Watch HDToday. At the heart of this true story is Damien Oliver, a young jockey who loses his only brother in a tragic racing accident, hauntingly reflecting of the way their father died 27 years earlier. After suffering through a series of discouraging defeats, Damien teams with Irish trainer Dermot Weld, and triumphs at the 2002 Melbourne Cup in one of the most thrilling finales in sporting history.