From the file

Halloween 2020 | Leaks, delays, mistakes and recrimination. This Halloween, there was nothing scarier than the British government’s handling of the second lockdown

The overspill

Wednesday 18 November 2020

This year, Halloween wasn’t just for 31 October. The horrors of that day reached into subsequent weeks – and contributed to the departures of two senior advisers


The Halloween headlines were, as Matthew d’Ancona has documented this week, a nightmare for Boris Johnson. News of an impending second national lockdown was emblazoned across both the Times and the Daily Mail – before any official announcement. “People were furious,” says one figure present in Number 10 at the time.

But the nightmare was to continue. Not only did the leak – or whatever it was – bounce Johnson into a second lockdown. It also spotlit the distrust and dysfunction at the heart of the government. The hunt for a culprit – if indeed there really was one – saw various factions turn on each other. Existing enmities boiled over. New ones emerged.

And a couple of weeks later, two of the prime minister’s most senior advisers, Dominic Cummings and Lee Cain, both veterans, like Johnson himself, of the Vote Leave campaign to depart the European Union, had been forced into another departure. They both left Number 10 for what appears to be the last time.

The departure of these aides, following a power tussle with the prime minister’s partner Carrie Symonds and the new Number 10 spokesperson Allegra Stratton, marks a new chapter for Johnson’s government. One on which the jury is still out.

The prime minister’s new press secretary Allegra Stratton arrives at Downing Street

The Halloween headlines were, as Matthew d’Ancona has documented this week, a nightmare for Boris Johnson. News of an impending second national lockdown was emblazoned across both the Times and the Daily Mail – before any official announcement. “People were furious,” says one figure present in Number 10 at the time.

But the nightmare was to continue. Not only did the leak – or whatever it was – bounce Johnson into a second lockdown. It also spotlit the distrust and dysfunction at the heart of the government. The hunt for a culprit – if indeed there really was one – saw various factions turn on each other. Existing enmities boiled over. New ones emerged.

And a couple of weeks later, two of the prime minister’s most senior advisers, Dominic Cummings and Lee Cain, both veterans, like Johnson himself, of the Vote Leave campaign to depart the European Union, had been forced into another departure. They both left Number 10 for what appears to be the last time.

The departure of these aides, following a power tussle with the prime minister’s partner Carrie Symonds and the new Number 10 spokesperson Allegra Stratton, marks a new chapter for Johnson’s government. One on which the jury is still out.

The prime minister’s new press secretary Allegra Stratton arrives at Downing Street

While Cummings and Cain have few true fans in the party, their sympathisers question whether Johnson will be able to function without them. Others are already cracking out the champagne. “All politicians have the ability to just move on from people,” says a government insider.

To assess what impact their departure will have, it’s worth rewinding the clock back not just to the turmoil of Halloween but to the beginning of Johnson’s premiership.

It has suited Johnson, since he entered Number 10 on 24 July 2019, to delegate the dirty work to others. As a consequence, he has been more accurately defined by the people he’s chosen to have around him than by his own words and deeds. Those people were, in large part, the Vote Leave team – and they set the tone.

The first 16 months of Johnson’s premiership were extremely combative: think of the prorogation of Parliament over Brexit, the sacking of Conservative MPs who wouldn’t toe the line, and blithe dismissals of international law and regulations. Though the prorogation was judged unlawful by the Supreme Court,  he and his Vote Leave supporters appeared to have the last laugh. In December, they secured an undoubted triumph  by achieving the largest Conservative majority in a general election since Margaret Thatcher. Having destroyed Jeremy Corbyn and conquered Labour’s “Red Wall”, Cummings & Co. looked untouchable

Boris Johnson returns to Number 10 after his election victory

Yet, in the past six months, to an extent that was unforeseeable on the night of that election victory, the terrain has become hugely more difficult. A global pandemic threw the Johnson team’s plans off course, lost them support among MPs and the public, and saw Cummings become Public Enemy No.1 for travelling from London to Durham during lockdown. The politics that triumphed in the referendum and the election were not much of a help for to the fiendishly complex problems posed by coronavirus.

But – to scroll back – few had predicted such prominence for Vote Leave at the time of Johnson’s leadership victory in July 2019. Plenty of his supporters at the time had presumed he would surround himself with a range of talents and listen to diverging opinions. It’s what he had done, after all, during his eight years as mayor of London.

Even fewer foresaw Cummings’ unique prominence and power. During the Tory-Lib Dem coalition years, he had been an adviser to Michael Gove, then education secretary, and the pair had remained close. Indeed, during the 2019 leadership contest, it was Gove, not Johnson, who was quizzed about Cummings and his prospective role – many Conservatives were concerned that a successful campaign for the former would mean a big job in government for the latter. Even the party’s Brexiteer MPs feared this outcome; Cummings had been contemptous of their efforts during the referendum battle.

No one had thought to ask Johnson. At that point, he and Cummings weren’t believed to have a strong personal relationship. In fact, the incoming prime minister had long believed that he needed the maverick adviser’s singular blend of aggression, intellect and theatricality to get Brexit over the line and beat Labour.

Dominic Cummings, dressed as Dominic Cummings

All became clear in July 2019, when Johnson entered Number 10, and Cummings sauntered up in a grey t-shirt and jeans. It is an understatement to say that he stuck out among all the men in suits. “[Johnson] had pulled the wool over our eyes,” reflects one Tory MP.

Lee Cain was a slightly different matter. He had first worked with Johnson in the Brexit referendum campaign, where he was by no means the most important figure at Vote Leave – Cummings and the campaign’s director of communications Paul Stephenson, a former government special adviser who is now a partner at public affairs company Hanbury, were the dominant personalities. But he learnt the ropes there and impressed enough to win a role as special adviser when Johnson became foreign secretary in 2016.

The strength of their bond increased after Johnson quit the Foreign Office over Theresa May’s Brexit strategy  and returned to the backbenches. They sat together in a pokey office in parliament, assigned to them by party whips, and they were an odd couple: an Old Etonian classicist and a state school scouser. At that time, in any case, a lot of Tory MPs had written Johnson off as just another pretender to the top job who had missed his chance. 

That time – described by some, as Johnson and Cain’s “Porridge days,” in reference to the prison sitcom – established a relationship of deep trust. “They’ve always seemed very jovial together,” says a former colleague. “You can’t underestimate the bond they forged on the backbenches – it is a very bizarre thing that you are suddenly in this poxy office, you have no power whatsoever, few friends and only each other for company.”

Sticking with Johnson paid off for Cain. He – along with other allies – helped guide him through those wilderness months to a successful leadership bid. Initially, it was lonely work. There was still a view that Johnson, while popular with the Conservative party’s grassroots, would struggle in the parliamentary stage of the contest in which Tory MPs have their say..

“Once it was clear he had [parliamentary] backing, the mood changed,” says a figure who helped on the campaign. “We went from spending our time trying to court support to everyone wanting to write op-eds about Boris for leader to try and ensure they got a look-in later down the line.”

In November 2020, Lee Cain becomes the story

Cain’s loyalty saw him rewarded with the most senior communications job in Number 10, from where he helped to preside over a reunion of the Vote Leave team – not just Cummings, but also advisers such as Oliver “Sonic” Lewis.

Power was quickly centralised. Cummings made sure that he didn’t have to answer to anyone other than the prime minister. Some in the building even questioned whether he answered to Johnson.

“[Johnson] knew delivering Brexit was crucial to his survival and thought the only person who could turn things around from where Theresa May had left them was Dom,” says one adviser.

The outcome? Those drastic tactics: from prorogation to a purge of uncooperative Conservative MPs. “What people often forget about these people is that they are pirates,” says a Downing Street source. “They’re not traditional Tories. They are happy to burn down institutions and break conventions with little thought to the long-term consequences.”

There were also changes that were welcomed. After years of drift under Theresa May, Cummings and Cain were credited – at least in the beginning – for bringing purpose to government. “When [Cummings] became de facto chief of staff, huge clarity was brought to government. He was so much better than Barwell [Theresa May’s Chief of Staff],” says a government aide from the time.

Cain shook up media strategy with some changes that are expected to stay in place. He reinstated the weekly all-media-spads meeting, meaning that aides had to come up with story ideas and pitch them to a room.

He also tried to move the emphasis away from simply feeding the 24-hour news machine to doing things more on the government’s terms. Some of this came from removing the middle man: a “people’s PMQs” in which members of the public could ask questions of Johnson. Some of it from simplifying existing arrangements: now only one minister does the round of Sunday morning news shows. “Things like that have brought clarity of message,” says a former colleague of Cain’s.

But Vote Leave’s Number 10 did have sharp edges. Some in employment at the time describe it as a reign of terror. The five-figure settlement handed to Sonia Khan – the special adviser frogmarched out of Downing Street under Cummings’ orders – is the most extreme example, but many complain of rough treatment. A particularly memorable meeting after Khan’s departure saw Cummings tell remaining aides: “If you don’t like how I run things, there’s the door. Fuck off.”

“I think he was fucking mad, to be honest,” says a one adviser from the time.

Staff also complained there was an impenetrable hierarchy. “If you were in Vote Leave, you could do what you want. If you weren’t, you’d get in trouble for things the others could do.” But even this broke down near the end. The Vote Leave group became strained, with some members demoted – or just departing.

The idea now gaining traction in Westminster is that the departure of Cummings, Cain and their allies will herald a more cuddly era of Conservatism. New aides will steer away from their combative approach.

But what about the common factor? Boris Johnson. After all, he was in charge when many of the problems were occurring. “This is what Boris Johnson does,” says a Conservative MP. “He shapeshifts when he needs to.”

The thinking among some MPs is that the times are changing. That the victory of Joe Biden in the US presidential election marks a new era – one in which the abrasive tactics of this group are out of whack. That populist governments all around the world are on the way out. This is what has allowed Johnson to break away from figures on whom he had once so heavily relied.

Some MPs suggest that Johnson has always been a liberal Conservative – he was just thrown off course. When I chaired the One Nation hustings during the Tory leadership contest, Johnson went on at length about his commitment to progressive values. He said asking him to pick one item from a list – a list that included the United Kingdom, Environmental Stewardship, and Law & Human Rights – was like asking a tigress to pick between their cubs.

Of course, many of the MPs in the room that day were left disappointed by the events that followed, with several being kicked out of the Conservative party for failing to toe the line on Brexit. They will not forget Johnson’s actions.

Boris Johnson in front of the infamous Brexit bus

This is why – even if Johnson is about to reconfigure, or at least try on a new suit for size – the story of Vote Leave’s ascendancy and takeover of Number 10 is as relevant as ever. It demonstrates how this Prime Minister can adapt and shake things off that would stick on others. “It’s not that he doesn’t believe in the things he’s been saying,” says one insider of the prime minister. “It’s that there is more than one side to him.”

Hence, despite the toxic briefing war currently playing out between the warring factions of Number 10, seasoned Westminster veterans believe that Cain, maybe even Cummings, could still return. “If [former adviser] Damian McBride can come back to the Labour party, Lee Cain can come back to the Tory party,” one predicts.

The Vote Leave team’s time as the dominant force in Number 10 has come to an end. But the saga may be yet to reach its conclusion.

Katy Balls is the deputy political editor of The Spectator.

Just what is a special adviser, anyway?

Read an Opinion piece by Laura Round, a former special adviser herself, on what the role entails – and what it could mean after Cummings and Cain.

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The PM’s press conference to announce a second lockdown was a dreadful affair. We asked a former Number 10 speechwriter to produce a better, alternative script

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