[8][11][12][13][14] Oakeshott describes Cameron as an influence on his thinking:[2] As a student he was a pretty interesting fellow but standing on his digs over some of the speeches and some of the sermons he used to give.

And in his parting speech to the students, he said, "I hope the great lesson I've taught you as the leader of this college is that you've got to stand up for what you believe in regardless of the consequences.

[6] He then worked as an administrative officer at the Road Transport Forum, for the lobbying company Resolutions, as a staffer for future 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.

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 (homosexuals)" were gaining too much influence in the party; he took particular offence to the former because his wife is of South Seas descent.

[2][6][8][25] He subsequently retained the seat as an independent at the 2003 New South Wales State election, gaining 69.75% of the primary vote, compared to 14% for the National Party candidate.

After preferences, he won 82 percent of the two-candidate vote, making Port Macquarie the safest seat in the legislature.

[27] There were suggestions that Oakeshott would stand as an independent candidate at the 2004 federal election against his former boss and future National Party leader Mark Vaile in the seat of Lyne, based on Port Macquarie, but he did not nominate.

In April 2008, following the defeat of the Howard government, Liberal Senator Bill Heffernan approached Oakeshott to consider standing as a joint Liberal-National candidate in Lyne should Vaile retire and a by-election be called.

[42] On 10 September 2010 he announced that he had turned down becoming the minister for Regional Australia, a portfolio created because of the agreement between himself, Tony Windsor and the ALP.

Oakeshott declined and Peter Slipper, a coalition MP, became speaker, allowing the Labor Party to continue in minority government.

He further stated that he would be prepared to work with whoever could provide stable government and would consider negotiating with the Liberal-National coalition to that end, although his preference would be to deal with former opposition leader Malcolm Turnbull over Tony Abbott.

Despite his large personal majority, both his federal and state electorates were still comfortably safe National seats in "traditional" two-party matchups.

Proving this, Besseling lost Port Macquarie to the Nationals' Leslie Williams at the 2011 state election partly due to voter anger at Oakeshott's support for Gillard.

[50] In February 2012, Oakeshott introduced a private member's bill to allow the Australian Minister of Immigration to authorise sending asylum seekers to any country that is part of the Bali Process.

In June 2012, following the sinking of two asylum seeker boats in the Indian Ocean within a week that resulted in significant loss of life, the bill was brought up for immediate debate in the House of Representatives.

[52] The bill, seen as a compromise between the Government's desire to allow processing of asylum seekers in Malaysia and the reinstatement of the Pacific Solution sought by the opposition Coalition, was not supported by the opposition or the Australian Greens on the basis that it would allow processing of asylum seekers in countries that were not signatory to the United Nations Convention Relating to the Status of Refugees.

[53] An amendment to the bill, introduced by the Shadow Minister for Immigration & Citizenship Scott Morrison, to limit processing of asylum seekers to nations that had signed the convention was defeated.

[58] In 2017, Oakeshott was among the first batch of students to begin studying a undergraduate medical degree at University of New South Wales's new Rural Clinical School Campus in Port Macquarie.