The masterpieces that helped Henry VIII pick wives

But such access was not without risk. Holbein arrived in England as the first of many court dramas was unfolding. The King’s forbidden love for Anne Boleyn, and Rome’s opposition to a divorce from Katherine of Aragon, was about to trigger a radical shift in the power dynamic between monarch and Church, and catapult the country into the Reformation. Those whose opinions were at odds with the King’s risked being tried for treason. “Holbein would have, very early on, witnessed some of Henry’s brutal treatments of dissenters,” says Moyle.

Survival at this turbulent time meant keeping your eyes and ears open, and your mouth firmly closed. “One of the reasons why he was so successful, is he must have been the embodiment of discretion,” says Moyle. “I suspect he did overhear an awful lot, and perhaps people unburdened themselves to him, a bit like a hairdresser.”

Navigating a treacherous terrain

Holbein deftly navigated the court’s shifting sands, moving stealthily between Protestant reformers and Catholics as they fell in and out of favour. He painted Sir Thomas More and the Duke of Norfolk (Thomas Howard), explains Moyle, as well as their arch-rival Thomas Cromwell – all three eventually locked up in Henry’s gruesome Tower of London, while Holbein slipped quietly onto the next client, ever-conscious, no doubt, of the family he had to feed back in Basel, and later also in London.

Holbein’s work required a dancing act between verisimilitude and diplomacy. At times, he appears to flatter his sitters. A comparison of the preparatory drawing and the finished portrait of Sir Henry Guildford reveals that Holbein elongated Guildford’s face, making Guildford appear, says Heard, “a much more authoritative, much more magnificent and a much more powerful figure”.

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