He then worked as an administrative officer at the Road Transport Forum, for the lobbying company Resolutions, as a staffer for National Party Leader Mark Vaile, and in public relations for the Coalition in Canberra before his own election to the New South Wales Legislative Assembly. NSW parliament He was elected as the National Party member for Port Macquarie at a by-election on 30 November 1996 after the retirement of National Party member Wendy Machin on 28 August, winning 46.71% of the primary vote against John Barrett, a former Liberal Party candidate who stood as an independent after the Liberals, then led by Peter Collins, decided not to run a candidate. However, the Nationals lost almost six percent of their primary vote from 1995, and their two-party majority fell to a marginal four percent. At his election, he was the youngest member of the NSW Legislative Assembly. He stood again at the 1999 election, increasing his primary vote to 56.05% and his two-party vote to 66.6%, enough to revert Port Macquarie to its traditional status as a safe National seat. Under Opposition Leader Kerry Chikarovski, on 19 April 1999 he was appointed as the Shadow Minister for Sport and Recreation and the Shadow Minister for Fisheries and Ports. Following a Shadow Cabinet reshuffle on 1 February 2000, Oakeshott lost Fisheries and Ports and took on the shadow portfolio of Gaming and Racing. However, he had become increasingly dissatisfied with the National Party, stating that he was the youngest person at most meetings he attended, and found himself in opposition to many of the party's policies. Almost immediately after his election to the legislature, Oakeshott identified a number of points of disagreement. He was not at home with the party's strong conservatism on social policy; he recalled being "massively heavied" not to support a Labor bill for a safe injecting room trial. He was also unnerved by a senior National claiming that "blacks and poofters" were gaining too much influence in the party; he took particular offence to the former because his wife is of South Seas descent. He was also pressured to fall into line on the Nationals' staunch opposition to a republic. He later said that he should have done "more due diligence" on the Nationals' ideology, saying that he would have never joined the party had he known about its conservative bent. He only did so because he