The Oatley story

Crosbie Lorimer | VOLUME 31, ISSUE 4
Bob forged his own sporting destiny on the waters of Mosman Bay and Middle Harbour
From humble beginnings, Bob Oatley became a trailblazing businessman, winemaker, philanthropist and a legend.

“Get back out there boys, you need to finish this!” said Bob Oatley to his young sons Sandy and Ian as they dragged their swamped Manly Junior ashore in the middle of a southerly buster on Sydney Harbour in the 1960s.

Many a father would have said the same to their children in varying sporting arenas, but one doesn’t have to look far into the life of Robert Ian Oatley to see that it was this competitive drive that propelled him from humble origins to become one of Australia’s most successful entrepreneurs and yacht owners.

Born in 1928, in what was then the working-class suburb of Mosman, Bob Oatley (who could trace his ancestry back to an English convict clockmaker, who had been transported to Australia) was brought up by his maternal aunt Muriel, following the death of his mother when he was one and in his father’s long absences from home as a travelling wool agent.

While Oatley’s father was a first-grade cricketer and footballer, Bob forged his own sporting destiny on the waters of Mosman Bay and Middle Harbour at the age of 11, having discovered that the addition of a makeshift sail to his canvas canoe – bought from a friend for two shillings and sixpence – made canoeing much more rewarding.

With his childhood friend Bill Buckle, who he still sailed with in his later years, Oatley went on to found the Balmoral Sailing Club and became a regular competitor in 12ft skiffs.

By the age of 15, Oatley was already in work, becoming an apprentice for Colyer Watson, which traded internationally in skins, hides and other commodities. While the company soon recognised the young man’s burgeoning business acumen, a nervous Oatley was less than confident about his prospects as he set off for his first day of work wearing shorts, having no long trousers to his name.

“I knew I was venturing into the unknown and I was scared. Right then, I just wanted to get up, dive over the side of the ferry I was on, and swim to shore,” said Oatley, recalling the day in 1943 that would kick-start a spectacularly successful business career spanning more than 70 years.

Under the guidance of Rupert Colyer, he soon moved on from filling inkwells and delivering mail, to early ventures in cocoa and coffee trading in Papua New Guinea. Such was his eye for business and the confidence he instilled in his employer that, in 1969 at the age of 41, Oatley acquired the New Guinea operations from Colyer.

“I was able to negotiate a very favourable deal that resulted in a slow transition to full ownership of the business, one where I wasn’t stretched financially. For me, it was as if I’d won the lottery,” said Oatley of the generous business terms, which he was to adopt many years later when selling his beloved yacht Wild Rose to his sailing friend, the late Roger Hickman.

Shortly after Papua New Guinea gained independence, Oatley sold his coffee and cocoa interests – but not before being awarded the British Empire Medal in 1985 by the PNG Governor General, in recognition of his contribution to the country’s economy.

Throughout this period, the Oatley family was based in Sydney, with all three children – Ros, Sandy and Ian – heavily involved in dinghy sailing at Middle Harbour. While their father was sailing a Yachting World Diamond keelboat, Sandy and Ian graduated from Manly Juniors and Flying Ants to Cherubs, before Sandy decided to build a Moth dinghy in his bedroom.

“Mum wasn’t too happy with me, because I had to take the window out to get the boat out of our house,” recalls Sandy.


In the late 1960s, the Oatleys bought a weekend getaway hobby-farm in the Hunter Valley with a view to setting up a small vineyard – a venture that, under the Rosemount brand, was ultimately to become one of Australia’s most famous and successful wine businesses.

With most of their weekends spent in the Hunter Valley, Oatley had sold his Yachting World Diamond and the family’s sporting interests centred more on rural pursuits, including waterskiing (Sandy held the Bridge to Bridge record), four-in-hand carriage racing and dressage, with Ros’s daughter, Kristy, becoming an Olympian.

By the late 1970s, and with the vineyard well established, Oatley returned to the sailing scene in Sydney, racing a Cole 43 with Bill Buckle.

In 1985, Oatley commissioned the design and build of the Bruce Farr-designed Wild Oats, a 43ft (13m) IOR yacht that was considered a lightweight and radical design in its day. Wild Oats campaigned on the East Coast and raced to Hobart, later enjoying great success as Wild Rose with her subsequent owner Roger Hickman, who had been among Oatley’s crew at the time.

After selling Rosemount Wines in 2001 and seeing an opportunity to create a world-class resort along the lines of his favourite sailing resort at Porto Cervo in Sardinia, Italy, Oatley purchased Hamilton Island. From here, the Oatley family commenced a long-term major build and upgrade program on the island that has included an eye-catching new yacht club, a spectacular golf course on Dent Island, and the award-winning, five-star qualia resort.

Oatley now focused on his passion for sailing. He raced with Sandy in the Davidson 59 Another Duchess, frequently competing against Neville Crichton, whose Duchess 59 Shockwave would be the first of many yachts under that name to establish a longstanding sailing rivalry with Wild Oats.


Oatley was also keen to pursue his interest in the nascent swing-keel technologies that were emerging in the USA.

The journey that would culminate in the construction of Wild Oats XI started in the early 2000s, with Oatley trialling the then radical canting keeler Schock 40 in San Diego. Having commissioned the first of a series of Reichel Pugh designs, the Oatley team retrofitted the RP60 with a canting keel and raced the boat at Hamilton Island in 2002, before campaigning her in England as part of the winning Australian team that brought the coveted Admiral’s Cup trophy Down Under in 2003.

Bob Oatley’s growing fascination with emerging technologies on the grand prix sailing circuit led him to commission John McConaghy to build the Reichel Pugh-designed, canting keel, 66ft (20m) Wild Oats X.

Wild Oats X enjoyed considerable success in Porto Cervo Sardinia, her canting keel enabling her to hold her own against much larger yachts. She is still regularly raced on Pittwater to this day.

Drawing on his favourite maxim ‘Lift the bar, tomorrow can always be better’, Bob Oatley began considering the next step up in size and technological advances. Hearing that Neville Crichton was considering selling his Reichel Pugh 98 Shockwave, which was under construction at the time, Oatley expressed his interest in buying the boat. When Crichton subsequently decided not to sell, Oatley was sufficiently impressed with what he’d seen to go his own way.

“Dad got really excited with the power and the technology in the boat and said ‘well, I need one of these’,” recalls Sandy Oatley. “He called John Reichel, Jim Pugh and John McConaghy and said ‘build me one’ and they said yes!”

Launched in 2005, Wild Oats XI has gone on to become one of the most recognisable and successful yachts in Australian sailing history, having won Line Honours in the Rolex Sydney Hobart Yacht Race eight times in 10 years, while also taking out the treble of Line Honours, Race Record and Overall Handicap winner on three occasions.


Very much a man for the big picture, Bob Oatley could see the significant synergies between the sport of sailing and the resort lifestyle of Hamilton Island. He developed Audi Hamilton Island Race Week as a family-friendly event, with onshore activities and spectator opportunities for all pockets – a vision that has been adopted by his family.

“We see Race Week as the Melbourne Cup of sailing,” says Nicky Tindill, Bob’s granddaughter and a key player in Race Week’s events program and management.

As with the Melbourne Cup, the program of events and activities is broad in appeal and varied in focus. The introduction over recent years of the Eat Street stalls on Front Street, sausage sizzles at the marinas and the free outdoor cinema has widened the options for event participants from the celebrity-chef dinners, fashion shows and champagne lunches that have been the popular mainstays of Race Week’s onshore program.

This inclusive approach to Race Week has undoubtedly resonated with sponsorship partners Audi and Club Marine, with both enjoying a mutually rewarding, 10-year-long relationship with the event.

Integrating the island’s onshore and offshore activities during Race Week and throughout the year has also been realised with the astute appointment of Olympic and America’s Cup sailor Glenn Bourke as the Island’s CEO in 2008. Bourke was the ideal choice for the position and was fully supportive of Oatley’s visionary plans for Race Week and the island.

“He was always a patron, a sponsor and a supporter and he loved seeing young Australians do well. He just loved the sport,” says Bourke.

Bourke’s appointment and enduring tenure mirrors that of Bob Oatley’s long-term skipper Mark Richards, who has taken Wild Oats XI to every one of her eight Line Honours victories in the race to Hobart. Richo, as he’s known to many, spoke warmly of his relationship with Bob Oatley prior to one of those many races south.

“We really enjoy each other’s company and going sailing together – and I love trying to get that boat to Hobart for him.”

Always seeking to maintain the appeal of Race Week, the Oatleys have consistently refreshed the event, attracting overseas entries that have included superyachts and ocean-racing trimarans.

Taking a boat and crew to Race Week from anywhere in Australia is a substantial investment, so the retention of a broad and evolving base of racing divisions is essential to the event’s ongoing appeal, as too is the Race Committee’s careful selection of courses to suit those divisions. The recent inclusion of dedicated multihull and trailable divisions responds to growth in those fleets around Australia, but the heart of the regatta’s patronage remains the large and enthusiastic cruising divisions, which are strongly supported by Club Marine.

Oatley’s commitment to competitive sailing was not confined to Race Week. He was also a strong supporter of the Australian Sailing Team, providing training facilities on Hamilton Island and purchasing new boats for the Olympic team – contributions that assisted in success for the team in Beijing (2008) and in London (2012).

Following both events, the victorious teams made Race Week a first stop on their return to Australia, enjoying a tickertape parade and the plaudits of the sailing community. This celebration will be repeated on the Friday of Race Week 2016, when the Olympians fly in from Rio.

With such a longstanding personal and public commitment to sailing, it was fitting and timely that in November 2015, Yachting Australia honoured Bob Oatley with a Lifetime Achievement Award for his contribution to sailing.

Away from sailing, Bob Oatley – or Popeye as he was known to his grandchildren – was a very private individual who, despite his considerable wealth, disliked epithets such as ‘billionaire’ and ‘millionaire’, concerned at the connotation of snobbishness, a trait not associated with his outgoing good nature.

Indeed, his under-the-radar, wide-ranging philanthropic activities remained unknown to most until they were detailed in the citation accompanying his appointment as an Officer of the Order of Australia (OA), in 2014, for services to the Australian wine industry, tourism and yacht racing, and for his philanthropic role in supporting medical research and the visual arts.

Bob Oatley enjoyed a strong constitution. Many will remember that, in 2014, aged 86, he sailed almost every day of Race Week from his specially designed, gimbaled seat near the helm of Wild Oats XI and was to be seen most evenings with his wife, Val, at the various functions and social occasions. Even in his last months, he was enjoying the weekly twilight race on Pittwater aboard ‘Baby Oats’ (Wild Oats X) and visiting McConaghy’s yard to watch progress on Wild Oats XI’s rebuild.

After a short illness, Bob Oatley died at his home in January this year, aged 87. His legacy is being carried forward by the next generation of Oatleys and remains for all of Race Week’s participants to enjoy in the years to come.

There will doubtless be a note of sadness in the welcome address for this year’s Race Week, but many will remember with a smile Bob Oatley’s genial, down-to-earth greeting over the years, eschewing the formalities of the ‘Ladies and Gentlemen’ tradition, with his hallmark: “Welcome, boys and girls!”