He was a National Party member of the New South Wales Legislative Assembly from 1999 to 2003, representing the electorate of Monaro.
Webb studied at Canberra Grammar School and Yanco Agricultural College, and was a grazier before entering politics.
[2] Campaigning on the state of the timber industry and the decline of rural infrastructure, he faced a very tight race against the Labor candidate, and emerged successful despite trailing for most of the count, in a result that was not known for days.
He once took a tray of local lamb to the American embassy to protest American agriculture tariffs, called for the abolition of the National Parks and Wildlife Service with the delegation of its responsibilities to local councils, and suggested letting the state's prison population tame wild brumbies in the Snowy Mountains.
He also had two vocal in-person clashes with Premier Bob Carr, and was once criticised for signing a petition by the Lyndon LaRouche-affiliated Citizens Electoral Council.