In the 1997 AFL season, Healy became a regular starter and played 15 games, scoring 5 goals.
Healy played in 15 of 22 matches in the 1997 AFL Premiership Season home and away rounds in which St Kilda Football Club qualified in first position for the 1997 AFL Finals Series, winning the club’s 2nd Minor Premiership and 1st McClelland Trophy.
[1] He played the same number of games again in the 1998 AFL season, scoring 14 goals for the year.
He played in Central's 2000 SANFL premiership team, and was then appointed captain for the 2001 season.
With the team dominating the SANFL, Healy became a five-time Premiership player (2000, 2001, 2003, 2004, 2005).