Whilst the nation continues to limp through one of the most unpredictable and turbulent times in our recent political history, one thing has always been a sure bet – Sadiq Khan would seek a second term as the Mayor of London.
It came as no surprise then when he announced his intention to do just that a fortnight ago, triggering the starting gun in the (admittedly long distance) race to City Hall.
With the deadline for completed nominations from would-be Conservative candidates set for Wednesday, and a number high-profile favourites, including Justine Greening, Ed Vaizey and Syed Kamall, already ruling themselves out, who are the faces that are looking most likely to throw their hats into the ring?
James Cleverly – The Bookies’ Choice
Despite appearing initially uninterested, speculation that Cleverly will put his name forward, either of his own volition or thanks to internal pressure from colleagues, is growing. And why wouldn’t he fancy his chances? He’s exactly the sort of young, energetic, social media savvy candidate the Tory Party needs, and thanks to a growing cult of admirers that will back him all the way, he has the support. With previous experience at the Greater London Authority (GLA), and now as the serving Deputy Chairman of the Conservative Party, he knows the London political scene inside out.
The question is: does he want it enough? It’s a long, relentless election slog; to be in with a shot you need to be hungry for the position. Indeed, Cleverly might be asking why risk it, given he’s already moving up the Party pecking order at a rate of knots. Will his strong pro-Brexit stance, in a city that voted heavily for Remain, be a further factor in the decision making process?
Shaun Bailey – The Outside Bet
Although an unknown at the national level, Bailey has been carefully developing his media profile over a number of years, and isn’t afraid to publicly take the fight to the Opposition (just look at how he dispatched Labour’s Emma Dent Coad when her “token ghetto boy” tirade against him emerged last year). Like Cleverly, he has experience of London politics having served as a Londonwide Assembly Member at the GLA since 2016.
However, the Conservative Party need a big name if they are to contend with the PR conglomerate that is Sadiq Khan. It might be an election cycle too early for him.
Kevin Davis – The Early Rider
With just two days to go, Davis is the only Conservative candidate to so far go public with his intention to stand. A former child actor who starred in the West End, until May he served as the Leader of Kingston Council, continuing now as Leader of the Opposition. Crucially, he was also, until recently, London Councils’ Executive Member for Health, so is extremely well connected across London’s local government network.
But, running under the banner “OneLondon Conservatism”, will his campaign have the panache needed to set the contest alight?
Joy Morrissey – The Dark Horse
American-born Morrissey has been a Conservative councillor in Ealing since 2014. The Conservative Party threw everything behind her when she took on Rupa Huq for the Ealing Central and Acton seat in last year’s General Election, and although unsuccessful then, she remains a familiar face within the Party, in part through her work for the Centre for Social Justice. In a wide open field, don’t be surprised to see other rising stars and former parliamentary candidates trying their luck.
Richard Tice – The Long Shot
Predictions that Tice, a property millionaire, would join the race have been doing the rounds for some weeks now, although he’s yet to officially put himself forward. Whilst he reportedly has the backing of some high profile Tory MPs, including Jacob Rees-Mogg and Priti Patel, it’s impossible to see him having any success against Sadiq.
For one, he’s a co-founder (with Arron Banks) of Leave.EU. Hardly a great ticket to stand on, even if he does bring with him a wealth of experience from the business and property worlds.
George Osborne – The Nuclear Option
Say no more.
???? – The Leftfield Option
The Tories have a few celebrity faces in their back pocket. Does Conservative HQ have the mettle, or nous, depending on your point of view, to play this trump card?
If they do, two names stand out: Karren Brady, businesswoman and Tory peer, more recently of Apprentice fame, and James Cracknell, two-time Olympic gold medallist and Conservative Party MEP candidate in 2014. Both are intelligent, respected individuals, and more importantly, could provide a well-known face to rival Sadiq’s cult of personality. The latter was seen in Portcullis House just last week chatting to James Cleverly.
Other Potential Riders
There are many, but look out for former MP for Enfield North, Nick de Bois (who ran Zac’s mayoral campaign two years ago); Munira Mirza, Boris Johnson’s Deputy Mayor for Education and Culture from 2012 to 2016; and Andrew Boff, London Assembly Member who has put his name forward before.
Whoever the Conservatives choose, it’s clear that they will need a politically intelligent candidate with a big personality. A readiness to play Sadiq at his own game, entering the social media fray and embarking on a presidential campaign, is also a must. Whether they can stick to the Party line and stand any chance of success is another debate entirely.
Let the electioneering begin.
Point of Order 
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