[4] He worked in the Ministry of Finance and Economic Planning of Kenya from 1968 to 1970, and served as a Labour councillor on Oxford City Council from 1972 to 1976.

[5] In 1972, Oakeshott became a Parliamentary Assistant to Labour's Roy Jenkins in Opposition; a so-called "Chocolate Soldier", funded by the Joseph Rowntree Social Service Trust.

He stood down as HM Government Treasury Spokesman by "mutual agreement" in February 2011, after his description of the Coalition's Project Merlin deal with the banks over lending and bonuses as being "pitiful".

[16] During the latter part of 2013, Oakeshott began to call for Nick Clegg to resign as Leader of the Liberal Democrats, even suggesting that the Coalition may have to break apart.

In April 2014 he privately commissioned ICM Research to undertake a telephone poll in each of four key Lib Dem seats: Clegg's own Sheffield Hallam; Cambridge; Redcar; and Wells.

After the poll results were leaked via The Guardian newspaper on 27 May 2014, and Clegg on 28 May accused him of seeking to "undermine" the Lib Dems and warned he faced disciplinary action,[18] Oakeshott subsequently resigned from the party and took a "leave of absence" from the House of Lords.

[18][19] In an attempt to "help save our country from a Tory government cringing to UKIP" in January 2015 he donated £300,000 in total to 15 Labour candidates in the 2015 General Election, £300,000 to 15 Liberal Democrats and £10,000 to the Green Party's sole MP, Caroline Lucas.