There are plenty who have been left bruised by May’s decade and a half at the top of the Conservative party, but even her worst enemies concede that the woman who is to become the next Prime Minister has shown a remarkable durability in high office. She’s the longest-serving Home Secretary in half a century, and has made a success of what’s very often a career-ending job.
A long-retired party grandee recalls May, then newly elected to Parliament, approaching him in 1997 to ask what she must do to succeed. ‘Ignore the little things,’ he replied. It’s advice that her critics reckon she has firmly ignored ever since. When he resigned as a Home Office minister, the eccentric Liberal Democrat Norman Baker described trying to work under May as ‘walking through mud’. There are Conservatives, too, including ones in the cabinet, who accuse May of being a territorial micromanager. But the wrath of her colleagues has only increased her standing with grassroots Tories.
‘She’s a boxer,’ says a Home Office mandarin. ‘She’s got her gloves up all the time. Not much gets through. Always defensive.’ ‘Any special adviser in Whitehall who didn’t make it their business to know exactly what is going on in their department is negligent,’ contends Nick Timothy, a long-term aide and friend. ‘She wants to know what’s going on and wants to have a handle on things.’
But the body count is high: Pauline Neville-Jones, the former spook turned security minister, lasted only a year in May’s Home Office. Ken Clarke felt her sharp claws when she publicly declared, ‘I lock them up, and he lets them out.’ No serious cabinet split in the past four years has had May’s name far from it and, as Michael Gove found out, she is very good at defending her territory.
Ask anyone about May and you get the usual ‘Merkel of Maidenhead’ stuff; she is famed for her kitten heels and penchant for expensive, punchy jackets and Vivienne Westwood tartan suits. These stories are partly a product of laziness — there are so few female politicians in the highest posts that facile comparisons are drawn — but May’s femininity cannot be ignored. ‘She refuses to apologise for her success,’ says her former spin doctor Katie Perrior. ‘She wears the clothes to show she is not the person you think she is. Her dress sense shows that risk-taking side. They are hidden signals. Her two fingers, a bit of control she has over her life.’
The tall, formidable yet softly spoken, almost regal May is popularly said to have surrounded herself with a praetorian guard of loyal and devoted aides. Dry in humour and incredibly stubborn, May does command a powerful loyalty from those who have worked for her — even after they have officially departed.
But there is plenty of criticism of her approach too. One phrase that never goes away is ‘risk averse’. ‘While some politicians fly by the seat of their pants, Theresa likes to have four parachutes next to the door,’ says a former staffer. Her supporters point out that this is just good practice, and planning is not the same as caution. She was nicknamed ‘Theresa May, or maybe not’, by detractors in opposition. ConservativeHome founder Tim Montgomerie writes: ‘It’s true that she doesn’t excite many people — either on TV or in personal dealings — but she’s the safest of safe pair of hands.’ Others are less kind: ‘She is boring. A technocrat. She is Philip Hammond with a fanny. Not interesting, but rendered interesting by circumstance. And that circumstance is that she is a woman. And in an age when the Prime Minister gets it in the neck for refusing to wear a fucking T-shirt that says he is a feminist, that is a rocket boost right underneath you,’ says a senior Conservative party official.
‘I think she is a massive risk-taker — huge,’ says her adviser and confidante Fiona Cunningham. ‘When she decided not to extradite Gary McKinnon, she knew the wrath from the States and by God, you know, the tornado that came out of Washington was immense.’ Reflecting on May’s 2012 decision to defy American demands to send over the autistic Pentagon hacker, Cunningham beams, ‘The call came at about quarter to six in the morning. Theresa simply said, “I’m not going to extradite him,” and I leapt out of bed with excitement. I don’t recognise why people say she’s not a risk-taker. Who is going to take a hard decision like that? Especially as a Home Secretary who has a bilateral arrangement on security with one of the most security-conscious countries in the world.’
Nick Timothy refuses to accept the May administration at the Home Office has been anything other than a risky business: ‘Are you kidding? She went out on a limb on Abu Qatada and never relented, despite various setbacks.’ Nor does he accept that his boss and friend is a technocrat: ‘Read her speeches. They go way beyond being a mere technocrat, they have a vision what the future should be about and what politics and the party should be about. It may be that earlier in her career she came across like that — when she was younger she may have been more diffident.’
Diffidence is something old timers agree on. ‘She was a very inexperienced politician,’ says a senior press official under Iain Duncan Smith, and was there the day May was plucked out of relative obscurity and made party chairman in 2002. ‘Very cautious.’ But it was her time as party chairman that defined the May brand. ‘There were the mods and traditional rockers,’ they recall, ‘and it was not a secret that she was a mod.’
Throwing down the modernisers’ gauntlet at their Bournemouth conference in 2002, May spelled out exactly how the party needed to change if it was to shake the tag of the ‘nasty party’. ‘She certainly needed persuading’ chuckles a party hand intimately involved in drafting the now infamous speech. The label instantly stuck, and has remained a lightning conductor for anti-Tory rhetoric ever since. All of these things had been said before, but it was extremely risky for the party chairman — traditionally a loyal attack-dog role — to be the one saying them. ‘It was more a case of, “We have nothing to lose here,” ’ says Katie Perrior, who was May’s media aide at the time. ‘She didn’t want the party taken over by right-wing nutjobs. Risk? No, it was desperate times. She knew it was controversial but I’m not sure anyone thought we would still be talking about it in ten, 15 years’ time.’
But in many ways, May’s gamble has been proven correct. The post ‘nasty party’ fallout cleared the path for the Cameron project and its relentless focus group-oriented ‘detoxifying the party brand’. There is barely a cigarette paper between Cameron and May ideologically — the current Prime Minister would claim to be socially liberal, while supporters of May put her on the ‘traditional wing of the social liberals’. Labour would love to be able to paint May as a right-wing authoritarian, but that attack line is hamstrung by her undoubtedly liberal moments in office, such as scrapping ID cards, reducing detention without charge to 14 days, reforming stop and search and pushing the Modern Slavery Bill. When the leading black newspaper the Voice described May ‘as fast becoming someone who the black and minority community can do business with’, it was evidence that she has been one of the most successful modernisers of them all.
‘As long as I have known her she has always refused to allow herself to be pigeonholed by saying she is in this club or that club or on this wing or that wing of the party,’ says Timothy. ‘It confounds some people, it especially confounds the Left, that you can be so sceptical about the European Court of Human Rights, but you can care so passionately about the rights of the citizen. It confounds them that she thinks immigration needs to be much lower, at the same time as introducing the first legislation of its kind on modern slavery. I don’t think that’s inconsistent, I think that she’s a sound conservative who believes in social justice.’
This is one of the secrets of May’s success. While she may be a defensive boxer with her gloves up, her feet are also moving incredibly quickly. That lack of pinpointing makes it very hard to define her, and thus attack her, though some will always try. ‘We will never ever forget the nasty party comment,’ says one prominent right-winger. ‘No matter how many terrorists she sends back or tough-sounding speeches she gives. She gave a name to our branding problem and it will be hung around our neck for decades by our enemies. It has damaged us as much as the misquoted “no such thing as society”.’ But while she may not be of the traditional right, there is certainly something very traditional about May as a person and as a politician. ‘If you say you are going to do a dinner, you can’t cancel it. She gets enormously annoyed if it looks like she might have to cancel something which has been a commitment she has given,’ says Cunningham. ‘I wouldn’t go as far as old-fashioned, but just a very traditional — do the right thing, you can’t let people down.’ ‘Strong sense of a proper way of doing things,’ echoes a friend.
This traditionalism may have more to do with her upbringing than her politics. Born a reverend’s daughter in Sussex in the late Fifties, before a spell at a convent and a grammar school and Oxford, she’s got a decade on Cameron, Osborne and Boris. Before the PM had so much as tried on his Bullingdon Club uniform, May had spent six years at the Bank of England, before becoming a Tory councillor and a financial consultant in 1986. By 1992, she was a parliamentary candidate — albeit in Durham, a Labour stronghold — and she ran again in the Barking by-election of 1994, where she was defeated by Margaret Hodge, before entering Parliament as the MP for Maidenhead in the Conservative party’s annus horribilis of 1997.
‘She is in her element when she is in the House, it’s her natural terrain,’ says Cunningham. But it’s hard to pinpoint a natural block of support on the Tory benches. There is no Mayite faction. There are complaints of coldness and an aloofness, and not just from politicians. ‘She doesn’t conform to a way that a lot of Westminster politicians behave,’ says a defensive Timothy. ‘So when it’s said that she is a less than interesting lunch date for a journalist, that isn’t because she doesn’t talk about interesting stuff, she doesn’t think about ideas. It’s because she doesn’t gossip.’
That tight-lippedness extends to her private life. The naffness of meeting her investment banker husband Philip at an Oxford Tory disco is negated by the fact they were introduced by Benazir Bhutto. ‘He absolutely admires her,’ says close friend Catherine Meyer. ‘There is no jealousy there as you might sometimes get. Not an iota of that, on the contrary.’ ‘Denis minus the drinks cabinet,’ says another friend. ‘He’s softer than Denis,’ adds Meyer. ‘There was a sense there that Margaret was the boss, but I can’t see that here. It’s a very harmonious relationship.’ ‘She is noticeably more relaxed when Philip is around,’ says Timothy.
While the couple have never had children, there is a remarkably maternal element to May’s politics. A lioness is how Cunningham describes her former boss, whose paws extend tightly around those closest to her. With that comes a tribal element. ‘She defends any minor incursion on to her territory as a direct attack,’ says a cabinet colleague. ‘The rows come when people camp on her turf,’ says a metaphor-mixing MP. ‘One thing you would not want to be is a cabinet minister with a drift into May’s area. It won’t be fun.’ A point all but conceded by Cunningham, who was sacked in spring 2014 after one such cabinet row descended into all-out war with the Department for Education over tackling extremism. It was a fight that gave a glimpse into Team May’s tactics: ‘She is very collegiate, and very, very loyal. Always happy to do whatever she needs to for her colleagues. Whether that is someone in a marginal seat needing her to go and do a dinner. She is genuinely someone whose immediate reaction is to be collegiate. But if someone wants to trample on her toes, then she will take a different tactic.’ In the spat that would ultimately cost Cunningham her job, that ‘different tactic’ included some low politics and mysterious late-night leaking of a dynamite letter. The claws are never far away. But May and Cunningham remained close, and she was drafted back to help the Home Secretary lead her charge into Number 10.
Those paws have been around for a long time, too. ‘Theresa didn’t just appear in 2010,’ says Perrior, ‘she has been doing this for years’, pointing to May’s desire to help out candidates — particularly women — and tour the country relentlessly for Tory functions. ‘Over weekends she has been working it’ for over 20 years. ‘She’s invested in friendship and loyalty.’ On the surface, she’s the ultimate party loyalist, devoting her life and time to the party. And now that investment has spectacularly paid off.
A version of this article first appeared in Spectator Life in November 2014