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20 November 2019updated 12 Oct 2023 11:02am

Theresa May’s might have beens

Evaluating Theresa May’s premiership.

By Steve Richards

Theresa May was an unlikely prime minister. She was shy, introverted, publicly awkward, mistrustful of colleagues and without much sense of ideological purpose. Most modern prime ministers are partly performers, fascinated by the political stage, their role on it and the wider context. May was indifferent to performance and not especially curious about what else was happening around her.

Her indifference, however, was not the same as lacking ego or ambition. One of the revelations in this extensive account of her premiership is the degree to which May ached to retain the thorny crown. She enjoyed what Anthony Seldon describes as the “trappings of power”, not least her regular sessions with the Queen. For May leadership was harrowing and yet she clung to the post resolutely. She was like the diner in the Woody Allen joke: “The food in this restaurant is terrible and the portions are so small.” May was tormented by her elevated role and she wanted more of it.

Her weaknesses make her leadership more interesting rather than less. They raise questions about where power lies in No 10, the relationship between prime minister, advisers, civil servants, cabinet ministers and parliament. Before the calamitous 2017 general election, May’s two chiefs of staff, Nick Timothy and Fiona Hill, had more power than any previous senior advisers including Alastair Campbell and Dominic Cummings. This is because May did not know what to do with power and they did.

Timothy in particular was innovative and ideologically daring. On economic matters he was to the left of David Cameron and George Osborne. In articulating his ideas, or being the public voice for them, May was potentially more of a moderniser than her prime ministerial predecessor, who was an orthodox Thatcherite. Her early leadership was punctuated with insightful proclamations about the good that government can do and generalised explanations about why markets do not always work.

 There were, though, two very big obstacles. May might have spoken what Timothy had written for her, but the level of her personal commitment was limited when faced with the policy implications. She was the cautious incrementalist urging her party to move closer to the radical ideas of Ed Miliband. The caution prevailed. There was a bigger obstacle. Brexit dwarfed all that followed.

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On this, Timothy, the committed Brexiteer in the tiny May entourage, was far less constructive than he was with his social and economic agenda. As Seldon shows, May had virtually no time to prepare for No 10 or Brexit. After another wacky Conservative leadership contest in 2016, she found herself in Downing Street within weeks of Cameron announcing he was going. On the advice of Timothy, and neurotically aware that she had been a Remainer, May moved towards a hard Brexit without fully realising that was what she was doing. Within months she had established impossible red lines and triggered Article 50.

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She did so without consulting widely. Quite often ministers in the newly established Brexit department did not know what was going on, let alone the wider government. As she set off on her course she knew little about the implications of the Irish Question or much else about the consequences of Brexit.

The election in 2017 transformed the context in which she led and, crucially, how she was perceived. Before the election only those who worked closely with her were aware of her fragilities: indeed, cabinet ministers, who were soon to make her life a hell, were in subservient awe at first. May’s poll ratings were stratospheric. There was a widely held assumption that she would be prime minister for years. Instead, the campaign that was supposed to reinforce her hold on power exposed her weaknesses. Behind the scenes she was indecisive and unable to decide on lines of command. The campaign was about her and she could not rise to the presidential focus. After she lost her party’s tiny majority she was doomed, dependent on the DUP and a fickle group of scheming ministers, and without Timothy and Hill to guide her through the storms.

May clung on for more than another two years, losing three votes in the Commons on her Brexit deal and suffering a bucket-load of ministerial resignations. After each daunting setback she carried on almost as if nothing had happened. At times she behaved like a leader separate from the storms rather than the one being swept aside by them. Inevitably, they got her in the end.

The external circumstances would have tested a political titan. May was no titan. To take one example, the never-ending resignations during her leadership were not unavoidable. The former Labour prime minister James Callaghan, a deeply unfashionable figure, suffered no cabinet resignations over policy throughout his turbulent tenure that lasted from 1976 to 1979, more or less the same amount of time as May’s. He knew how to manage colleagues even though his restive ministers were more challenging figures compared with the shallow egotists that walked away from May’s team.

Most fundamental of all, May misread the political rhythms. She chose to act weakly when she was politically strong and then had no choice other than to be assertively strong when she was pathetically weak. Before the election, when she was walking on water, she meekly told her party what it wanted to hear; that they could have their cake and eat it. She would end free movement, leave the customs union and single market, step aside from the European Court of Justice, and yet maintain the same convenient arrangements with the EU as now. She was hailing a fantasy.

Then, this spring, she began to do what she had the power to bring about at the beginning. She reached out to a Labour leadership desperate to move on from Brexit and made the case for compromise. She did so when her internal opponents were ready to remove her.

The unwritten British constitution demands that Anthony Seldon writes accounts of PMs soon after they leave office. While other authors might struggle for access to every adviser, minister and senior civil servant, Seldon secures interviews with virtually all of them. A lot of them agree to be identified as the interviewee, rather than an anonymous source. Understanding the complexities of leadership, and no doubt grateful for the access, Seldon seeks to be sympathetic to his subjects. But even he struggles with May. This is his most critical account of a prime minister so far. He notes approvingly her sense of duty and her deep seriousness, but his hero is the late Jeremy Heywood, the most senior civil servant who worked tirelessly and deftly to keep the haphazard regime together.

Heywood functioned behind the scenes. Where the elected May also succeeded in hiding behind the curtains, Seldon draws them open and casts disturbing light on a prime minister who too often preferred to rule in the comfort of darkness.

Steve Richards’s most recent book is “The Prime Ministers: Reflections on Leadership from Wilson to May” (Atlantic). He appears at Cambridge Literary Festival, run in association with the New Statesman, on 1 December

May at 10
Anthony Seldon with Raymond Newell
Biteback, 706pp, £25