Oakeshott was the political editor of The Sunday Times and is the co-author, with Michael Ashcroft, of an unauthorised biography of former British prime minister David Cameron, Call Me Dave, and of various other non-fiction titles, including White Flag?
[17][18] In 2019, she wrote a series of articles for The Mail on Sunday based on leaked diplomatic memos written by the British Ambassador to the United States Sir Kim Darroch, in which he criticised the Trump administration.
[20] In July 2019, The Guardian amended an article by its parliamentary sketch writer John Crace which contained a sentence that had potentially implied that Oakeshott obtained the Darroch emails by sleeping with Nigel Farage or Arron Banks.
[27] In October 2024, several disability organisations, including the charity Long Covid Support and the Black Triangle Campaign, referred Oakshott to Ofcom and called for reforms to the UK's hate crime laws after she criticised Chancellor Rachel Reeves for failing to announce a “crackdown” on young people on sickness benefits in the 2024 Budget, and described young disabled people on out-of-work benefits as “parasites”.
[30] Call Me Dave, co-written with Michael Ashcroft, is an unauthorised biography of former British prime minister David Cameron.
[31] One of the details in the book – that Cameron, during his university days, allegedly performed a sex act involving a dead pig – caused controversy upon publication.
[37][38] Oakeshott helped former Health Secretary Matt Hancock write his book, Pandemic Diaries, The Inside Story Of Britain's Battle Against Covid.
[39] Oakeshott then passed more than 100,000 of Hancock's WhatsApp messages to The Daily Telegraph, who began to publish them in February 2023 in a series called the Lockdown Files.
[41] The files revealed details of the health and public-order decision-making during the COVID-19 lockdown, and various political figures and civil servants including Hancock himself, then Prime Minister Boris Johnson, the UK's most senior civil servant, the Cabinet Secretary Simon Case, Chief Medical Officer, Chris Whitty and Chancellor of the Exchequer, Rishi Sunak.