He was a Liberal member of the New South Wales Legislative Assembly, representing Mosman from 1984 to 1991 and North Shore from 1991 to 1993.
Smiles contested the preselection but was opposed by the local mayor, Dom Lopez and Malcolm Turnbull.
[2] In 1991, his seat was abolished, and he contested North Shore and defeated the Independent member, Robyn Read.
[6] Smiles was acquitted on appeal, but the court did not find him innocent and thus refused to order the Tax Office to foot his legal bills.
On 6 June 2005, registrar Sue McIllhatton declared him bankrupt, in part because he hadn't paid Moon a single cent of what he was owed.