The beasts of Bass Strait come in the night. Waves looming larger than the Sydney Opera House like grey giants in the moonlight. Waves so big that in 2005 they smashed the windows on the Spirit of Tasmania and caused it to turn tail. Waves that toss and torment sail boats with no steel superstructure to hide inside, and yet still, every year, they come. The crazy brave men and women who choose to tackle the Rolex Sydney to Hobart Yacht Race.

Mark Richards is the Peter Brock of the event, having won line honours a staggering nine times on various iterations of the Wild Oats super maxis. While Richards sounds like he’s got huge gusts of wind in his sails, when you enquire about what makes this internationally famed ocean race so tough, he suddenly becomes becalmed.

“It’s strange, you know, but a lot of issues in the race, and I’ve had some very difficult moments, they happen at night—that’s just a weird thing about it, and maybe it’s that time of year, it’s the thermal conditions that create the big weather in the night,” he recalls, gently, like someone describing a particularly painful past car crash.

“And then there’s the challenge of just crossing Bass Strait, it can be absolutely brutal. But while anyone can sail during the day, it’s not that easy at night, particularly when the winds get fresh and you’ve got a lot of gear up and you can’t get it down, because it’s just too dangerous in the dark.”

Not only are competitors being thrown almost blind into walls of water, they’re doing so at speed, and they can’t slow down because if they send someone up to drop the sails it might just cost them their lives.

“Those are some interesting times and that’s why you have to really try and get some rest during the day, while the race is going on, so you can get ready for the night time, because that’s when the shit hits the fan,” adds Richards.

The incredible thing about the popularity of the Rolex Sydney to Hobart is we seem to know about Bass Strait—we’ve culturally absorbed a strange sense of pride about having one of the world’s most dangerous stretches of water, yet we never get to see the truly terrifying parts of the race, what the competitors experience, on television.

We just know the stories, particularly those from the 1998 horror show when six people died, five yachts were lost and 55 sailors had to be plucked from the sea in the largest peacetime search-and-rescue effort ever seen in Australia.

That sense of peril—a contrast to the festive start in Sydney Harbour and the joyous celebrations in Hobart—have inspired average Australians to take an interest in sailing, even if only once a year.

Commodore Noel Cornish of the Cruising Yacht Club of Australia (CYCA), which runs the event, says Australians tend to think of the race’s popularity as having been built over time and repetition from its 1945 inception. He too thought this—until, that is, he looked back into its history.

“I wondered whether it just got more popular as time went on after starting quite low key,” offers Cornish. “One thing that intrigued me when I read about the history of the race was that even in 1945, it really captured the attention of Australians; that first race was very much
in the headlines, ‘where are the boats? How are they going?’ It was very much in the news, and then one boat wasn’t seen for four days, then it was found.”

It captured the collective imagination, arguably spurred by a post-war need, and has, as Cornish adds, “continued on through the 75-odd years—it’s quite incredible.”

The feeling of warmth that frames the race, emotions tightened and felt even more among the close-knit yachting community that takes part, made last year’s decision to cancel the Rolex Sydney to Hobart, for the first time ever just days before the off, particularly heartbreaking.

“We’d just had the 75th anniversary, a milestone year and a wonderful celebration, and then COVID hit and around the middle of the year it looked like mission impossible. But we decided we’d get our heads down and keep trying, and the closer we got to the race, the more likely it looked, but then we had the [Sydney] Northern Beaches outbreak and then Tasmania closed its borders, and the decision was made for us,” recalls Cornish. “We were all in shock for a very long time and Boxing Day was a very hollow day for those of us that do the race.”

One might assume that part of Cornish’s dismay would have been dealing with some very unhappy sponsors, but he says that while it “certainly wasn’t ideal”, the race is very closely tied to those who back it.

“We have wonderful sponsors. It’s called the ‘Rolex’ Sydney to Hobart for example, and these are people who are very loyal to us and we cherish those sponsorships and it’s something that extends well beyond the race itself, it’s the promotion of the event throughout the year. Rolex is a wonderful sponsor and it’s a brand that’s all about the sense of human endeavour and adventure, and we provide an exciting and challenging adventure for human beings in that race, because there certainly are a variety of different challenges you need to overcome, not to win the race, but just to complete the race.”

The Sydney to Hobart stands Mount Everest-like above other open-water events. For Cornish, who has skippered a crew in the event a dozen times and describes competing as one of the greatest thrills of his life, says the race has become a bucket-list event for yachties.

“Just to do a Sydney to Hobart, just to make it, even once, that’s something a lot of people come for—that’s how it starts, that big tick on the bucket list, but the next thing you know they’re coming back again, and again; the allure of the race is really strong for a lot of people. And there are many different levels to it—it’s not just about winning or line honours, there are many different levels of aspiration, races within races, different classes you can enter.”

Cornish says that while the media spotlight illuminates the winner of line honours, for the yachties in the fleet it’s all about the Tattersall Cup—which goes to the overall winner on handicap.

In 2005, Richards and wonder-boat Wild Oats XI combined to become the first, since Rani won the inaugural event in 1945, to take the trifecta of line honours—setting a record time for the trip and grabbing the coveted Cup. It’s no wonder that most of his memories about the Rolex Sydney to Hobart are hugely positive, particularly those related to the start that stops the nation (albeit a nation moving at fairly sluggish speed given that it’s Boxing Day).

“I’ve done all the big races many times but the Sydney to Hobart is special, it’s just such an amazing race,” says Richards. “And obviously being part of the Australian culture is special and that in itself creates passion and desire of a totally different level.”

The famed skipper points to the dramatic Harbour start. “It’s just such a massive thing—one of the biggest sporting events in the country; the people watching, the boats in the Harbour, the TV, it’s just a massive day, and it’s pretty cool.

“It can be stressful for us in the bigger boats, because the spotlight is on us, and I’ve had fantastic moments and bad moments at the start, and people remember. I met someone this week and they said, ‘oh, do you remember that tack you made that time at the start, what were you thinking?’ And then you’ve got all the challenges it throws you on the way down, and then the finish, and there aren’t many in the world like that, where literally tens of thousands of people come out to the Derwent in Hobart to cheer you on. It’s special.”

Another famous competitor with a deep enthusiasm for the event is Neville Crichton, who raced Touring Cars at Bathurst in the ’80s before switching to ocean racing where he was so successful—winning events all around the globe—that he was named the ISAF Rolex World Sailor of the Year in 2003.

Crichton, 76, has raced in five Sydney to Hobarts—claiming line honours twice in 2002 and 2009 in his boats Alfa Romeo and Alfa Romeo II. In 2017, he became the oldest man ever to compete at the age of 72.

Ask Crichton which one is harder—the high-speed endurance of The Great Race at Bathurst or skippering a boat for a few days of equally dangerous dicing with the elements on the high seas—and he can’t split them. “I’ve been lucky to have a bit of success in both and they’re both tough,” he says. “Yachting is more of a team sport. You’ve got a team of 22 people on a super maxi and everyone’s got to know what every other person on that boat is doing. The helmsman gets all the publicity, but everyone on that team is just as important … But it’s not that different at Bathurst, because the preparation of the car is just as important and it’s still a team sport, with pit stops and so on, and if one person makes a mistake, you’re stuffed, but it’s the driver’s mistakes that get the most focus.

“And in motor racing, it only takes a second here or there and it can cost you the race. But the Sydney to Hobart can be very competitive as well. I remember one year dicing with Wild Oats the whole way—we were in sight of each other at every step. And with racing like that, it’s not just about finding the fastest way down, you’ve got to cover your tail, you’ve got to cover the whole field, think about racing tactics and what your competitors are up to.”

There’s obvious passion in Crichton’s voice—and as his record in two different endeavours shows, he loves winning (which also translates to business, having amassed a personal fortune of $500 million). When he talks about the newcomers who’ll be taking part in this year’s race for the first time, the two-handed racing crews, Crichton is excited about the challenges they’ll face, and almost as if he wouldn’t mind having a crack at it himself.

“The boats the two-handers use are very, very fast and they’re very talented sailors—so it’s not as if it’s a Sunday sailor out there, it’s going to be difficult for two people to do a race like that—if one of you gets hurt, you’re going to have big problems.”

Despite the extra level of difficulty, Commodore Cornish says there’s been heavy demand from two-handed crews keen to be part of the famous race.

“The CYCA is always trying to respect our history and at the same time look for developments and improvements in how we go about doing things. So we decided to introduce two-handed racing to the fleet and it’s proven very popular—we’ve got 104 boats racing this year and 20 of those are two-handed,” says Cornish.

“It is a very tough form of racing, while one of you is resting the other one is on deck making it all happen alone, so they are people who know how to function continuously with very little sleep. They’re amazing boats and amazing people and we’re very much looking forward to seeing them in the race this year.”

Indeed, after the longest break in its history, everyone is looking forward to the Rolex Sydney to Hobart this year.

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