Who is Isabel Oakeshott? Understanding the Westminster whistleblower who exposed Matt Hancock – Screen Shot
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Who is Isabel Oakeshott? Understanding the Westminster whistleblower who exposed Matt Hancock

On 28 February 2023, UK-based newspaper The Telegraph published the first of an extensive series of articles containing over 100,000 private WhatsApp messages obtained from former Health Secretary Matt Hancock. The highly damaging messages exposed a systemic mishandling of the COVID-19 pandemic crisis by the British government.

The publication’s revelations are currently being signed off by a group of journalists who’re calling themselves ‘The Lockdown Files Team’—seemingly in hopes of becoming the British press’ answer to The Avengers. However, behind this faceless tagline, is a freelance journalist whose prolific past as a whistleblower has made her Westminster’s single biggest political threat.

Who is Isabel Oakeshott?

Armed with the secrets of some of the most powerful men in the UK, Oakeshott has managed to create a controversial name for herself in the British political scene. Long-standing Tory and strong supporter of Brexit, Oakeshott has mingled with almost every high-ranking Conservative MP in the country.

Jumping from deputy political editor at The Sunday Times to the Daily Mail’s political editor-at-large, Oakeshott has had her fair share of experience when it comes to juggling the private lives of politicians. And one thing has remained consistently clear: she has zero issue with airing the dirty laundry of any official she can get her hands on.

‘Call Me Dave’ and ‘The Bad Boys of Brexit’

For over a decade, the political commentator has been at the helm of a dozen or so political scandals and has helped write a number of autobiographies for prominent Tory players. In 2015, Oakeshott co-authored Call Me Dave—a nonfiction book which has been deemed the unauthorised autobiography of former Prime Minister David Cameron.

In the book, Oakeshott, alongside fellow author and former life peer of the House of Lords Michael Ashcroft, revealed the infamous story involving Cameron allegedly performing a sex act on a deceased pig. Yeah, that story.

In 2018, the journalist was hired to write a diary-style book detailing the EU referendum from the eyes of prominent Brexiteer, businessman and co-founder of the Leave.EU campaign, Arron Banks. The inside account, accurately titled The Bad Boys of Brexit, ended up being an explosive political football when, during the writing process, Oakeshott obtained documents which linked Banks himself to Russian officials and businessmen.

As reported by The Guardian, Banks, who gave 12 million to the Leave campaign, became the biggest donor in UK history and has repeatedly denied any involvement with Russian officials, or that Russian money played any part in the Brexit campaign. However, The Observer has seen documents—evidently leaked by Oakeshott—which a senior Tory MP says, if correct, raise urgent and troubling questions about his relationship with the Russian government.

Whistleblowers aren’t an unusual sight within the British media establishment. From marital affairs to misogyny, there’s always been a journalist waiting in the wings, ready to pounce on any story in the name of public interest. However, Oakeshott’s methods have always been highly tactical and while I may not align with her political views, I have to respect her ruthlessness when it comes to unearthing the truth—whatever it may be.

Working with Matt Hancock on ‘Pandemic Diaries’ and the WhatsApp leaks

In 2022, Oakeshott approached her most challenging venture yet, trying to humanise disgraced former Health Secretary Matt Hancock. Working together for months on end, they ultimately created an account of Hancock’s perspective on the COVID-19 pandemic titled: Pandemic Diaries, The Inside Story Of Britain’s Battle Against Covid.

The book itself was relatively uninteresting. As predicted, Hancock botched his one opportunity for minor redemption by throwing a glorified temper tantrum—using the entirety of the account to lament over how he was treated during the pandemic.

When the book was first released, Oakeshott’s name for the most part stayed out of the headlines. However, as soon as The Telegraph released those private messages, her name skyrocketed into the spotlight.

According to Sky News, the journalist—who passed over more than 2.3 million words from exchanges the former Health Secretary and his colleagues had about COVID-19 policy at the height of the pandemic—has admitted that she directly violated her non-disclosure agreement (NDA) with Hancock when she chose to share the messages.

Some of the most important revelations have included: insight into the political, rather than scientific, reasoning behind some of the country’s most intense lockdowns, top officials mocking travellers who were forced to isolate in government-run hotels, and catty in-party fighting (including contemplating “locking up” Nigel Farage, which wouldn’t have been the worst idea to be honest).

Oakeshott continues to vehemently defend her decision to release the WhatsApp messages, citing that it was within the public’s interest that they be privy to these inner government conversations.

Hancock, on the other hand, has stated that the leak was a “massive betrayal and breach of trust.” While Oakeshott has received quite a bit of support from the British population for taking such a risk, the media community has been slightly less kind. Some have deemed her decision to hand over the messages to a newspaper who were overtly anti-lockdown during the pandemic as problematic.

So, wherever you sit on the entire fiasco, the question remains: Why on earth do prominent politicians keep hiring Oakeshott to write their autobiographies? While I’m always going to favour the whistleblower over the Westminster puppet, you have to question why any of these men didn’t see it coming? I guess that pretty much sums up British politics for you.

From Donald Trump to Matt Hancock, reality TV is ruining democracy one viral show at a time

From Donald Trump to Matt Hancock, democracy and reality television are becoming increasingly intertwined—and it’s increasingly worrying and corrosive to our core political principles.

Of course, celebrity and politics have long been close personal bedfellows: Ronald Reagan was a Hollywood actor before he was the Governor of California, a post later occupied by Arnold  Schwarzenegger, aka the Terminator. Meanwhile, across the pond, Boris Johnson was a regular guest host of the long-running British panel show, Have I Got News For You?

Not all overlaps between celebrity and politics are negative though: Volodymyr Zelensky, president of Ukraine since 2019, was a comedian and actor before he was a politician—playing a fictional Ukrainian president in the satirical show Servant of the People from 2015 to 2019.

But reality TV presents a different challenge, not least given the ongoing blurring of lines between reality and fiction. The early wave of reality television arrived in the 1990s—most significantly The Real World, which aired on MTV from 1992 to 2017—but quickly exploded in the new millennium. Documentary format programmes also came thick and fast: The Osbournes (2002), The Simple Life (2003), Keeping Up with the Kardashians (2007), etc.

Competitive shows with public votes spawned and soon spread internationally: Simon Cowell and  Pop Idol (2001), The X Factor (2004), and various Got Talent competitions (for instance, Britain’s Got Talent started in 2007). Voting became commonplace, even if it was primarily a way for the channels to make money from calls and texts. People would vote for the strange and stupid, occasionally  celebrating the eccentric but also resulting in multiple dogs being hailed as the greatest talent this country has to offer (no offence, Pudsey). Expert advice was ignored in favour of impulsive and emotive decisions. And some of the most successful acts after the fact—One Direction, anyone?— failed at the time to win enough public support.

So, did such patterns of behaviour have long-term impacts? It’s hard to know for sure. A 2015 study found that more 18 to 22-year-olds in the UK voted on reality TV shows than were planning on voting in that year’s general election. This does seem to have shifted in the years since though, perhaps due to divisive events such as Brexit and even more divisive individuals like Trump—after all, gen Zers were the key in stopping the predicted ‘red wave’ in this year’s US midterms.  

Then there’s The Apprentice—hosted and produced from 2004 to 2015 by the disgraced former US President, which helped catapult him to household celebrity name status. Ivanka Trump, Donald Trump Jr., and Eric Trump all starred on the show in various capacities, and would go on to play a number of roles in their father’s administration.

Trump was only fired by NBC when he announced his candidacy for President because the network disagreed with remarks he made about Mexican immigrants. No one intervened when he made his scurrilous foray into politics by spreading birther conspiracy theories that questioned Barack Obama’s American citizenship. He later appeared on Good Morning America and The View to further emphasise these arguments—appearances that elevated his political profile in the years leading up to 2016. He was essentially the first reality TV president, now the question is—will he be the last?

The Apprentice UK has been hosted since 2005 by Lord Alan Sugar. The British businessman is hardly compatible with Trump in terms of his affect on national politics, but the show still gives him influence and a national platform—despite spewing sexist and racist abuse on Twitter, such as that time he compared the Senegal World Cup squad to people selling sunglasses. It’s also worth noting that he remains a lawmaker in the House of Lords for life. Plus, the show was ultimately responsible for Katie Hopkins, surely one of the most abominable so-called commentators to have been featured in British public discourse. Can anyone remember a winner?

Politicians Ed Balls and Ann Widdecombe both memorably appeared on BBC’s Strictly Come Dancing. The latter went on to appear on Celebrity Big Brother in 2018, coming second to Australian drag queen Courtney Act.

Widdecombe was subsequently elected as a Member of the European Parliament (MEP) for the Brexit Party in the 2019 European Parliament elections, serving until the UK left the EU on 31 January 2020. Meanwhile, Penny  Morduant, who ran twice to be Conservative leader this year and is the incumbent Leader of the House of Commons, appeared on the short-lived diving reality show Splash! in 2014, donating all of her £10,000 appearance to charity.

I’m a Celebrity… Get Me Out of Here!, which has aired annually on ITV since 2002, has regularly  pushed the limits of what it means to be a celebrity in the public eye. In 2012, Nadine Dorries took part in I’m a Celeb, without informing the chief whip. She lost the party whip as result, but it was returned in 2013 and she was readmitted to the parliamentary party. Dorries subsequently served as Secretary of State for Digital, Culture, Media and Sport from 2021 to 2022 under Boris Johnson—literally putting her in charge of television for the government.

Remember when Ant and Dec used the show to criticise Johnson over Partygate? What’s become of political journalism when such platforms become vital satire?

Matt Hancock—the health secretary who served during most of the COVID-19 pandemic, oversaw tens of thousands of excess deaths, and was forced to resign after breaking his own lockdown regulations—entered the infamous jungle this year. He too had the whip removed but is still a sitting MP, despite being entirely unable to serve his constituents for the duration of the show. Hancock has used his primetime to ask for forgiveness and evidently promote his autobiography —why has he been granted this right?

Multiple members of the Trump administration have also sought rehabilitation in the public eye  through appearances on reality television: Sean Spicer, the disgraced former press secretary,  appeared on season 28 of Dancing with the Stars. Rudy Giuliani—once the respected Mayor of New York City but better known now as Trump’s personal lawyer and peddler of 2020 election  conspiracy theories—was revealed to be Jack in the Box earlier this year on the American version  of The Masked Singer.

Several judges walked off immediately and the internet responded in shock,  but given that the show is produced by FOX Entertainment and aims to create the most shocking reveals possible, perhaps this isn’t as surprising.

Politicians are using reality television to raise and rehabilitate their public profiles. Reality TV  regularly courts controversy to increase viewership and generate discussion on social media.  These interlinked dynamics create a vicious and damaging cycle—in turn, elevating and often  celebrating the fringe and the controversial.

Should reality television and politics ever operate in the same sphere? Increasingly, the genre is becoming more divorced from reality—‘surreality’ television might be a more apt name—while the real world effects of politics are becoming more direct and brutal. At the end of the day, it’s important to be able to separate the two. The stakes are too high otherwise.