The Cameroons resent May – but her conservative convictions are more deeply held than theirs

It is easy to understand Cameron’s frustrations with May. But her convictions have been tested over a long period than his.

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The attack on Theresa May’s conduct in the EU referendum campaign by Craig Oliver, David Cameron’s communications director, reflects badly on the spin doctor. Instead of damaging the new Prime Minister, it has weakened the Cameroon case. Setting aside the selfish timing of his book, Unleashing Demons: the Inside Story of Brexit – which was rushed out to coincide with the party conference season – revisiting the febrile atmosphere of pre-referendum politics works against those who created that political context in the first place.

May’s strategy can be interpreted as genuinely conservative. After all, arguing a case with appropriate fervour – or lack of fervour – is a distinctly conservative tradition. So the current tensions between May’s camp and the Cameroons are subtly revealing. Beneath the resentment, they hint at two different types of conservatism.

The serialised extracts from Oliver’s book give us details of the case against May without telling us much that is new. The Leave campaign nicknamed the former home secretary “Submarine May” for allegedly torpedoing Cameron with her withdrawn and non-committal stance on the EU vote. “Amid the murder and betrayal of the campaign,” Oliver writes, “one figure stayed very still at the centre of it all . . . Now she is the last one standing.”

What is so telling about Oliver’s comments is how flat they sound in the milieu of post-referendum politics. During the campaign I, too, was sceptical of May’s reluctance to come out from the shadows and fight for Remain. Now I feel differently: her judgement has been strengthened by subsequent events, and so has her career. Perhaps the ghastly referendum debate, as distinct from the gravity of the decision, merited lofty disdain. What Oliver calls May’s “stonewalling” now comes across not just as self-interest but also as the appropriate response to a toxic campaign.

It is easy to understand Cameron’s frustrations with May. In cricket, I have seen on countless occasions how a vice-captain or a senior player can undermine his captain merely by doing nothing to help.

It is also true, however, that it is tempting (and dangerous) for any leader to confuse the personal battles they have picked that will define their career and reputation with what matters to their colleagues and team-mates. It is a symptom of a captain who is nearing the end when he sees anything less than 100 per cent support as casual betrayal. Leadership must always balance the competing needs of loyalty and authenticity. Sometimes, allowing people to go their own way holds greater rewards than demanding that they toe the line.

Cameron’s problems in “handling” May during the referendum debate accidentally demonstrated how he might have done things differently. Had he been less partisan and less personally attached to “winning”, her nuanced position would not have been such a problem for him.

When Oliver’s book was serialised, I was rereading Michael Oakeshott’s celebrated philosophical essay “On Being Conservative”, published 60 years ago. It made me think more deeply about the referendum debate than a gossipy, blow-by-blow insider account could. According to Oakeshott, a true conservative “understands it to be the business of a government not to inflame passion . . . but to inject into the activities of already too passionate men an ingredient of moderation; to restrain, to deflate, to pacify and to reconcile”. By that logic, if Cameron had presented himself as the referendum’s referee (albeit a slightly biased one) rather than its principal player – more Harold Macmillan, less George Osborne – he could have simultaneously improved Remain’s chances of winning and his own prospects of surviving a defeat.

In Cameron’s defence, Oakeshottian conservatism – the disposition “to indicate assent or dissent, not in absolute, but in graduated terms” – is not easily adapted to modern political strategy, which encourages making a “clear” case and then smashing the point over and over again with a sledgehammer. Even the most complex positions have to be argued with total conviction, as though the counter-argument were absurd.

Graduated argument, or conceding any ground to the opposition, is ridiculed as fence-sitting, or a “lack of conviction”. Yet the opposite can be true, even for someone in high office. The best thinkers stand out not only for reaching good judgements, but also for arriving at those positions with an appropriate degree of conviction. Reducing all political issues to “for” and “against” is like marking every exam script as “Pass” or “Fail”, with no grades along the spectrum.

One of the fascinations of the transfer of power from Cameron to May has been how the change has illuminated that the deepest qualities of conservatism are not ideological. The question “Who is more conservative: Cameron or May?” is not answered satisfactorily by a long list of policy positions.

Conservatism is always about personality, mood and disposition. Cameron’s partisan position during the referendum increasingly looks unconservative in its prescriptiveness and lack of scepticism. There will certainly be bumps in the road ahead, but Britain has not imploded after voting for Brexit, and it was never going to.

Would Cameron have fought a more sceptical and avuncular campaign had he been older? Oakeshott argues that “politics is an activity unsuited to the young, not on account of their vices but on account of what I at least consider to be their virtues”. The appeal of pragmatic leaders is stronger when their pragmatism has been fully lived, rather than merely adopted in the absence of an ideology. May is almost exactly ten years older than Cameron. We are now sensing that her conservative convictions, tested over a longer period, are more deeply held.

Ed Smith is a journalist and author, most recently of Luck. He is a former professional cricketer and played for both Middlesex and England.

This article appears in the 29 September 2016 issue of the New Statesman, May’s new Tories