Rolex Sydney Hobart: sailing in memory of 1998, twenty years later

Peter Dean was 15, his brother Nathan 17, when their dad John - or ‘Deany’ as family and friends called him - set sail on Winston Churchill that day. The yacht and crew received more than the usual attention because Winston Churchill was in the very first Sydney Hobart in 1945 and finished second over the line – nearly a day after the line honours winner, Rani. Their vertically striped crew shirts were also quite eye catching.

She was a famous old yacht, and one that I personally had a lot of fun sailing in the Winter Series at the Cruising Yacht Club of Australia that year, joining a cast of old regulars who loved the beautiful wooden Percy Coverdale design as much as I did.

Her crew in 1998 was mainly made up of old sailing mates, some of whom grew up with owner, Richard Winning; Deany and Michael ‘Banno’ Bannister among them. Jim Lawler was to come later. Deany had done the race previously, and as a friend, I remember him getting a late call up to sail on Apollo in the late 1970s.

Nobody could have guessed on that day in 1998 how the race would unfold. In the end, all it took was one rogue wave in 60-70 knot winds to sink Winston Churchill, leaving her crew to scramble into life rafts. In one of the rafts, Deany, Banno and Jim Lawler, did not survive. Devastatingly for the family and friends, Deany was never found.

Peter Dean, whose early life had revolved around sailing and the water, has not stepped foot on a boat since. But 20 years on, he has made the courageous decision to sail in memory of his father. He will be surrounded by close family friends and others who care. All are experienced sailors.

John ‘Herman’ Winning Jr, a year younger than Peter, is skippering Matt Allen’s Carkeek 60, Ichi Ban, renaming it Winning Appliances for the race. Aboard is his dad, John ‘Woody’ Winning, who has done five Sydney Hobarts on yachts such as Love & War, Ballyhoo and Apollo. It’s Woody’s boat, JBW, which has operated as the race’s Radio Relay Vessel since 2005, generously loaned by him.

The Winnings are close friends of the Deans, and have crafted a team around Pete as he retraces the path his father took in that fateful race.

“The whole reason I’m going is the anniversary of the 20th year since Dad was lost. I asked the Winnings if they could help. I thought they’d be sticking me on the boat of anyone they knew who’d take me. Instead, I find out Herman has organised a boat to take me…

“I hadn’t sailed until now,” he said on the eve of the Cabbage Tree Island Race in early November.

“Yeah, I’m scared, anxious, nervous and excited all at the same time,” Peter says. Twenty years is a long time – there are a lot of stages you go through. I didn’t think I’d ever get on another boat.

“But in having my own kids (four and a half and 17 months) who ask why they don’t have a grandfather and why I don’t have a father – doing this (the race) will answer some questions.”

Is he ready? “Yes, I’ve done a lot of work personally to deal with it (his dad’s death), and I watch the start every year. It’s always been part of my life – sailing – I’ve grown up with it.

“Mum (Penny), Nathan and my family are very supportive of what I’m doing. In the past I’ve sailed with Dad, Herman and Woody – so it’s a nice touch to have them on board with me.”

After his first sail on Winnings Appliances, Peter said: “I was sh***ing myself, but Peter Calligeros (he’s done 16 Sydney Hobarts) took me under his wing – he really watched out for me. It was a bit strange, sailing, but after a few more times, I’ll be fine.”

On Boxing Day, Pete took something to leave in the sea in memory of his father. It will be a poignant moment shared with friends. He looked happy – and excited – as they prepared to leave the dock at the Cruising Yacht Club of Australia to set sail on this special journey.

We hail those who survived the 1998 race, mourn those we lost, and laud the courage of the families who have soldiered on without their loved ones.

Twenty years on, we remember: Bruce Raymond Guy and Phillip Skeggs (Business Post Naiad, 27 December 1998); John Dean, James Lawler and Michael Bannister (Winston Churchill, all drowned, 28 December 1998 – John never found); and Glyn Charles (Sword of Orion, drowned, 27 December 1998 – never found).

And we remember those before them who lost their lives at sea.