‘Out with old, in with the new’ - how Eton’s ‘woke’ headmaster is challenging elitism

Simon Henderson is tasked with bringing Eton College into the modern day - but is he too woke?

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In 2015, Simon Henderson became the youngest ever headmaster of Eton College at the age of 39. The job comes with the task of bringing the 600-year-old institution into the modern day but Etonion detractors complain he’s turned the school ‘woke’. Mr Henderson doesn’t mind being called woke. In fact, he says he’s ‘guilty as charged’. But the Winchester and Oxford-educated teacher does want to challenge the political climate which, he says, is reducing people to “polarised, binary positions’.

Modernising an institution takes collaboration. All hands steering the wheel and an open door for fellow commuters along the way. Eton College wasn’t designed with this in mind but it’s certainly a logical step the fee-paying, public school needs to take. Henderson wants to lead with ‘kindness, understanding, respect, tolerance, decency, and empathy’. But is the culture for turning?

In 2021, a recent graduate of Eton College criticised the headmaster for sacking English teacher Will Knowland, after he refused to take down a controversial lecture on patriarchy from his YouTube account. Francis Emerson, now studying at Oxford, wrote in the Critic Magazine that Mr Henderson had behaved like ‘a petty tyrant’ and was transforming the school into a place of ‘ideological homogeneity’. The graduate also claimed pupils were asked to consider taking part in a “protected” ‘gay and transgender day’.

Speaking to the Big Fish podcast, Mr Henderson denied using any form of ‘ideological framework’ to educate the students but supports the idea of celebrating events such as Pride and Black Lives Matter. “Why wouldn’t we celebrate the experience of significant groups within our community, some of whom have perhaps been marginalised over time,” he said. “Those are things we’re proud to do and I think part of being a modern institution.”

In 2015, Simon Henderson became the youngest ever headmaster of Eton College at the age of 39In 2015, Simon Henderson became the youngest ever headmaster of Eton College at the age of 39
In 2015, Simon Henderson became the youngest ever headmaster of Eton College at the age of 39

Eton College is frequently criticised for perpetuating elitism, engendered by an ability to churn students set to one day enter the chamber. After the 2019 general election, almost half the Conservative Party consisted of MPs from fee-paying schools with etonians such as Boris Johnson, Jacob Rees-Mogg and Kwasi Kwarteng holding major positions in cabinet.

The school has a long-established affiliation with Conservatism and Classical Liberalism but the culture is shifting, and values now associated with the Conservative Party show little sign of collaboration. Four years on from the general election and a roll call of departures (Philip Hammond, Nicky Morgan, Rory Stewart, Ken Clarke, and more) later, the party’s centre has been pitted out. A space which emerging students could soon rediscover.

Tweaks to education over the years have demonstrated sizable changes to the political landscape. ‘Widening participation’ and ‘fair access’ were key principles for Tony Blair when he introduced the Higher Education Act in 2004. This meant people from working-class and ethnic-minority backgrounds - who disproportionately voted Labour in the 1997 election - finally had an institutionally supported pathway into politics. Likewise, the voices represented in top UK universities widened and the culture of elitism continued to shrink.

As for the state of affairs at Eton College, it will be fascinating to see how future Etonians look back on their time under the guise of Simon Henderson. Eton’s recent inspection report said pupils are ‘outstandingly socially aware’ and show a ‘greater respect for others, regardless of background, culture, tradition or sexual orientation.’ Whether it’s all a strategy to silence the radicals or not, Mr Henderson could play a genuine role in contributing to a Parliament to be proud of.