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Sunday, 23 November 2025

The double life of George Downing

Republican, royalist, chaplain, schemer, spy – the builder of Downing Street was a man of multiple identities

No one seems to like George Downing, the “shameless” turncoat of this book’s title, very much – not least his biographer. A spy for Cromwell and a baronet under Charles II, Downing was, Sewell tells us, a “liar, blackmailer, seducer and thief”. His peers called him Judas; Samuel Pepys thought him “a perfidious rogue”, and history has tended “to shoo him into the footnotes like an embarrassing relation”. If anyone knows anything about him, it is for lending his name to Downing Street. In the 1650s, he took a risk on some land just off Whitehall, where he later built four brick houses: numbers 10 and 11 still stand. Famously stingy, he skimped on the mortar.

Sewell makes no apology for an unsympathetic biography and does not attempt to rehabilitate Downing. But he does succeed in bringing him out of the shadows and evoking his “convulsive” times. As it turns out, Downing’s shrewd development of the future home of British prime ministers is one of the least interesting facts about him.

Downing was born in 1623 in Dublin and grew up in London. At the age of 15, he emigrated with his family to Salem, Massachusetts. (His uncle was John Winthrop, leader of the “Great Migration” of English Puritans and governor of Massachusetts Bay Colony settlement.) After excelling as a member of Harvard’s first graduation class, Downing again moved overseas to preach in the Caribbean. He clocked, with approval, the buying of African slaves. When the civil wars hit England, the 22-year-old Downing sailed home and became a chaplain in the New Model Army. He did not sign Charles I’s death warrant, but he rose through the ranks to become Cromwell’s biddable scoutmaster general, rooting out military intelligence of the highest quality.

This is the story of Downing’s “spying and scheming” for the British republic. In Scotland, he infiltrated the Marquis of Argyle’s circle, who were plotting with the future Charles II to overthrow England’s king-killers. Downing maintained his cover as a chaplain, only arousing suspicion when someone noted that he had never once been seen to pray. He posted back ciphered letters to London, favouring word-substitution as his code: Charles was “Robinson”; Cromwell “Mrs Wisdom”. After the royalist-crushing Battle of Dunbar – during which Downing was badly wounded – Cromwell secured Edinburgh Castle thanks to Downing’s smart recruitment of the castle’s governor as an agent. Dispatched abroad as an ambassador, Downing wormed his way into Princess Mary of Orange’s household in the Hague. As the exiled Stuarts hatched plans for uprisings, Downing kept John Thurloe, Cromwell’s spymaster, up to speed. It was dirty, dangerous work and Downing insisted on round-the-clock bodyguards.

His peers called him Judas; Samuel Pepys thought him ‘a perfidious rogue’

When the republic fell apart, following the death of Lord Protector Cromwell and the swift resignation of his son, Richard, Downing switched sides. Exactly when or how is unknown – Sewell offers three possible versions – but, as a restoration of the monarchy looked likely, Downing found a way to offer Charles II a grovelling apology, some valuable secret intelligence, and a promise to serve as long as he could keep his job. Downing’s overture was accepted and he was duly knighted.

Downing was not the only one to trim his sails. His close ally was General George Monck, who used his post as commander of the republic’s forces in Scotland to help facilitate Charles II’s restoration. But, for Sewell, Downing’s “turn” is of a piece with his unscrupulous and ruthless self-interest. Still in the Netherlands, Downing hunted down regicides who were on the run, exempt from the Act of Indemnity and Oblivion. Downing shipped three men responsible for killing Charles home to face their execution, earning himself a baronetcy and pioneering the extrajudicial process of “extraordinary rendition”. But one of the three was Colonel John Okey, whose regiment Downing had once guided as their wartime chaplain. Sewell does not probe his subject’s malice, but he does hint several times at Downing’s formative years in Puritan New England. From this colony of speculators and supposed saints – his dad was a “crook” and the master at Harvard “a deranged and brutal sadist” – Downing emerged “a demon”.

A spy’s life is necessarily obscure, and Sewell cannot always locate Downing. There are no private thoughts, and little is known about his home life. He married into the Howards – one of England’s grandest, Catholic (and mostly royalist) families – but his wife Frances also remains a mystery. The best bits of this book are when we can hear Downing’s voice from his letters, chilling battle reports, or quips in parliament. Sewell does not linger on Downing’s post-Restoration activities, but he had learned from his time in the Netherlands the secrets to Dutch wealth. The tax and credit reforms he introduced in Britain were revolutionary: he increased the country’s revenue by diminishing the power of the monarch.

Downing Street may have been, as Winston Churchill said, “shaky and lightly built”, and yet Sir George played his part in building the modern British state.

Turncoat: Roundhead to Royalist, the Double Life of Cromwell’s Spy by Dennis Sewell is published by Atlantic Books (£25). Order a copy from The Observer Shop for £22.50. Delivery charges may apply

Alice Hunt is author of Republic: Britain’s Revolutionary Decade, 1649-1660 (Faber & Faber)

Painting of George Downing courtesy of Alamy

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