Oliver's Winterbottom win was his 115th G1 strike as he moves ever closer to what is widely regarded as an Australian jockey’s record (held by George Moore) of 119 triumphs at the highest level.
George Moore’s record is open to debate as, of course, he hung up his boots before the introduction of the Pattern system. The Pattern has always been a moveable feast, so conferring retrospective Group One status on some of his feature-race victories is a subjective matter.
However, what is clear is that Moore’s record was outstanding, not least because his big wins were spread so far and wide, his many great days in Australia being complemented by triumphs in Europe in such great races as the Derby, Prix de l’Arc de Triomphe, Prix du Jockey-Club, Grand Prix de Paris, 1,000 Guineas, 2,000 Guineas, King George VI And Queen Elizabeth S. and Ascot Gold Cup. To win ten Sydney jockeys’ premierships while spending so much of his career overseas was truly remarkable.
Supreme achievements
The achievements of Damien Oliver, however, stand supreme among those of jockeys currently riding, his consistency and longevity matching the natural talent which he showed from the outset.
Born in Western Australia in June 1972, Damien Oliver hails from a racing family but tragically neither he nor his elder brother Jason could be tutored by their father Ray, a successful jockey who lost his life in a fall in the Kalgoorlie Cup in 1975 when his sons were still young.
Their father’s death, however, did not deter the boys from choosing the same career, and they signed on as apprentices with their step-father Lindsey Rudland on leaving school. While Jason remained in the west, though, Damien headed east once he had ridden a few winners in WA, having his indentures transferred to Lee Freedman in Melbourne when he was still 16.
Lee Freedman and Damien Oliver after winning the 2003 G1 Thousand Guineas with Special Harmony
Changes in Melbourne
It transpired that Oliver had arrived in Freedman’s Flemington stable at just the right time. Since the mid-‘70s, racing in Melbourne had been dominated by the Hayes family. South Australia’s leading trainers Colin Hayes and Bart Cummings had both established permanent stables at Flemington, but as Cummings focussed his attentions largely on Sydney, Hayes came to dominate in Melbourne, winning his first trainers’ premiership there in 1978. C. S. Hayes remained Melbourne’s champion trainer until his retirement in 1990 when he handed over the license to his younger son David, who was champion trainer in each of the next four seasons until relocating to Hong Kong and passing on responsibility (and the premiership) to his elder brother Peter.
Nothing, however, lasts forever. From the late ‘80s onwards Lee Freedman emerged as the prime challenger to the Hayes’ domination, and Damien Oliver was the stable’s patently gifted apprentice. He was still aged only 18 when winning his first Group One race, the G1 Show Day Cup (now Sir Rupert Clarke S.) at Caulfield in 1990 on the Lee Freedman-trained Submariner (NZ) (Sea Anchor {Ire}), the horse’s 49 kilos meaning that Freedman’s senior riders could not take the mount.
"From the late ‘80s onwards Lee Freedman emerged as the prime challenger to the Hayes’ domination, and Damien Oliver was the stable’s patently gifted apprentice." - John Berry
Damien Oliver aboard Submariner in the G1 Show Day Cup
At the time Freedman was regularly using Darren Gauci on his better horses, while Shane Dye was on board Tawriffic (Tawfiq {USA}) when the gelding led home a Freedman-trained quinella in the 1989 G1 Melbourne Cup, Gauci having understandably opted to ride the runner-up Super Impose (NZ) (Imposing). Damien Oliver had his first Melbourne Cup ride in the race, but on the Sydney-trained long-shot Salisopra (NZ) (Three Legs {GB}) who carried 48.5 kilos, started at 250/1 and fell.
Establishing himself as a leading rider
Damien Oliver, though, was riding an ever-increasing proportion of the stable’s runners, as well as getting plenty of outside rides. He was still an apprentice when securing his first Melbourne jockeys’ premiership in 1991, ending an extended spell in which the title had almost automatically gone to Colin Hayes’ principal jockey, having been won through the previous decade by, successively, Brent Thomson, Darren Gauci and Michael Clarke. (Lee Freedman finally wrested the Melbourne trainers’ premiership from the Hayes family in 1997).
"Arguably the horse who did most to establish Damien Oliver as a leading rider was Mannerism." - John Berry
Arguably the horse who did most to establish Damien Oliver as a leading rider was Mannerism (Amyntor {Fr}), one of several very good horses whom Freedman trained for popular Victorian owner/breeders Barrie and Midge Griffiths. The stable was now awash with high-class horses, with one of the best being the now-legendary Subzero (Kala Dancer {GB}).
Subzero was among one of the best in the Freedman stables
Subzero was a difficult ride as a young horse and, ridden by Damien Oliver, his waywardness cost him the race when narrowly beaten by Dark Ksar (Ksar Royal) in the G3 VRC St Leger in the autumn of 1992. Greg Hall was in the saddle next time when the grey ran straight and true to win the G1 South Australian Derby in Adelaide. The following spring ‘Subbie’ and Hall won the Melbourne Cup with Oliver finishing last on a lesser-fancied Freeman-trained runner, the former WA-trained Heroicity (Cheraw {GB}).
Taking the Caulfield Cup
In the interim, though, Damien Oliver had landed a famous victory in the G1 Caulfield Cup on Mannerism, with Subzero and Hall back in fourth. Winning a ‘major’ gives a massive boost to the career of a young jockey, but this was particularly special: this was the Cup in which Mannerism, ridden faultlessly, turned over the hot favourite Veandercross (NZ) (Crossways {GB}) on whom Shane Dye steered an extremely wide course, prompting head-scratching which still rumbles on 28 years later. In the two minutes and 34.9 seconds which it took to run that race, Damien Oliver’s position as a major-league big-race rider became cast in stone.
"Winning a ‘major’ gives a massive boost to the career of a young jockey, but this was particularly special." - John Berry
Watch: Damien Oliver winning the 1992 Caulfield Cup aboard Mannerism
Damien Oliver was now regularly on board Lee Freedman’s best horses in Melbourne such as the brilliant sprinter Schillaci (Salieri {USA}), notwithstanding that Greg Hall was the rider of the mighty Mahogany (Last Tycoon {Ire}) largely because of his friendship with the gelding’s owner Lloyd Williams. Oliver rode Freedman’s next Melbourne Cup winner, 1995 hero Doriemus (NZ) (Norman Pentaquod {USA}) on whom he had won the G1 Caulfield Cup 17 days previously.
The trainer/jockey partnership had nearly completed the same double the previous spring, with Paris Lane (Persian Heights {Ire}) taking the Caulfield Cup before chasing home the David Hayes-trained Jeune (GB) (Kalaglow {Ire}) at Flemington. For his Sydney raiders, though, Freedman generally looked elsewhere, using Mick Dittman, Greg Hall (twice) and Glen Boss on the stable’s four consecutive Golden Slipper winners, 1993 to ’96 inclusive.
A 'go-to' hoop
During the subsequent decades, Damien Oliver has graduated into the senior figure of Australia’s jockeys’ ranks.
He has remained a ‘go-to’ hoop for pretty much everyone, whether that be Lee Freedman for horses such as the outstanding filly Alinghi (Encosta De Lago); Dermot Weld or Gai Waterhouse for the Melbourne Cup winners Media Puzzle (USA) (Theatrical {Ire}) and Fiorente (Ire) (Monsun {Ger}); Katsuhiko Sumii or Luca Cumani for the Melbourne Cup runners-up Pop Rock (Jpn) (Helissio {Fr}) and Purple Moon (Ire) (Galileo {Ire}); Bart Cummings or Fred Kersley for the Cox Plate winners Dane Ripper (Danehill {USA}) and Northerly (Serheed {USA}); John Hawkes for the Inghams’ 2007 Golden Slipper winner Forensics (Flying Spur); Kris Lees for Lucia Valentina (NZ) Savabeel {Aus}) in the G1 Queen Elizabeth S. in the Championships at Randwick in 2016; or, most recently, Darren Weir for Voodoo Lad over in Perth.
Damien Oliver celebrating his victory in the G1 Winterbottom S. on Voodoo Lad
A jockey’s life is a tough one, and there is far, far more to putting together a long-term career at the highest level than merely being able to ride well. In pretty much any endeavour, staying at the top is even harder than getting there, and jockeying probably tops the lot in that respect.
The physical and mental toughness required to cope with both the highs and the lows is extreme. And lows there have definitely been, Damien Oliver’s all too many falls headed by a dreadful accident at Moonee Valley in 1996 in which he fractured several vertebrae.
"In pretty much any endeavour, staying at the top is even harder than getting there, and jockeying probably tops the lot in that respect." - John Berry
The death of his brother Jason in a fall in a trial in Perth only a few days before Media Puzzle’s 2002 Melbourne Cup victory tested his stoicism and resolve to the limit. Almost as traumatic, albeit in a very different way, must have been his 10-month suspension imposed by the stewards after the 2012 Spring Carnival for having been found to have placed a $10,000 bet on the winner of a race at Moonee Valley two years previously in which he had ridden one of the beaten horses.
The big race jockey
Through it all, though, Damien Oliver’s ability to ride winners, particularly on the big occasion where nerves of steel are required, has never waned. Ten Melbourne jockeys’ premierships between 1991 and 2015 tell the tale, as do the nine Scobie Breasley Medals (for excellence of riding on Melbourne’s racetracks) between 1996 and 2014, and the 115 (111 in Australia and four in New Zealand) Group One winners from 1990 to the present day.
Australia’s best jockeys nowadays rarely compile the outstanding overseas records which they did through the middle of the 20th century when many of them called Europe home for extended periods, but even so Damien Oliver can still boast a respectable list of international achievement.
Damien Oliver after winning his 9th Scobie Breasley medal
In 2000 he enjoyed a successful two-month stint riding for Aidan O’Brien, highlighted by success in the G3 Railway S. at the Curragh on Honours List (Ire) (Danehill). Along with Greg Hall and Craig Williams, he was one of three Australian jockeys to ride at Royal Ascot that year, and he has made several flying visits to Europe since then, including to ride Nicconi (Bianconi {USA}) for David Hayes in the G1 July Cup at Newmarket in 2010.
It is likely that the much-loved and much-missed ‘Professor’ Roy Higgins, winner of eleven Melbourne jockeys’ premierships between 1965 and 1978, will always be revered as Victoria’s greatest jockey. When we are all dead and gone, though, Damien Oliver’s name will still be mentioned in the same reverential breath. No jockey could ask for an honour greater than that.