Damien Oliver: Courage Against All Odds


Just days before the 2002 Melbourne Cup, champion jockey Damien Oliver received devastating news.

His brother Jason, also a jockey and mentor to his younger sibling, had suffered head injuries in a training accident and wouldn’t survive.

“The challenge of losing your brother and then having to turn off his life support machine, it was just really overwhelming at first and difficult to deal with,” Oliver told PickStar’s Off-Field podcast.

“And then I was faced with the decision should I ride (in the Melbourne Cup), what will people think if I do ride?

“But the way I followed my brother into the sport, it was through him, his experiences that I learned and got a lot of the opportunities … and having a great chance of winning that Melbourne Cup, if I had been sitting at home and not taking part in it, I just know his thoughts would have been 'you idiot, what are you doing?' So that was one thing that resonated with me.”

It wasn’t the first time that tragedy had struck the Oliver family. Damien was just three when his father, Ray, also passed away in a horse racing accident.

Before committing to ride in the Melbourne Cup, he sought advice from his mother, Pat.

“I think she was just very supportive of whatever I chose to do and once we discussed the reasons why I chose to ride in that Melbourne Cup, she was really supportive,” Oliver said.

Finally, the hall of famer had to decide whether he was emotionally and physically up to the challenge.

“I'm sure mentally I probably wasn't quite as sharp as I normally would be but I just had to keep pushing myself and remind myself ‘just stay in the moment and ride the way you normally would’.”

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But his Spring Carnival build up was far from perfect. Oliver said he struggled and even questioned whether he’d made the right decision to get back on the horse.

But when the clock struck 3pm on that first Tuesday in November, and Oliver sat aloft on Media Puzzle ready to race for the Melbourne Cup, something special was about to occur.

While touted as an outside chance to win, the field miraculously opened up for Oliver.

“I’d never ridden in a race that has gone so to script, or so perfect, would you believe it was divine intervention? It was probably as close as you'll ever get on that day,” Oliver said.


In what has become one of Australia’s most memorable sporting moments, Oliver crossed the finished line then pointed and looked to the sky, in the ultimate tribute to his brother.

“It was probably more relief than anything, because there was so much build up and emotion to that race,” he said.

“I've won two other cups and those cups were just the overwhelming emotion of joy and celebration, whereas this one was kind of just relief and hard to actually enjoy because of the circumstances. But it was still an amazing tribute to my brother and something I'm really proud and glad I did.”

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