As news has spread in U.K. political circles that Steve Hilton will be the Republican candidate for governor of California — with an outside chance of taking power in one of the United States’ biggest and wealthiest states — reactions among friends and former colleagues, including former government ministers who spoke to The Standard, have ranged from admiration to something close to bewilderment.

Those who worked with the shaven-headed “blue sky” thinker in the Conservative Party from the early 1990s and, 20 years later, watched him operate as director of strategy for then-Prime Minister David Cameron, are impressed that a former Briton could have made such strides in U.S. politics since leaving the U.K. in 2012. 

But many also roll their eyes. The Hilton they knew was an environmentally friendly, liberal Conservative who dragged Cameron to the Arctic to film him driving a pack of huskies through the snow and made environmentalism central to Tory rebranding. The idea that he is now a Donald Trump ally and MAGA standard bearer strikes many of them as perplexing and, to some, a quite shocking.

As Hilton, the man who helped shaped modern British conservatism, emerges as a political force in California, his old colleagues back home are using the moment to ask a question they never quite resolved when they worked with him: Was Steve Hilton a political genius or a radical, restless thinker more interested in blowing up the system than in building another to replace it?

It is not just his ideological journey that has turned heads in the U.K. Many also remain skeptical that someone so memorably mercurial during his time in British politics could successfully govern a U.S. state more than one and a half times the area of the U.K. with a population almost three-fifths its size and an economy that is the fourth largest in the world.

“He’s a gadfly rather than a serious operator,” Sir Vince Cable told The Standard. Cable is the former Business secretary in the Conservative-Liberal Democrat coalition government from 2010 to 2015, when Hilton worked in No. 10 Downing St.

Those who watched him at the time remember Hilton as a restless mind, a scruffily dressed disruptor who could light up a room with a concept and then lose interest the moment it required patience, compromise, or bureaucratic navigation to execute. 

Guto Harri, who became a good friend of Hilton and dealt with him extensively while serving as communications director for Boris Johnson when Johnson was mayor of London (before Johnson became prime minister), cannot quite picture Hilton, the radical thinker, becoming a hands-on governor.

“He always seemed to regard the execution of actual policy as rather pedestrian, rather beneath him, rather like he regarded ever wearing a suit in Downing Street as not for him. I can’t see it really.”

Hilton, however, is still held in awe, even by those in the U.K. who find it impossible to imagine him running California. His legacy as a radical Tory strategist is impressive. Almost single-handedly, he masterminded the branding revolution that transformed the image of the Conservatives from that of a “nasty party (opens in new tab)” into one able to take power in coalition with the Liberal Democrats in 2010 after 13 years of Labour government.

A few of his former colleagues even believe that if, by some outside chance, he wins California, he might turn out to be a different Steve Hilton once the executive tools are fully and exclusively under his control.

Ameet Gill, a former speechwriter for Cameron, can see Hilton succeeding. Gill says Hilton found it difficult to make the switch from being in opposition, where he was hugely powerful and close to Cameron, to government, where he was part of a much larger team and more distant from his friend and boss.

“Power dissipates when you get into government. You are not as close to the principal as you were in opposition,” Gill said. “I think Steve’s frustration was more with David Cameron than the civil service. If he is elected and gains control of the California government apparatus, he could get things done.”

Another friend and former colleague was similarly hopeful.

“If he is shrewd enough to appoint the right people on the delivery side, I think he will be a success. His biggest concern should be that he is impatient. Impatience is a good thing in some ways, but he has to realize that change will take time.”

The British commentator and journalist Ian Birrell, who covered Hilton during his U.K. political career, spent three days with him on his campaign last year, when, as Birrell puts it, most people thought his campaign was “a joke.”

“I was surprised to see his ease as a campaigner, even in rural California farmlands. He clearly enjoys all the glad-handing and speeches, and people seemed to like him, while I was repeatedly told his British accent makes him sound smart.”

Hilton and Cameron first began working together as young advisers in the Conservative Central Office in the early 1990s. One friend of both men told The Standard, “They were always incredibly fond of each other, very close indeed. But it fell apart quite quickly in government.”

Cameron’s bitterness toward Hilton comes across powerfully in his 2019 memoir, “For the Record,” in which he describes his former friend as a “disruptive force” in government and his ideas as “one part brilliant to several parts bonkers.”

• Steve Hilton (probably) can’t win California. That doesn’t mean he’ll be a loser

• Hilton advances to November governor’s race to face Becerra

“I knew that to be successful in government you have to play the game. And he had no interest in playing the game, just tipping it over and throwing the pieces all over the floor.”

Hilton left Downing Street to join his tech entrepreneur wife, Rachel Whetstone, in the United States in March 2012. He wrote Cameron a valedictory note detailing his discontent with what he saw as the prime minister’s lack of ambition. Their relationship worsened further in 2016 when Hilton returned to the U.K. to campaign for Brexit, an outcome he would have known could destroy Cameron’s premiership, as indeed it did.

Cameron resigned the morning after U.K. voters chose to leave the European Union by a 52% to 48% margin in a referendum he had called to settle the question of EU membership within his own, often anti-EU, party. It settled the issue, but not in the way he had hoped. The result was an early tremor of the populist wave that would soon reshape politics across the Western world.

One of Hilton’s central — but ultimately unsuccessful — ideas for Cameron’s Conservative government, and one he had hoped would come to define liberal Cameronism, was what he called the “Big Society.” It was designed to get “real people,” as opposed to politicians and civil servants, involved in running things, shifting what he saw as the bloated state out of the way. Cameron, however, was never convinced, and the idea faded away without being implemented.

Andrew Cooper, now Lord Cooper, was Cameron’s pollster both when the Conservatives were in opposition and later in government, where he worked alongside Hilton. He recalls the difficulties he had trying to sell Hilton’s Big Society vision.

Have thoughts on this story?

“He never really succeeded in fleshing out what it actually meant,” Cooper told The Standard. “When we tested it on people, they would look at us as if we were mad because basically what it meant, if it meant anything, was, ‘We want the state to pull back from running things.’”

Cooper added: “Libraries were one idea. People would say, ‘But I don’t want to run a library. I’m busy. I’m working hard, I have a family. I don’t know how to run a library.’ It was all a bit faddish, dreamy, and conceptual. In my job, I found it frustrating because I was trying to face up to where the country was and how voters viewed the party, and he didn’t really want to engage with that.”

As well as the Big Society, Hilton pushed other, even less practical schemes, such as cutting the civil service by 70%. He subsequently told friends he had actually wanted to reduce it by 90%. Hilton hated elites and bureaucracies, with the European Union representing the quintessence of both in his mind.

Lord Darroch, the former U.K. ambassador to the EU and later to Washington, remembers a call from a colleague in No. 10 asking whether he would host Hilton for a day in Brussels to try to change his anti-EU views.

“He hates the EU. Could you persuade him that it’s not so bad?” the official asked.

Darroch said: “The visit was a spectacular failure. I suspect Hilton hated every moment. His face was fixed with a look of utter contempt.”

Damian Green, the Immigration minister in the early Cameron government, remembers having to tell Hilton that one of his ideas for dealing with immigration would have been all very well — were it not clearly illegal.

Hilton protested.

“Steve just said to me, ‘I don’t like being told I can’t do things!’ which I couldn’t help likening to the reaction of a spoiled toddler,” Green said.

Hilton’s determination to break the mold of British politics expressed itself in other eccentric and more personal ways. He insisted on walking around Downing Street barefoot, wearing dirty T-shirts and scruffy shorts, leaving the normally serene head of the civil service, Jeremy Heywood, in a state of mounting fury.

The former Conservative MP and minister Rory Stewart recalls in his memoir “Politics on the Edge” visiting Hilton in Downing Street, where the chief of “blue sky” thinking was dressed in a tight V-neck T-shirt and no shoes. A frenetic high-energy Hilton told him that he wanted to “blow up the Foreign Office” and get rid of all the ambassadors, before he quickly moved on to discussing technology and the European Union and then lay on the floor staring at a map saying: “Fuck me, look how big Scotland is. This is just fucking mad, man.”

All of this, unsurprisingly, led Hilton to become the subject of media satire. Most memorably, he was the inspiration for the character Stewart Pearson in the popular BBC satire “The Thick of It,” which dealt with the chaotic and dysfunctional nature of modern government. Created by Armando Iannucci, who later made “Veep” for HBO, the series ran from 2005 to 2012.

In one memorable episode (opens in new tab), his character arranges an offsite “Think Camp” to better explore some blue sky thoughts. Pearson (Hilton) sits cross-legged in a circle on the floor across from a government minister who is clearly not a fan of his radical musings. Pearson suggests “doing away with computers.” The government minister shouts back, “That is fucking mental” — only to revise his opinion when he realizes he would no longer get any of Pearson’s emails.

After arriving in the United States, Hilton took on a role as a Fox News host. He became a U.S. citizen in 2021. In his campaign for governor, true to previous form, he is promising to slash taxes and red tape. His mantra is that he will make the state “Cal-affordable” through economic reforms.

Hilton is the son of Hungarian immigrants who sought asylum in the U.K. and insists that, despite supporting Trump on immigration, he will stand with legal immigrants and help them climb the ladder to success like everyone else.

As for Hilton’s political shift from liberal conservatism to Trumpism, those friends who remain most loyal say that while it may look like betrayal and opportunism, there are threads of consistency stretching back to his early days.

“Steve’s political root beliefs are all about accountability for ordinary people and empowering them, dislike of bureaucracy, ending red tape, pushing elites aside, blowing up the old ways of doing things,” one former colleague noted. “It is not a million miles from elements of the Trump way of thinking.”

Birrell, the British journalist, challenged Hilton on his political transformation when he accompanied him on the campaign trail last year. “He argued to me that his views have not changed in his weird journey from architect of greener, softer conservatism in Britain to MAGA flag-bearer conservatism,” Birrell said, adding that he found Hilton’s explanations “sometimes, but not always convincing.”

Andrew Cooper, with memories of his chaotic days dealing with Hilton in Downing Street still vivid, is more contemptuous, describing Hilton’s embrace of Trump — and Trump’s embrace of Hilton — as “completely extraordinary” and perhaps evidence of something broader.

“My view was that he was always fundamentally not a very serious person and that he had a very flirtatious view about politics.”

Everyone in the U.K. who knows and worked with Hilton is aware that wherever he goes and whatever he does he will not go unnoticed. The U.K. is witnessing the rise of the right-wing Reform Party under Nigel Farage, and another former colleague wondered whether Hilton’s political journey could take another turn, were he to lose in November. “I can’t help thinking,” said the ex-colleague, a senior figure from the days of the Cameron government, “that he might end up embracing Reform and Farage. If Reform took power there could be a role for him in the U.S. as, say, as Farage’s ambassador to Washington? I am pretty sure the race to be governor of California won’t be the end of the Hilton story.” 

Toby Helm is a former political editor of The Observer (UK), 2009-2025. Previously he worked as a political journalist and foreign correspondent for the Daily Telegraph in London.