Sydney to Hobart’s John ‘Woody’ Winning, John ‘Herman’ Winning in family quest on Andoo Comanche
He won the Sydney to Hobart the first time he raced it on a supermaxi with his son. But this famous sailing senior citizen isn’t sure he will be back for another crack.
John ‘Woody’ Winning said he had the time of his life racing on the supermaxi Andoo Comanche with his son and skipper John Junior and a group of the best sailors from Australia and overseas.
But that doesn't mean he will be rushing back to defend the line honours title with his son next year.
Winning, who has contested multiple Sydney to Hobart’s in the past, reckons he might be pushing his luck by coming back.
Incredibly, he reckons both races he has done with his son in 2022 and in 2018 on the 60-footer Winning Appliances have been the easiest he has ever done.
“If you knew it was going to be this easy you’d do it every year.,’’ he said.
“I've had two easy ones … I don’t want to push my luck.
“All the others have been pretty tough.
“I might do the odd race with them. But there’s too much to fit in and not long to go.’’
Winning, who made his Sydney to Hobart supermaxi debut at age 70 and will be returning to his favoured 18-footer racing on Sydney Harbour in a week or so, said he was immensely proud of his son putting together a great crew and winning the 2022 Sydney to Hobart on their first attempt.
“It was an amazing crew. There were no prima donnas. Everyone did their work. The guys up the front and in the middle just worked their butts off, he said.
“There wasn't one balls up.’’
WORLD'S OLDEST SUPERMAXI ROOKIE ABOARD ANDOO COMANCHE
He races one of the fastest and wettest boats on Sydney Harbour and has done so for more than 50 years. Now he’s jumping on one of biggest and wettest in the Sydney to Hobart - at age 70.
John “Woody’’ Winning could well be world sailing’s oldest supermaxi rookie.
At 70, the popular Sydney sailing institution is one of the senior members of the fleet. At an age where others retire to a bar stool, not tackle a new challenge.
But the lure of racing with his son John Junior, or Herman as he is universally known in sailing circles, aboard one of the most extraordinary racing machines, was simply too much for Winning to resist, even though he has mixed memories of the famous race.
“After 20 years sailing against him it will be nice to be sailing with him,” said Woody, who still races his 18-footer each week against his son from the Double Bay 18-foot skiff club. but will join him on the supermaxi Andoo Comanche this year.
“Initially I could beat him but I struggle to do that nowadays.”
But it still happens, with Woody beating 38-year-old son Herman in race three of the recent NSW skiff titles to the delight of the entire fleet, who jokingly ask Woody to “check his passport’’ from time to time when he finds himself racing sailors up to 50 years younger.
Woody has raced in six previous Sydney to Hobart’s and also motored south on the Radio Relay ship, his beautiful launch JBW, which will again be heading south as the fleet mothership.
“The first one I did was the most terrifying,’’ Woody said of his Sydney to Hobart past.
“I hadn’t done a lot of offshore racing at the time. It was 1974 and I was on Apollo. Warwick Rooklyn was skipper (the youngest ever at just 17) and the instruments were saying 60 knots.
“We had just had a nice steak and we had a shoot (spinnaker) on and we saw a front and thought we might go around it. Then we changed out mind and just managed to get everything down in time.
“We ended up in a storm for about 18 hours, down to a No. 6 headsail, no mainsheet and in enormous seas. It was a shock to the system.”
Over the years Winning has sailed with some well known names including Bob Miller, who later changed his name to Ben Lexcen and designed Australia II’s winged keel, and Jack Rooklyn, the eastern suburbs poker machine entrepreneur.
One of the most special - and easiest - was sailing with son Herman in 2018 on the 60-footer Winning Appliances. Herman is the CEO of the family business Winning Appliances.
“It was the first time I haven’t seen 50 knots in a Sydney to Hobart,” Woody said.
“It was the easiest race I have ever done and it was great doing it with Herman.’’
Winning has been out training aboard his supermaxi ride south with the 100-footer a previous Sydney to Hobart line honours winner under original owner and Netscape founder Jim Clark from the US and then Australian Jim Cooney.
“When Herman told me about it I jumped at the chance,” Woody said of being aboard one of four supermaxis in the 2022 race.
“I’m looking forward to it. I’m no expert but this is an amazing boat.
“It’s fun to sail and we are really blessed to be able to do this.
“Herman has put together a great team, going to sea with good people is always the safest way.’’
“He’s good at it. He puts a good people together. He’s a far bigger thinker than I am.’’
Sailing alongside the Winning’s will be Iain Murray, a multiple winner of the race and America's Cup and Olympic campaigner, and a crew of experienced sailors and young guns hoping to make their mark.
Also in the crew are Winning family friends, Nathan and Peter Dean.
Their father John Dean was one of six sailors lost at sea in the deadly 1998 Sydney to Hobart Yacht when forced to abandon ship off the famous old yacht Winston Churchill, skippered by Woody’s cousin Richard “Diesel” Winning, when it started to sink after being pounded by wild wind and waves.
“It will be very special doing it with the boys,” Woody said.
“Peter sailed with us in 2018 but Nathan is doing his first this year.’’
Woody got his nickname as he started his career as a carpenter.
His son Herman was given his nickname at a far earlier age.
“Mine started as Woodchop because I was a carpenter and then got shortened to Woody,’’ said Woody who also sails a Historical 18 called The Mistake each week.
“When Herman was a baby he started to walk and he walked like Herman Munster.” he said.
“That’s how we got his name and its stuck.
“He could tighten the bolt on his neck before he could walk.”
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