Jody Harrington, the headmaster of Byford Primary, recalled Oliver’s inspiring message to the students: “Damien told the students that you can achieve anything you want in life, believe in yourself, and trust in your abilities.” Harrington and her staff were impressed by how the older students connected with Oliver, showing a genuine curiosity about his life since leaving school and becoming one of the college's most celebrated alumni.
Earlier this year, Oliver announced his retirement at the age of 51, capping a remarkable 35 years in the saddle, and three Melbourne Cup victories. This all came from hard work and talent, but a chance meeting with trainer Anthony Freedman early in his career at a local yearling sale in Perth was a pivotal moment. Over coffee, they forged a partnership that would become one of racing’s most successful collaborations.
“I spoke to Anthony and mentioned my progress in my first year of riding. They had a connection to me through my brother Jason, so it was decided that I would come to Melbourne,” Oliver recounted. The Freedman brothers, known for their racing prowess, saw potential in Oliver that could complement their team. “I was performing well back in Perth, and having a 2.5-kilogram allowance for the Freedmans gave me a strong advantage as I climbed the ranks. It was a challenging time, being homesick and moving to the other side of the country at just 16, but the Freedmans were tough and hard working. It was a time when everything fell into place, and I was fortunate to be part of their success,” Oliver reflected.
Oliver’s career has been nothing short of spectacular, with 128 Group 1 victories, which far surpasses his rivals. He’s claimed 11 Scobie Breasley Medals, an award recognising the most accomplished rider of each season. His early years as an apprentice were equally impressive, as Richard Freedman noted. “People underestimate what a superstar he was as an apprentice. If you ask who the most successful apprentice rider in Australian racing history is, you get names like Malcolm Johnston, Des Lake, and Darren Gauci. But while Gauci had three Group wins as an apprentice and Des Lake had nine, Damien Oliver had 18. He was truly remarkable, perhaps the greatest apprentice in Australia and possibly the world.”