His critics say he’s a ruthless menace who will ensure that he finishes what he started and ram Brexit through by Oct. 31, come what may. His mercurial style has reminded observers of not only Rasputin, but also ousted Trump adviser Stephen K. Bannon and Cartman from “South Park.”
Johnson is arguably the most divisive British prime minister since Margaret Thatcher. Many observers thought that, once in office, he might tack to a more moderate position, but his choice of Cummings as his chief strategist quickly signaled the opposite: The public could expect more polarizing behavior, not less, and the vow to steer Britain out of the E.U. by Halloween, “do or die,” was anything but Johnsonian bluster.
Cummings is unconventional. He wears T-shirts and sneakers to work, loathes many lawmakers and doesn’t kowtow to authority. He retweets personal criticisms. In 2014, he said in a speech that the idea of a permanent civil service was one for the “history books.”
His gadfly image was cemented in the HBO film “Brexit: The Uncivil War,” in which Benedict Cumberbatch played him as a socially awkward but strategically brilliant campaign organizer who used data-driven tactics to help his side prevail against the odds.
Placing a combative strategist with a winning track record at the heart of the government has led to speculation that Johnson could be gearing up for an early general election.
“He is there to help Boris Johnson win the next election and to navigate the route through to Brexit as quickly, efficiently and brutally, if necessary, as possible,” said Steven Fielding, a political historian at the University of Nottingham.
Fielding also noted that Cummings, like Bannon, sees himself as someone who can tap into “real, working-class voters … the so-called left behind.”
“In some sense, there is a broad comparison with someone like Steve Bannon,” he said. “He wants to drag everything back to year zero.”
But analysts also note there are many differences between the two.
“I imagine Cummings would see Bannon as being quite crude and being quite a politician, and I imagine Bannon would see Cummings as a policy wonk who is fixated with detail and data algorithms and the latest innovation in Silicon Valley,” said Matthew Goodwin, a professor of politics at the University of Kent.
Stuart Wheeler, a political donor who was one of those who called Cummings in the summer of 2015 and urged him to lead a pro-Brexit campaign, said that Cummings is “absolutely a power behind the throne” who will ensure that Johnson delivers Brexit.
“He has tremendous determination and energy and a willingness to upset anybody, no matter how important,” he said.
Cummings may be abrasive, but he has loyal supporters. Several of the people The Washington Post spoke to about him declined to give their names but nonetheless emphasized that they liked Cummings and found him to be fiercely intelligent and an engaging listener.
In “All Out War,” a book about the 2016 E.U. referendum, Tim Shipman writes of Cummings: “If no other special adviser sparked such loathing, none generated the same levels of loyalty either.”
Despite his high profile, Cummings doesn’t give interviews. A Downing Street press officer said that The Post could submit questions but that Cummings would be bound by the special adviser “code,” meaning he wouldn’t be able to answer them.
But with all eyes on Brexit, pundits are examining Cummings’s own words for insight into how he might shape Johnson’s thinking about the how and when Britain will quit the E.U. That includes combing through his Twitter account and voluminous posts on his blog, some of which run to tens of thousands of words.
The picture that emerges is a complex one. Sometimes, Cummings takes surprising positions on Brexit. He appears to favor, for example, a second vote on the issue, for a simple reason: He thinks he could nail a second win.
Elsewhere he strays into sprawling discussions of technology, philosophy and futurism. In some posts, he seems to praise the way autocratic societies such as China can get things done at a rate that Western democracies cannot.
“China erects skyscrapers in weeks while Parliament delays Heathrow expansion for over a decade,” he wrote in 2017, referring to London’s largest airport.
He has also offered candid — and sometimes confounding — reflections on Twitter.
In an exchange of tweets with David Allen Green, a British lawyer and writer who is often critical of Brexit, Cummings appeared to accept that Britain’s exit from the European Union may not necessarily be a good thing. “In some possible branches of the future leaving will be an error,” he wrote.
John McTernan, a journalist with the Financial Times and former adviser to the Blair government, said he met Cummings when the latter was a relative unknown working for the Education Department.
“Dominic is a lightning conductor” who will try to move fast and break things, he said, adding: “Johnson is a swashbuckler, and so is Dominic.”
Cummings studied ancient and modern history at Oxford University, where he impressed professor Robin Lane Fox. Asked by the BBC who was the cleverer student, Cummings or Johnson, Fox said: “Dominic, by a long way … a different class altogether.”
Cummings moved to Russia after university, where he reportedly tried, and failed, to set up an airline. Back in the U.K., he worked on political campaigns before taking up roles as a political adviser.
“I like him a lot — he’s not the ogre he’s been described as,” said one former colleague who worked with him in 2004 on a successful campaign against the establishment of a regional assembly. He said their campaign deployed simple, clear messages and effective visual stunts, such as branding the idea it was opposing as a “white elephant” and then touring the region with an inflatable white elephant.
Cummings grew up in Durham, in northeastern England, the son of an oil rig project manager and a special needs teacher. The former colleague speculated that some people in London might misunderstand him because he’s from the north, “where we are more plain-spoken and less concerned about finessing our language.”
Ralph Woodward, a childhood friend, told The Post that Cummings could be scornful of people who were not as clever as he was and “wouldn’t back down in an argument.” He also stood out for voicing support for Thatcher, then the Conservative leader and a deeply polarizing figure, he said.
Woodward isn’t surprised that Cummings is now one of Johnson’s top advisers.
“He was always bright and single-minded,” he said. “I’m not saying he’s ‘evil’ or a ‘genius,’ but I can see how he could do the Machiavelli stuff behind the scenes and find ways to get his viewpoint across and get actions taken.”