This article is taken from the October 2023 issue of The Critic. To get the full magazine why not subscribe? Right now we’re offering five issues for just £10.

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I have followed the progress of Sunak from constituency MP to PM over the past decade with personal as well as professional interest. We were, after all, at school together, albeit in different houses and in different years; he was at Bramston’s, known informally as Trant’s, from 1993 to 1998, and I served my time in Kingsgate House (Beloe’s) from 1994 to 1999. 

Yet I came to know Sunak a little through my classmate James Forsyth, one-time Spectator political editor, Sunak’s closest friend in and out of politics and now his senior political aide at Downing Street. I have been asked many, many times what the man once known as “Dishy Rishi” was like at school, and my stock answer, alas, is a disappointing one. “Utterly charming, very likeable, and that very rare thing at Winchester — a man apparently without enemies.” People then slope off, disappointed, asking darkly if I’ve been nobbled by the higher echelons of the Conservative party. 

No money, or similar favours, has ever changed hands. I liked Sunak, as far as I knew him — which was not very well at all — but he was not someone who I ever expected to reappear in my, or the nation’s, consciousness. 

Yet looking at his rise to prominence and premiership, there are certain traits and patterns of behaviour that seem inimitably Wykehamist, and make me believe that, for all of his much-ballyhooed love of trash culture (Riders and Emily in Paris) and the like, the lessons and traditions of his alma mater have stuck just as fiercely to him as they have to many of its alumni; provided, of course, that they have not entirely abandoned the school’s teachings and now insist that they attended the local comprehensive. 

When I look back on my time at Winchester, at the tail end of the twentieth century, it seems astonishing that a public school could get away with actions that now seem reprehensible and bewildering. When I was a pupil there, displays of eccentricity — mainly, but not exclusively, by the teaching staff — were talked about with amusement, sometimes leavened by incredulity, but never with any serious anguish. 

Yet after I left, the real world collided with this eccentricity, with predictable results. One history teacher and housemaster, whose behaviour was regarded as beyond the pale even by Wykehamist standards — he was said to join the boys in the showers, in an “all lads together” spirit — was eventually put on trial on charges of cruelty to children. The case was dismissed when the prosecution failed to offer evidence, but he was then sacked after another allegation of assault came to light; he stamped on a boy’s foot during a lesson, and was thrown out by a no doubt relieved school. 

The incident was serious, but compared to what occurred during the time that Sunak and I studied there, it would almost have been run-of-the-mill, something discussed in whispered tones as we walked between our boarding houses and the main teaching area — a red-brick, Butterfield-designed Victorian assembly of classrooms known as Flint Court — but little more than that. 

The teachers at Winchester when I was there were a strange mixture of former Oxbridge dons, keen to take on roles with greater pay, less academic responsibility and, in many cases, a sumptuous Georgian house provided for their accommodation, and eccentrics who seemed to have chanced into pedagogy almost on a whim; imagine Hector from Alan Bennett’s The History Boys, remove the most obviously pederastic tendencies, and multiply him by a few dozen, and you have the teaching staff of one of the country’s most prestigious (and expensive) schools. 

That winchester maintained one of the most enviable academic records of any educational institution in the country, routinely sending between a third and half of its sixth form — including Sunak —to Oxbridge lies in several factors. Firstly, its admissions process is tough; it has its own entrance exam, considerably harder than the Common Entrance process used by most independent schools, and only admits those who score highly. 

It’s also ruthless about dispatching underperforming pupils, many of whom left the school during my time. As someone who did poorly in his GCSEs, especially in the sciences, I expected the hand on my shoulder and the figurative P45 from my housemaster; but thankfully the school was sufficiently enlightened to believe that I would eventually come good during my A-levels, with intensive, near-Oxbridge level tuition in small groups, and so it proved. And secondly, many of the teachers were brilliantly able men (and, occasionally, women) who maintained an air of other-wordliness as a façade. Strip away the jokes and irony that they majored in, and you had keen, engaged people who would rise to the occasion, so long as you didn’t bore them.

We called the teachers “dons”, one of the school’s many linguistic affectations, known as “notions” — there were so many that there was an entire book dedicated to them — and they would often play up to self-created roles. 

One man, Cattermole, was a stern disciplinarian and would take especial delight in trying to find schoolboys in the pub on a Saturday evening; an offence that would usually be punished by “gating”, or being confined to the boarding house for a while. He rode a black bicycle known as the “Catterbike” and was fond of offering miscreants apparently impossible choices, such as telling one unfortunate drinker that, if the boy could return to his house before the advent of the Catterbike, he would go unpunished. The enterprising pupil, seeing Cattermole’s vehicle of doom outside the pub, simply punctured its tyres and thus continued a leisurely progress back to the boarding house. The teacher was, by all accounts, amused rather than infuriated by this display of nous. 

It is often noted of sunak that he regards himself as the cleverest person in the room, and that he becomes exasperated or weary when he is faced with a line of questioning that he finds intellectually frustrating or facile. This, undeniably, remains a Wykehamist trait, established in the classroom and passed on to pupils. Boys were not taught to be authoritative about a few major issues, but to have a wide range of opinions about a huge number of subjects, learning worn lightly, even superficially, but nonetheless impressive at first glance. 

It worked beautifully for later life, whether for Oxbridge entrance or for entrancing dinner party conversation, but what it did not do was to instil rigorous learning in its “men”, as we were called. Like Bunthorne in Gilbert and Sullivan’s aesthetic parody Patience, I can “discourse in novel phrases/Of a complicated state of mind”, and hope that those around me will gasp “If this young man expresses himself in terms too deep for me/Why, what a very singularly deep young man this deep young man must be!” 

… high office has exposed both his tetchiness at being questioned on matters he may not be as informed about as he might wish

It is clear that Sunak has a similar outlook, and alas high office has exposed both his tetchiness at being questioned on matters he may not be as informed about as he might wish — a tendency he shares with his predecessor but one as PM — and a worrying lack of depth to many of his statements. 

There were genuinely brilliant, simpatico and witty boys around me, especially in the scholars’ house, College, but the house structure often discouraged friendships and most of my peers were (to, I believe, their lasting credit) fundamentally un-Wykehamist in that they refused to buy into the school’s ethos of conspicuous intellectual achievement, accomplished languidly with one eyebrow raised, before heading off to see Parsifal or King Lear or some other work of the Western canon. 

It is one of the few schools that had an unexamined daily class, “division” or “div”, where boys were taught whatever their teacher was interested in. For one year, I studied Schopenhauer, George Formby and the Russian revolution, more or less in tandem. I don’t remember much about Schopenhauer or revolutionary politics, but I still know an awful lot about Formby. 

Sunak remains a loyal Old Wykehamist (or “OW” as we are known), giving large sums of money to his former school and speaking highly of it in interviews. It’s changed a great deal since our day, going co-educational and now appointing its first headmistress (or “Head Man” as she must be known, in the school’s parlance). It is less mad, less inimitable and altogether more conventional. From a perspective of simple sanity — and educational rigour — this is to be encouraged. Yet I cannot help thinking that the grounding that it gave the Prime Minister, and me, quixotic though it may have been, is unlikely to be passed onto another generation. 

Did I enjoy my time at Winchester? I’ve been asked that many times and the answer I always give is “I don’t know,” a typical get-out that the school would have been annoyed by. But for better or for worse, Sunak and I were both there at a fin de siècle period. We shall not see its like again, and perhaps that is a loss.