An Australian documentary revisiting one of the most tragic chapters in the history of the Sydney to Hobart yacht race has opened in cinemas nationwide, telling a deeply personal story of grief, friendship and resilience more than two decades after the disaster that claimed six lives.
Directed by Dave Klaiber and produced by Will Alexander, True South centres on lifelong friends Herman Winning and brothers Nathan and Peter Dean. Their bond stretches back to childhood in Sydney’s eastern suburbs, long before the devastating 1998 Sydney to Hobart race in which Nathan and Peter’s father, John Dean, died at sea.
The documentary arrives as the race marks its 80th anniversary and revisits the 1998 event, widely regarded as the darkest chapter in the race’s history. Those who remember the race will recall a powerful east coast low struck the fleet in Bass Strait, generating extreme weather conditions and waves up to 90 feet, turning an elite sailing contest into a survival battle.
Alexander, who grew up with the Winning and Dean families and has known them for more than three decades, said the tragedy had a profound impact both on their community and on the broader sailing family.
“There’s a long-standing friendship between us all, and around the ’98 tragedy, we’re all a very tight knit community, and that really tore us all apart,” he said.
“There was this idyllic upbringing around the Sydney Harbour, mucking around on boats around the eastern suburbs, and then ’98 hit and that really drove a big wedge through.”
The families’ connection to sailing stretched back generations. Alexander said the boys had grown up around the harbour and were introduced to sailing at an early age.
“Their fathers made them start sailing [and] from the time they could walk really, they were on the water,” Alexander said. “The Winning family particularly have a long lineage of very famous sailors. It’s sort of in their DNA.”
John Dean, who died in the race, had played an important role in the lives of many of the young sailors around him.
“He played a hugely influential role in both the lives of his sons, as you’d imagine, but also in the Winnings’ kids,” Alexander said. “They all looked up to him like an uncle… he was a great man. He was larger than life.”
Dean’s death understandably devastated those closest to him and left a lasting impact on the families.
“The loss was just devastating. It destroyed their families in many ways…shattered them,” Alexander said.
Almost 25 years later, after a period where each person had travelled their own personal and professional path, fate brought Herman Winning, Nathan Dean and Peter Dean back to the Sydney to Hobart race together. Their decision to compete again – retracing the path where tragedy struck – became the emotional core of True South.
Alexander said the film initially began as a project following the campaign of the Supermaxi yacht Comanche during the 2022 race but quickly evolved once filming began.
“When Nathan Dean arrived on set, there was this reunion of all the boys from our childhood coming back together, and the penny dropped that Herman’s brought this team together for something much greater,” he said. “It wasn’t about our winning line on it…this was much deeper.”
Instead of focusing solely on the race, the filmmakers shifted their attention to the personal journey of the families and the legacy of the 1998 tragedy.
Director Dave Klaiber added the story grew beyond sport to become a film about the people behind the race.
“The boat race just became a part of the story. The real story was about the people and the emotions and really having these really big conversations,” he said.
For an outsider, as Klaiber was, he said gaining the trust of the men involved – many of whom were reluctant to discuss their emotions publicly – was one of the film’s biggest challenges.
“They’re either big powerful businessmen who are media trained and can give you very slick answers or they’re real Aussie blokes who don’t talk about their feelings,” Alexander said. “So how do you get those polar opposites into a place where they felt comfortable enough and wanted to tell the story.”
Revisiting the events of 1998 also proved emotionally difficult for those involved in making the documentary.
“It was gut-wrenching reliving it all…going back through all the archival interviews and newspaper articles,” Alexander said. “They still hit me every time.”
For a dose of star power, True South has been narrated by legendary Australian actress Sigrid Thornton and features an original score by composer Elena Kats-Chernin, whose work the filmmakers say helped elevate the emotional tone of the story. Both women had been previously recognised with an Order of Australia for their contributions to the performing arts.
Klaiber said the aim was to create a film that both honours those affected by the tragedy and takes audiences on a powerful emotional journey.
“I think the whole idea with this film is to take viewers on a journey. It acts in a very cathartic way of bringing closure to the situation,” he said.
True South is now screening in cinemas across Australia.