The Rory Stewart I knew: why it was inevitable he’d be knocked out of the Tory leadership contest

Rory StewartI’ve been following the Conservative leadership race with uncommon interest: I knew Rory Stewart quite well about 25 years ago. We were students a year apart at Balliol College, Oxford, in the early 1990s, and though we moved in different circles and were never friends, his idiosyncratic social status as a student may provide clues about why he has been knocked out of the contest rather earlier than his supporters were hoping.

Rory Stewart was not the only Balliol graduate in the running to become Prime Minister of course: the front-runner Boris Johnson also studied at the college, several years before Stewart (or I) arrived there. But whereas Johnson trod the familiar path of the Oxford Union and the University’s Conservative Association on his long march towards elected office, Stewart shunned them both: he was in fact a member of the Labour Party (albeit an inactive one as far as I know).

Both Johnson and Stewart were also, of course, educated at Eton. A lot of nonsense has been written about Balliol in the last few weeks, mentioning it in the same breath as Eton. Although in the 1990s the majority of its students were public school, Balliol is a very different sort of place. Although Balliol has produced many senior Tories – Macmillan and Heath, as well as Boris – it was by the 1990s an almost painfully left-wing place, much prouder of its Labour products – Denis Healey and Roy Jenkins – and the journalist Christopher Hitchens, then at his irreverent peak. Although there was much snobbery at Balliol, almost all of it was of the intellectual kind, and most public schoolboys deliberately played down their social graces (one Wykehamist I knew spent most of his first year wearing a football shirt).

The most prominent clique at Balliol in Stewart’s day was the Left Caucus, a mixture of state school and public school lefties, who vied with each other to be the most right-on. A Left Caucus slate usually dominated Balliol’s Junior Common Room committee, which held much more power than most colleges’ (Balliol’s main bar was, and still is, student-run, and the JCR also ran its own cafeteria, the Pantry, competing with the college’s formal Hall). When I arrived at Balliol the JCR had just introduced the “Tampax tax”, a levy on all students to fund the bulk purchase of sanitary products to end the discrimination against menstruating women. Although it was theoretically possible for male students to opt out of paying the levy, the few who did so were subjected to derision and ridicule. I am sure Stewart was not among them.

Public schoolboys who wanted to lead a Brideshead Revisited existence were in evidence of course, but they frequented the Buttery, Balliol’s college-run bar, which was only open in the early evenings before dinner. Although Stewart was definitely not a part of the Left Caucus, he wasn’t one of the so-called ‘Buttery Boys’ either. In our time the college’s only exclusive dining society, the white-tie-and-tails Annandale, was effectively driven underground, its antics no longer reported in the college’s Annual Record on account of its invitation-only status.

I honestly can’t remember whether Stewart was ever a member of the Annandale, but I suspect he wasn’t: flaunting himself was never his style. Nor was he a habitué of the Bullingdon Club,  a similar Oxford dining society which both Johnson and David Cameron notoriously belonged to. “I definitely don’t like people who are sort of aggressively posh… I don’t like that look,” Stewart told the New Yorker’s Ian Parker shortly after his election to parliament in 2010. He added that he did consider joining the Bullingdon, but changed his mind after only one dinner: “I didn’t want to be part of it, as soon as I saw it up close.”

Nor was Stewart a member of Balliol’s other dining club, the subversive Academics (which I presided over for a couple of terms). The Academics was a debating society that claimed to be the most egalitarian. Membership was open to everyone, and the dress code was sub fusc: white tie and black suits, and commoner gowns – the formal wear that everyone was obliged to wear for exams, thereby presenting no financial hurdles to those attending, most of them Left Caucus types with their tongues firmly in their cheeks. Describing a white-tie dining society as “egalitarian” because it does not expect its members to shell out on tails may seem perverse, but Balliol’s that sort of place.

But Stewart was the president of the Arnold & Brackenbury, a Balliol debating society which only served copious amounts of alcohol, not dinners, at its evening meetings. Debauched it wasn’t: if anything its debates on motions like ‘This House would rather be Ancient rather than Middle-Aged’, proposed by hoary old dons and seconded by undergraduates, were, with hindsight, contrived and rather boring. Stewart was once very charitable to me when I made an awful speech at one of its debates, which had done nothing to raise the boredom threshold.

I’ve written before about how I didn’t particularly enjoy my time at Balliol, academically at least. Maybe Stewart didn’t either: he studied Modern History for his first year, before switching to Philosophy, Politics and Economics, the usual course studied by aspiring politicians. But while it is no surprise that he went on to become a successful diplomat and author, few would have expected him to become an MP, yet alone been a serious contender for the Conservative leadership while still in his mid-40s. He was a real one-off, who couldn’t be pigeon-holed, either socially or politically.

I can’t claim to have ever known Stewart very well, and aside from a brief conversation in Parliament in the early 2010s, I have not met him for the last 20 years. We only had two real mutual friends when were students. The first was Harriet Jaine, now a BBC producer, who read English in my year and dated Felix Martin (a good friend of Stewart’s who is now a macro-economist and fund manager, and author of the 2013 book  Money: the Unauthorised Biography). The second was Palash Davé, a student at next-door St John’s College, who was close to many Balliol lefties. Like Stewart, Palash had gone to Eton, but as the British-Indian son of a south London doctor he was hardly a typical Etonian. And apart from Palash I don’t recall Stewart ever spending much time with old Etonians at Oxford, most of whom were arrogant bores.

The two are obviously still close: at Stewart’s 400-strong rally on the South Bank last week, he called a question from Palash, who has now been described on Twitter as a “Corbynite Marxist”, who pointed out that Stewart had defended him from racism at Eton. I can’t think of any other Tory candidate able to plant such a question.


Stewart was already rather famous by the time I first met him in 1993, having spent a summer vacation acting as a sort of tutor come role-model to princes Harry and William, who were still not yet in their teens. He already had a Lawrence of Arabia aura: during his gap year in 1991, he had completed a short service limited commission as a second lieutenant in the Black Watch, and he had an agelessness and unworldliness about him. He was neither a party animal nor a show-off.

Everyone seemed to think Stewart was the son of a Scottish laird who owned much of the Highlands. Then as now, the reality was just as intriguing as the myth. In fact Stewart is not an aristocrat: his grandfather Redvers Buller Stewart was a Calcutta jute merchant, but his father Brian Stewart was the assistant head of MI6. Although Stewart was of relatively humble origins in financial terms, he was always a citizen of the world, born in Hong Kong, and he spent much of his childhood in Malaysia, where his father ran the Rubber Growers Association, having failed to get the top job at MI6 and retired.

But it is really what Stewart did after leaving Balliol that makes him so fascinating. After graduating he joined the Foreign Office, which in those days seemed to only recruit people just like Rory Stewart: of all the people I knew at Oxford who went on to the Foreign Office, all were public schoolboys. Doubtless they all turned out to be skilled diplomats, but Stewart’s ascent through the ranks was swifter than anyone else’s and cannot be put down to the Old Boy’s network. Early on he worked at the British embassy in Indonesia at an auspicious time – the run-up to the referendum on East Timorese independence – before being appointed, aged only 26, as the British Representative to Montenegro in the wake of the Kosovo campaign. He then spent two years walking across central Asia, arriving in Afghanistan shortly after the Twin Towers fell. At about this time, many have claimed, he joined MI6 just as his father had (though he may have joined much earlier: the late Maurice Keen, a Balliol history fellow, was known to be an MI6 recruiter).

After the 2003 invasion of Iraq Stewart became the Coalition Provisional Authority governor of two provinces in southern Iraq – overseeing elections development projects, resolving tribal disputes, and once having his compound besieged by Sadrist militia – for which he was later awarded an OBE. In late 2004, Stewart became a fellow at the Carr Center for Human Rights Policy at Harvard University’s John F. Kennedy School of Government, and in July 2008, he was appointed as a Harvard professor and made director of the Carr Center, positions he held until his election as MP for Penrith and the Border in 2010. In the meantime, in 2005 he had joined the Turquoise Mountain Foundation, an NGO in Afghanistan established by the Prince of Wales and Hamid Karzai, rising to become its executive chairman.

It is an extraordinary CV, unlike that of any other 21st-century politician, most of whom have had dull jobs as lawyers, political aides or management consultants. Anyone doubting his intellectual rigour should read any of his three books – Can Intervention Work?, Occupational Hazards or The Places in Between (the award-winning account of his Asian walk) – and reconsider. Indeed, his backstory is so fascinating and Byzantine that quite a few profiles don’t even mention that he went to Eton or Balliol: if anything, where he went to school and university are the least interesting things about him. Although he has led a life of extraordinary privilege, he has also courted physical danger and has an intimate knowledge of those dealt a less favourable hand in life: a little-known fact is that his younger sister Fiona has Down’s Syndrome.

As soon as he entered parliament in 2010, Stewart was tipped for high office, and even for the premiership. In 2014 he became chair of the Defence Select Committee, and after the 2015 election he quickly started ascending the ministerial ladder, helped by a fair bit of luck – his stint as an environment minister coincided with widespread flooding over the winter of 2015-16 – and rare candour: as prisons minister in 2018 he vowed to resign if violence in jails was not reduced soon. But he was not around long enough to find out if he had to: in May 2019 he was promoted to the cabinet as International Development Secretary, in the reshuffle that followed Gavin Williamson’s sacking.

As soon as he launched his presumptuous leadership bid a month later he was feted by the media. Here was a youngish, fresh face – apart from the fact that his hair has recently become a lot neater, he looks exactly the same as the gawky student I first met more than 25 years ago – ready to speak truth to the nation, about the difficulties of Brexit and the lack of headroom for tax cuts. His campaign videos and un-stage managed walkabouts – talking to imams, walking across the Northern Irish border, and being thrown out of Hampstead Heath – immediately acquired cult status.

Why then did he fail to reach the final two? It certainly isn’t inverted snobbery against a second Etonian (Jeremy Hunt was head boy at Charterhouse and, as the son of an Admiral who rose to be Commander-in-Chief of the Royal Navy fleet, is if anything from a more privileged background). Stewart is wrong to state, as many of Boris’s backers have, that his Etonian schooling has been a handicap to overcome. Of course, even the possibility of an all-Eton, all-Balliol, duo in the final ballot of Conservative members says much about Britain’s entrenched privilege and lack of social mobility.

The real reason why his star has not risen any further – for now at least – is his refusal to be pigeon-holed, and his reluctance to join cliques. Although the Rory Stewart I knew 25 years ago was, and arguably still is, an Etonian dandy, he was also a thoughtful guy capable of great kindness: he once invited a good friend to stay (platonically) in his rooms for several weeks while going through a personal crisis. He didn’t just mix with Balliol’s public school types, and had a small but ecumenical range of friends. Although he is now fabled for his networking, charm and confidence, he was never an extrovert, and he was, if anything, rather shy.

If I was a Conservative member, and if Stewart had made it through to the final two candidates, I would vote for him without hesitation. But I am not, and he hasn’t: most Tory members, unlike me, are died-in-the-wool Leavers, socially conservative and insular. Stewart’s compulsive honesty, distaste for tax cuts, and refusal to countenance a no-deal Brexit meant it was always very unlikely he would become Britain’s next Prime Minister. The real surprise is not that he was knocked out in Round Three, but that he had made it to Round One.

He was really campaigning in the nation, not among the tiny pool of Tory members, and the even tinier pool of Tory MPs, who had votes. A more orthodox, and ambitious, Conservative would have pitched rightwards for now, stressing his foreign and military experience, and only pitched leftwards once he had secured the leadership.

But Stewart has succeeded in widening the Overton Window of what modern conservatism means. In the wake of his ejection from the leadership contest, he’s already calling for centrists to join the Tory party en masse and help make it more electable – and, no doubt, more likely to elect someone like him as its leader. Someone who has spent most of his career outside politics is just what political parties now need. I wrote a few years ago that ‘the age of Balliol superiority is now over’, but now realise I was wrong: if Boris Johnson becomes Prime Minister and then has to bow out in disgrace, as many expect, Rory Stewart could well succeed him.

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9 Responses to The Rory Stewart I knew: why it was inevitable he’d be knocked out of the Tory leadership contest

  1. Tricia says:

    Yes ! I am a devoted Stewart fan but just wish he (and you) would follow Chuka into the LibDems and forge a new alternative party quickly ! We owe it to our children and grandchildren to ditch the manifestly useless and self serving “main” parties ASAP.

  2. Julian says:

    Timely – Simon Kuper wrote a piece in the FT today around his experience of being in Oxford around the same time as Johnson, Reece-Mogg and others. Provides some food for thought into how and why the UK is where it is today.

  3. pacelli58 says:

    Really interesting post Alex, thank you. Pat

    Sent from my iPhone


  4. Marc says:

    Mark Field would get my vote. Reading GS & St Edmunds Hall!

  5. yasminjananjum says:

    Dear Alex

    I found your article on Rory Stewart just a few hours ago.

    There is something wonderfully different about him.

    What do you think of him running as an independent candidate for Mayor of London and the way he’s canvassing & gathering information in order to make a manifesto for his campaign.


    • Alex Grant says:

      I still rate Rory highly, and while his pragmatic approach to Brexit was close to mine, I fear he is not “Remain” enough for London voters (of which I am no longer one): I think that even though Brexit is done, it will still be a key factor in the 2020 race. Sadiq Khan has many weaknesses as mayor, and Shaun Bailey is a very poor candidate, but I fear that Rory’s bid is probably doomed, as he simply does not have enough name recognition, or a close enough association to London, to cut through as an independent as Ken Livingstone did in 2000. He may well come third ahead of Siobhan Benita, but she is among the most plausible of candidates so he may come fourth or even fifth. London will always be a Labour city for the foreseeable future, as Johnson is a less metropolitan PM than he was London mayor – and it was Ken that really lost in 2008 and 2012, not Boris who won, in my view. Sadiq is competent enough to win by a wide margin.

      • yasminjananjum says:


        Sorry Alex, I didn’t realise til someone showed me today, nearly a year later, that you’d replied. Thank you.

        Alot has happened since then though

        Rory has pulled out of the Mayoral race in London when he couldn’t sustain his independent campaign due to Covid.

        He’s been teaching at Yale University since end of last August ( 2020 ). Amongst other things he’s teaching Politics


  6. Cricket Kemp says:

    More information about this wonderfully different gentleman. Very sad that we have lost him from Cumbria for now.

    • Alex Grant says:

      When you say “for now” does that mean that you think he plans to return to Cumbrian politics after his (probably doomed) London mayoral bid?

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