The Sydney to Hobart’s top-10 unforgettable moments this century
The Sydney to Hobart yacht race never fails to deliver on excitement, colour, courage and triumph. We countdown the top-10 unforgettable moments since 2000.
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The Sydney to Hobart yacht race never fails to deliver on excitement, colour, courage and triumph — it is a magnet for interest whether or not you are into sailing.
It also comes with danger, near-misses and sometimes, tragedy.
Since it started with nine intrepid crews in 1945, the “Hobart” has delivered in spades, from the biggest ocean racing fleet in history — 371 starters for the 50th event in 1994 — to the terrible storm that ravaged the fleet and tragically took the lives of six sailors in 1998.
The 628 nautical mile kicks off again at 1pm on Boxing Day for the 79th edition of the blue water classic.
Here are some of the races’ triumphs and tragedies this century.
10. THAT SINKING FEELING (2006)
When award-winning yachting photographer Ian Mainsbridge arrived over Queensland yacht Koomooloo on the News Corp helicopter, little did he know what emergency was about to unfold.
In Mainsbridge’s incredible photo, he captures Koomooloo skipper Mike Freebairn on his phone calling for help, crew frantically bailing water out of the cockpit, while the navigator is down below on the radio with race officials, and a helmsman steers the yacht ultimately to its doom.
The chopper stayed overhead until the Koomooloo’s crew could be rescued.
But 51 minutes later the classic timber yacht, winner of the Sydney-Hobart in 1968, went to the bottom of Bass Strait.
9. TRIPLE TREAT (2005)
Marked the arrival of the most successful yacht in the history of the blue water classic.
Wild Oats XI was commissioned by Australian wine billionaire Bob Oatley as a distinctively narrow downwind flyer specifically-designed to win the Sydney-Hobart.
Launched in December that year, Wild Oats won line honours, broke the race record and also claimed the race on overall handicap.
The 100-foot supermaxi broke the race record three times, holds the record for the most line honours win with nine, including an unprecedented four in a row from debut.
8. CHEATING DEATH (2000)
Tasmanian yachtsman Matt Clougher holds the dubious honour of being the first Sydney-Hobart sailor washed over overboard in the 21st century.
A huge wave swept the professional boat engineer from the deck of Sydney yacht Ninety Seven, line honours winner of the storm-battered race of 1993, off Tasmania’s northeastern tip.
Known as “Gerble”, Clougher was not attached to the boat’s lifeline, he was not wearing a life jacket or inflatable clothing. His bib-and-brace style wet weather gear and sea boots were fast filling with water.
But Clougher, 30 at the time, refused to believe it was the end.
“It was a big surprise to find the boat floating away,” he said. “I didn’t see the wave coming. I just got knocked across the deck and over the side.
“I was hanging on to the fence [safety rail] so hard with both hands but the force of the water was so powerful I was over, end of story, and I couldn’t believe it.”
The crew threw two life rings to Clougher.
“Most of the time I was in the water I had a life ring in my hand,” he said. “As soon as I was off the boat I could see the wheels go in motion to get me back.
“They stopped the boat within about five or six boat lengths. It was so fast I was totally amazed. Then they turned around to pick me up.”
7. BEATEN IN THE BOARDROOM (2017)
A one-hour time penalty saw Wild Oats XI stripped of her ninth line honours win in what is still one of the greatest controversies of the race.
Comanche was declared the line honours winner after a protest against Wild Oats XI over a near collision in Sydney Harbour was found to be valid by an independent international jury.
The jury found that Wild Oats should have given way to Comanche but failed to do so.
The Wild Oats crew could have chosen to perform a 720-degree self-imposed penalty turn, which would exonerated her from any post-race penalty.
“Everyone’s a genius in hindsight,” said skipper Mark Richards.
“We made our decision and have to live with them. We’ll get back up on the horse.”
The following year Wild Oats took line honours again, but held onto the win only after surviving another protest, this time from runner-up Black Jack, which claimed their opponent had failed to “turn on its Automatic Identification System during the race”.
6. PEUGEOT CRASHES (2002)
Tasmanian yacht Valheru claims to have one of the shortest races in Sydney-Hobart history.
Less than 30 minutes into the 2002 event, and still on Sydney Harbour, Valheru was T-boned by French entrant Peugeot Racing in a manoeuvre gone wrong.
Tasmanian crewman Peter Fletcher was thrown overboard in the crash, and was lucky not to be crushed between the two yachts before he could be plucked from the harbour.
Valheru’s owner-skipper Anthony Lyall was in disbelief.
“I thought we were going to be cut in half,” Lyall said.
“We were doing a starboard tack out to the [offshore] turning mark and Peugeot Racing started coming towards us.
“We were on starboard tack and obviously in the right. They started to bear away to go behind us, and next thing we know it came straight back up into us.
“That was it. Their boat came virtually halfway through Valheru. It’s a mess.”
5. THIS ONE’S FOR YOU DAD (2024)
Just for a moment, Peter and Nathan Dean forgot about the Sydney to Hobart yacht race and that they were leading the 628nm classic on Comanche to focus on something more personal.
As their 100-foot supermaxi powered across Bass Strait on day two, the brothers paid special tribute to their father, John, one of the six sailors lost in the fatal Sydney to Hobart in 1998.
John was never found, so the only “grave” the family has is a set of co-ordinates on the ocean where his yacht, the Winston Churchill, was last sighted.
John Dean, 47, died at sea during 1998 disaster. A member of the crew of the Winston Churchill he was swept from a life raft after the boat sank
The Dean boys drank a rum toast to their dad and could only imagine how frightening John’s final moments must have been.
“There was never a body found so that’s his grave out there, so we had a drink and threw a wreath,” Nathan said.
4. PLANE TRAGIC (2014)
A light aircraft carrying well-known local photographer Tim Jones crashed into the sea near Cape Raoul on the Tasman Peninsula on December 29 during a flight to capture images of the yachts.
Pilot Sam Langford, 29, and 61-year-old Jones, died in the crash and the wreckage sank to the ocean floor.
It took weeks to salvage the light aircraft and even longer for the inquest and air safety investigation.
The ATSB found the aircraft had made a steep climbing turn at just 50 feet above the water where it stalled and spun out of control, and the “exceptionally low height” of the plane at the time was a breach of air safety regulations.
3. MISSED IT BY THAT MUCH (2023)
It was the second-closest line honours victory in the 78-year history of the Rolex Sydney-Hobart, and the greatest comeback inside the Derwent River that the race had ever seen.
As race leader Comanche passed the Iron Pot at the entrance of the Derwent, 11nm from home, it had both hands on the line honours trophy.
The closer it got to the finish, the slower it went. And not travelling mush faster, LawConnect staged an incredible challenge for the title.
It was not until the final 2nm that LawConnect was taken seriously as a challenger for the win, but as they crept up beside Comanche, it became walking-paced thriller.
Sometimes they two yachts event stood still in the water, and several times they drifted backwards.
It was a rolled gold thriller that saw LawConnect pip Comanche by just 51 seconds — the closest finish since 1982 when Condor of Burmuda beat Apollo III by seven seconds.
2. UP THE SPOUT (2001)
Swedish skipper Ludde Ingvall’s green machine Nicorette was brilliantly-poised in the 57th Hobart, leading the race for line honours ahead of a fleet of 60-foot around-the-world flyers _ until the unexpected happened. As the sun set on the opening day, the crew of Ingvall’s maxi saw a sight that sent shivers down their spines — a water spout headed their way as it sailed off Jervis Bay in the NSW South Coast.
“Even the fastest sailors in the world couldn’t get out of the twister’s day,” Ingvall said. “It seemed to be chasing us across the ocean.
“I could see the water vapour circulating within the twister and then the yacht sailed straight into it.”
Ingvall said the yacht was knocked flat on its beam ends, with another crewman describing seeing a couple of large lightning strikes and sounding “like a thousand people screaming”.
Nicorette’s mainsail was destroyed by the spout, and the crew only had a lesser “delivery sail” to fall back on, significantly handicapping the speed of the maxi. It was beaten to line honours by 9m17s.
1. BELLY UP (2004)
Few fans of the great race could hardly forget the sorry sight of Grant Wharington’s supermaxi Skandia up-side-down in the Tasman Sea after losing its keel.
Skandia led the race at the time but when its 25-ton keel parted company, it destabilised the 98-footer sending the crew went into survival mode.
Wharington refused to get off his boat, famously saying that he would not abandon ship until he had to “step up into the life raft” – meaning not until his boat was about to slip under the waves.
The crew was plucked from their life rafts but a Tasmania Police rescue vessel and taken to Flinders Island. They made it to Hobart by light aircraft.
Skandia was left floating belly-up 80 nautical miles east of Flinders. Wharington dispatched a tugboat to salvage to stricken vessel.
Originally published as The Sydney to Hobart’s top-10 unforgettable moments this century
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