The Inside Story: How Theresa May’s Personal And Political Flaws Finally Forced Her Downfall

Brexit didn’t mean Brexit after all. Reality catches up with the PM as her long goodbye becomes a short one.

The moment after that big black door closed, Theresa May was greeted by a gaggle of No.10staff whose tears matched her own. They broke into brief applause before she headed into the bowels of the tardis that is Downing Street. 

Within minutes, upstairs in the Pillared State Drawing Room, she spoke to a semi-circle of her special advisers. Underneath a huge oil painting of an imperious Queen Elizabeth I, the UK’s second female prime minister looked a diminished figure, but retained the strong affection of her team. 

After a short speech thanking them for their hard work behind the scenes, she was applauded one more time before she prepared for the ministerial car waiting outside. “It said a lot about her that she made us all feel a lot better, despite having just gone through what she had,” one insider said.

Yet despite all the tweeted tributes from Cabinet ministers praising her “dignified” resignation, plenty of Tory MPs were just relieved that May had finally put them out of their misery. Like Margaret Thatcher before her, they had come to see her as a toxic liability and she had reluctantly, finally agreed she couldn’t go on.

Even her normally loyal Scottish secretary David Mundell welcomed her departure. “As Mrs May herself acknowledges, she has, however unfairly, become an impediment to the resolution of Brexit, and was no longer being given a hearing by parliament.”

In fact, despite all the theatre of her Downing Street announcement and its market-moving reaction, few knew that May had already made her momentous decision on Wednesday night. 

The previous day, she’d tried one last gamble to get her Brexit plans approved, offering Labour MPs a second Brexit referendum and a temporary customs plan. But the scale and ferocity of the backlash from her own MPs, particularly from moderate loyalists, convinced her that she’d reached the end of the parliamentary road.

In Downing Street, she told her closest aides, Gavin Barwell and Robbie Gibb, that she would finally admit defeat and set a fixed departure date of June 7. The circle of trust was small and only a tight number of aides were informed of the news. Crucially, however, some members of the 1922 committee executive of Tory grandees were also tipped off. For once, it didn’t leak.

But, in a pattern that typified her premiership, the Cabinet had no idea that May’s mind was made up. She held meetings with Jeremy Hunt and Sajid Javid, heard them urge her to pull the Brexit legislation, and didn’t utter a word about her leadership decision. All that Hunt was told was that May would indeed be still PM for the coming state visit by Donald Trump.

Boris Johnson,
Boris Johnson, PM-in-waiting?

While May’s exit plan was highly confidential, the worst kept secret in Westminster was that Hunt and Javid, along with Boris Johnson, Michael Gove and countless others, had been mobilising for weeks to replace her. 

Parliament’s arithmetic was the real obstacle, yet her closest aides began to realise that the impasse could only be resolved with a new leader. Exasperation gave way to an air of resignation, in both senses of the word.

On Friday morning, before anyone knew of the exact timing of the coming announcement, a shredding company van arrived in Downing Street at 8.45am.  It conjured up an unfortunate image of a PM going through the wringer. 

Just after 9am, Tory vice chairwoman Helen Grant quit her post via Twitter and then announced she was backing leadership contender Dominic Raab. At 9.15am, Sir Graham Brady, the chairman of the 1922 Committee of Conservative backbenchers slipped quietly through a secret entrance to Downing Street, avoiding TV crews huddled elsewhere.

In the No.10 ‘den’ that is her office, Brady and the PM held a cordial meeting, not least as they both knew what the other was going to say. They chatted for fifteen minutes, agreeing that it was best to sort a shorter leadership election than a long one. 

At 9.42am, the first any of the media knew that an announcement was imminent was when No.10sent out an email to Lobby reporters headlined ‘Theresa May Statement’. It turned out to be blank, and sent in error. Within minutes, the famous lectern was set up in Downing Street and the world knew May’s announcement was very close.

In her speech, the PM tried desperately to list non-Brexit achievements that she clearly thinks will form her legacy of nearly three years at the top: mental health, housing, domestic abuse, a race audit and gender pay gap reporting. Even the public inquiry into the Grenfell Tower tragedy was on the list.

Yet in almost every case, such policies have been bogged down by the quagmire of Brexit, just as much as her own leadership has. Paralysis across Whitehall has led to dither and delay. On housing in particular – where once May famously said “I will dedicate my premiership to fixing this housing problem” – almost no progress has been made.

Tory 1922 Committee chairman Sir Graham
Tory 1922 Committee chairman Sir Graham Brady

Watching the speech on TV, one of Jeremy Corbyn’s team uttered a hollow laugh of contempt when May declared: “Never forget that compromise is not a dirty word.” It was May’s own failure to reach out to the Opposition after the 2017 general election disaster that has in many ways led to her demise, many Labour MPs believe.

Compromise wasn’t just a dirty word to May for much of her premiership. It wasn’t even in her vocabulary. From buckling to Eurosceptic pressure to push for an early trigger of Article 50, before any Brexit plan had been devised, to her infamous “no deal is better than a bad deal” hubris, there was little room for consensus with Remain voters or other parties.

Anand Menon, of the UK in a Changing EU think tank, said: “She is certainly not an innocent in all this because she went in hard from the first without talking to anyone. She didn’t reach out after the general election at which point it was obvious she wasn’t going to get this through on Tory numbers alone.”

The new timetable for the Tory leadership contest, with a successor in place by the time MPs go off for their summer break on July 24, means that May will be gone quicker than some expected. One minister paraphrased Shakespeare’s Macbeth, saying: “If it’s to be done, it’s best to be done quickly.”

Yet in many senses, May’s departure has been a long goodbye, one that began with that disastrous decision to call a snap election in June 2017, almost exactly two years ago. 

This has been a slow, painful political death, not a mercy killing. Losing her Commons majority, as well as her authority, meant that just a handful of Tory Brexiteers could block any plan she had.

Politicians are meant to campaign in poetry and govern in prose. May could do neither. Her tin-eared response to the Grenfell disaster was both a personal and policy failure.

Labour’s Yvette Cooper, May’s main political foe over many years, said: “Theresa May’s resilience has been her greatest strength and greatest weakness – it prevented her from properly reaching out. She is leaving now not because she tried to get compromise and consensus this spring, but because she didn’t build consensus and compromise at the start.”

Chris Wilkins, May’s former director of strategy and speechwriter, says that 2017 really was the beginning of the end – of Brexit progress and of her premiership. “In that election she was not the unifying leader we wanted her to be. She became quite a partisan, divisive figure who embraced a hard Brexit.”

After that defeat, May told a packed meeting of her MPs: “I got us into this mess, and I’m going to get us out.” She added she would stay on as leader only for “as long as you want me”. They made crystal clear in the last few days that they certainly didn’t want her any more.

Even Tories who have worked closest to May say that her fundamental problem was a failure to connect with others, combined with “tunnel vision” and brittle political judgement. Add in her tendency to be inflexible and to prevaricate and it’s clear why many of her MPs felt frustrated.

The tunnel vision worked on issues like security, with her response to the Russian poisonings in Salisbury a case in point. But on something as complex as Brexit, it was a disaster. Her narrow focus on the details of her Withdrawal Agreement Bill, rather than the wider politics was what led to her downfall. 

“She only ever looks at the thing right in front of her but can’t see what’s staring her in the face beyond it. She can see the trees, not the wood,” a former official said.

While many initially admired her refusal to be ‘clubbable’ or to hang around Westminster’s male-dominated bars, May’s lack of support in her own party stemmed from her chronic inability to befriend others. 

In Westminster and Whitehall, the business of catching someone’s eye and clutching their elbow to get them onside is often the key to progress. Policy can be a science, but politics is the art of persuasion and May was artless.

One former aide said: “She never pulled people aside and said ‘I’ve got your back’. That’s the kind of thing that helps in Brussels as much as Westminster. 

“When the boss of Nissan flew to Downing Street she couldn’t quite understand why he wanted to see her face to face. But he wanted to look her in the eye and shake her hand. It was about trust, trust that she wouldn’t go for no-deal.”

Yet May is more complex than the ‘Maybot’ caricature for which she is famed. 

She could be stubborn to most, yet strangely malleable to a few. Socially, she was shy rather than cold. She would build up incredibly close relationships with aides and then cut off all contact once they left.

“She has a racy sense of humour and can crack a joke back if you lob her a joke,” one insider says. 

“But she does have real trouble at reading signals. I never once heard her say to a politician ‘I need your help’. I never heard her say ‘I’m sorry, I was wrong’. In her mind, that would admit a vulnerability, a weakness she never wanted to show.

“And yet when you saw her with Philip, you could see how truly loving they are, a relationship most people would be jealous of,” one aide said.

May with border collie
May with border collie Blitz

Some strong leaders can survive a lack of really close partnerships with other politicians. US President Harry Truman once famously said: “If you want a friend in Washington, get a dog!” 

Still, May couldn’t even get a dog of her own. One well-kept media secret is that all those Sunday photos of her playing with a dog outside the Church in her local village were only possible because a photographer brought along his pet – to get more ‘interesting’ photos and to make the PM smile.

Many felt the lack of people skills really was the reason for her shallow support in parliament. “You’d look round the Cabinet table and realise no one had her back, really. Going to the Cabinet once a week was like going to the dentist. Everyone had their say, but you learned nothing about what she wanted. 

“She’d say ‘Thank you Andrea, thank you Karen’ then end the meeting. It was like a really bad self-help group where they all paid a lot of money to a shrink, thinking he was going to have some answers but in fact he just let you do all the talking.”

Others point to May’s lack of political self-confidence. It opened a gap which officials and advisers filled, but MPs didn’t. 

“When Nick and Fi [her former chiefs of staff] left, [Mark] Sedwill [the National Security Adviser and later Cabinet Secretary] effectively replaced them,” one former official said. 

“He saw from his Home Office days how she could be pushed around. Other civil servants did too.

“She relies on people who then manipulate her. Gavin Williamson was brilliant at it. Penny [Mordaunt] was nailed on to get the [Defence Secretary] job when Fallon quit, but Gavin persuaded her he should get it. And he did.”

Another insider who knows May well said she has less ego than any politician they know, yet it was obvious that she had wanted to be PM since she was a schoolgirl. All political leaders get a God complex, but in her case, it was more subtle. 

“She had a really religious sense of duty, maybe that came from her father [an Anglican vicar]. But even that at times felt like she had a ‘higher calling’. And it occasionally came across as a need to be superior.”

In an infamous Sunday Times magazine interview that she gave during the early days of her tenure, May let slip that the fact she had no siblings had left an impact. “Being an only child, you don’t feel the need to be in a big group…you’re given more of a sense of…relying on yourself a bit more.”

The sight of May nearly breaking down in tears on Friday, the moment that will now be replayed on endless loop, was as much a shock for her close allies as it was for her enemies. “Oh, crikey,” said her husband Philip, as he saw her voice crack with emotion.

Her emotional defences were often rigidly maintained. An aide once tried to prepare May for an interview by asking her reaction to losing her parents at a young age (her father died in a car crash, her mother of multiple sclerosis a few months later). 

“‘It was very sad,’ was all she could say.  This is someone who came off stage after that awful conference speech and just shrugged her shoulders and said ‘oh, well that was one of those things’.”

A former Cabinet minister was more brutal. “Politics is her life. She has nothing else really. I don’t know what on earth she will do,” he said. One former aide said that verdict smacked of sexism because May had no children. Yet they conceded her lifelong focus on the Conservatives as a ‘second family’ really would make her ‘retirement’ very difficult indeed.

“Ever since their twenties, she and Philip have been part of the fabric of the Tory party. For the party to have been treating her like a leper, as it has lately, has been very hard to take,” said one who knows her well.

“She’s always been busy. When she was party chairman, her diary was stuffed with rubber chicken events. As shadow education secretary, and as Home Secretary, she was constantly working. Being PM was that with even less time for anything else. I don’t know how she’s going to cope outside office.”

But, as one of her backbenchers Lee Rowley put it to her in a heated meeting of Tory MPs last December, “stamina is not a strategy”. And on Europe, May seemed to think for a long time if she just kept wearing down her party it would eventually accept her Brexit deal. 

Although her coalition-building skills were dreadful, it wasn’t a lack of empathy as much as the brute forces of political gravity that really brought May down. With no parliamentary majority, and Brussels a formidable negotiating bloc, there were inherent flaws in her attempt to get a Brexit that was half-in, half-out of the EU.

The great irony of losing her majority is it plunged her into the thing she’s most unsuited for – daily and weekly horse trading both with her own party, the DUP and with Labour and Brussels. ‘Brexit means Brexit’ was the meaningless soundbite that ultimately proved as empty as many feared. 

Now, after Thatcher, Major and Cameron, May is the fourth Tory prime minister to be broken by the issue of Europe. She never forgot that her very occupancy of No.10 was born out of the Leave vote in 2016, but it falls to her successor to take on the task of sorting Brexit. 

There was an unseemly haste with which several leadership contenders came out of the traps on Friday. Barely three hours after May’s emotional exit, Hunt told his local newspaper he was running. Then even Brady announced he had quit as 1922 Committee chairman because he was “considering” running as leader.

Game of Thrones superfan Michael
Game of Thrones superfan Michael Gove

Friday happened to be Brexiteer Jacob Rees-Mogg’s birthday and May’s resignation announcement was the perfect present.  And it is Rees-Mogg’s favoured candidate, Boris Johnson, who is the biggest beast lurking in the shadows. 

With a new haircut, a new partner, a slimmer frame and – crucially – new found support among Tory MPs desperate to stop the Brexit Party’s Nigel Farage, Johnson is undoubtedly the front runner. “I couldn’t get him to tuck his shirt in in four years,” his former spin doctor at London’s City Hall, Will Walden, joked today.

As typified by that photo of him on a zip wire, Johnson has defied political gravity before, notably in winning twice as Mayor in the Labour-leaning capital city. His major task now will be to somehow get a Brexit deal that eluded May. 

He can test to destruction the theory that Brussels will somehow change position on the issue of Northern Ireland if only a new leader added some grit to the negotiations. Brits abroad shouting louder in English to make Europeans understand them is not often a recipe for success. 

But the Tory leadership race is almost certain to turn into a contest between a no-deal candidate and an anti-no-deal candidate. At a conference in Switzerland on Friday, Johnson put down a clear marker: “We will leave the EU on October 31 – deal or no deal.” 

Raab, who has plenty of support among MPs, will challenge him for that no-deal mantle. And it may be Michael Gove or Hunt who emerges as the compromise candidate. Whoever becomes leader may have to trigger an autumn general election if there is no movement in Westminster or Brussels.

Gove, who memorably ‘knifed’ Johnson back in 2016 after their Vote Leave campaign triumph, is known among civil servant and friends alike as a superfan of Game of Thrones.

The blood-and-swords drama may be over as a TV series, but it’s only just getting under way for the Tory party. And for many who fear a Johnson premiership will lead to isolation and a chaotic exit, winter is coming.

It’s perfectly plausible that when Donald Trump visits the UK next month, he will ask to meet Johnson, who is rare among British politicians for having expressed admiration for the US president. Never afraid to rub salt into an open wound, Trump may be unable to resist an endorsement for both Farage and Johnson when he holds a joint press conference alongside May.

After her heartfelt exit let the world finally see how passionate she was about her job, May’s close allies felt that the tragedy of Macbeth was again apt: “Nothing in his life became him like the leaving it.” “It’s such a sad day,” one said. “She meant it when she said she leaves with no ill-will. And she did it with a grace and dignity that a lot of other people couldn’t manage.”

As May’s ministerial car left Downing Street to take her back to her constituency on Friday, Britain’s second female PM was just yards from hundreds of teenage girls on a ‘schools strike’, chanting and marching in Parliament Square. 

Their day-long protests about the climate change crisis often drowned out the TV circus covering May’s exit. The prime minister missed them all. She had left No.10 – by the back door route.

All Rights reserved for Paul Waugh.

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