Isabel Oakeshott
Isabel Oakeshott is a prominent British political journalist, author, and commentator known for her fearless investigative reporting and involvement in numerous high-profile political stories. From her early career in local newspapers to her role as one of the most influential political commentators in the UK, Oakeshott’s career has shaped British political discourse for over two decades. Along the way, she has earned a reputation for her controversial reporting, ghostwriting political books, and a significant presence in the world of public speaking.
This article provides a deep dive into Isabel Oakeshott’s life and career, touching on her professional achievements, controversies, net worth, and personal life, as well as her influence on the media and political landscape.
Early Life and Education
Isabel Oakeshott was born on June 12, 1974, in Westminster, London. Raised in a family with a strong background in education, Isabel attended St George’s School in Edinburgh and Gordonstoun School in Moray, Scotland. Known for its rigorous academics and prominent alumni (including members of the British royal family), Gordonstoun shaped Isabel’s early worldview and character.
After completing her secondary education, she went on to study History at the University of Bristol, where she graduated with a degree in 1996. This academic foundation in history and politics would later become a cornerstone of her career in political journalism.
Journalism Career: Isabel Oakeshott Climbing the Ranks
@Isabel Oakeshott’s career in journalism began in the late 1990s, as she moved from Scotland to London and took on reporting roles at various local and regional newspapers. Her early work included positions at the East Lothian Courier, the Edinburgh Evening News, the Daily Record, and the Sunday Mirror. These initial stints in local media provided her with the foundational experience necessary to succeed in the competitive world of national journalism.
The Sunday Times and Breakthrough in Political Journalism
Oakeshott’s career took a significant leap forward in 2006 when she joined The Sunday Times, one of the most prestigious newspapers in the UK. She was initially hired as the Deputy Political Editor and worked her way up to become the Political Editor in 2010.
During her time at The Sunday Times, Oakeshott earned a reputation for her fearless investigative reporting, particularly in the realm of politics. One of her most notable scoops involved exposing Chris Huhne, the then Liberal Democrat cabinet minister, for arranging for his wife to take driving penalty points on his behalf. The story eventually led to a criminal trial and imprisonment for both Huhne and his ex-wife, Vicky Pryce.
Oakeshott’s reporting garnered several accolades, including Political Journalist of the Year at the 2011 Press Awards. Her career continued to rise as she gained recognition for her ability to break stories, analyze political developments, and offer bold commentary on public affairs.
Later Roles and TV Appearances
After leaving The Sunday Times in 2014, Oakeshott joined the Daily Mail as Political Editor-at-Large, where she continued to cover British politics and offer analysis. In addition to her newspaper roles, Oakeshott has made regular appearances on BBC’s Question Time, Sky News, and various political discussion programs, further solidifying her presence as a political commentator on television.
In 2022, Oakeshott took on a significant new role as the International Editor at TalkTV, a platform known for its bold approach to news and political analysis. Her role at TalkTV allows her to cover international political developments, offering her a global stage on which to continue her work as a commentator.
Books and Writing Career
In addition to her journalistic work, Isabel Oakeshott has made her mark as a writer and ghostwriter. Her books have often delved into political figures, public policy, and controversial political events. Oakeshott has written or co-authored several books, which include:
- Inside Out: My Story of Betrayal and Cowardice at the Heart of New Labour – Co-authored with Peter Watt, this book gives an inside view of the workings of New Labour and the scandals that surrounded it during its time in power.
- Farmageddon: The True Cost of Cheap Meat – Written with Philip Lymbery, this book explores the environmental and ethical implications of industrialized meat production, highlighting the issues surrounding factory farming.
- Call Me Dave – Co-authored with Michael Ashcroft, this unauthorized biography of former Prime Minister David Cameron contains sensational claims about his personal life and youth, including the infamous “piggate” controversy.
- The Bad Boys of Brexit – Oakeshott ghostwrote the memoir of several key Brexit campaigners, providing an insider’s view of the dramatic political event that reshaped the UK’s relationship with the European Union.
- Life Support: The State of the NHS in an Age of Pandemics – Written with Michael Ashcroft, this book evaluates the state of the UK’s National Health Service and its ability to cope with future crises, particularly pandemics.
Oakeshott’s writing style is known for its boldness and willingness to tackle controversial subjects head-on. Whether investigating the internal workings of political parties, government policy, or societal issues, Oakeshott’s books often seek to expose truths that are not immediately apparent to the public.
Isabel Oakeshott Controversies and Major Leaks
Isabel Oakeshott’s career has not been without its share of controversy. She is known for her investigative reporting on stories that have had significant political consequences, and her work has often stirred public debate about journalistic ethics.
Call Me Dave and the “Piggate” Scandal
One of the most controversial moments of Oakeshott’s career came with the publication of Call Me Dave, the unauthorized biography of former Prime Minister David Cameron. The book contained an anecdote about Cameron allegedly participating in a bizarre initiation ritual at Oxford University in which he placed his genitals in a dead pig’s mouth. The claim, which was unsubstantiated, quickly became the focus of tabloid headlines, leading to the “Piggate” scandal.
The story sparked fierce debates about the ethics of publishing unverified stories and whether the incident was truly in the public interest. Despite the controversy, the book’s release cemented Oakeshott’s reputation as a journalist unafraid to tackle sensitive subjects, even if it meant facing backlash.
The Lockdown Files Leak
In 2023, Oakeshott made headlines once again when she leaked over 100,000 WhatsApp messages from former Health Secretary Matt Hancock during the height of the COVID-19 pandemic. The messages were provided to Oakeshott by Hancock, who had written a memoir about his time managing the crisis. Oakeshott passed the messages to The Daily Telegraph, which published a series of articles revealing behind-the-scenes discussions of government ministers during the pandemic.
The leak caused a public uproar, with Hancock accusing Oakeshott of betrayal. However, Oakeshott defended her actions, arguing that the messages were in the public interest and that the public deserved transparency about the government’s handling of the crisis. The leak led to widespread debates about government accountability, media ethics, and the role of journalists in exposing political wrongdoing.
Isabel Oakeshott Net Worth
Estimating a public figure’s net worth can be tricky, but based on her long and successful career in journalism, authorship, and media, Oakeshott’s estimated net worth is believed to be between £1 million and £2 million. This wealth comes from her high-profile media roles, her book royalties, and income from her frequent public speaking engagements.
Oakeshott has maintained a lucrative career, particularly through her television work, book deals, and her presence at major media outlets. While her exact net worth is difficult to pinpoint, her ability to generate revenue from various sources—whether through freelance journalism, speaking engagements, or book royalties—has contributed to her significant financial success.
Isabel Oakeshott Public Speaking and Media Appearances
Beyond journalism, Oakeshott has gained recognition as a public speaker. Known for her strong opinions and insightful commentary, she is often invited to speak at conferences, corporate events, and political forums. Her speaking engagements typically focus on topics such as political analysis, the media’s role in shaping public opinion, and the ethics of journalism.
Her work as a keynote speaker has allowed her to share her views on current affairs, political leadership, and government transparency. Her speaking style is known for being direct, engaging, and accessible, making her an effective communicator for both political audiences and general public forums.
Personal Life: Family, Husband, and Relationships
Isabel Oakeshott’s personal life has also attracted public interest, particularly her relationships. She was previously married to Nigel Rosser, with whom she has three children. The couple later separated, but Oakeshott maintains a relatively private personal life.
Since 2018, Oakeshott has been in a long-term relationship with Richard Tice, a businessman and prominent political figure. Tice, who is the leader of Reform UK and a supporter of Brexit, is also involved in politics, which has made their relationship a subject of public interest.
In early 2025, Oakeshott and her family moved to Dubai, where she resides with her children. The move was reportedly motivated by changes in UK taxation laws regarding private school fees. Despite her relocation, Oakeshott continues to play a significant role in British political discourse through her media work and writing.
Isabel Oakeshott Legacy and Influence
Isabel Oakeshott’s career trajectory has positioned her as one of the most influential journalists in modern British politics. Known for her investigative zeal, bold commentary, and significant impact on public policy debates, Oakeshott has made a lasting contribution to the political landscape of the UK.
Her work continues to spark conversations about government transparency, the ethics of journalism, and the importance of holding power to account. While controversial at times, Oakeshott’s reporting and writing have undeniably shaped the way the public views politics, media, and governance in the 21st century. As she continues to rise in prominence, her legacy as a fearless journalist will likely only grow.
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