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If you read Boris' famous school report they knew back then what a shit he was and I doubt that view has changed.
I think @christianSpaceman has in mind the culture of privilege and entitlement that the school fosters generally. That headmaster may have seen Johnson for the shit he is, but he probably didn't see how the school's culture made him (and Cameron and the rest) even worse.
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I don't feel like there are that many parallels between Johnson and Cameron despite their very similar backgrounds. Cameron quite bright but lazy / dropout, Johnson thick but carried by a flashy way with words?
I don't remember quite such contempt of standards in public life from Cameron and you got the sense that there was some kind of consistent ideology running through what he and Gideon were trying to do (like their idol Thatcher). Johnson appears to lurch from crisis to crisis with whatever sticking plaster stupid fucking policy he can think of.
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Yes, I suppose I'm curious about how comfortable they feel about their association with this particular generation of students.
The Head's a good example - the 2010-20's are an era of Etonian prime ministers, does he feel Johnson is a reflection on his leadership at all? Do the PPE-type subject teachers recognise the influence they've had on current events? Is the economics teacher happy about having taught those responsible for such economicaly illiterate policies?
There's presumably some professional pride for teachers at having a past student achieve any degree of greatness (right word?). I wonder how they celebrate this cohort.
If you read Boris' famous school report they knew back then what a shit he was and I doubt that view has changed.