Cover image courtesy of Western Racepix
On Saturday afternoon, the curtain will come down on the career of arguably the greatest jockey of all-time, Damien Oliver.
Fittingly, the proud Western Australian’s final ride will take place in Perth, with ‘Ollie’ to partner the Nick Ryan-trained Munhamek (GB) (Dark Angel {Ire}) in the race named in his honour - the G3 Damien Oliver Gold Rush (1400 metres).
Oliver - a son of father Ray and mother Pat - was destined to be a jockey. Ray won the 1958/59 and 1959/60 Perth apprentices’ titles, before landing Perth Cups on Rendition (NZ) (Count Rendered {GB}) in 1958 and Fait Accompli (Little Empire {NZ}) in 1972. Tragically, Ray lost his life in a race fall at Kalgoorlie in 1975 when Oliver was just three. Oliver’s grandfather, Gerry, was also a jockey and won the 1965 Kalgoorlie Cup aboard Colour Correct (Cyrus {GB}).
Damien Oliver, a proud West Australian, will have his final ride in Perth on Saturday, December 16 | Image courtesy of Western Racepix
Oliver experienced further family devastation in 2002 when his brother, jockey Jason, was also killed in a trial fall in Perth.
Oliver’s glittering career began in 1988. Indentured to his stepfather, Lindsay Rudland, he notched his first win on March 15 of that year at Bunbury, as a 15-year-old apprentice, on Mr Gudbod (Gielgud {USA}) for trainer Bruce Kay.
Kay told TTR AusNZ he is honoured to be a small part of Oliver’s remarkable story.
“It is very special, I was just the lucky one that had him for his first ride,” Kay explained.
“It is very special, I was just the lucky one (trainer) that had him (Damien Oliver) for his first ride.” - Bruce Kay
“His brother Jason used to do a lot of riding for me; he was suspended so he told me to give Damien a go.
“How he got that horse to win, I don’t know. He was a maiden in a Class 5, so he was well out of his grade. He went around at 70/1 and never won another race after that.
Bruce Kay | Image courtesy of Western Racepix
“Jason and I always thought he was special, but never did we imagine he would reach the heights he has. For him to do what he has done, and through the tragedies, it’s quite amazing.
“Jason (Oliver) and I always thought he (Damien Oliver) was special, but never did we imagine he would reach the heights he has.” - Bruce Kay
“He’s a wonderful guy and hopefully he can bow out on Saturday with a winner or two.”
Kay recalled a special moment five years ago when a message out of the blue took him by surprise.
“It was March 15, 2018 and I was sitting in my lounge room at home. I got a text message from Damien, saying, ‘Hi Shagga, forever grateful, 30 years today, can’t thank you enough’. How is that, hey? He didn't have to do that, but that’s the sort of guy he is. He’s just a lovely bloke, he’s never changed.”
Ollie and FBI - a formidable force
A little more than a year after his maiden victory, Oliver was thrust into the limelight, joining the all-conquering Lee Freedman stable in Melbourne. Lee was the face of the business, but brothers Michael, Richard and Anthony were all an integral part of the team, which was dubbed ‘Freedman Brothers Incorporated’ (FBI).
In 1990, aged 18, Ollie chalked up his maiden Group 1 triumph, claiming the Show Day Cup (now the G1 Sir Rupert Clarke S.) on Submariner (NZ).
Soon after, Oliver won the G1 Caulfield Guineas on Centro (NZ) for the Freedmans.
For a decade, Oliver and the Freedmans were almost unbeatable. They combined for 24 elite-level successes between 1990-97. During this time (in 1991), Oliver won the senior Melbourne Jockeys’ Premiership at the age of just 19, and by the time he had completed his apprenticeship, Oliver had ridden 18 Group 1 wins on his CV and two Jockeys’ titles (he would go on and win another eight). This was at a time when Greg Hall, Michael Clarke and Darren Gauci, to name just a few, were all competing in Melbourne.
| Derby Day | 209 | 30 | 23 | 26 |
| Cup Day | 204 | 21 | 22 | 13 |
| Oaks Day | 174 | 24 | 23 | 14 |
| Stakes Day | 175 | 13 | 17 | 22 |
| TOTAL | 762 | 88 | 85 | 75 |
Table: Damien Oliver's success across major Melbourne Cup week racedays
In 1992 star mare Mannerism (Amyntor {Fr}) handed Ollie his first major when she was first home in a controversial running of the G1 Caulfield Cup, one where Shane Dye lost his compass aboard the 5/2 favourite Veandercross (NZ) (Crossways {GB}).
In 1994, Oliver and Freedman lifted the Caulfield Cup again, this time with Paris Lane (Persian Heights {GB}).
The following year, Oliver won the first of three G1 Melbourne Cups, partnering Freedman’s great stayer Doriemus (NZ) (Norman Pentaquad {USA}) to glory.
Damien Oliver won three G1 Melbourne Cups, the first aboard Doriemus (NZ) (pictured) in 1995 | Image courtesy of The Image Is Everything
Schillaci (Salieri {USA}) won eight Group 1s between 1992-95, and in the autumn of 1992, Oliver piloted the crack Freedman-trained sprinter to elite-level triumphs in the the Lightning S., Oakleigh Plate, Newmarket H. and The Galaxy.
In 1996, Oliver won the first of 11 Scobie Breasley Medals, which recognises Victoria’s leading jockey of the season.
Damien Oliver with Schillaci | Image courtesy of Sportpix
“It seems not all that long ago, even though it was, that he came over as a fresh-faced teenage apprentice. We all camped in together there, pretty much in the one house. It was an amazing ride,” Michael Freedman told TTR AusNZ.
“It didn’t take him long to establish himself. By his second year, he was considered as good as any of the seniors.
“It didn’t take him (Damien Oliver) long to establish himself. By his second year, he was considered as good as any of the seniors.” - Michael Freedman
“He had 18 Group 1 wins by the time he finished his apprenticeship, which is by far the biggest tally of any apprentice in history.”
Freedman said Oliver’s competitive drive was one trait that stood out.
“He had a certain cockiness about him, but he wasn’t arrogant. It was a strong belief in his ability and he was fiercely competitive,” said Freedman.
“I can remember the odd occasions where he didn't mind voicing his opinion, perhaps when he shouldn’t have. That’s all part of growing up, maturing and learning.
“He had a real steely resolve, even from a young age.”
“He (Damien Oliver) had a real steely resolve, even from a young age.” - Michael Freedman
Freedman lauded Oliver’s ability to absorb pressure. He explained that some of the top-line horses he rode for the Freedmans were expected to win, often starting at short odds.
Michael Freedman | Image courtesy of Ashlea Brennan
“The fact that he was capable of taking on the pressure of those mounts… some of them went around in those big races at pretty short odds, particularly a horse like Schillaci. He just didn’t let it faze him at all, he just went out there and did his job. It would be rare to see a relatively inexperienced, young apprentice, take on that challenge and be totally unaffected by it,” Freedman commented.
The King of the Flemington
Just last month, Oliver had his final ride at Flemington - a track he made his own over a sustained period, especially at carnival time.
Oliver will retire as the winningest Melbourne Cup Carnival jockey of all-time, and some of his stats are quite extraordinary.
He bows out with 88 Cup Week wins from 762 rides, a strike rate of 11.54 per cent.
Damien Oliver's Melbourne Cup carnival statistics
88 - A record 88 Melbourne Cup carnival winners
26 - A record number of Group 1 winners over the four days of the Melbourne Cup Carnival
3 - Melbourne Cup wins
6 - Victoria Derbys
7 - VRC Oaks triumphs
5 - Champions S. (formerly Mackinnon S.) successes
3 - Wins in the Coolmore Stud S. (formerly Ascot Vale S.)
Twenty-six of Oliver’s record 129 Group 1s took place during Cup Week.
He won the G1 Melbourne Cup on three occasions - Doriemus in 1995, Media Puzzle (USA) (Theatrical {Ire}) in 2002 and Fiorente (Ire) in 2013.
The 51-year-old is a seven-time winner of the G1 VRC Oaks - the same as Bobbie Lewis. Oliver’s Oaks triumphs came aboard Northwood Plume (Military Plume {NZ}) in 1994, Kensington Palace (Kingston Rule {USA}) in 1997, Special Harmony (Spinning World {USA}) in 2003, Jameka (Myboycharlie {Ire}) in 2015, Miami Bound (NZ) (Reliable Man {GB}) in 2019, Personal (Fastnet Rock) in 2020 and Willowy (Kermadec {NZ}) in 2021.
Furthermore, he won the G1 Victoria Derby on six occasions and the G1 Black Caviar Lightning no less than five times.
Perhaps Oliver’s finest moment and one of the most memorable in the history of the sport was when the champion rider guided Media Puzzle to an emotional victory in the 2002 Melbourne Cup, just days after brother Jason died in Perth. Oliver bravely pushed ahead, wanting to honour his late brother. Wearing Jason’s breeches, Oliver produced a well-executed ride, and the Dermot Weld-trained runner was far too good. After crossing the line, Ollie stood in the irons and blew a kiss to Jason, vision that is now part of racing folklore.
With tears running down his face, Oliver said: “The Melbourne Cup doesn’t mean anything to me any more. I’d give it away right now to have my brother back. But I know it was the right thing to ride. Jason would have wanted that.”
Other notable accolades
In 2007, just two years after breaking his spine, Oliver became just the eighth jockey in history to claim the ‘Grand Slam’ of Australian racing - the G1 Golden Slipper S., G1 Caulfield Cup, G1 Melbourne Cup and G1 Cox Plate. Ollie registered the historic feat when guiding Forensics (Flying Spur) to a brilliant win in the Slipper.
Oliver has two Cox Plates in his trophy cabinet, having won aboard Dane Ripper (Danehill {USA}) in 1997, then Northerly (Serheed {USA}) in 2001.
Damien Oliver returns to scale after winning the G1 Golden Slipper aboard Forensics in 2007 | Image courtesy of The Image Is Everything
He has four Caulfield Cups - Mannerism in 1992, Paris Lane in 1994, Doriemus in 1995, Sky Heights (NZ) (Zabeel {NZ}) in 1999.
In 2008, Oliver was inducted into the Australian Racing Hall of Fame.
Oliver retires with more than 3150 wins to his credit, plus $256-odd million in prizemoney.
In both 1992/93 and 2001/02, he notched nine Group 1 wins.
