Having lost his brother Jason in a Perth track accident only days before, Oliver needed to call on all his reserves to win the coveted Loving Cup Trophy.
And knowing he had not ridden well on Derby Day three days earlier, there was much speculation as to whether Damien should take the mount on the Dermot Weld-trained stayer. Yet it was like the script was already written, as Damien placed the Irish stayer in the best positions throughout and, at the top of the straight, all punters were screaming for Media Puzzle to win.
There was hardly a dry eye at Flemington as Oliver saluted crossing the finishing line and calling to the heavens, ‘My boy, my boy’, an affectionate exchange between two brothers who had endured a lifetime together. Damien Oliver would return to Perth the next day to bury his brother. It was the heart-wrenching story of the decade.
In winning the Cup, Media Puzzle (trained in Ireland) became the first of nine international horses to win the Melbourne Cup between 2000 and 2019. Others would include: Delta Blues (2006, Japan); Americain (2010, France); Dunaden (2011, France); Protectionist (2014, Germany); Rekindling (2017, Ireland), Cross Counter (2018, United Kingdom), Twilight Payment (2020, Ireland) and Verry Elleegant (2021, New Zealand).