The Prince

Written in 1513 while Machiavelli was out of a job and out of Florence, dedicated to a Medici who probably never read it, and not actually published until after he was dead. The subject is holding onto power, and the reason it still winds people up five centuries later is that he simply declines to ask whether the ruler deserves to have it. Cruelty gets assessed purely on whether it works, and on getting it over with in one go rather than dripping it out. Being feared beats being loved if you can’t manage both, but most importantly never be hated. Keeping your word once it has stopped serving you is treated as a mistake rather than a virtue, though one must always seem honourable. He also reckons about half of everything is luck, and the other half is being ready for when it runs out.

Reading it, I started recognising these tactics in people with power I’ve come across over the years, whether they’d read him or not, and it’s helped me understand how they got their positions, kept them, or lost them. That it still holds up says Old Nick understood the human animal pretty well.