There were no caricatures of Theresa May, only understatements. She was a catastrophic and uniquely isolated prime minister

The end of Theresa May’s tenure as British prime minister is unique in modern times. Not because her political life has ended with a dramatic political failure; the same could be said of Margaret Thatcher, John Major, Gordon Brown and David Cameron. It is that, even today, as her staff still sit at their desks in Number 10, they barely bother to defend her tenure.

Yes, she was dealt a tough hand. But political players want to be at the centre of things during important moments. She also had opportunities. She led the Tories to a huge opinion poll lead – enough to make a snap election seem riskless. And she blew it.

In truth, the reasons for her catastrophic tenure as the head of the UK government were largely those that made her so astonishingly popular in the first place.

Why this story? Through his brilliant reporting for our “Defeated by Brexit” series, Chris Cook identified an important – and alarming – truth: when Theresa May said that “Brexit means Brexit,” she didn’t really know what she meant. Months of prime-ministerial vacillation followed, leading to pretty much nowhere. We still can’t be certain how or whether Britain will depart from the European Union. What is certain, however, is the end of May’s premiership. She will depart Downing Street within days, to be replaced by, most likely, Boris Johnson. What better time could there be, we thought, for Chris to return to the subject of her premiership and its failings? Again, the reporting is brilliant. Again, it is alarming. Peter Hoskin, editor Read more Read less

May rode the stereotypes she was perceived to embody. Her father was a clergyman, and she has remained a loyal Anglican. As a result, she was automatically assumed in popular discussion to have a sense of sturdiness, seriousness and community-mindedness. A vicar’s daughter. The acme of a sort of diligent, buttoned-up English woman.

When she launched her leadership bid, she said: “I don’t tour the television studios. I don’t gossip about people over lunch. I don’t go drinking in parliament’s bars. I don’t often wear my heart on my sleeve.”

And she did not want an informal “sofa government” or “kitchen cabinet” in Downing Street. After the easy to-ing and fro-ing of the Cameron premiership, she wanted things done by the book. One former aide said: “She has a strong sense of what is right and what is wrong – and that’s true of everything. It’s as much about righteousness as anything.”

When she was all-powerful, we kept hearing how she was “diligent” and “across her brief”. She “gets through her box”, it used to be said. That is to say, she reads her papers each evening and responds to queries from officials. She had been one of Cameron’s ministers; there would be none of his hands-off leadership.

Another stereotype cemented her image: women who lead the Tory party. Thatcher remains the touchstone of Toryism and May had, the Daily Mail said, “The Steel of the New Iron Lady”. When she called an election, the Mail cheered her on: “Crush the Saboteurs,” it bellowed.

The problem with May, though, was not that these descriptions were wrong. It is that the folk depiction of her was not caricature but understatement.

No, she did not tour the TV studios or drink in Westminster. In fact, she spoke to vanishingly few people. There were almost no MPs who might be said to be her outriders. No columnists who could unpack her vision of the world. She does not trust other politicians.

She had almost no relationship with David Davis, her longest serving Brexit secretary, whose work would be the core of her premiership. Part of this was personal: “I don’t think they ever bonded… They are both instinctive political loners,” one of her allies told me. But when she had choices as to whether to bring him in or shut him out, she always shut him out. But she always shut everyone out.

My reporting suggests that she privately ruled out leading Britain out of the EU without an agreement at some point in 2017 – mostly because of the harm it would do to the United Kingdom’s internal union. This is the view of senior aides and officials who dealt with her. It is also otherwise difficult to understand why she conceded so much so readily to the EU at that time.

But, in public, she kept saying: “No Deal is better than a bad deal.” Perhaps she wanted the EU to believe this notion. But she never let on that she believed this to be a lie, even to cabinet ministers who agreed with her. Her judgment on this issue only emerged when she was facing an actual No Deal exit, and she moved to avert it. A strange part of her legacy will be the normalisation of the idea that a No Deal Brexit is a benign outcome, despite her own misgivings.

When she had a Brexit deal to sell to MPs, she was hopeless at building alliances. When she had to collar fellow European leaders, she was a dismal schmoozer.

One of her former aides told me: “She has an expectation that other people will come around to her viewpoint… an impatience. It’s a self-belief thing. It’s a lack of realism about the reasons why people have different viewpoints. She doesn’t know why people believe in things…” Another aide was more caustic: she is prone to “sanctimony” and “too easily assigns bad motives to people who disagree with her”. Her meetings with Leo Varadkar, the Taoiseach of Ireland, have become the stuff of diplomatic legend. Officials from Dublin and London wince at the mutual awkwardness; neither is clubbable. A back-channel between their deputies had to be set up to allow the two governments to maintain a dialogue.

Even within Downing Street, she was something of a sphinx. She relied heavily on a tiny inner core. The constants were her husband, Philip, and her chiefs of staff – Nick Timothy and Fiona Hill before the mid-2017 election, Gavin Barwell afterwards – and their deputy, JoJo Penn. Sir Jeremy Heywood, the late cabinet secretary, and his successor, Sir Mark Sedwill, were in the inner sanctum. But there were few beyond that.

One of her political advisers told me that, in order to get a paper on to her desk prior to the 2017 election, their submissions needed to be filtered through two deputy heads of the policy unit, the head of the policy unit, the cabinet secretary and the chiefs of staff. They used to joke that a fire could break out in the basement, and it would take two weeks for the prime minister to be told.

One aide said that “avoiding causing offence” along that chain was the key to getting things in front of her. Things are easier now. Hill and Timothy resigned after the 2017 election debacle, and these processes, brought in with her from the Home Office, softened.

They made more sense in that department. One aide said: “The Home Office has a tendency to hide things in the fifth paragraph of the sixth annex of documents which can blow up home secretaries. You want a lot of pairs of eyes on it.”

Theresa May walks along Downing Street in 2017, ahead of that year's disastrous general election

But, even as the strictures have relaxed, the inner circle has not expanded. The flow of information is still torpid. One of her personally appointed advisers – someone who, in another Downing Street, would be said to be close to the PM – told me it is still difficult to get an informal or broad steer from her on a topic.

When she was home secretary, this sort of process was not a problem; the security machine would simply slow down to work at her pace. But when Downing Street operates like this, it becomes a bottleneck. Part of its role is to chivvy indecisive ministers, to prevent ministers from going off-piste, and to keep them from butting heads. But that requires a certain amount of speed.

Even her much-noted diligence was a double-edged sword. Yes, she read her papers – and digested them carefully. One former aide said: “She had a tendency of sending things back at the Home Office, and was quite pedantic about the types of information that she wanted to enable her to make decisions.”

Less discussed was another important attribute that several of her appointees told me about: she valued “keeping options open”. She places great store in future flexibility.

But one person’s diligence and desire to avoid being tied down is another’s decision-avoidance. “You have to get used to meetings ending without coming to a conclusion,” another of her advisers told me. As one senior civil servant told me: “She always wants to know what the ‘right’ or correct answer is. But politics isn’t a mathematical equation.” She was loath to actually make leaps based on her own judgment.

The clearest example of this hesitance came from the Brexit negotiations. May will leave office with her government’s position on Brexit being the so-called “Chequers” plan. Some of her cabinet wanted to be in a customs union with the EU, some out. So she split the difference incoherently. A cabinet minister told me: “If you’ve got a fundamental choice, do you risk annoying sections of the Tory party? She will seek a third way.”

May chairs a cabinet meeting – back when Boris Johnson was still foreign secretary, and not just poised to depose her

What the Mail saw as evidence that she was an Iron Lady, officials saw as inflexibility. Her experience of negotiating was within cabinet and with other European interior ministers. Being stubborn was an asset in those scenarios. She delighted in being called a “bloody difficult woman” by Ken Clarke, a veteran Europhile Tory.

But this is not how large-scale, high-profile EU negotiations work. She was not able to respond to the realisation that her red lines were clashing, nor the reality of life after the 2017 election. Indeed, it was a lack of flexibility which led to her grim election performance. Labour was able to pull together a coalition of people sceptical about her – and she was unable to allay their concerns.

Someone very close to her told me: “It wasn’t that she lacked decency or even had unreasonable values – it is just that the other characteristics meant these qualities rarely shone through. In small groups, in private, she was funny, passionate and clear, but I never saw this if you put someone outside the inner circle in the room.” (On her private charm, another said: “Well, don’t go overboard.”)

Still, these “vicar’s daughter” attributes do not explain everything.

First, you must understand the role of her advisers. She did make some bold sallies during her career.

As home secretary, for example, she defied official advice to pursue the extradition of Abu Qatada, an extremist preacher. She resisted an extradition request from the US to deport Gary McKinnon, a man who hacked into US government systems looking for evidence of alien life. But that was all Hill’s initiative, not hers.

As prime minister, she risked Tory ire by pressing forward with an active industrial policy, something they usually eschew. But this was Timothy’s part of the project. She took risks when she was given advice to be bold.

In happier days: May, surrounded by Conservative MPs, as she becomes leader of her party and country

Second, never underestimate her tribalism. “She is a Conservative to her core and the party has been a huge part of her social life and sense of identity,” one friend puts it. And she is enormously rooted, in particular, to her constituency (“her flock”, as one aide put it).

This is a thread within her that explains how, for all her indecision and caution, she triggered Article 50, starting the countdown to leaving the EU, without a plan for managing the negotiation. She did it against the advice of her lead civil service negotiators and officials. But she was getting advice that she should press ahead from the political side – and felt under pressure from the party to press on.

She wanted to own Brexit for her party. This is partially why she did not reach out to Labour early on. It is why she worked so hard to paper over cracks in her own cabinet – even at a cost to the British negotiating position. The Withdrawal Agreement was rejected by both pro-Remain and pro-Leave MPs, but it was Tory Leavers she sought to win back.

Britain was engaged in a task that required a leader who could lead, convince, innovate, be agile, break party lines and work swiftly. In its place, it got one who was a strange combination of isolated, tribal and indecisive.

Photography by Getty Images