22 Farewell Ollie “What stands out the most is how driven and mentally strong he is. Lee Freedman once said he’s like kryptonite that can’t be broken. One example was when he had a fall at The Valley on a Friday night. I thought there was no way he’d ride the next day at Flemington, but after being cleared and discharged in the early hours of Saturday morning, he not only rode, but won the first race!” Tragedy struck during Oliver in 2002 when his older brother, Jason, was killed in a race fall in Western Australia. While the racing world mourned, Oliver managed to mentally compartmentalise his grief to win the Melbourne Cup shortly after the accident. “I’ve thought about this a lot. I was younger and without a family when I lost Jason, and I don’t think the true impact of grief hit me as it would today. I have a family now, and they mean everything to me. If something were to happen to them, I would be devastated,” he revealed. As Oliver steps away from the limelight, he leaves behind an impressive legacy in Australian racing, from dominating two-year-old races to clinching the Melbourne Cup three times. His family will now take centre stage in his life, along with new challenges. Yet, Oliver’s enduring message is that you can achieve anything if you desire it strongly enough, a sentiment echoed by Richard Freedman, who said, “To have been a three-time leading jockey as an 18-year-old and to have ridden 18 Group 1 winners … it’s hard to fathom how exceptional he was.” (Left) SEVENTH HEAVEN: Ollie joins legend Bobbie Lewis on seven VRC Oaks wins after he guided Willowy home in the 2019 edition of Australia’s first fillies classic. (Vince Caligiuri/Getty Images) (Right) NUMBER 6: Aboard Warning after winning the 2019 Victoria Derby for a sixth time. (George Salpigtidis/Racing Photos)
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