In 2014, a year and a half before he finally lost his head, David Cameron threw a rave at Chequers. The Prime Minister danced, in an open necked shirt, to a DJ known as ‘Hard Bitch’, with film stars and a foul-mouthed TV presenter, on a dance floor set up in the Great Hall. A portrait of King Charles I stared down at him and if Cameron had met the glance of this melancholy van Dyck, he might have paused to consider how the mighty fall. Later on – when hestood accused of ‘acts of self-indulgence bordering on decadence’ – perhaps he wished he had. But the party raged on until 3am, as civil war brewed outside the doors.

A year on from the shock Brexit victory, half the nation is still violently unhappy at having to leave the EU. These are people who know how to ski, watch the BBC on iPlayer and agonise on Twitter – while the other half hates their guts. The Establishment is at war with the Peasants Who Revolted. There are fresh skirmishes by the day between those who drink Premier Cru and those who prefer lager. It’s Waitrose v. Lidl, ‘sofa’ v. ‘settee’, avocado on toast v. HP sauce, Eton v. the bog-standard comprehensive, Range Rover Woman v. White Van Man. Or to encapsulate the two sides in all their manifold complexity: Cavaliers v. Roundheads.

This terminology is borrowed from the English Civil War – the bloodiest conflict in British history. War broke out in 1642 when King Charles I declared war on his own parliament. ‘Cavalier’ derives from the Spanish word ‘Caballeros’ meaning ‘horsemen’ and applied to the aristocrats who fought for Charles. The ‘Roundheads’ (whose severe haircuts made their heads look round) fought for Parliament.

King Charles was keen on Europe (in the form of his very French queen), introduced unpopular taxes, manipulated the honours system, alienated the Scots, chillaxed too much and kept picking fights he either lost or failed to win decisively. As Theresa May might put it, ‘remind you of anybody?’

Eventually, Parliament chopped Charles’s head off. Some Cavaliers – like today’s City banks – fled England altogether. Others sulked – such as the ex-Chancellor George Osborne, who sits on the back benches, in an attitude of despair, ‘waiting for it all to go tits-up for Theresa,’ as one of his confidantes assures me it most definitely will.

Many Cavaliers felt frightened that the killing of the King would bring about the End of Days – much as the Governor of the Bank of England, Mark Carney, predicts the economic Apocalypse.
The Cavaliers should have made mincemeat of the Roundheads. They had all the money, power and privilege on their side. But they were out of touch with the common people and had no idea how ferocious the Roundheads would prove in battle. Oliver Cromwell, like Theresa May, hadn’t started the war; but rose swiftly from MP to leader of a cavalry regiment to commander of Parliament’s New Model Army. He relied heavily on his allies’ messianic zeal, much as May depends on her special advisors Nick Timothy and Fiona Hill, whose ruthlessness helped her survive the Home Office, the graveyard of so many political careers.

Cromwell’s Roundheads were sober and serious and about as much fun as May’s grim-faced Chancellor, Philip Hammond, appears to be. Their rallying cry – for parliamentary sovereignty and individual liberty – is echoed by May’s Brexit ministers, David Davis and Liam Fox.

For a Cavalier to socialise with a Roundhead was unconscionable – and vice versa: the same is true today. Even on Tinder, ordinarily a sexual free-for-all, millennials often state if they were Remain or Leave so they don’t accidentally sleep with the enemy. In real life, it can be hard to spot your natural compadres. Expensive dress is not a reliable indicator. Our Roundhead PM, for instance, has been photographed in £995 gold leather trousers, and owns dozens of pairs of kitten heels. Haircuts are a more reliable indicator. Cavaliers were proud of their ringlets and today’s equivalent pride themselves on their floppy manes (both Boris Johnson and Donald Trump, with their blond hair soufflés, reveal themselves as Cavaliers pretending to be Roundheads for electoral gain).

But while Cavaliers are ordinarily feckless, spendthrift and the life and the soul of the party -right now they’re in a state of shock. Whilst Roundheads, who tend to be dour, humourless and somewhat unimaginative are, all of a sudden, tremendously pleased with themselves. The clearest signal as to whether you’re speaking to a Cavalier or Roundhead is whether your interlocutor appears astonished and petrified – or smug and self-satisfied. If the former, then you are talking to a Cavalier, unable to believe in this sudden reversal of fortune; if the latter, you’ve unearthed a Roundhead rejoicing in Little England.

The difference between the two factions is most neatly encapsulated in the lives of their leaders: Cameron and May. The son of a millionaire, Cameron, as we know, was educated at Eton (and still demands that the crust is cut off his toast). At Oxford, he joined the Bullingdon Club. According to his arch-enemy Lord Ashcroft, it is possible he violated a pig’s head at a party. After getting his First, he swanked off into the Conservative Party Research Department, and then became a special advisor, before abandoning politics – very temporarily – for a highly paid job at Carlton Television where he learned the dark arts of PR. At every point in his career, he had his path smoothed by significant phone calls to significant people. His rise from stockbroker’s son to Prime Minister was inexorable.

Theresa May, by contrast, thrust herself towards greatness. The only child of a vicar, she won a place at Oxford thanks to her grammar school education. At Oxford, there are no wild tales of Theresa; when I contacted the press office of her biographer Rosa Prince in the hope of fresh revelations I was told, quite cheerfully, that there weren’t any. By all accounts, she worked hard and – in the words of one Old Wykehamist – felt fortunate ‘to meet the sort of people she never would have met had she not gone to Oxford’ – including her future husband, Philip May.

While Cameron is famous for his Notting Hill cabal, May made a few friends at Oxford who remain allies, like the Work and Pensions Secretary, Damian Green, and the Minister for Foreign & Commonwealth Affairs, Alan Duncan, but she’s never been a networker. At the same age as Dave was when he drank Bolly in the Bullingdon, Theresa was listening to visiting Tory speakers at the Union. (Certainly, she liked to go back and speak there herself. The Tory grandee Jonathan Aitken vividly recalls her wiping the floor with the hate preacher Abu Hamza in a debate some years before she deported him.) After leaving Oxford, May went to work for the Bank of England – so she has held down a ‘real job.’ She first went head to head with David Cameron in 1994, when they both sought selection for the safe Tory seat of Ashford, and were both beaten – by Damian Green.

The defining Cavalier characteristic is a love of the good life. Crises often hit Westminster during the summer and Cameron’s MPs would complain that the only way to get hold of him was ‘to hire a Cornish ice-cream van and set up on the beach.’ In the summer of 2013, a humanitarian crisis was escalating in Syria. There was no time for chillaxing. And yet that July, an image surfaced of Cameron, on Instagram, fast asleep on a four poster bed with a Red Box by his feet. Earlier in the day, he’d apparently left the same box unattended on a train while he nipped off to the buffet car. That August, Cameron was hoping to persuade President Obama into military intervention but he failed to put in the necessary effort to win over parliament. When the vote was held in the House of Commons, the government was defeated on a matter of war – for the first time since 1782.

But Cameron simply couldn’t resist taking time out to socialise. He loved nothing better than hanging out with his fellow Cavaliers – and has now swanned off into the sunset with them. On New Year’s Eve, David and Samantha Cameron decamped to Burford Priory, the home of the multi-millionairess Elisabeth Murdoch, daughter of Rupert, who threw a party that involved ‘an entire theatrical set, complete with revolving floors, an entrance made of flowers, cocktails on tap and roving graffiti artists spray painting the toilets mid-party with guests’ names,’ and reputedly cost half a million pounds. ‘Nobody is not a celebrity,’ Jonathan Aitken told me. ‘[Cameron] is in his element.’ The Camerons’ love of partying in a circle that included the disgraced former News of the World editor, Rebekah Brooks – alarmed even their Cavalier friends; Lord Ashcroft’s controversial book ‘Call Me Dave’ labelled them ‘the Chipping Snorton’ set.

May, however, barely socialises at all. She is always at work: even on Christmas Day, when she doesn’t eat her dinner until she’s gone to the old folk’s home in Maidenhead to raise a glass of sherry with the residents. Even at the Conservative Party Conference, ‘when most politicians were out courting newspaper editors,’ the LBC radio host Iain Dale recalls, ‘Theresa May was in Cafe Rouge, having dinner with her husband.’ Aitken recalls inviting May, then Home Secretary,
to visit a charity in Maidenhead called Blue Sky, a rehabilitation scheme for ex-offenders, during the New Year recess in 2011.

‘The date suited nobody except those who had to be there,’ he recalls. ‘Everyone else was off skiing or on holiday and it was the filthiest day I can remember. The wind was blowing and the rain pouring – we might as well have been in a trawler on the North Sea. All she needed to do was stay inside and say a few words but she spent no less than an hour and a half going round talking to ex-cons, asking questions such as ‘how deep is that ditch?’ And I’ve never seen anyone do it better – there was not a scintilla of artificiality about her.’ When I ask Aitken how May compares to that other Tory Roundhead – Mrs. Thatcher – he says it’s too soon to say. ‘On that day, she was almost like the Queen.’

Cavaliers believe above all, that they are born to rule; Roundheads take advantage of insurrection – mounted by furious plebs. The Brexit vote was, in the first place, an act worthy of Charles I himself. Charles believed in the Divine Right of Kings while Cameron seemed to believe he was entitled to premiership. First, he promised a vote, to appease his backbenchers. Then, when he won an unexpected majority at the 2015 election, he rushed into holding the vote even though his most trusted advisor, Chancellor Osborne, advised him very strongly against it. Privately, Cameron assured EU leaders, ‘we’re going to win – maybe 70-30.’

Throughout his entire political career, Cameron behaved like a cocky undergraduate, so sure he’d ace the test, he didn’t bother to cram until the very last moment. And this technique had worked so many times – most nail bitingly in the Scottish referendum. When he lost he resigned in a fit of pique, allegedly demanding of his aides: ‘Why should I have to do the hard shit for someone else, just to hand it over to them on a plate?’

Certainly, ITV’s Robert Peston caught Cameron on camera outside Downing Street ‘humming a Winnie-the-Pooh style hum as he says goodbye to the cares of office.’ While that other Cavalier ex-PM Tony Blair has returned to urge fellow Remainers to ‘rise up in defence of our beliefs’ Cameron has stayed schtum. Had not his wife, Samantha, popped up to give so many interviews to promote her fashion label, Cefinn, one might have assumed he’d come to as sudden an end as Charles I himself.

Theresa May, it must be remembered, did not want to leave the EU – much like Oliver Cromwell had not wanted to start a civil war. She voted Remain and must now do her best to clear up the mess her predecessor created which she is doing with teeth gritted. Of course, she is helped by the fact that she faces no domestic opposition. She has either purged or handicapped her Cavalier rivals – Chancellor Osborne was dispatched with particular brutality while she has stripped her Foreign Secretary, Boris Johnson, of his grace and favour home and two of the key responsibilities of his office – forcing him to share both with Liam Fox and David Davis. But she was equally merciless to her Roundhead opponents – she finished off her old enemy Michael Gove and political insiders claim he’ll never recover.

May – like Cromwell – has also been lucky in some of her battles. Labour is currently in an unelectable state thanks to its leader Jeremy Corbyn (who ought to be martialling the Remain-ing opposition but is, instead, making out like a militant Puritan.) Meanwhile, potential Charles II’s – the Tory Tom Tugendhat, a dashing former British army officer, who some fancy as Cameron’s heir – keeps very quiet on the backbenches and Labour’s great Cavalier pretender, the handsome, voter friendly, Tristram Hunt, has surrendered his parliamentary seat to become director of the V&A. In this context, it is perhaps not surprising that May enjoyed a 17 point lead in the spring polls.

Cavalier forces needed to regroup – and urgently – if Remainers were to exert any sort of influence on May’s Brexit deal. But they are too easily distracted by the finer things in life… Cameron’s disappearance, for instance, is largely to be accounted by his need to make money – he had often complained that he’d paid for his love of politics ‘with a pay cut before I even started.’ On standing down as an MP, and not having to declare his income in the Register of Members’ Interests, he hit the lecture circuit hard. ‘His agent told him he’d be the most wanted speaker in the world,’ a gossip tells me. ‘But only until January 20th – and then Obama would be… So he made a whole bunch of speeches for a lot of money but no publicity. He has to, because he does hang out with this group of very rich people. And money is how you keep score.’

Cameron was one of many Cavaliers who came a cropper during the 2009 expenses scandal. (Despite his private wealth, he claimed more than £80,000 on his second home, plus a £680 bill for clearing wisteria.) Roundheads – including, one doesn’t doubt, Theresa May – were appalled. She was one of the very few MPs to emerge almost utterly unscathed. The Telegraph’s report on her was three un-damning sentences long: stating that she’d claimed £15,000 in mortgage interest to which she was perfectly entitled.

But Cameron’s most blatantly Cavalier act was his dabbling with the honours system. He awarded OBEs both to the woman who put his Chancellor on the 5:2 diet and the stylist who picked out his wife’s clothes. One cannot imagine May doing this: she’s formidably trim and chooses her own outfits. Like one of Cromwell’s Ironsides, she knows her armour is vital. Many have sought to gain insight into her personality by examining her shoes. (As Iain Dale observes, it’s quite incredible that ‘after 19 years she’s still an unknown quantity.’) But far more can be gleaned from the state of her fingers. May is adept, tough and entirely self-sufficient: she never goes to a manicurist because she’s learned to paint her nails immaculately herself.

The perception is that she ‘is very middle class,’ as Dale explains. ‘But – anecdotally – she has an appeal for working class voters that David Cameron never had. He always seemed that little bit slippery. But callers to my show say they trust her. Even Labour voters trust her.’ In fact, May has been far more radical than she is perceived – and so suits the Roundhead masses. It was she (not Cameron) who first urged the party to modernise in 2002, telling the Tories that they were unelectable because voters thought they were the ‘Nasty Party.’ She also came up with the idea for an ‘A’ list of potential MPs because she knew how difficult it was for female and ethnic minority candidates to gain selection for Tory safe seats. She helped host a launch party a fortnight before Cameron became leader. (Steve Hilton, then Cameron’s strategist, said it was the first party he’d attended ‘full of normal people.’)

Even last year, May did not win any plaudits for introducing the law against coercive control – even though it was astonishingly popular, thanks to a controversial domestic abuse storyline on Radio 4’s, The Archers. May may not shout about her feminist credentials but she’s always done her bit for the Sisterhood.
She has, though, now reached a critical moment – and Cromwell’s reign, it must be remembered, was exceptionally brief. May was welcomed into Number 10 because of the reputation she had built as Home Secretary as ‘the safest of safe pair of hands.’ Yet all of a sudden – in January – her right one was grasping the tiny hand of Donald Trump – horrifying pretty much everyone. No one knows what kind of deal she’ll manage to cut with the EU.

Most famous for claiming that ‘Brexit means Brexit’ she is also fond of the phrases ‘negotiations are negotiations’, ‘you will see what we publish when we publish it’ and ‘I gave the answer that I gave.’ Chequers, under May, will never – but never – witness another rave. But this summer it is likely to be used to host something far more ruinous to any Prime Minister’s reputation: a politician who transcends all historical precedent or description – President Donald Trump.