Oliver’s Cup pain: ‘I don’t think I’ll ever enjoy it’

The sequence of life-changing events - brutal and euphoric - still melts Damien Oliver signature stoicism.

In the 17 years since Oliver lost his brother, Jason, in a racetrack fall and won the Melbourne Cup eight days later on Media Puzzle, the double-edged nature of life's harshest realities haunt him still.

Sitting in an ante room at Flemington, Oliver reflects on a victory which will always be the most memorable of his 2463 wins (as of August 31) but, for the most tragic reasons, will never be regarded affectionately.

 

Stream over 50 sports live & anytime on your TV or favourite device with KAYO SPORTS. The biggest Aussie sports and the best from overseas. Just $25/month. No lock-in contract. Get your 14 day free trial >

 

Damien Oliver rode an inspired race to win the 2002 Melbourne Cup on Media Puzzle. Picture: Colleen Petch
Damien Oliver rode an inspired race to win the 2002 Melbourne Cup on Media Puzzle. Picture: Colleen Petch

 

"It's obviously the most memorable but it's hard to say it's my favourite because of what happened," Oliver said. "I don't think I'll ever enjoy it because it's the memory of losing my brother more than winning the Cup.

"You can still see now how emotional I get and it's 17 years ago."

The winner of three Cups - Doriemus (1995), Media Puzzle and Fiorente (2013) - Oliver can smile about runner-up finishes on Paris Lane, Pop Rock and Purple Moon. But there is fraught introspection when those hellish eight days from the spring of 2002 are revisited.

Media Puzzle's triumph resonates so powerfully because of the ghastly toll exacted on a family shaped by a sport which has given plenty, but taken far more.

Jason and Damien Oliver followed their father Ray into racing despite his death in a race fall at Kalgoorlie in 1975.

Jason Oliver was fatally injured in a trial at Belmont on October 29, 2002.

"He was on life support for a few days but I had to turn off the life support a few days later," Oliver said of his rival and hero.

"He was someone I always looked up to, especially with my father dying early.

"There was always a rivalry there but I followed him into racing and he was always helping me along the way. The circumstances in 2002 were obviously exceptional, losing my brother the week before the Cup."

 

Damien Oliver blew a kiss to the heavens for his brother Jason after his win on Media Puzzle.
Damien Oliver blew a kiss to the heavens for his brother Jason after his win on Media Puzzle.

 

Oliver agonised over whether to ride on Derby Day and also on Cup Day.

Fretting over public perception and aware of family sensitivity, he said: "I was probably at the height of my career at that stage and it (Jason's death) really threw everything into disarray.

"I didn't know what to do, what to think and what people would think if I rode.

"I sat down with my mum (Pat) and obviously my brother was a huge inspiration.

"My mum and I both thought about it and came to the conclusion that if I was sitting on the couch at home watching the Melbourne Cup, Jason would have been saying 'You bloody idiot, what are you doing?"

Despite an imposing book of rides, Oliver struggled on Derby Day.

"I had one placing from eight rides and I was starting to question whether I'd made the right call," he said. "I rode most of them OK, but there was a lot of noise on the outside. People were good to me but at times it was difficult to focus.

"I was most comfortable when I was on a horse.

 

Damien Oliver admits its hard to say Media Puzzle’s Cup win was his favourite considering the heartbreaking personal circumstances around the victory. Picture: Mark Stewart
Damien Oliver admits its hard to say Media Puzzle’s Cup win was his favourite considering the heartbreaking personal circumstances around the victory. Picture: Mark Stewart

 

"Your instincts take over when you're riding but it's hard not to be distracted when you have quiet times."

Having convinced Dermot Weld he was in the right frame of mind to give Media Puzzle the best winning chance, Oliver's emotions were again clouded on Cup Day.

"There were a few rides and not much success and there were more questions, but I assured myself I'd done the right thing and things would work out well," he said.

"In the Cup itself, I had a beautiful run and if you wanted to script a Melbourne Cup as the way you wanted it to go, this was it.

"Coming to the turn, I knew I was in with a big chance. Then I cruised up and halfway down the straight I knew I was going to be hard to beat.

"But it was probably inside the last 100m, you realised you had it won but it was quite a strange emotion and not one you could enjoy.

"It was relief more than anything."

 

Trainer Dermot Weld and Damien Oliver celebrate Meda Puzzle’s Cup win.
Trainer Dermot Weld and Damien Oliver celebrate Meda Puzzle’s Cup win.

 

Wearing his brother's jodhpurs, Oliver rose out of the saddle as he crossed the line and pointed to the heavens. It was the most poignant moment in Cup history, but not premeditated.

"Not at all. It was a fantastic tribute to my brother," Oliver said.

"(Wearing Jason's jodhpurs) was something I really wanted to do because I felt like I was riding for him, for his memory."

Left to navigate muted post-race celebrations, Oliver had a far more important assignment the following day.

"They were humble celebrations that night after the Cup," he said.

"We caught up with the connections of the horse for drinks and dinner, but I flew out early the next morning for my brother's funeral.

"Looking back, the human emotion and all the other factors are the things that makes it stand out the most. "It still affects me now, as you can see."

Oliver famously said at the time he would happily surrender the Melbourne Cup to have his brother back.

Those words ring as loud today as they did in 2002.