As I write, the field of candidates is being whittled down. It is Rishi Sunak’s contest to lose, and the best-placed “Stop Rishi” candidates, according to Westminster consensus, are Penny Mordaunt and Liz Truss. Tugendhat and Kemi Badenoch have caught much attention, but they are unlikely to make it the final run-off. Nor are Zahawi, Hunt, or Braverman. Although the momentum today seems to be with Mordaunt, after a slick campaign launch this morning, it could well be Truss and Sunak on the ballot paper that goes out to Conservative party members. An MP since 2010 – five years before Sunak arrived in parliament – Truss has been courting party members up and down Britain for more than a decade. Many expect she may become Britain’s next Prime Minister.

Can she be defeated at the next general election? Most definitely she can. I should know: I have defeated her twice in elections for public office. Long before she became an MP, Truss and I stood against each other at council elections in the London Borough of Greenwich (in the safeish Labour Vanbrugh ward in 1998, and in the ultra-marginal Blackheath Westcombe ward in 2002).

On both occasions I was elected, and Liz Truss wasn’t. I won 500 more votes than Truss at our first encounter in May 1998, and 400 more votes than her in 2002. I became a Labour councillor in Greenwich, serving for 16 years until I stepped down in 2014, and Truss didn’t join me in the council chamber until 2006. I am now a freelance writer, living happily well away from Greenwich, and Westminster, while Liz Truss is foreign secretary, and may be about to become our prime minister.

The head start I had over Truss clearly gave me no advantage. Being a councillor in Greenwich turned out to be the peak of my political career: for Truss it was merely a stepping-stone to selection in a safe parliamentary seat (South-West Norfolk), and then ministerial office. But what does Truss’s time in Greenwich tell us about her, and her strengths and weaknesses as a politician? Much has been said about Truss’s early years as a young Lib Dem activist in the 1990s, and about her career in Westminster from 2010 onwards. Much less has been said about the intervening years, in which she lived in Greenwich and stood for election there three times.

Liz Truss and I had a lot in common when we first encountered each other in 1998. Both of us were Oxford graduates in our early twenties (Truss, then in the Lib Dems, had been in the same year as me at Oxford in the mid-1990s, though our paths had never crossed). Both of us had been born in the mid-1970s the children of liberal parents who worked in education, and we were now running for election for the first time in the same council ward.

But there the similarities ended. My candidacy in Blackheath was almost dynastic; my parents had moved there in 1980, when I was only six, and aside from three years away at university I had lived there ever since. I was encouraged to stand by many locals, and was advantaged by the fact that my family was deeply embedded in SE3 (my father, then a supporter of the ascendant SDP, had nearly stood for election to Greenwich Council himself in the 1980s).

Liz Truss was very different: born in Oxford but brought up in Scotland and then Leeds, she had no roots in Greenwich and was just passing through. There is nothing wrong with that, but if you are standing in a winnable ward it normally pays to attempt to win it.

The intriguing thing about Truss is how little I remember about her, compared to the many rivals I stood against as a councillor in SE3. Remarkably for someone who is now standing for party leadership, she did not seem to really want to be elected. Greenwich has never been easy territory for Conservatives, and 20 years ago they often made extravagant gestures to get elected: two of them would get themselves photographed dredging a pond a few months before local elections, to highlight the Labour council’s neglect. With no social media in 1998, local elections were won or lost on the doorstep, but Liz Truss never put her waders on.

Labour councillors had been elected in the previously Tory Vanbrugh ward since 1986, but never with huge majorities. There was a possibility that, with both Labour incumbents standing down, the Tories could regain it. One of Vanbrugh’s Tory candidates in 1998 was a youngish man called Douglas Ellison, who worked in the City, had previously stood for the Referendum Party, and looked like he should be wearing a straw boater. Others saw Douglas as the local Labour party’s irritant-in-chief, but I always had a sneaking admiration for his energy and chutzpah. With the Internet in its infancy, Ellison once produced several risographed issues of Greenwich Watch, a thinly-disguised Conservative newsletter, and made a fuss when the council refused to allow it to be made available in its libraries. At a hustings meeting, on an estate at which the council had recently closed down an under-used communal laundry, Douglas came armed with quotations with Rumbelows, arguing that the council could easily reopen the laundry with cheaper machines (he failed to point out, of course, that machines for communal use need to be much hardier than what Rumbelows had to offer, and that most residents had their own washing machines by the late 1990s).

I don’t recall Liz Truss turning up to that hustings, or having any hand in Greenwich Watch. All I remember of Truss in the 1998 election is photographs of her, alongside Douglas, in the Tories’ local newsletter, Vanbrugh Voice. Truss gesticulated by a road sign, promising to “spend money on vital services, instead of bureaucracy” and “stop the transport nightmare”. But I don’t think I ever met her until the count.

Douglas Ellison gave Labour a fright, coming within 360 votes of victory in Vanbrugh, but his campaign was a one-man band. Truss had made no impression at all. Somehow I got almost double the votes that she did.

Four years later I found that Truss and I were both standing in Blackheath Westcombe (a new three-member ward, created by boundary changes, which swallowed up Vanbrugh with lots of Tory voters thrown in). Here was an opportunity for the Conservatives to make advances: the new ward turned out to be the most marginal in London (from 2002 to 2022 it always had a mixture of Labour and Conservative councillors).

Truss (billed as a “Conservative local government spokesman”) was nominally editor of SE3, the Tories’ renamed newsletter (risographed in black and white on flimsy A4 paper). SE3 carried smudged photos of Truss posing by bottle banks, looking disapprovingly at brick walls covered with graffiti, or lurking outside the Royal Standard, the ward’s only pub. Her Pooterish biography revealed that she “works for a major telecoms company, negotiating contracts”, has “been active in local affairs for many years”, and “plays tennis in Blackheath and is a DIY enthusiast”. But again, Truss was largely invisible during the campaign. In the end, it was a photo finish in 2002 and I was elected alongside another Labour councillor and a single Tory, who wasn’t Liz Truss.

I can remember going for a conciliatory drink soon after the election with the victorious Tory, a cantankerous accountant called Rhodri Harris. When I asked after his running-mate Geoffrey Brighty, an incumbent Tory councillor who had been defeated, Harris reacted angrily, accused me of gloating, and suggested that Labour had committed some kind of crime by defeating him (the hard-working Brighty was elected four years later, and was a Blackheath Westcombe councillor for 16 years until May 2022, when Labour finally won all three of the ward’s seats). I don’t recall there being any mention of the other Tory candidate who’d lost, Liz Truss. She seemed to have been quickly forgotten about.

I was later told that Truss and Harris had fallen out during the 2002 campaign, and she had consequently done little work to get him, or herself, elected. This was endearing because no one found Harris easy to get on with. But all in all it was an odd start to Truss’s political career: do little work in a potentially marginal ward, and then even less work in a hyper-marginal four years later. You’d have thought Truss would have wanted to burnish her CV by either beating Labour, or at least being seen to work hard and come close. Sometimes you meet young politicians and immediately sense that they’re destined for great things. Truss was not one of them.

The 2006 election campaign in Blackheath Westcombe was a much more fascinating, and bitter, contest than four years before. The cantankerous Harris stood down, and the Tory candidates were Brighty and two newcomers, Alex Wilson and Peter Whittle. Labour gave Whittle, a neo-con journalist, some schtick for having written a piece in the Sunday Times entitled “How my Neighbourhood was lost to the multi-culture”, which described parts of Greenwich as “carved up by immigrant groups”. When Labour called out this nonsense, Whittle threatened to serve us with a libel writ. One Labour leaflet was withdrawn, but no apology was made. On polling day I survived, outpolling Whittle by more than 100 votes, but the Tories won the other two seats. The Conservatives cried foul afterwards, but did not challenge the election results in the courts. They went through the motions of demanding my resignation for allegedly slandering the hapless Whittle, but they soon became embarrassed by him when he defected to UKIP (he stood as UKIP’s mayoral candidate in 2016 and served on the London Assembly, firstly for UKIP and later as a sort of independent culture warrior, until 2021).

Where was Liz Truss in 2006, as a heated culture war broke out in her former stamping ground in Blackheath? Just as Blackheath Westcombe politics got really interesting, she was nowhere to be seen in SE3: she was busy getting herself elected in Eltham South ward, two miles away. To be fair to Truss, it was not a safe Tory ward then: in 2002 a Lib Dem councillor and two Tories had been elected, and at the 2006 election it returned three Tories, including Truss, by very slim majorities (you can find the results here). But I sensed that Truss (who lived in Greenwich proper, much closer to Blackheath than to Eltham) felt more at home in a leafier suburb, not the more mixed, and unpredictable, streets of Blackheath Westcombe.

She wisely stayed silent about the Whittle affair after the 2006 election. In fact, she made very little impression at all. I have no memory of any maiden speech, any hard-fought campaigns to expose Labour incompetence, or for that matter any gaffes or scandals. Some Labour councillors felt that Truss was entitled and petulant, but I always found her friendly and polite. If she was running late for meetings of the planning committee that I chaired, she would reliably send me her apologies by text message. I once went to a conference in central London and was greeted by Truss (in her day job in public affairs). We had a friendly chat, wryly amused that we’d met each other outside Greenwich, and that it was Truss who ticked my name off a clipboard and gave me a name badge, not the other way around.

Truss did not seem arrogant in any way, and she won some sympathy in Greenwich after her affair with the married Tory MP Mark Field came to light, soon after her election in 2006. Truss was by now married herself, and Labour councillors in Greenwich dissuaded our leader, Chris Roberts (not a natural diplomat), from making a lame joke about “Playing the Field” to embarrass Truss during a debate about development on a playing field in her ward.

I don’t think Truss turned up at that council meeting. Within a year or two of her election in 2006 she was seldom seen in Greenwich, as she had been selected to stand in South-West Norfolk, having already stood in two safe Labour seats in Yorkshire: Hemsworth in 2001 and Calder Valley in 2005. Once Gordon Brown bottled an early election she did not become South-West Norfolk’s MP until 2010, when she did not seek re-election in Eltham South ward. After sanctimonious Conservative members there (dubbed the “Turnip Taliban” by the media) tried to deselect Liz Truss as their candidate in 2009 over her extra-marital affair, I felt enough camaraderie with Truss to send her a supportive “Don’t let the buggers get you down” email, which she graciously thanked me for. Liz Truss’s eldest daughter is very close to mine in age, and in about 2008 I once found myself beside Liz in Greenwich Park’s playground, pushing our infants on adjacent swings. But I don’t recall ever going for a drink or meal with her. We weren’t friends, simply because Truss had little interest in Greenwich politics, whereas with hindsight I probably had too much. For me, being elected and re-elected in Blackheath Westcombe ward meant an awful lot: for Truss it was of no importance at all.

It was hard to dislike Truss. But it was equally hard to see her as a future MP, let alone as a credible minister or prime minister. She always seemed to be a bit bored in Greenwich, impatient to become a Tory MP for a safe seat in Middle England, and keen to put the fruitless work of being a Tory councillor in a safely Labour London borough behind her. If someone had told me that 20 years later Truss would be on the threshold of Number 10, I’d have choked on my muesli. She’s having the last laugh now.  

Politicians tend to look outwards to voters, or inwards to their parties. Boris Johnson was an outward politician, winning for the Tories in places (like London and the Red Wall) which are naturally Labour’s turf. Theresa May was an inward politician, who ultimately failed even to hold her party together, let alone unite or enthuse the country. Jeremy Corbyn was a bit of both, and Keir Starmer is arguably a bit of neither. I see Truss as an archetypal inward politician, great at bridging rifts in the party (she voted Remain in 2016 but has since been a keen Brexiteer), and telling the membership what they want to hear, rather like a Tory version of Ed Miliband. But she has never seemed to be remotely interested in campaigning, or winning, in marginal electoral contests. Her qualities may well see her elected as leader of the Conservative Party. Whether she can then win a general election is much more doubtful.

A shorter version of this article was published in the Times Red Box on September 2 2022: see https://www.thetimes.co.uk/article/liz-truss-can-be-beaten-i-should-know-ive-defeated-her-twice-rpnb2t8rz