John Winning Jnr.
John Winning Jnr skippers Comanche in defence of the Sydney to Hobart line honours crown. Image by Dean Lewins/AAP PHOTOS
  • sailing

30 skydives: How champion skipper prepared for Syd-Hob

Jasper Bruce December 26, 2023

Even for an adrenaline junkie like Andoo Comanche skipper John Winning Jr, a skydiving binge is unusual preparation for the Sydney to Hobart yacht race.

Winning’s Comanche is the reigning line honours champion and favourite for this year’s Sydney-Hobart, a 100ft behemoth that ranks among the most powerful monohull yachts in the world.

Come Boxing Day, three other supermaxis, LawConnect, Wild Thing 100 and SHK Scallywag, will fight to stop her from becoming the first boat since 2014 to clinch back-to-back Hobart line honours wins.

John Winning
 John Winning Jnr is out to repeat last year’s Sydney-Hobart line honours triumph aboard Comanche. Image by Linda Higginson/AAP PHOTOS 

As the hunted, you’d think Winning would’ve spent the lead-up studying weather charts and getting some rest.

Instead, he found himself in the United Arab Emirates jumping out of a plane enough times to give himself back pain.

He can thank the crew behind an upcoming feature documentary that follows Comanche’s 2022 Sydney to Hobart triumph.

The as-yet untitled Comanche film takes a behind-the-scenes look at the people behind the four-time Hobart line honours-winning yacht.

“There’s only so many people who are interested in watching a sailing movie. But there’s lots of people that are interested in watching a human-centric movie,” Winning told AAP.

“There’s definitely some personalities on the boat, I can say that first-hand.”

Winning is a keen skydiver, with 500 jumps worth of experience, but rarely films his exploits.

With the movie in its final stages of production, the director was eager to capture some shots of the skipper in his element. 

So Winning found himself bound for Dubai to meet with members of the extreme sports team sponsored by Andoo, one of the companies he owns.

“They were able to organise for me to do a lot of jumps in a day. If I do it in Australia, I’m getting about four or five jumps in a day, over there I can get about 10 or 11,” he said.

When the skydiving drop zone in Dubai closed for two days, Winning, who had already jumped 20 times in two days, made his way to an Abu Dhabi military base to keep going.

“I got almost 30 jumps in over four days,” Winning said.

“My back feels every one of those jumps. It’s a lot of up-and-down, up-and-down and hunched over with a pack. It’s like a small brick on your back and then pulling it bends my back.”

Winning has had to juggle massages, stretching and physiotherapist appointments with his tactical race preparations, which have included scoping out the competition.

SHK Scallywag returned to the water in October after extensive modifications, while Wild Thing owner Grant Wharington only recently finished upgrading his own boat from an 80-footer.

For Winning, one challenger is a clearer threat to Comanche’s title defence than the others.

“It’s LawConnect for us. They’re just a very solid team,” Winning said.

“I think Scallywag’s a bit of an unknown. 

 LawConnect has been tipped as the biggest line honours threat to Comanche. Image by Dean Lewins/AAP PHOTOS 

“We’re not too worried about Wild Thing, unless three of us are off-shore and Wild Thing’s the only one in-shore or three of us are in-shore and Wild Thing’s the only one off-shore, then they might be a threat.

“We don’t want lotteries, we know this boat’s fast. 

“But we can’t control it if we’re in 15 knots different breeze or sailing upwind when others are sailing downwind. 

“We want to control what we can control and that’s staying near the other boats where we can and when we can’t, it’s making calculated risks.”