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My life at Eton under Trendy Hendy’s woke revolution

Like all my football games at Eton, Simon Henderson’s time as headmaster started off okay but rapidly went downhill. 

I joined the school as a pupil at the same time as he started as head. My early impression of him was as an unremarkable but likeable headmaster, known chiefly for once mangling an anecdote about Incy-Wincy Spider in his first assembly to the new boys.

Yet in my five years there – I left in June – he transformed Britain’s most famous and arguably most historic school into a place which reflects right-on preoccupations befitting his nickname ‘Trendy Hendy’.

He’s achieved this with an ‘Executive Leadership Team’ holed up in a hideous greenhouse of an office block, separated from the rest of the school by a locked door and a wall of silence.

We boys snickeringly referred to it as the ‘Tower of Power’ but as its ideas have taken root in every aspect of school life, it now seems a lot less funny.

Eton headmaster Simon Henderson transformed Britain’s most famous and arguably most historic school into a place which reflects right-on preoccupations befitting his nickname ‘Trendy Hendy’

I went to Eton on a scholarship. I can still remember the awe I felt seeing the chapel, strewn with vast shadows in the autumn sun; my house, in all its Victorian splendour; and fellow pupils striding about in their white tie and tails.

A boy arriving this year might have noted a member of Pop (Eton’s prefects) wearing a school-issue Black Lives Matter waistcoat – they’re a bit sinister, actually, white lettering on a black background – or wondered why the old phone box outside Eton’s Bekynton building, which was always meant to be painted Eton Blue, was also BLM black.

In fact, the phone box, which was celebrating Black History month in October, has now been painted purple, since November 18 to December 18 is Disability History Month.

(One wag wrote in Instagram: ‘Why spend £100 repainting it when you could use that money to pay for Henderson’s taxi outta here…’).

So the Eton landscape has, both literally and metaphorically, taken a turn for the bizarre.

It started at the end of my first year with the mystery departure of the senior chaplain, the Reverend Canon Keith Wilkinson.

There had been, we heard, a row between him and Eton’s provost, the former Tory Cabinet Minister Lord Waldegrave.

Hundreds of pupils gathered outside the main building – what Etonians call a ‘Leggit’ (imagine a buffalo stampede in white tie and tails) to protest to masters about the chaplain’s disappearance.

A Leggit is rare, a powerful gesture which is supposed to give boys a voice. But it was the headmaster’s response which was the most curious thing: He seemed to pretend it hadn’t happened, despite some of England’s smartest families baying for an explanation because the chaplain had been such a respected member of the school community.

Eton headmaster Simon Henderson (pictured) was accused of implementing a progressive 'woke' agenda and suppressing free speech after sacking English teacher Will Knowland

Eton headmaster Simon Henderson (pictured) was accused of implementing a progressive ‘woke’ agenda and suppressing free speech after sacking English teacher Will Knowland

In contrast, one of the teachers promoted under Mr Henderson was Hailz Osborne, head of drama, who is keen to point out that she spotted the early potential of a young Eddie Redmayne when he had a non-speaking role in a school production of The Madness Of George III.

She was chosen as the school’s new director of inclusion education, charged with appointing a committee of boys to shape school policy around issues ‘focused on, but not limited to, race, faith, sexuality, gender, disability, age and outreach’.

Hailz says her greatest achievement at Eton is how proud she is of seeing the Pride flag being flown on the official flag pole above the school’s gateway.

Interestingly, when asked about her career goals, Hailz once said she’d like to see the BLM flag flying over the college gateway, too. I’m gay and I can say with certainty that Hailz’s interventions on sexuality didn’t help me.

One of the teachers promoted under Mr Henderson was Hailz Osborne (pictured), head of drama, who is keen to point out that she spotted the early potential of a young Eddie Redmayne when he had a non-speaking role in a school production of The Madness Of George III

One of the teachers promoted under Mr Henderson was Hailz Osborne (pictured), head of drama, who is keen to point out that she spotted the early potential of a young Eddie Redmayne when he had a non-speaking role in a school production of The Madness Of George III

In my early years at Eton, being gay wasn’t a big deal. Then we became a ‘protected’ community, singled out for attention. By my final year, a kid four years younger than me was running around calling us all ‘fags’. 

Realising I was gay at the age of 12 was terrifying. It’s not that my parents are conservative – one’s a therapist and one’s a musician – but like most boys on the cusp of their teens, I felt as if the world expected me to grow up and have a wife and family one day.

That dissolved when I went to Eton. I found the boys in my year were more open and more liberal than I could ever have expected. I never heard them say anything homophobic in my presence.

This gave me the courage to be honest about my sexuality and by the end of my first year, aged 14, I was ready to come out.

However, by then the headmaster’s progressive policies were embedding themselves in the school. 

As this culture consolidated, with the notion of ‘protected groups’, gay people at Eton became seen not as individuals who happened to be gay, but as part of a monolithic community with the same aims, the same politics and the same beliefs.

It was as if people in general are defined by who they choose to sleep with. Being brilliant at rugby, or music, or debating, or computer coding all seemed to take second place to this ‘protected’ characteristic.

As a result of this shift, and a sense of being labelled or categorised, I no longer felt able to come out, and ultimately I spent another miserable year and a half in the closet. When I eventually plucked up the courage to tell my family and friends, it all happened in the space of a week.

I still wonder today, now I’m 18, how it would have been if I’d been able to do it more organically, over time.

I can’t fault the headmaster’s intentions. He wanted to make gay pupils and staff at Eton feel included in a diverse community.

For me, though, it had the opposite effect. I was worried I’d be isolated from the boys in my year, ostracised for being a member of a ‘protected group’.

Sadly, those fears were realised and it was only through intense personal effort that I felt I could be seen as someone in my own right, rather than as a ‘gay person’.

I’m now at university and happy in a long-term relationship, but I worry about other boys currently at Eton who might be facing the same paradox as me.

I’d say it was during the first coronavirus lockdown, my last term, that the great ‘awokening’ of Eton became public knowledge. It had been embedding itself in the school’s curriculum and policies since Simon Henderson’s arrival, but suddenly it was manifest beyond the school walls.

A video released to celebrate Pride in June included a short clip of the incoming prefects being forced to say: ‘I Support Pride.’ Then they wore Black Lives Matter waistcoats, followed by the saga of the painted phone box. Now, there’s the fallout from the freedom of speech row over a lecture by English teacher Will Knowland and his sacking.

Knowland, who taught me and is a brilliant and popular teacher, posted a controversial lecture online about gender differences and the patriarchy on a school platform. Somebody complained.

He duly deleted it from the course for which it was intended but wouldn’t remove it from his personal YouTube channel.

He got fired.

Now there’s a petition of 2,600 names, many of them Eton pupils, asking for his reinstatement, and £55,000 has been donated to help with his legal fees, should his appeal against dismissal fail on Tuesday.

It has caused a public furore for a fortnight because one of the things Eton has always been famous for is the quality of its debates, of the opinions aired in its chamber and points of view fought over.

Like it or not, it’s an important school with almost 600 years of history.

As someone wisely said last week, Eton is ‘meant to be a bastion of learning and free speech – not a place for cult groupthink’. They added: ‘George Orwell went to Eton. What would he think? 1984 was meant to be satire, not a how-to manual.’

Dozens of our Prime Ministers have been educated there, so were Princes William and Harry. Its alumni usually succeed, regardless of their chosen field.

‘Trendy Hendy’ has undoubtedly made some valuable changes. The expanded scholarship programme will help bright boys from less well-off backgrounds secure a place at Eton and enjoy the outrageously good facilities and generous privileges which come with it.

But what I fear the headmaster is going to be remembered for is capitulating to the plagues of liberal society in 2020 where intolerance is dressed up as tolerance, bullying is cloaked by moral self-righteousness and there’s a less-than-critical acceptance of the doctrines of radical political movements.

If it is to flourish, as its motto Floreat Etona commands, Eton doesn’t need human resources consultants, or an army of middle-managers, or an ‘awokening’.

All it needs is to extract the genuinely good points from the progressive causes it supports while discarding the politics which have captured them.

It should commit itself to teaching its pupils to respect people’s individuality, engage with difference and disagreement, and keep in the back of their minds the good, old-fashioned ideal of common sense.

Painting that phone box Eton blue would be nice, too.


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