests and Webb’s second victory in Perth. 

The 1926-27 victory gave Webb his third victory in the Mark Foy Challenge Cup. 

Foy’s original intention was for the Mark Foy Challenge Cup trophy to be presented to whoever won five times, but when he realised this was not going to be possible, he reduced the number and recognised Chris Webb’s four victories (one in Australian III and three in H.C.Press II) and insisted that the trophy become the property of George Press, the owner of H.C.Press II. 

During the 1929-30 season was accused by the SFS of refusing to answer his flag and accused of holding his boat back until Britannia (the scratch boat) had started. 

Webb answered the charges, “I have sailed in this club since it was formed and for twenty years have never taken a start.  I am not a one-day champion, have always been a champion, and consider I should always be on scratch.  Whilst I am boat sailing, if I can’t win without a start it is time for me to turn the game up.” 

Chris Webb contested his last Australian Championship in 1936-37 and the World Championship for the J.J. Giltinan Trophy in 1938, both in Collaroy. 

He was described in the media at the time as being, short, quiet (nicknamed ‘Rowdy’), moustached and pipe-smoking, was ‘cool, skilful and reliable’, and wore a rather thoughtful expression. 

Webb won his last ‘eighteen’ race in Sydney, the Cock O’ the Harbour, in March 1942 (aged 75), and died on 9 June 1948. 

(credits: Robin Elliott ‘Galloping Ghosts’, John Steamer Stanley,  Webb Wagg Family in Australia) 

Frank Quealey
Australian 18 Footers League Ltd.