Through triumph and tragedy, Damien Oliver is racing’s great survivor

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This story was first published by this masthead about two years ago (November 2021) and was republished on Wednesday in light of Damien Oliver’s announcement of his impending retirement.

The skin is drawn tightly over his face, his expression remains sharp, but his features are more weathered, the hair not quite as brown as it was a decade ago.

None of this is surprising for a man who will turn 50 on his next birthday; a man who, for more than 30 years, has put his body through the physical strains and mental pressures of being one of the world’s leading jockeys.

Champion jockey Damien Oliver.Credit: Getty

Damien Oliver – the man in question – is as focussed, driven and determined to win as he was the day he arrived in Melbourne from Perth as a 16-year-old apprentice to join the then-emerging Freedman brothers training combination.

His timing then, as it has been every race day since, was auspicious. The Freedmans were producing a conveyor belt of track stars. Oliver didn’t ride all of them, but he established his name on the flying grey sprinter Schillaci and the Caulfield Cup winners Mannerism, Paris Lane and Doriemus, who did the cups double in 1995.

This year, he has teamed up again with the Freedmans and will ride Delphi in the Melbourne Cup on Tuesday.

Oliver has been at the top of the tree seemingly forever – as he proved his genius again last Saturday when he landed a group 1 double on Derby Day aboard James Cummings’ mare Colette, and Superstorm for Danny O’Brien.

Both were rides of craft, guile, patience, nerve and strength. as the two trainers, both of whom have forged a strong relationship with the rider, acknowledged after the respective races.


“He’s been very focussed all spring and this is his big week,” O’Brien says of Oliver.

Damien Oliver, centre, en route to victory in the Kennedy Cantala during Derby Day. Credit: Getty Images

“I have known him since he was 16, I saw him start here as an apprentice working for Lee Freedman. He is a super competitor, he is elite at what he does, but he is very focussed on winning. All those one percenters that really elite athletes pay attention to, Damien does that, says O’Brien.

Sydney-based Cummings concurred. “You can’t teach ability, and he has got that in spades. He is a confident guy, he thinks about what he is doing, he speaks well, talks me through his thinking.

Damien Oliver salutes his late brother after winning the 2002 Melbourne Cup. Credit: Sharon Smith

“He has helped our Melbourne team out, and it’s good that we can have someone to rely on in the squad when I am trying to steer the ship from nearly 900 kilometres away.”

The man himself seems embarrassed when he is asked how it feels when punters clamour for him on social media, posting his name with a meme of a goat (GOAT being the acronym for greatest of all time).

“I am not into social media.

“I don’t see the good or the bad things from that so much, so it doesn’t really concern me,” he says.


For all his success and undoubted wealth from the big wins he has achieved – four Caulfield Cups, three Melbourne Cups, a Golden Slipper and two Cox Plates – Life has not always been easy for Oliver.

His father, Ray, was killed in a race fall in the Kalgoorlie Cup in Oliver’s native Western Australia, when Oliver was a toddler, in 1975.

Damien Oliver after winning the Kennedy Oaks aboard Willowy at Flemington in 2021.Credit: Getty

His elder brother Jason was also tragically killed after a fall in a barrier trial just days before the 2002 Melbourne Cup. when Oliver was due to ride the strongly fancied Media Puzzle for Irish maestro Dermot Weld. He won that day and one of racing’s enduring images is him smiling and waving his whip in a skyward salute, in tribute to his brother.

Oliver, too, has suffered a series of injuries over the years in race falls, and has also had to face public scorn after his infamous betting ban nine years ago.

Yet he remains driven, talented and very much in demand.

“You do look around, and you notice there are not many people left in there that I have been riding with throughout my career,” Oliver says. “It doesn’t feel like I have been riding that long. You hear old footballers say that it all goes very quickly, and you probably don’t realise that when you are young.

“But as you get older you look back and think, ‘Where has all that time gone?’”


Oliver is diplomatic when asked about his biggest race thrill or the best horse he has ridden.

”I can’t put it down to one, There are so many. Obviously, all the Melbourne Cups are great for different reasons,” he says.

Still got it: Damien Oliver won the Empire Rose Stakes with Colette. Credit: Getty Images

“I think the biggest fact that I am proud of is that I have been able to compete at a high level in all different states and countries for so long.

“The longevity is important for me, and also to have done it outside my own home state. It’s easy to do it in your backyard, but to do it in other states and countries is something that I am pretty proud of.”

But surely the personal tragedies and injuries must put a strain on a rider’s nerves, especially as he gets older?

Veteran jockey Damien Oliver pictured after riding Superstorm to victory. Credit: Getty Images

“I am not indestructible, but once you get on the horse, and you are in that kind of competitive atmosphere, you don’t really think about those kind of things, you just think about the job at hand,” Oliver says.

“Over a long period of time I have come through ups and lows, and you can condition yourself through the hard times. I think I have been able to do that well.”


Over such a long period in the saddle, he has competed against some of the best jockeys of the past 50 years – those who were established when he was young, and those who have come through since.

Ask him who his toughest rivals were, and the names he rattles off are mainly from the 1980s and 1990s.

Damien Oliver with trainer Danny O’Brien pictured after Miami Bound’s 2019 VRC Oaks win.Credit: Eddie Jim

“Internationally, the ones I respected and had some time for were [Irish riders] Mick Kinane and Johnny Murtagh. And locally, guys like Mick Dittman early in my career, Brett Prebble, Darren Beadman, Darren Gauci and Michael Clarke,” he says.

“Those sorts of riders are the ones that probably stand out to me, along with Craig Williams, of course, in recent times, and we have great young jockeys coming through, like Jye McNeil as well. But it’s just as important to have a good horse as a good jockey.”


No story on Oliver would be complete without the incident that threatened to completely derail his career and tarnish his reputation for good – the betting ban that left him outed from race riding for 10 months after he was found guilty of backing a horse in a race at Moonee Valley in 2010, in which he was riding a fancied opponent.

“It’s definitely something that I am not proud of. I did the wrong thing, I was pretty embarrassed about it,” Oliver says.

“In racing and in life in general you do get chances to redeem yourself. I have worked hard the last eight or nine years to try and earn that faith and respect back from the racing community.

“You can build a good reputation over a long period of time, but you can ruin it over such a short time. That’s one thing that I learned from that.

“I feel proud of how hard I have worked over the last eight years to have success again and to earn the trust of the racing community.”

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