John Winning – one of three greats in 18 Footer history

There have been many champion competitors, builders, designers and administrators involved with the 129-year-old sport of 18 footers racing, but three men with the foresight, positive thinking and financial wisdom to promote the 18s to the masses, stand out as the real champions of the sport: Mark Foy, James J Giltinan and John Winning.

Mark Foy was the first. He is the man who revolutionised sailing on Sydney Harbour in the 1890s when he established a boat and action-packed type of racing which would excite spectators enough to become regular followers of the 18 footers.

‘Woody’s’ 2000 JJ Giltinan victory with AMP Centrepoint – Bob Ross pic – 18 Footers League

James J Giltinan was the second. He was the man who agreed with local competitors that the original style boats had become outdated by the early 1930s and that there was a need for a faster, less costly boat with a smaller number of crew to sail them.

When the controlling club refused to accept the registration of the new style boats, he organised a meeting of a number of unhappy competitors and boat owners and ultimately formed the NSW 18 Footers Sailing League (now known as the Australian 18 Footers League).

Within three years of the formation of the new club, Giltinan organised the first World 18 Footers Sailing Championship. He was an integral part of the boost in which the Club’s 1937-1938 season attendances approached the 200,000 mark, with up to seven ferries following the Club’s races on Sydney Harbour.

‘Woody’ (Travelodge Hotels sponsored Pacific Harbour Fiji) in the late 1970s – 18 Footers League archive

The sport maintained a high level of popularity over the next forty years, but like many high-performance sports, the cost of technology and the on-going search for excellence by designers, builders and competitors took a heavy toll on the fleets around the world.

During the 1990s, even the strong Australian 18 Footers League fleet was suffering. The Club had to take the action of introducing a one-design hull to try and reduce some of the cost, increase the longevity of the hull and make the boats more accessible, to more competitors, around the world.

The League’s initiative was successful, but it needed ongoing direction and sponsorship support from the administrators at the Australian 18 Footers League to ensure the future of the 18s.

Another Mark Foy or James J Giltinan-type individual was required to steer the class through a very difficult period.

Enter John ‘Woody’ Winning, the third of ‘the big three’, a JJ Giltinan world and Australian 18ft Skiff champion. A man with a great respect for the history of the 18 footers and the people who have given so much to the sport along the way, and manager of a very successful whitegoods family business.

Since taking over the role of President of the League in 2004, Woody’s DNA can be found in every area of the sport, and he is responsible for its present stability and growth.

‘Woody’ and crew ‘send’ Yandoo in a stiff breeze – 18 Footers League

Woody has been a central part of the League’s successful racing program for the full 17-year term of his presidency, and together with his family’s initiatives, and financial support, has been a significant part of the League’s success.

John and his wife Kerrie, together with the late Bob Killick, were the original trio who had the vision of presenting 18ft Skiff Racing to the world, and Woody funded their idea. The result is that every 18ft skiff race on Sydney Harbour is now a livestream production from the race track to the world.

The Winning Group, the family business name, has also been the major financial backer for each JJ Giltinan Championship since 2007.

Former Australian 18-footer champion and class historian, John ‘Steamer’ Stanley, has nothing but the highest praise for the man they call ‘Woody’:

“John Winning puts far more back into the sport than he takes out of it. He is extremely generous with his time and money and is always prepared to help fellow sailors or anyone who needs it.”

‘Steamer’ is also quick to add how much ‘Woody’ appreciates the history of the 18s: “John and I went for a sail on a replica of the historical 18, Aberdare, and we were both hooked on the challenge of sailing on such a boat.”

“Woody had a replica built of Australia I, the 1946-1947 Australian champion, on which his father and uncle were in the champion crew. That was the start of a rebuilding program to preserve and recreate the rich 18 footer history.

“As usual, he was prepared to back his belief with his own cash, and still owns or has an interest in five or six boats in the present Historical 18s fleet.”

Aside from his marvellous administration and financial support, John has been an equally incredible competitor who joined the 18 footers in 1975-76, in a skiff sponsored by Travelodge Motels. This was after he won the 1971-72 Australian 12ft Skiff Championship with Yandoo and the 1974-75 Interdominion 12ft Skiff Championship for the Travelodge company.

In the 18s, he won the JJ Giltinan world Championship and Australian Championship in 2000 skippering AMP Centrepoint to victory with teammates Euan McNicol and Anthony (Jack) Young, and has won international 18ft Skiff championships in Europe, the USA and New Zealand.

His international victories in Yandoo include three European championships (2001, 2004 and 2011), the Mark Foy Trophy at Sonderborg, Denmark in 2011, the International Championship in San Francisco in 2004 and the ANZAC Regatta at Auckland in 2010.

‘Woody’ was also runner-up to the legendary 18-footer champion, Iain Murray, in two JJ Giltinan world and three Australian 18 footer Championships, and his record would have been even greater had he not taken several years away from the 18s to concentrate on his business commitments.

‘Woody’ (right) and son John Jnr (Herman) -partners in business – opponents on the water – 18 Footers League

With his son, John Jr. now in charge of The Winning Group business, Woody has more time to concentrate on his sailing activities. One of the challenges he faces each week is the contest against John Jr. in the League’s fleet.

At 68 years, ‘Woody’ is still very competitive in both the League’s ‘modern skiff’ fleet on Sunday, as well as the Sydney Flying Squadron’s Historical 18s fleet each Saturday and is looking forward to the start of the 2021-22 season in October.

The ongoing success of Australia’s iconic 129-year-old sport of 18ft skiff racing on Sydney Harbour owes much to the incredible action and support of John ‘Woody’ Winning, the Winning family, and the Winning family’s business.

The class is fortunate that its success and longevity is mainly due to the foresight, positive thinking, and financial wisdom to promote the sport to the masses, by three positive-thinking men.

Frank Quealey, Australian 18 Footers

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