Who is responsible for Labour’s recent woes? For some Conservatives, the answer is obvious – Sheridan Westlake. He is that rarest of beasts: an effective Tory operator who has served every leader since John Major. Flaxen-haired with an impish grin, he is spoken of by colleagues as part myth, part political mastermind. Yet ask him what he does, and the stock answer is modest: ‘I simply do the photocopying.’
‘He just likes getting up in the morning and kicking socialists. He’s in it for the love of the game’
The resignation of Angela Rayner last month is widely attributed within Conservative Campaign Headquarters (CCHQ) to an effective campaign by the party’s attack team. Westlake, a 30-year veteran, is part of the five-man squad who worked on exposing Rayner’s tax affairs. His experience of a similar story involving John Prescott was a factor in the party pursuing lines of inquiry to keep the story alive over the summer.
What began as a simple written question in April slowly turned up the pressure on the former deputy PM. One longtime Westminster ally compares Westlake’s tenacious harrying of Labour to ‘the federal prosecutors who brought down Al Capone. He followed the plumbing and the wiring – then he acted on it’. One admiring peer adds: ‘He puts the bullet in the gun, and he likes to see someone else fire it.’
The Tories were forced to downsize these resources after last year’s landslide defeat, but are now replenishing them. Some 17 staff sit in the press and research department teams, with Westlake helping to train up the new intake. Having held seemingly most titles in CCHQ at different points, his latest one – ‘promoter’ – ensures it is Westlake’s name that is emblazoned across the attack ads churned out by the party machine.
His political life began at the Oxford Union – the ‘only institution he loves more than the party’, according to a friend. Cherwell archives chart both his remorseless politicking and others’ endless fascination with his hairstyle. His Tory contemporaries included Liz Truss, whose hen do he attended, and Chris Philp. When Westlake was press officer at the Oxford Union, O.J. Simpson came to speak. Press snaps of the grinning Westlake next to Simpson were a precursor to a lifetime beside the great and the not-so-good. During the 1990s and 2000s, he worked his way up the CCHQ ladder. His distinctive name – which one grandee described as sounding like ‘a chain of cheap motels’ – sparked inevitable Patricia Routledge quotes from Keeping Up Appearances. But Westlake impressed other aides with his Tigger-like enthusiasm and encyclopaedic memory. ‘He knows the politics in any policy,’ says one. A former MP recalls loudly moaning about the state of opposition research in a meeting with Westlake. Four hours later, an email with more than 200 suggested questions arrived in their inbox.
In the coalition government, Westlake worked on local government under Eric Pickles: his relentless focus was on bins, flags and public toilets. Liberal Democrats were exasperated by what they saw as his Nimbyism; Tories respected his instinct for retail issues. In 2015, Pickles told his leaving party: ‘It has been a pleasure working for Sheridan.’ Thereafter followed nine years in No. 10 under the premierships of David Cameron, Theresa May, Boris Johnson, Liz Truss and Rishi Sunak.
Like a good cricketer, he knows how to block – and when he can hit a six. ‘Sheridan was the one who actually read the ministerial write-arounds,’ says one aide. ‘He had an oppositional mindset,’ says another. ‘He took that from opposition and simply applied it to the civil service to stop a lot of their stuff.’ His roving brief meant he could help unlock problems too. When the Greensill inquiry published Cameron’s texts, it was no surprise that he had asked Westlake about ‘a looming problem you can help solve’.
Among his talents is the ability to craft the perfect parliamentary question. One peer says that learning from Westlake was ‘like listening to a medieval knight describing his kit’. Countless stories are attributed to him: ‘Now a tax on treehouses!’ was one memorable Daily Express splash following a little-noticed question in the Lords in 2008. Much of his talent lies in reading vast 300-page reports pumped out by officialdom, and spotting the killer detail buried halfway through. ‘He just likes getting up in the morning and kicking socialists,’ says an ex-colleague. ‘He’s in it for the love of the game.’
Loyalty is another reason for his endurance. In a party renowned for regicide, Westlake avoids factional fights, declining to work on leadership campaigns. Colleagues have long regarded him as their ‘shop steward’. Former special advisors praise him for helping in the interminable Whitehall wars and contract disputes with officials. ‘We don’t get HR like they do,’ explains one. He has long organised the Tories’ Thursday night drinks, dispensing wisdom and chinking glasses over a ‘cheeky pint’ of Amstel or Foster’s.
In an ever faster-paced political world, Westlake’s institutional memory counts more than ever. Younger Tories appreciate how he will ‘dive into his notebook and find something from Blair in 2002 which created a precedent’. Older ones praise his ability at keeping up old friendships and providing a strand of continuity between iterations of the Tory party. ‘He’s like Dorian Gray,’ says one. ‘Ageless amid corruption.’
Now back in opposition, Westlake has seen his career go full circle. Fuelled by his favourite Pret tuna sandwiches, he works tirelessly to defend his party and tear down its enemies. As one old colleague puts it: ‘Not everybody can be a Sheridan Westlake. But everybody in government needs a Sheridan Westlake.’
Who is the real Sheridan Westlake? Political editor Tim Shipman joins the Edition podcast to explain why he describes him as ‘the cockroach of Westminster’:
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