‘I can’t imagine going through that today’: In his final Cup carnival, Damien Oliver looks back at his most famous win

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Even at the end of the most remarkable of careers, Damien Oliver is still, as the cool kids like to say, bringing the drama. Perhaps Melbourne Cup day wouldn’t be the same without it.

Be it his first time, in 1989, where he fell on longshot Salisopra mid-race, or his final outing, 34-years on where he awaits the fitness of his roughie, Alenquer, the greatest Australian jockey of his generation’s day will by no means be dull.

Damien Oliver is in the thick of his final Melbourne Cup carnival as a jockey.Credit: Eddie Jim

In a lifetime in the saddle, which has so far yielded 129 group 1 wins – the most ever in Australia – and just shy of $250 million in prize money for connections, it will be his heroics on the first Tuesday in November that will be remembered as long as the race survives.

His triumphs and tragedies have played out on the TV screens in family living rooms. In a sport which has slowly but surely drifted away from mainstream Australian culture, he has been as close of a household name as Scobie Breasley or Roy Higgins – the great jockeys who came before.

Oliver jumping off Media Puzzle after his incredible 2002 Melbourne Cup win.Credit: Fairfax

Racing has taken plenty from Oliver, who lost both his father and brother to the sport in tragic race falls, but he has rarely stopped giving back. In his last weeks in the saddle he has rarely turned down interview requests, even if they are conducted, like this one, in between sauna sessions.

“I’m probably sick of talking about myself now,” he told this masthead. “But racing has been my life. You know it’s part of the job, but I dunno if I will miss this part of it.”

Oliver remembers first listening to the Cup as six or seven-year-old at school. His racing pedigree was well known. He was the go-to person when it came for a tip.

But that first Melbourne Cup in the saddle still plays on the mind of the now 51-year-old, who rode two winners on Derby day just to remind punters he is going out on top.

“I remember I got to about 2000m and Richard Jolly, who was riding Saratov in front of me, found some interference and he was trying to hang onto his horse,” Oliver said.

“I was sure I was going to get around him and the next thing … he lost his grip and fell off, and my horse tripped over him and I came down. I was as flat as a tack that night.”

Oliver would win 18 group 1 races as an apprentice but would have to wait six years before his first Cup win in 1995 on Doriemus – for his long-time boss Lee Freedman – beating Victoria Derby winner Nothin’ Leica Dane and 1993 Cup winner Vintage Crop. Coincidently the two trainers the pair beat home that day would train the next two Oliver winners – Dermot Weld’s Media Puzzle in 2002, and Gai Waterhouse’s Fiorente in 2013.

“Thinking back to that first one, it was just huge thrill for me – and a relief,” Oliver said.

“I had run second the year before on Paris Lane, and Doriemus had won the Caulfield Cup but then it came up wet for the Melbourne Cup and we didn’t really know if he would like it. But, as it turned out, he loved it.”

Oliver says it’s hard to split his trio of Cup wins – saying its like being asked to pick your favourite child. His win on Media Puzzle, 21 years ago, is among the most famous victories of all, having lost his brother Jason just days prior. The story became a book and a big-budget film.

“I was obviously in my 30s and without a family when I lost Jason, and I don’t think the true impact of grief hit me as it would today. I have a family now, and they mean everything to me. I can’t imagine going through that today,” he says.

Oliver, himself, has suffered a series of injuries over the years in race falls, and has also had to face public scorn after betting on a rival horse, Miss Octopussy, 11 years ago.
But he says he is proud of having always fronted up, never running or hiding from media scrutiny.

“I guess sometimes you feel hard done by, but other times it was your own mistakes,” he says. “I have never liked letting people down but I think, ultimately, I have lived a public life and you can’t really complain too much about it.”

Waterhouse, who has partnered with Oliver for six group 1 wins, said this week the retiring champion hoop was “a one-off”.

“He is a champion jockey – you only have to look at his record,” she says. “He knows how to place horses, or where he thinks they’re placed. He really is a masterful jockey.”

Oliver says the Cup has benefitted from the international field it now attracts, where he has been able to test himself against the world’s best jockeys including Frankie Dettori and Ryan Moore. He admits he would relish one more Cup win before retiring in December, which would put him alongside Bobby Lewis and Harry White with the record four.

“There’s been some great rewards and camaraderies among the jockeys as well, and you know the risks when you go into it. Fortunately, touch wood, I’ve been able to get through it OK.”

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