In the 1840s he bought land in the Nineteen Counties in partnership with his brother Francis Oakes who also became a member of the Legislative Assembly.
He then traveled extensively in Europe On 13 May 1861, in an attempt to swamp the upper house to carry his land reform bills, the premier, Charles Cowper, nominated Oakes to a limited-time appointment in the Legislative Council .
However, he could not be sworn in as the President of the New South Wales Legislative Council, William Burton, walked out of the chamber in protest at the government's actions.
When the council again met in June, Oakes refused to take his seat due to objections to the conditions that Cowper had placed on his appointment.
[1] As a result of his anti-sectarian stand and opposition to Parkes, Oakes failed at several attempts to re-enter the Assembly but was eventually elected as the member for East Sydney at the 1872 by-election caused by the appointment of Saul Samuel to the Legislative Council.
[citation needed] Oakes married Mary Ann Shelley at St John's Church of England, Parramatta, on 25 May 1837 and she died in 1865.