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Lessons from the court of Henry VIII for America's CEOs

The Straits Times

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October 27, 2025

Wolf Hall, on precarious times in the Tudor court, offers a useful guide to survival in the age of Trump.

- Adrian Wooldridge

Every era of business history brings an appropriate big book. In the 2000s, it was Tom Friedman’s The World Is Flat (2005). In the 1980s, it was Michael Porter’s Competitive Strategy (1980). Today it is not a business book but a novel - Hilary Mantel’s great trilogy about English statesman and lawyer Thomas Cromwell, Wolf Hall.

Since US President Donald Trump’s reelection, America’s chief executives have, to all intents and purposes, put a crown on Mr Trump’s head and turned themselves into courtiers. He’s Henry VIII in a golf buggy, and they are so many slavish bag carriers.

Not content with all the fawning and mega-donations, CEOs have even started to dress to please Mr Trump, unconsciously following the advice of the greatest how-to-book on courtly life, Baldassare Castiglione’s The Book Of The Courtier (1528), which recommends that, before anything else, courtiers must make sure that they look the part.

Most conspicuously, tech executives have abandoned their trademark hoodies and sweats in favour of real-estate mogul-style suits and ties and bling. Meta CEO Mark Zuckerberg, who praises Mr Trump as a “badass”, has taken to wearing a US$895,000 (S$1.16 million) Greubel Forsey watch.

There are compelling reasons for such behaviour. The US government can make or break businesses, either by allocating billion-dollar contracts or, more negatively, by raising tariffs or passing troublesome regulations. The government can also put businesspeople through the nightmare of an Internal Revenue Service audit. Mr Zuckerberg even has to worry about Mr Trump’s threat that he could “spend the rest of his life in prison” for sponsoring voter turnout programmes in 2020.

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