In the summer of 1985–86, the new private owner of the Sydney Swans, flamboyant and controversial doctor Geoff Edelsten, had been frantically signing talent on massive contracts to play for his team. Rioli was announced as one of his many signings. It was the salary cap that saved Rioli from leaving for Sydney. After rumours that he would either join or return to South Fremantle, he eventually returned to the Tigers midway through the 1986 season. Rioli performed patchily through the season and the next, when Richmond finished last for only the third time in its history. Rioli captained Western Australia in the state game that year against his teammate Dale Weightman, who led Victoria.