A brilliant footballer who could tear any side to pieces on his day, Osborne spent most of his career at Fitzroy. Leaving the Lions he spent a season with Sydney where he sustained a horrific head injury and had to be moved from the ground by ambulance. He then spent three years with Footscray before finally, in 1997, making it to Collingwood - the club he had barracked for as a kid. His pace, marking and long kicking skills did not diminish greatly even after years in the game. Represented Victoria seven times in state of origin games.