Simon Madden was one of the greatest ruckman to play the game, and certainly the most durable. In all he played 378 senior matches, the most by any Essendon player, and fourth most league history (behind Michael Tuck, Kevin Bartlett and Robert Harvey). In addition to playing in the ruck, Madden was a handy part-time forward, kicking 575 goals in his career, a club record that stood until it was broken in 2003 by full-forward Matthew Lloyd.
Madden won four Essendon best and fairest awards (1977, 1979, 1983 and 1984) and captained the side in the 1980 and 1981 seasons. He played in the back-to-back premiership sides in 1984 and 1985, winning the Norm Smith Medal for best on ground in the 1985 Grand Final. In 1986 he rejected an offer of a $500,000 contract by the Sydney Swans to remain with Essendon for his entire career. He was also named in the All-Australian Team on three occasions (1983, 1987 and 1988). Madden captained the Victorian interstate team in 1989-91 and in 1990 received the Simpson Medal for best on ground in the Victoria v Western Australia match played in Perth.
He was named in the ruck in Essendon's "Team of the Century" and named as the fifth best player ever to play for the club in the "Champions of Essendon" list.
Simon's brother Justin was also a top class ruckman for Essendon and Carlton, and they are the only set of brothers to both play 300 games of league football. Both brothers had their secondary schooling at St Bernard's College, Essendon, a school renowned for its sporting prowess. (The school is the only to ever produce three 300-game players, with Simon and Justin Madden joining former Bomber Garry Foulds in this achievement.)
Simon became head coach of St. Bernards Old Collegians Football Club in 2005.