Episode Details

The way James McDonald is reeling off Gr 1 wins it seems certain he’ll need only two more full seasons to seriously threaten Damien Oliver’s record of 129 Australian wins at the elite level. Until that happens we can continue to appreciate the distinguished record “Ollie” left behind when he retired from race riding seventeen months ago. Those 129 Gr 1’s were the highlights of a magnificent career tally of 3189. Throw in 14 Scobie Breasley medals, 10 Melbourne jockey’s premierships and an induction into the Racing Australia Hall of Fame at age 36, and you’ve got one hell of a record. Damien’s Melbourne Cup win on Media Puzzle in 2002 came just days after the death of his jockey brother Jason who’d suffered multiple injuries in a Perth barrier trial fall. The story of the tragedy behind Media Puzzle’s win made news around the world and remains a part of Australian racing folklore. A podcast seemed the best way to identify and document the many facets of the fascinating life of one of our best ever jockeys. “Ollie” was happy to oblige and we caught him in reminiscent mood. 

He begins by admitting he still gets an occasional withdrawal symptom when the big races roll around.

Damien talks of his final day in the saddle- a four race international jockey’s series in Saudi Arabia.

He looks back on his final Melbourne Cup carnival. Three wins over the week consolidated his all time record of 88 wins for the four day carnival.

The former ace jockey looks back on his final day of riding in Australia. From seven rides at Perth’s Ascot track he won the last three races to the delight of 10,000 racegoers. It was an emotional day for the WA born horseman.

He talks about the death of his father Ray in a Kalgoorlie race fall in 1975. He was just three years old.

Damien reflects on his original apprenticeship to step father Lindsay Rudland, and the unforgettable thrill of his very first winning ride at Bunbury.

He recalls the manner in which negotiations played out for his transfer to the Freedman stable in Melbourne. He says the experience was intimidating in the beginning.

The multiple premiership winner reflects on the first of his 129 Gr 1 victories. He was just 18 years old at the time. 

He agrees that Mannerism’s Caulfield Cup win in 1992 was the one to propel him onto the big stage.

Damien is happy to admit his first Melbourne Cup appearance finished in a disaster.

He’s still in disbelief that he was able to win 18 Gr 1’s before completing his apprenticeship.

Damien reflects on the first of his three Melbourne Cup wins on Doriemus in 1995. He pays special tribute to the top class stayer.

He was happy to revisit the incredible Media Puzzle story of 2002. The death of brother Jason following a freak accident in a Perth barrier trial and the reason for his decision to ride the Irish stayer in the Melbourne Cup. He remembers the race, the emotion, the aftermath and the release of a movie called The Cup nine years later.

He recalls the circumstances leading up to his engagement for Fiorente in the 2013 Melbourne Cup. He’d never ridden the horse in a race but played a major part in the stallion’s preparation leading up to the big race.

Damien talks of three second placings in the famous event.

He reflects on some favourite moments from his Gr 1 journey beginning with his first Cox Plate success on Dane Ripper in 1997.

Damien remembers his second Cox Plate win on the great West Aussie Northerly. He had to survive a double protest.

The champion jockey has won some major races several times over. He looks back on multiple victories in races like the Victoria Oaks, the Victoria Derby, and the 1000 Guineas. 

Damien talks of several great sprinters he got to ride with special mention of the powerful grey Schillaci.

Oliver won 5 races on the brilliant Testa Rossa including 3 Gr 1’s. He reflects on one famous