There aren't many obscure political strategists who get to be played in a film by Benedict Cumberbatch. But perhaps that’s because there aren’t many like Dominic Cummings, the man now running Boris Johnson’s ‘do or die’ mission to deliver Brexit by 31 October – as they put it, ‘come what may’.
He’s barely been in Number 10 a fortnight, but is already ruffling feathers, whether lurking in the background of official photographs in a scruffy T-shirt or summoning ministerial aides to pre-breakfast lectures about the evils of leaking to journalists. In a world of Tory stuffed suits, Cummings is invariably the one shambling around with his shirt hanging open, quoting the black civil rights activist Malcolm X’s line about succeeding ‘by any means necessary’.
To some, Johnson’s new special adviser is a creative genius, with a knack for solving problems in ways that sound crazy but work – never more so than during the Brexit referendum, when as head of the official Leave campaign, he helped pull off a life-changing victory against the odds. (The Channel Four film Brexit: The Uncivil War, starring Cumberbatch, tells the story of how he did it.) But to others, Cummings is a loose cannon who doesn’t much care what get broken in pursuit of his pet ideas; a ‘career psychopath’ as the former PM David Cameron only half-jokingly put it. One previous colleague joked last week that he’s had so many texts from panicking special advisers – or SpAds – about how to handle Cummings that he should set up shop as a full-time SpAd whisperer.
Where both camps agree, however, is that Dominic Cummings knows how to get things done in a hurry – even if sometimes, it’s best not to ask how. And for a Prime Minister with less than three months to deliver Brexit or watch his government go up in flames, that’s priceless. ‘He does it by ruthless prioritisation. There are things he’s interested in, which he’ll spend an awful lot of time on, and there are things he will just let go,’ says one source, who worked closely with Cummings during his time as special adviser to then education secretary Michael Gove. ‘One of the things about Dom, and he’ll slightly cringe about this, is he’s capable of inspiring great loyalty from those who work with him. He has very, very good judgement.'
And while Cummings may be impatient, driven, and intensely focused, he isn’t, the source adds, deaf to reason: ‘I don’t think I’ve ever seen him lose his temper, except for comedic effect. And it is possible to win an argument with Dom, he’ll totally listen.’ While he prides himself on challenging the establishment, Dominic Cummings’s CV is conventional. Private school in his native Durham, history degree at Oxford, and marriage to the Spectator deputy editor (and baronet’s daughter) Mary Wakefield. He first hit Tory MPs’ radar in his late twenties, while working for the Eurosceptic pressure group Business for Sterling, and in 2002, the then Tory party leader, Iain Duncan Smith, made the decision to hire him as director of strategy.
It wasn’t a happy pairing. Cummings lasted eight months before quitting in frustration, complaining that the shadow cabinet just weren’t ready to listen to his radical ideas. (He’s never held back on his views about senior Tories, portraying David Cameron as lightweight, Iain Duncan Smith as incompetent, and the former Brexit secretary David Davis as ‘thick as mince’. If he ever does fall out with Boris Johnson, we’re likely to hear about it.) But he impressed some Tory modernisers, and in 2007, Gove hired him as an adviser. Cummings served through three years of opposition and four of coalition government before quitting amid growing tensions with Number 10, which reportedly saw him as being out of control.
This time it looked as if his political career really was over. Cummings went to ground and began spending his days reading up on everything from Russian novels to genetics and mathematical theory, while writing incredibly long, exasperated blogs about everything he thought was wrong with Westminster. But friends say it was this time out that let him step back and see the political shifts others were missing; insights he used effectively when he was unexpectedly hired to run Vote Leave. Cummings prides himself on not following the herd, and before accepting Johnson’s job offer, is said to have demanded the freedom to do things his way.
‘The key thing for Dom will be: is the principal willing to take his advice? If not, I think his feeling will be, “Well, you’re not listening; what’s the point of me being here?”’ says an ex-colleague. ‘He’s not remotely interested in the trappings of power or being in the front car of the motorcade. There are many other subjects he finds as interesting as politics, so he’d be perfectly capable of walking away.’
Or, to put it another way, if the decision to hire one of Westminster’s most unpredictable talents ends in tears, they won’t necessarily be his.