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Thu, 28 January 2021

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By Chris Sear
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Theresa May’s premiership: where it all went wrong

Theresa May’s premiership: where it all went wrong
14 min read

Theresa May’s true legacy is that her successor will now be dealt an even worse hand than she was, writes Sebastian Whale

Andrea Leadsom, flanked by her campaign henchmen, read out a statement on the steps of 13 Cowley Street in Westminster. It was 11 July 2016, and the environment minister was announcing her withdrawal from the Tory leadership race. The contest, which was due to finish on 9 September, came to a premature end following a newspaper interview in which the Brexiteer talked about why being a mother made her suited to lead the country.

Two days later, Theresa May addressed the nation from Downing Street. Parking her tanks firmly on Labour’s lawns, the newly minted Prime Minister pledged to build a better Britain. She entered No10 with hopes of remoulding the country she believed had been too heavily skewed in favour of those with disproportionate means and influence. Her Majesty’s Government, it seemed, was in pursuit of a meritocracy.

At the same lectern less than three years on, a tearful May announced the timetable for her resignation. The optimism that followed her into the famous black door in the summer of 2016 was replaced with regret for a tenure that never truly got going, let alone extinguish the burning injustices that she had so readily identified.

This is the story of where things went wrong.


On launching her bid to replace David Cameron, May, dressed in a tartan suit, spoke proudly of being someone who doesn’t gossip in the tea rooms or schmooze with lobby journalists. Once viewed as a positive, this aversion to the realpolitik would hamper her leadership.

May’s first reshuffle illustrated her lust for loyalty over flair and pizazz. Gavin Williamson, who helped run her campaign for the leadership, was made chief whip. James Brokenshire and Karen Bradley, two ministers who had served under May in the Home Office, joined the Cabinet as Northern Ireland and Culture Secretary respectively. Long-term allies David Lidington and Damian Green (an old friend from Oxford) also joined her top team. Philip Hammond was moved to the Treasury. Fiona Hill and Nick Timothy, close confidants, were made her joint chiefs of staff.

May displayed an element of ruthlessness by unceremoniously cutting ties with key figures from the previous government, creating enemies in the process. She sacked George Osborne in Downing Street, and aides would later brief out that she encouraged the former chancellor to get to know his party better. Michael Gove was another high-profile casualty – along with Dominic Raab and Nicky Morgan (both of whom backed Gove’s bid for the leadership). No space could be found, too, for business minister Anna Soubry and other Cameroons.

Taking power away from the Foreign Office, she created the Department for Exiting the European Union, known as DExEU, to be led by David Davis. In setting up the Department for International Trade, the PM signalled her intentions on Brexit. If the UK was to remain inside a customs union, it would not be able to strike its own free trade deals. By placing Liam Fox (another to have supported her leadership bid) in charge of a department whose purpose was to do exactly that, May showed her first bit of leg.

In one of her most consequential appointments as Prime Minister, she made Boris Johnson, the spiritual head of the Leave campaign, foreign secretary. Johnson’s performance (including his remarks over dead bodies in Sirte, and his handling of Nazanin Zaghari-Ratcliffe’s imprisonment in Iran) would come back to haunt May, who, following the 2017 election, would find herself too weak to do anything about the bombastic former London mayor. The final humiliation came when Johnson quit on his own terms in July 2018. Her inability to deal with Johnson – or her cautiousness at not doing so – only sought to highlight her vulnerability.


As May settled into the new job, she came under pressure over the triggering of Article 50. Brexiteers were keen to get things moving and European leaders insisted that no negotiations could take place beforehand.

On the eve of the 2016 Tory conference in Birmingham, May – who would not come to an agreement with the Cabinet on the future EU relationship for almost two years – confirmed that the Article 50 process would be initiated on 29 March 2017. In doing so, she committed the UK into a set of negotiations to which she was unsure of her desired end outcome. In the first of two conference speeches, May attacked the “citizens of nowhere”; a remark that her critics would deploy against her thereafter.

The Government’s insistence that Article 50 should be triggered unilaterally without parliament’s authorisation was challenged in the courts by campaigner Gina Miller. The case ultimately ended up at the supreme court. The row, which featured prominent attacks on the judiciary, triggered many pro-Remain Tory MPs to turn against May for her treatment of parliament. This was a theme that would run throughout her premiership, culminating in a vote of contempt against the Government last December.

Given where we are now, it is remarkable to think that MPs would not have been allowed a say on both initiating the Brexit process and signing off on the Withdrawal Agreement, as per May’s original intention.

“We’ve had the curious situation since the referendum where we have an executive claiming it’s acting in the will of the people without a majority in parliament to carry out its decisions,” Dominic Grieve, the former attorney general, remarked to me recently. “Inevitably it’s been leading to friction. In my view, the Government has been mistaken in not trying to extend a more conciliatory role towards Parliament.”

Though the supreme court ruled in favour of Miller, the Government continued to take a combative approach (May famously watched on as peers in the House of Lords debated the Article 50 bill for the first time). This drew praise from the more hawkish British press, where May was dubbed the new iron lady. But the PM had done little to address the chasm that had opened up in British politics following the referendum. Indeed, keen to prove her worth on Brexit after backing Remain, she often deepened the divide.

Following sustained pressure to flesh out her Brexit vision, May outlined her views at Lancaster House. The January 2017 speech was crucial as it set the parameters of the negotiations. Gone was membership of the single market and the customs union (though May was largely unspecific on this latter point), with pledges to retain control of the UK’s laws, borders and money. She warned Brussels that seeking to “punish” the UK would be an “act of calamitous self-harm”. For the first time, she used the phrase “no deal is better than a bad deal”.

Brexiteers were ecstatic. Nigel Farage said: “I can hardly believe that the PM is now using the phrases and words that I’ve been mocked for using for years. Real progress.”

Lancaster House was a pivotal moment. The referendum result and Brexit itself had yet to be defined. For months people had looked to the PM for guidance; for months, all she had said was that “Brexit means Brexit”. Brexiteers would now see anything less than what was committed to as a betrayal. Those who had previously advocated a softer Brexit hardened, knowing they could get more than they might otherwise have coveted. Now, they were dealing with a PM who had said they would be willing to leave empty-handed.

Remainers, isolated, felt May had courted the 52 and shown short shrift to the 48. She had taken one group with her on a journey she would ultimately be unable or unwilling to fulfil – and left the other behind.


May, however, was riding high in the polls. Very high. Jeremy Corbyn’s Labour party were, according to some surveys, lagging by more than 20 points. Behind the scenes her joint chiefs of staff had alienated many MPs and officials in Whitehall but, with the party surging ahead, little was said about it publicly.

After spending Easter walking in Wales with her husband, Philip, May returned to Westminster having made up her mind. The PM, who The Economist had once referred to as Theresa Maybe, would call an election. On 18 April 2017, she announced the news to the public, accusing the opposition parties of trying to jeopardise her government’s preparations for Brexit.

She said of a snap election: “I have concluded it is the only way to guarantee certainty for the years ahead.”

For a campaign that was built entirely around her personal brand, May proved to be a major hindrance. Her ad hominem attacks on Brussels and Jeremy Corbyn showed her preference for short-term gain over concern for long-term impact. The party’s manifesto fell apart as it touched air. There was no running theme to her domestic agenda and little positivity. May’s love of obfuscation was on full display; as the social care proposal unravelled – and was quickly amended – she insisted: “nothing has changed”.

Politically and personally humbled, May returned to Westminster not as she left it: weak, without two of her closest aides and short of a majority. Her lack of political antennae was on display during a speech outside Downing Street, when she failed to praise or apologise to the many Conservatives who had lost out and was largely tone deaf to what had just taken place. This failing was ruthlessly exposed in the aftermath of the Grenfell Tower tragedy days later, where May’s lack of a human touch infuriated an already outraged community.

Far from strengthen her negotiating hand, the election results – which saw the Conservatives enter a confidence and supply agreement with the DUP – emboldened the Commons and undermined May’s standing overseas.

May centralised powers for negotiating Brexit to the Europe Unit in the Cabinet Office, headed by Olly Robbins, a senior civil servant. Much to the chagrin of Davis, the Brexit Secretary, she succumbed to the EU’s timetable for the negotiations. Now, no trade arrangements could be discussed until the divorce bill, citizens’ rights and the Irish border issue were resolved. During her second major Brexit speech, this time in Florence in September 2017, May finally committed to a two-year implementation phase (another policy she had resisted and then committed to).

While Florence was largely a success, the same cannot be said for May’s keynote address to the Tory party conference in Manchester. She coughed and spluttered her way through 45 painful minutes as the set collapsed around her and a prankster handed her a P45. Despite Grant Shapps’ best efforts to use the real-life anxiety dream as a catalyst to get rid of May, few Tories put pen to paper.

Though May had brought in Gavin Barwell to reconnect with the parliamentary party as part of a new look No10 team (a senior Tory source says the former MP actually became “one of the biggest blockages between Tory MPs and Downing St”), Brexiteers, who had been front and centre of the negotiations, were suddenly more isolated. No10 drifted “towards more civil service-based policy” after the 2017 election, David Davis told me last year. “I don’t vilify people for that,” he explained. “What it means is you’re ending up with a sort of Remainers’ Brexit.”

In December 2017, the Government signed up to a joint UK-EU report that contained a commitment to ensure “full alignment” with the rules of the customs union and single market that uphold the Good Friday Agreement in the absence of a future agreement. The mechanism, known as the backstop, was Britain’s brainchild.

Davis warned No10 at the time that harmonisation between the UK and the EU was “contrary” to the wider Brexit strategy. According to the former Brexit secretary, May said it was about “full alignment of outcomes, not full alignment of every single rule”. The Cabinet signed off the on the document.

In July 2018, more than 15 months since Article 50 was triggered, May finally brought her Cabinet together for a meeting at Chequers to go over the Government’s vision for Brexit. Davis, who had argued that the UK should diverge from the EU on rules and regulations, was the first to resign. Brexit minister Steve Baker followed, and Boris Johnson a day later.

Brexit had drifted from what many Leavers felt comfortable with. While previously onside, many could not reconcile themselves to May’s “180-degree pivot”, as one put it to me. The PM had failed to communicate the choices on offer and had moved away by stealth.


May began 2018 with a reshuffle of her top team. The appointments highlighted her innate caution and value for competency over apparent suitability. Karen Bradley was moved to the Northern Ireland Office despite never having visited the region. Lidington was made the de facto deputy PM.

Two months earlier in November, May overlooked Penny Mordaunt (a rising star with a military hinterland) in favour of Gavin Williamson (who had never spoken at the despatch box) to replace Michael Fallon as defence secretary. Mordaunt would go on to replace Priti Patel at DfID, and succeeded Williamson in the MoD in May of this year.

Meanwhile, May’s approach to the Commons was becoming a particular sore point. The Government had decided not to oppose contentious Opposition Day motions to avoid damaging defeats. This sparked some Labour creativity. The party started to deploy an antiquated procedure called a humble address to get ministers to produce documents. When the Government failed to publish the full Brexit impact assessments last December, the Commons found it in contempt of Parliament.

Nevermore had Theresa May needed parliament on side – she had just struck a Withdrawal Agreement with Brussels. But little to no courting of the necessary MPs had taken place. The DUP were left incandescent at the existence of the backstop and their belief that May had continually ignored their concerns. Scores of Brexiteer Tory MPs and Remainers alike had reconciled themselves to voting against the Government. Labour MPs who could have been won over had free rein to vote down the deal knowing it was going to lose.

May had two choices following the historic 230-vote defeat; to pivot towards other parties in the Commons or try to secure nearly all of the available Tory and DUP votes. She chose the latter, pledging to get further assurances on the backstop that ultimately (and perhaps inevitably) were not forthcoming. This came after the Commons passed the Brady amendment, which called for alternative arrangements to solving the Irish border question in place of the backstop. Senior Tories claim May’s “failure” to put alternative arrangements to the EU in the weeks after the vote sealed her fate.

After a third defeat, she moved towards the Labour party, but by then few believed the talks would come to any fruition, or that she had the political dexterity to do business with Jeremy Corbyn, who too faced the same charge. If May had been serious about securing a Brexit deal with Labour’s approval, the work would have begun sometime earlier.

Perhaps her most controversial intervention came on 20 March, after her deal was defeated for a second time. In a speech inside No10, May pitted MPs against the public by laying the blame for the Brexit impasse squarely at their feet. MPs on all sides had been facing widespread scrutiny during a feverish period in politics. The PM once more showed she was incapable of unifying the House, other than in opposition to her.


May survived a vote of no confidence in December but, in typical fashion, gave an obtuse assurance about her future. Trust in her word had all but dissipated, which, for a prime minister, is terminal. While it is unclear what her successor can do to deal with parliament such as this, it became self-evident that she had run out of road.

Britain needed a unifying prime minister after the divisive referendum, one who could bring people back together. The biggest indictment of May’s premiership is that we are now further apart. Faith in the establishment is at an all-time low. As a result, the choices are whittling down to two extremes; no deal, and revoke.

May’s grand ambitions to tackle the burning injustices remain unfulfilled; plans to address systemic issues in social care remain on the cutting room floor. She joins the legion of Conservative leaders to have their domestic agenda overshadowed by the question of Europe.

No one can doubt her commitment to public service and fortitude in the face of resistance. And far from all the blame for the Brexit quagmire can be laid at her feet.

But May’s true legacy is that her successor will now be dealt an even worse hand than she was on that blustery July day in 2016. 


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