“Do you think you’ve made the right decision this time?”
That is the question The Smiths ask in their hit song London. The song continues with the lines “did you see the jealousy in the eyes / Of the ones who had to stay behind?” It is, perhaps, the perfect set of lyrics to describe James Cleverly’s current predicament.
A man who, over the weekend, waved goodbye to his Shadow Cabinet colleagues in the hopes of clawing back the capital for the Tories, one must wonder if he’s constantly asking himself if he made the right decision. The answer, judging by what his Parliamentary colleagues have said, is undoubtedly ‘yes’.
“James would be an AMAZING Mayor” one Shadow Cabinet member texted me, adding that “London deserves a mayor with capability and personality – Cleverly’s the guy.” Another quipped that “James is our best chance” at turning the city blue. Indeed, there is something that is inherently statesmanlike about him.
You could chuck him into one of those low-budget, sophisticated-story-lacking action films as the British Prime Minister and no one would bat an eye. Think London has Fallen or White House Down. Perhaps it’s his time spent in the Army Reserves. Perhaps it’s the knighthood. Perhaps it’s the fact that he has served in two of the four Great Offices of State. Nobody really knows the specific reason, but anyone who looks at him thinks to themselves that this is a bloke that means business. Whether that’s enough to win over the champagne socialists of Hampstead and Highgate is anyone’s guess.
But aside from winning back London, many within the Party also see Cleverly as the antidote to the illness of dwindling coffers. As ConservativeHome reported on recently, the Conservatives raised just shy of £15 million in donations in 2025, a drop of 46.8 per cent from the year before. Cleverly, many argue, can rectify this issue. He will “attract donations” one MP tells me, whilst another adds that his “name recognition” will “attract donors.”
Whether he wins the keys to City Hall is really beside the point, however. He may well secure the Tory nomination, but in doing so he may well be laying the groundwork for a possible leadership campaign far into the future. Whilst those close to him reject that such a trajectory is in his mind, it is far from an outlandish prediction. Stepping away from the Shadow Cabinet, developing and refining the ‘Cleverly image’, amassing a series of donors – whatever his team says, they’d have to accept that it is the perfect concoction for a post-Kemi leadership bid.
And it’s a path well trodden too.
Boris Johnson used the position as a springboard into Cabinet, and Sadiq Khan used it as a means to attract national attention, albeit only taking the final leap back into Parliament via the Lords. Even our Andy made the jump from Mayor of Greater Manchester to PM. But whilst Cleverly may not possess the theatrics of Johnson nor the limitless love for Oasis of Burnham, City Hall offers him a very real opportunity to go further – to prove that he is competent, a trait which is so lacking in modern-day politics.
Being in the Shadow Cabinet is useful, yes, but ultimately he is overshadowed by those higher up the food chain. Despite slowly eking up the League Table, going from +48.6 to +52.5, he still falls well behind the likes of Coutinho, Timothy and Philp. Stepping away from the hubbub of it all provides him the perfect opportunity to refine his personal image.
He would, were he successful in his campaign, go from shadowing Angela Rayner to governing one of the biggest cities in the world. Four years spent building relationships and proving to the British public what he can do when he is handed the reins of power. A litmus test of governance, if you will.
This does all, of course, rest on the question: is Cleverly able to actually win?
He may well have to do battle on the left, jostling with Dawn ‘I adore Corbyn’ Butler, or Sir Sadiq Khan who has remained quiet on whether he’ll run for election yet again. On his right, he would be forced to have it out with Reform’s Laila Cunningham, a woman whose recent social media spree has seen her become an epileptics’ worst nightmare. Whoever the runners and riders may be, Cleverly’s route to City Hall is by no means guaranteed.
The project is undoubtedly a risk.
London has shifted from a city that could be decided by a coin flip to one that has leaned more heavily towards Labour. But with the Greens splitting the progressive vote, the Tories surviving May’s local elections in some parts of the capital, alongside the complexities and opportunities of the Supplementary Vote system, there is a set of scenarios that provides Cleverly with the chance to secure victory.
Yet, whether he is successful or not, Cleverly has achieved something rather substantial, for he has made himself interesting again.
He is no longer just that guy in a suit who talks about housing and planning regulation. He is James. To be a real person in modern politics is a difficult task, but Cleverly has given himself the perfect opportunity to do just that.
Everyone knows that Badenoch will remain in place until the next election. No one is bonkers enough to challenge her. People admire her no-nonsense, Thatcher-esque attitude. And, in recognising this, Cleverly has positioned himself really rather well. He has stepped off the Shadow Cabinet stage where the spotlight only shines on the lead actor and into an arena where he can show himself off to the world.
It is difficult to imagine a better apprenticeship for someone who might be harbouring ambitions of challenging for the leadership in a post-Kemi world. Almost everyone is in agreement that Cleverly is the right person for the candidacy. That’s by no means an endorsement, but rather a recognition of the state of play.
London-based heavyweights like that of Susan Hall have already bent the knee, and Tory grandees have been quick to fly the Cleverly flag. Such bountiful support may provide a false sense of comfort, however. The former Foreign Secretary should seek out a contest. There are at least two others who are known to be thinking of running: Festus Akinbusoye and Alex Challoner, both of whom have written for this site.
But, the thing is, nobody is entirely comfortable with a coronation anymore.
People want some type of choice – a different box to put their X in. One needs only look at the recent coronation of the King In the North to see that waltzing into the nomination would be a misstep. This is, after all, the first time since Boris that the Tories have put forward a big beast for the position, but that shouldn’t dissuade other people from running. Competition is a healthy thing – a Conservative thing.
For you see, the story here is not whether Cleverly is the right person for the job, nor is it whether he can win the keys to City Hall. It is how Cleverly uses the political vehicle that is this contest, then the race and, if successful, the London Mayoralty to shape his political agenda. As one former PM once said, “if the ball came loose from the back of a scrum” he wouldn’t say no to a challenge.
The Smiths asked whether the right decision has been made. One suspects Cleverly knows what the answer is.