The path to power is often easier than the journey of maintaining it. Whether in Renaissance Italy or modern democracies, new rulers face a common set of challenges: how to consolidate their authority, manage opposition, and transform temporary advantage into lasting control. Machiavelli's insights into these challenges remain remarkably relevant, even as the nature of political power has evolved from direct territorial conquest to more subtle forms of political and economic dominance.
A new ruling party, much like Machiavelli's prince, must navigate between different power centers, manage popular expectations, and neutralize potential threats. The initial momentum of victory—whether through election, revolution, or conquest—quickly gives way to the complex reality of governance. The new ruler must decide how to treat the old guard: whether to co-opt them, marginalize them, or destroy them entirely. They must balance the demands of their supporters with the practical necessities of rule, and transform their campaign promises into actionable policies without alienating crucial constituencies.
Most challenging of all is the question of how to handle those who remember—and pine for—the old order. This is where Machiavelli's advice becomes particularly pointed and controversial. His solution to dealing with people who have known freedom is stark: either destroy them completely or find a way to make them forget what they've lost. While modern political systems rarely resort to such extreme measures, the underlying challenge remains: how does a new power establish legitimacy in the face of resistance from those who preferred the previous regime?
Commentary on Chapters 3-6
But in republics there is greater vitality,a more hatred, and a stronger desire for revenge; they do not forget, indeed cannot forget, their lost liberties. Therefore, the surest way is to destroy them or else go to live there.
One of Machiavelli's shocking claims is that a free people are better destroyed than ruled. If you conquer a republican city used to living in freedom and managed by its own citizens, you may win the battle, but they will always remember their life of freedom and want to set themselves against you. Your only recourse, according to Machiavelli, is to simply raze the city to the ground. You don't have to scatter the citizens to the winds, but when it's rebuilt, it's rebuilt on your terms.
There's a certain kind of conqueror who shows dominance by razing his opponents' cities to the ground and killing anyone who resists - The Mongols and Timur come to mind - Machiavelli might cite them approvingly as conquerors who brook no dissent.
Given the difficulties encountered in holding a newly conquered territory, the following facts may cause surprise. Alexander the Great became master of Asia within a few years and, not long afterwards, died. It might have been expected that the whole region would then rebel; nevertheless, Alexander’s successors held it, and had to contend with no other difficulties than those arising from their own ambitious schemes.
Earlier Machiavelli talked about how a non-hereditary prince is more likely to come to power because of luck than because of talent and energy. Nevertheless, he says if a talented prince comes to power he's more likely to keep it. Machiavelli is very interested in both the question of how to acquire power and what are the qualities it takes to retain it. He continues along those lines by asking what are the kind of principalities that are easier to conquer and what are the principalities that are easier to retain under your rule once you conquer it.
And because for a private citizen to become ruler presupposes that he is either able or lucky, it might seem that one or other of these would, to some degree, mitigate many of the difficulties. Nevertheless, rulers maintain themselves better if they owe little to luck.
The question that’s on all our lips: is Trump a beneficiary of luck or a man of destiny? I don’t have a good answer. His first win surely had an element of luck to it, but anyone who comes back to power after losing (and being a sore loser) and all those legal troubles must have some talent. I just don’t know what that talent is - it’s clearly not persuading me.
Here he has an interesting point to make that principality in which power is distributed, where the king is not a supreme authority but rather has barons and others who are under the king but nevertheless have independent sources of power, versus the Turkish Sultanate in which the Sultan is a supreme authority and no one else has independent power. Machiavelli thinks that it's harder to conquer the Turkish kingdom, but once you've conquered, you're more likely to be able to retain it because all you have to do is to get rid of the ruling family and put yourself in place.
Contemporary Reflections
One of the amazing things about the modern nation state is how unlikely it is that a disgruntled opposition figure or a local leader invites a foreign power to invade you. Wars are rarer now than they used to be, but even when they happen, they are between nation states, but it's hard to imagine a modern nation state being physically conquered by an opponent who is assisted by a traitor within. Don't get me wrong: regime change happens all the time with outside support. It happens within countries for sure - I can't count the number of times the BJP (or the Congress in its heyday) has broken the opposition by bribing a disgruntled or opportunistic second in command. It also happens across national boundaries - the United States has backed its favored leaders in other countries, sometimes electorally, and sometimes with a coup, but it's still different from physical conquest.
Machiavelli's insights into power, conquest, and political control remain startlingly relevant in our contemporary world, even as the mechanics of political domination have evolved beyond physical conquest. While modern nations no longer face the threat of cities being razed to the ground by invading armies, the fundamental dynamics of power that Machiavelli described—the tension between freedom and control, the role of luck versus skill in political success, and the challenges of maintaining newly acquired power—continue to shape global politics.
Today's political landscape offers fascinating parallels to Machiavelli's observations. Consider how modern authoritarian leaders must grapple with populations that, like Machiavelli's republican citizens, have tasted freedom and resist its loss. We see this in Hong Kong's resistance to Beijing's control, in Russian and Ukrainian opposition to Putin's regime, and in the ongoing struggles for democracy worldwide. Israel’s treatment of Gaza is closest to the city destroying methods advocated by Machiavelli. If you leave that exception aside, the methods of control have become more sophisticated: instead of destroying cities, modern rulers employ surveillance technology, information control, and economic leverage to maintain their grip on power.
Here’s Henry Farrell talking about how Trump is destroying the infrastructure of US economic dominance
Machiavelli's analysis of different power structures—from distributed authority to centralized control—finds new expression in today's varied political systems. His insights about the relationship between luck and skill in political success remain particularly relevant, as we witness political figures like Trump, whose rise to power combines elements of both fortune and ability, much like the princes Machiavelli analyzed. Moreover, his observations about the role of internal discord in enabling external intervention resonate in an era where foreign influence operations and cyber warfare have replaced traditional conquest as tools of international power politics.
The Pauper's Perspective
What's fascinating about reading Machiavelli from below rather than above is how his insights about republican resistance become a blueprint for civic resilience. When he warns princes about the impossibility of subjugating people who remember freedom, he's inadvertently identifying the core strength of democratic movements. It's rather like an immune system – once you've developed antibodies to authoritarianism, they're remarkably persistent.
But we have to be more sophisticated about how this applies today. Modern autocrats have evolved beyond the crude methods Machiavelli described. Instead of razing cities, they're more likely to deploy what Evgeny Morozov would call "digital authoritarianism" – surveillance capitalism meets political control. The contemporary equivalent of destroying a republican city might be flooding it with disinformation until civic trust collapses.
I find his analysis of mixed principalities particularly relevant to our moment. Think about how modern power structures operate: they don't need to maintain territorial control so much as they need to manage systems of influence. When Machiavelli talks about the difficulty of holding conquered territories, he's really describing what we might call the friction coefficient of power – the energy required to maintain control over a population that remembers alternative possibilities.
This brings us to his distinction between fortune and virtue in leadership. The contemporary parallel is striking: movements that arise purely from momentary outrage or viral social media campaigns tend to fizzle, while those built on sustained organizing and deep community relationships have staying power. It's rather like the difference between day trading and building a sustainable business.
What's particularly interesting is how his advice about maintaining power can be inverted for democratic purposes. When Machiavelli suggests that princes should either destroy republican cities or inhabit them, he's acknowledging that power requires presence. For us, this translates into the need for robust civil society institutions – what Antonio Gramsci would later call the war of position rather than the war of maneuver.
And that’s why authoritarians go after civil society institutions the minute they can.
On Memory and Freedom
The modern equivalent of his armed citizenry isn't just about physical force – it's about creating resilient networks of mutual support that can resist both economic and political coercion. In essence, where Machiavelli's prince sought to consolidate control, our task is to distribute it; where he advised destroying democratic memory, we need to actively cultivate it. The art of the pauper, if you will, lies in making centralized control impossible while building horizontal structures of democratic power.
The relationship between memory and freedom is particularly crucial in our digital age. When Machiavelli spoke of people who "cannot forget their lost liberties," he was describing something fundamental about human nature that takes on new urgency today. Our collective memory of freedom – whether it's the memory of a free press, independent courts, or the simple ability to speak truth to power – acts as a kind of social DNA that carries the blueprint for democracy across generations.
Ultimately, the purpose of fake news isn’t to circulate falsehood. It is to break down trust and to destroy collective memory. Digital media is particularly pernicious since it’s more than capable of infusing false memories at scale.
The key is that these memories need to be living rather than merely preserved. They must be practiced, debated, and renewed through actual democratic participation. When people regularly exercise their democratic muscles – through local organizing, participatory budgeting, or collective decision-making – they create not just memories but embodied knowledge of what freedom feels like in practice.
Lovely read sir! Some paragraphs made me laugh as well, but more importantly, most others, made me think, deeply. That's what the best writings are capable of 😊