John “Herman” Winning jnr’s speedometer pushes into triple figures as he plummets toward earth.
Dubbed “Herman” by his father before he could talk because he waddled like The Munsters patriarch, the fourth-generation multimillionaire steps out of the Appliances Online blimp.
And he’s in free fall.
Pre-flight, John Winning jnr moments before take-off.
It might be the Adelaide Hills below. Or the outer suburbs of Melbourne. The view from almost a kilometre above has blurred the cities together over the years.
Terminal velocity – roughly 120km/h – is his tipping point.
“But it’s quite nice, that free-falling feeling,” Winning tells the Herald and The Age.
“Skydiving out of a plane, you hit the air at pace. Out of the blimp, it’s dead silent. It’s like you’re falling off a cliff, it’s quite peaceful. You gain speed, hit terminal velocity and pull your chute.”
Except Winning doesn’t. It’s his ninth jump of the day. Half a second longer, and it’s his last.
“There’s a safety device that releases your parachute at 1000 feet [300 metres from the ground],” he explains.
“It only goes off if a skydiver is unconscious, something’s gone seriously wrong. You don’t want it going off at all.
“I pulled my own chute late and when I’ve hit the ground, the safety officer ran over, looked at my digital altimeter and it read 1050 feet.
Above it all: Andoo Comanche skipper John ‘Herman’ Winning jnr in full flight solo skydiving.
“I was less than a second away from having two parachutes deployed, those two chutes inevitably getting tangled, hitting the ground and in that scenario, you’re dead.
“That was me done for the day, I learned my lesson and have been jumping plenty of times since then, that was five or six years ago.”
Winning is telling the tale beer in hand, off the back of another yarn spun upstairs at Double Bay’s Cruising Yacht Club of Australia.
Andoo Comanche’s eye-watering near-collision with Sydney to Hobart rival Law Connect, a $50 million, 60-tonne crash with Winning at the helm has the skipper considering the nature of risk and reward. Or at least being questioned on it.
“We actually do work with a neuroscience company that analyses the different personalities in our crew,” Winning says.
“I’ve got a high-risk profile. I don’t mind those adrenalin-pumping situations and understand that I can move on and that I put myself in more dangerous situations than most.
“But then we balance that with someone like [Comanche’s sailing master] Iain Murray, his profile is high guard. He’s more risk averse, he’s more sceptical to dangerous situations and more cautious in his approach.
“We work out that balance and the individuals on a boat. Iain said afterwards, ‘I wasn’t comfortable with what happened [when the two super maxis almost collided], maybe that’s more high guard personality, but I’m not comfortable going out and having that happen’.
All hands on deck onboard Comanche.Credit:Andrea Francolini
“So we stopped and said, ‘Iain, you can be in charge’. To help rebuild that confidence in the boat and our sailing.
“Don’t get me wrong, these things happen all the time on yachts. But on these yachts, people die in that situation. And at the same time, there’s egos and a lot of money in these boats too. Any mistake, the owner can very quickly move someone on and there’s a lot of pressure to it.
“‘If I don’t hit a podium, I’m probably losing my place in the team’ – there’s that pressure for a lot of people, so boundaries can and will be pushed.”
War stories from the water and above cast perceptions of sailing and its enthusiasts in a different light to the linen and boat shoes that will engulf harbour vantages when the boats take off on Boxing Day.
For every risk Winning takes, a reminder of the stakes looms large.
His uncle Richard Winning was skipper of Winston Churchill in the 1998 Sydney to Hobart. Tragically three of the six sailors who died that year were on the boat.
Matt Munting, the “dear friend” who helped found Winning’s extreme sports venture Andoo X and introduced him to wingsuiting – when a webbed jumpsuit is used to glide through the air, died earlier this year when a jump in Italy’s Northern Alps went wrong.
He was 35. Winning himself is now 38 and has been sailing since the age of four. “Before I could swim.”
Winning jnr at the helm of Andoo Comanche.Credit:Fraser Edwards
He took up skydiving on his 14th birthday, the first day he was legally able to in Australia.
Aside from a blown-out knee after crash-landing into a hedge in Dubai, Winning has walked away from hundreds of jumps in one piece.
Both pursuits can turn deadly in an instant.
Every precaution and quadruple-check will be conducted by Comanche’s crew over the next two weeks to ensure this year’s Sydney to Hobart doesn’t.
Running a close second in the preparations is claiming line honours, as the genteel sailing stereotype is left to those on shore.
Andoo Comanche enters this year’s Sydney to Hobart as clearcut favourite to claim line honours.Credit:Janie Barrett
“I understand that perception for sure, and I’d say tennis can be like that, and golf can be like that too,” Winning says.
“But when you’re at the top level of competing, we’re not certainly not cracking open the oysters and champagne on Comanche. It’s a highly competitive sport like tennis or golf at the top level, you’re not there to schmooze.
“You do consider; ‘how much do I push safety to win?’ Obviously, everyone is as safe as they can be. I’ll avoid a collision all day. But you better believe I’m not giving you a free ride either, everyone wants to win.
“And at the same time, there’s those moments when you’re reminded, you are not invincible.
“You keep reminding yourself of that. You need to know your role because people’s lives are in your hands.”
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