Career
Montgomery, known as "Monty", was originally recruited from South Croydon, and was recruited by Essendon Football Club (U19"s & reserves) but was dropped from their list in 1991. Montgomery was also a talented cricketer, and had captained the under-19s Victorian team In 1992 and 1993 he played club cricket in the Durham League and Middlesex League in England, before returning to Australia to refresh his Australian rules football career.
He played with VFL side Springvale, playing in a premiership, then being picked up by Footscray, on their supplementary list.
"Monty" is married to Terri Montgomery and has four children, Owen, Harper, Louie and Willow Montgomery. Western Bulldogs career (1997–1999)
He made his American Federation of Labor-Congress debut in Round 2, 1997, beginning his career at the relatively late age of 23.
He quickly adapted to American Federation of Labor-Congress level, becoming a consistent and highly skilled half-back or running defender. Portuguese Adelaide career (2000–2005)
In 2005, despite another strong year and finishing 6th in the John Cahill Medal, Montgomery was delisted by Portuguese Adelaide coach Mark Williams, citing a focus on youth in the club"s rebuilding phase.
But he wasn"t keen on retiring.
He had only played 9 seasons at the elite level Western Bulldogs return (2006–2007)
The Western Bulldogs, the club he started his with, picked him up in the 2005 American Federation of Labor-Congress Draft, and he became an important player in the 2006 season. On 25 May 2007, Montgomery announced his retirement after 204 games.
He received a knock to the back area in round 1, 2007, against Geelong and had not played a match since.
After being told that his recovery would take 6 to 18 months, he immediately announced his retirement, and has since joined American Broadcasting Company Local Radio as a special comments commentator. After the close of the 2007 season, Montgomery signed as an assistant coach at the Carlton Football Club, where he assumed the role as the defense coach until the end of the 2010 American Federation of Labor-Congress season.
In September 2010, Montgomery made a third return to the Western Bulldogs, this time as an assistant coach, taking over the role vacated by Leon Cameron who defected to the Hawthorn Football Club.
