A new family rivalry takes centre stage in the Sydney to Hobart
Racing supermaxi yachts is an expensive game. Why their owners are willing to put in the big bucks comes down to a number of factors. Freud would have a view on one of them.
“Imagine yourself standing under a cold shower with unlimited $100 bills, just tearing them up and dropping them down the drain,” says John Winning Jr, quoting a well-worn sailing adage. “That’s a good analogy of what it feels like to own a 100 foot Maxi that is doing the Sydney to Hobart.”
Racing supermaxi yachts is an expensive game.
A bottom of the range 100 footer will cost at least $2m and building a decent one as much as $40m. Then there is the upkeep during an annual campaign, which could total $4m depending on the need for new sails and where the boat is racing for lead-up events.
Winning Jr will be racing Andoo Comanche, while the Oatley family will contend with Wild Oats XI, the Beck family will sail LawConnect, and Peter Harburg has Black Jack rounding out the super maxis aiming to be first up the Derwent River into Hobart.
Altogether 115 yachts ranging from 100 to 30 foot – the latter costing as “little” as $20,000 – will set sail from Sydney Harbour on Boxing Day, including 22 that are contending in a handicap for two-people crew.
It all combines to make fantastic eye candy. A spectacular mix of colourful spinnakers, nimble carbon fibre boats, and elegant timber ladies all jostling for position as they spill out between North and South Head into the Pacific Ocean.
Why the supermaxi masters are willing to put in the big bucks to try to win the race comes down to a number of factors. Freud would have a view on one of them.
“We’d be naive to say that anyone in the competitive level of sailing with a lot of money doesn’t have an ego,” says Winning Jr. “As much as it probably is a battle of egos, it feels more like a really fine friendly competition.”
The 38-year old Winning Jr has had Andoo Comanche on a leasing arrangement for six months and believes he knows the yacht – the current Sydney to Hobart record holder – well enough to be a contender.
“I’m definitely not one of the best sailors in the world, but I’m pretty quick to pick things up on a boat,” he says. “I usually need to spend less time in a boat than most people I know. It doesn’t feel like I’ve had to do much sailing to get a feel for it.”
Comanche’s record was achieved in 2017 when it was owned by Jim Cooney and his wife, Samantha Grant, who sailed it into Hobart in 1 day and 9 hours, compared with the three day average. Conney won again with Comanche in 2019 before selling it to a Russian buyer.
Cooney admits that he and Grant and their two children – who will sail with them this year in their mini-maxi Willow – were sad to sell Comanche after owning her for three years but felt they didn’t have the time to focus on getting the best out of her anymore.
“Something as sophisticated as Comanche takes a long time to understand,” says Cooney, who clearly takes a different approach to Winning Jr. “We spent an awful lot of time doing sailing trials and taking the boat offshore with the full crew, experimenting for days to understand what are the things you can tweak? What are the changes you can make to the rig settings to the water balance.”
Cooney doesn’t believe he can take out line honours in this year’s Sydney to Hobart on Willow, which the family has owned for six years, because at 70 foot, she is just too small.
“Size matters,” he says. “It’s purely the physics and the power rate ratio. The bigger the boat, the bigger the sails you can carry so in terms of raw speed and line honours the first boat home will always be one of the super maxis.”
That doesn’t mean he is just in it for the fear of crossing the Bass Strait at night though. Cooney is very much angling for handicap honours, which is more prestigious among the sailing fraternity anyway.
“If we have moderate to strong winds, it’s what our boat was designed and built for, so we would be a reasonable prospect for a handicap win,” Conney says.
What Cooney sees as the attraction of this race is more nuanced.
“While at least one person on the boat needs enough money to compete, everyone else is the crew and you can have six to 15 amateur or non-professional people who just enjoy each other’s company and enjoy sailing and being on the water.”
“It’s quite a spectacle on Sydney Harbour on a bright sunny day when the spinnakers are filling and there is also an element of danger and element of excitement involved taking on the Bass Strait and the storms that can confront you and the teams of people pushing through that sort of adversity.”
For anyone of a certain age that adversity will always be associated with the tragedy of the 1998 Sydney to Hobart when a storm cell created category 2-style gusts. Waves were reported at 10 to 15 metres, six people lost their lives, seven boats sank and 30 civil and military aircraft helped rescue 55 people from 12 yachts.
Cooney was not racing that day, but says he has certainly been afraid, when racing the Sydney to Hobart in 2010 and was forced to retire sailing Brindabella when the boat found itself in 60 knot winds and 11 metre seas.
“We were taking a serious beating,” Cooney recalls. “The boat was bashing into these enormous waves that were washing over the boat and at times we had a metre of water coming over the bow and washing down the length of the boat, hitting us in the face and pushing us on the rails. That was frightening.”
Not so frightening that he isn’t letting his two sons join him and his wife in contesting the race this year though.
“If we win the Tattersalls Cup, the handicap win, it would be much more of an achievement than the race record,” says Cooney.
Taking a much lower key approach is Christian Beck, who purchased Perpetual Loyal – now known as LawConnect – from Anthony Bell in 2017 for $1.6m after enjoying Sydney’s low key summer evening races in the harbour frequently largely by corporates.
“I’m probably not a fair dinkum sailor,” says Beck. “I used to do the Twilight Races and was just looking around for a 50 foot boat, and then it ended up that Perpetual Loyal was for sale and it was fairly cheap, so I bought it and it was a big jump for me.”
Beck sounds super casual when he talks through his approach to the race, which unlike his super maxi competitors doesn’t seem to include a large stack of professional sailors on crew.
His crew includes three who had their names drawn from a hat at his legal information company, plus “a good IT guy” who had his name drawn in a previous Sydney to Hobart office draw, who managed to fix the internet onboard that year when the computers got wet.
Beck says its because his boat is so big and heavy, weighing 35 tonnes, that it can handle a more relaxed approach to crewing.
“It’s so heavy anyway so the weight doesn’t make much difference compared to a lighter boat like Black Jack or Wild Oats,” Beck says.
His boat did win once when called Perpetual Loyal, when Wild Oats pulled out due to damage.
But to win again? “It’s not that easy or likely,” says Beck, who has come in second on the boat twice.
And even though he is the skipper, largely for legal reasons, Beck says his second in command, Tony Mutter, is really the man who calls the shots.
“I’m happy to say I don’t know that much about sailing,” he says. “The people that are doing 5000 miles across the Southern Ocean and see the Sydney to Hobart as an overnight sail – all these boats will have those kinds of guys on them – when the s... hits the fan they are the guys that get you through it.”
Rival super maxi owner Sandy Oatley probably does know a thing or two about sailing, even though he won’t be joining his crew in racing Wild Oats this year.
Sandy’s father Robert Oatley, who made his fortune founding Rosemount Winery, was one of Australia’s most prominent yachting supporters and won eight Sydney to Hobart races before passing away in 2016.
Bob Oatley’s family have parallels with the Winnings. John Winning senior is also a famed sailor and both men’s families have granddaughters pursuing equestrian Olympic dreams in dressage and showjumping respectively.
Sandy says that even though the Sydney to Hobart is generally contested by the same group of people it is still an absolute pinnacle to win.
“It’s like going to the Olympics where you are competing against the same countries,” Oatley says. “You are trying to better yourself on every outing, and we also find great camaraderie once the race has finished catching up with old friends. We are together and enjoying it and when we get out on the water we try to beat each other.”
There are very different tactics depending on the style of boat being sailed, but Oatley says the best ocean racing in the world can still grind to a halt if you hit the wrong conditions coming into the mouth of Hobart’s Derwent River.
If the tide is going out, competitors can and do frequently catch up to the leaders.
“You might stop and everyone catches up to you and then you start again,” Oatley says. “That happens quite often. Sometimes you could throw a cricket ball across to the other boats.”
In one case his father Bob had to take extreme measures.
“One time in the Derwent when the tide was going out and there was no wind, my father told me that he actually had to throw the anchor out to stop going backwards,” Oatley says. “There’s been lots of monumental sailing duels going up the Derwent.”
It just goes to show that for all the millions of dollars in sails and 1170 kilometres of racing, the race really isn’t over until you cross the finish line.