When I meet Cleo Watson at the Corinthia Hotel in Whitehall, she’s feeling bruised: Sarah Vine has just published a column in the Daily Mail whose headline cautions all men to “be wary of the wiles of doe-eyed lovelies” like her. “My husband said, ‘I didn’t know I should beware—it’s too late for me!’” In her former job, as an aide to both Boris Johnson and Theresa May, that kind of headline would be a disaster. “As a special adviser, any media attention is basically bad news,” she says. “Exposure is scary.”
This new exposure comes from the fact that Watson has just written a book: Whips, a novel set in SW1, filled with sex and political scandals. I ask if some of the scenes—including one involving a very public tryst at Chequers between a minister and his colleague’s wife—could ever happen. “I think for really weird ardent politicos that is a bucket list thing,” she laughs. Some plotlines proved to be a bit too realistic: a fictional MP who watched porn in the chamber was cut after Neil Parish, the Conservative MP for Tiverton & Honiton, ended up quitting over the same offence in spring 2022.
One character seems particularly familiar: Percy Cross, an upper-class, bumbling, ex-Tory prime minister who has had numerous affairs, resigned in disgrace and now “makes his living off poorly researched hagiographies of his favourite historical figures and GQ, Playboy and Telegraph columns.” Watson protests that not all the similarities with a certain former prime minister are intentional. “When I wrote that character, that was when it looked like we’d have several more years of Boris—not like he’d be running around doing nothing.”
Watson, who grew up in Hay-on-Wye and studied politics and economics at Cardiff, interned for Barack Obama’s 2012 re-election campaign, before joining Vote Leave in 2015 after being recruited by Dominic Cummings. She then worked for Theresa May in Number 10 while May struggled to control her fractured party. “There was genuinely a sense that you might be here for three years, you might work three weeks, like they could collapse at any point,” Watson says. Although May’s lack of majority meant constant difficult compromises, she found her easy to deal with: “she did all her work. She was really nice—we almost exclusively talked about shoes and clothes.”
After May left office, Cummings invited Watson to work for Boris Johnson in Downing Street, where she became his co-deputy chief of staff. Adjusting to the new prime minister’s lack of discipline was difficult. “It was extremely annoying, because you are the prime minister and there’s just certain stuff you need to do.” She found it was easiest to “nanny” Johnson to get him to focus. “It was the equivalent of a mum thinking, ‘Oh, I’ll hand him my iPad,’ because she’s trying to have a nice lunch with her friend.”
“It was just what he responded to. It’s weird, and I’m not sure it makes a particularly good prime minister but I think it complemented my skillset.” During the pandemic, especially while Johnson was recovering from his own bout of Covid, getting him to focus on the task at hand became more difficult. I ask what Watson would say. “‘I know, I know,’” she coos. “‘You can lie down on the sofa and read the Spectator, but first you have to do these three things in your box because they’re massively important.’” She laughs. “God, it sounds so much worse when you say it out loud.”
Watson has a certain sympathy for Johnson. “He’d just gambled everything [in the 2019 election] and was settling down ready to have quite a nice time. There was a sense of, ‘why does everything happen to me? This isn’t my fault.’” She believes the competitive, privileged environment he grew up in has affected his psyche. When discussing the other Old Etonians in his party, Johnson would reference where they had finished in the school year. “Like, how old are you?”
The full chaos of the Johnson administration only became apparent to most people after the Partygate scandal emerged. Watson had been involved: in June 2020, on Carrie Symonds’s request, she organised a gathering with food and alcohol for a 20-minute celebration on Johnson’s birthday. “In retrospect, obviously fucking stupid,” she says. “Everyone worked together, it was just before the next meeting, it was in the day. It seemed like a much greyer area than some things.” The celebration resulted in Johnson, Symonds, Rishi Sunak and Watson all being fined in April last year. She found it “deeply uncomfortable” to explain it to her non-political friends.
She blames Johnson for attempting to cover Partygate up. “I suspect if he’d done a real, ‘mea culpa, it happened on my watch, the culture is set from the top, I’m in charge, massive misjudgement…’ I wonder whether people would have got over it,” she says. It has tainted her experience of working there. “If you say I worked in Number 10 in that time—this is how I feel anyway—it feels embarrassing and shameful.”
In November 2020, Cummings left following a reported power struggle with Symonds. For the next two weeks, Watson didn’t see Johnson, who was self-isolating. Then, in the Cabinet room, he said he wasn’t sure it was working anymore, and told her she reminded him of an “ugly old lamp” left over at the end of a marriage. “I still can’t quite tell if I quit or I was fired,” she says. “He did immediately bombard me with messages saying, ‘I can’t believe this has happened, this is so sad. Come back and work on Cop[26].’”
While preparing for Cop26 in Number 9 Downing Street, she worked on Whips. She’s now planning a sequel—one that takes in the Labour party as well as the Conservatives. She doubts she will return to her old job. “I’m the kind of special adviser that I hope we don’t need any more,” she says, adding that she doubts Sunak and Keir Starmer need to be cajoled into doing their jobs. But she doesn’t want to regret her time with Johnson. “We should have seen what he was about a little bit better,” she says. “But I’m sure tonnes of people will think, ‘we’ve known this for years.’ It’s hard to be too frustrated—he was true to form.”
