18ft Skiffs – Winning by name, a winner by nature

High achieving individual from a high achieving family

It’s never easy for a young man to follow in the footsteps of a famous father, but it’s not impossible if you are John (Herman) Winning, the son of 18 Footer sailing world champion and legend, John (Woody) Winning.

What ‘Herman’ has done is both unique and incredible.

With a sailing and business pedigree, it wasn’t surprising that ‘Herman’ was successful from an early age when he became the 29er world champion as an 18-year-old in 2002 and later moved into the 18s where ‘Woody’ was still competing at the highest level.

Andoo's winning crew at the 2023 JJs (Michael Chittenden, Sail Media photo)
Andoo’s winning crew at the 2023 JJs (Michael Chittenden, Sail Media photo)

When ‘Herman’ led the Andoo team (Seve Jarvin and Sam Newton) to victory in the 2023 JJ Giltinan world 18ft Skiff Championship, which concluded on Sydney Harbour last Sunday, ‘Woody’ was also a competitor, who finished in sixth place overall.

The victory in the 131-year-old iconic Australian sport also led to ‘Woody’ and ‘Herman’ becoming the first father and son to skipper World Championship-winning boats, since the first championship regatta was sailed on Sydney Harbour in 1938.

As the fourth generation of the high-achieving Winning family, ‘Herman’ had already established himself as a champion sailor when he took over as CEO of Winning Appliances in 2011, and has since displayed organisational and promotional skills of an entrepreneur on behalf of the business.

Winning Group skiff races past the Appliances Online-sponsored video Camera Cat in 2019 (Frank Quealey photo)
Winning Group skiff races past the Appliances Online-sponsored video Camera Cat in 2019 (Frank Quealey photo)

Like the generations of the Winning family before him (R.W. Winning & Co began business in 1906) ‘Herman’ has progressed the family business to a new level, with a modern direction to take advantage of new technologies and styles, while maintaining the values of customer service set by his predecessors, particularly his father.

The pressures of the move to the top of the business side of his life, however, has naturally had an effect on his ability to compete more regularly in the 18 footer sailing side.

He first came into the 18s in the 2005-06 season with a skiff sponsored by Appliancesonline, an online, market-rattling, white goods and home appliances retailer, which he founded in 2005, and immediately recorded top-five placings in a very competitive international fleet of some 30 teams.

At the 2009 Giltinan World Championship, ‘Herman’ and his team were in contention to become the overall winner until the final stages of the last race relegated the team back into fourth place.

Increased pressure from his appointment as CEO of Winning Appliances reduced his 18 footer racing career until the 2018-19 season when he returned as skipper of Winning Group, with Seve Jarvin and Sam Newton.

Winning Group finished runner-up behind the three-time Giltinan champion Honda Marine team, led by David McDiarmid, at the 2019 JJs. The same team, racing as Yandoo Winning Group, was again runner-up in 2021, this time behind Michael Coxon’s Smeg.

In a bold, but not surprising, move, ‘Herman’ became involved in a Supercars Championship V8 sponsorship, through Appliancesonline, with the Walkinshaw Andretti United team which won the biggest prize in Australian motor sport – victory by Chaz Mostert and Lee Holdsworth at the iconic 2021 Bathurst 1000.

In 2022, the Winning Group launched a new online retail platform aimed at furniture, bedding and home entertainment, as well as appliances, which was named Andoo.

Although ‘Herman’ was unavailable to sail the 2021-22 season in the Australian 18 Footers League fleet, he organised a team of Seve Jarvin, Sam Newton and Matt Stenta to crew the brand-new skiff, which was managed by six times Giltinan world 18 footer champion, Iain Murray.

Andoo became the 2022 JJ Giltinan world champion.

John 'Woody'Winning at the helm of AndooComanche (archive)
John ‘Woody’Winning at the helm of AndooComanche (archive)

Next, when an international situation led to the opportunity of leasing the 100ft ‘supermaxi’ Comanche, it wasn’t surprising that being an entrepreneur and having a strong sailing heritage, ‘Herman’ could not resist the opportunity to lease the 100ft ‘supermaxi’, re-brand it as AndooComanche for racing in Australia, and become a winner, again.

This time, it was another iconic Australian event, the 2022 Sydney Hobart Yacht Race, when John Winning Jr skippered AndooComanche to Line Honours victory.

This time victory for ‘Herman’ was even more satisfying as he did it with ‘Woody’ beside him on the deck of AndooComanche.

Typical of the Winning family, ‘Herman’ is not the only successful offspring of ‘Woody’ and Kerrie Winning.

Like ‘Herman’, his sister, Jamie (Jamie Winning-Kermond), is also a very successful sportsperson, an accomplished equestrian.

Ironically, it’s Jamie and her mother Kerrie Winning’s involvement with equestrian which originally led to the introduction of the livestreaming video coverage of 18ft skiff racing to the world, that we have today.

Kerrie saw what the equestrian sport was doing and, with the co-operation of the late Bob Killick, generated the idea to video tape 18 footer racing.

Since those early years, the Winning family has ‘put its money where its mouth was’ and financially backed the ever-developing technology and logistical changes necessary to continually improve the standard of the overall product.

Today, wherever you are in the world, you can view Sail Media’s livestreaming coverage of the 18ft skiff race, directly from the Sydney Harbour course, with expert commentary by seven times-world 18ft skiff champion, Andrew Buckland, and professional commentator, Peter Shipway.

'V' for victory last Sunday (Michael Chittenden, Sail Media photo)
‘V’ for victory last Sunday (Michael Chittenden, Sail Media photo)

Following successfully in the footsteps of a father who is regarded as a champion in 18 footer sailing and business is very difficult but, as John ‘Herman’ Winning has shown, it’s not impossible.

Frank Quealey
Australian 18 Footers League Ltd.

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