Jacotine was an unlucky player considering his credentials. He wasn't picked up until no.41 in the 1998 AFL Draft, when people thought he would have been picked up at a younger age the year before. He captained the Vic Metro U18 side in 1998, and played at U18 level in the TAC Cup for 2 seasons with Dandenong. He made his debut with Collingwood on ANZAC Day against the Bombers in the traditional blockbuster. He started off well in his debut season, and was regarded early on as a future leader by captain Nathan Buckley. His form went down-hill in 1999 after stringing most of the season together since his first game. In 2000 he would only play 2 games, spending most of his season at Williamstown after he was outed by injury. He was delisted at the end of the year.