"Close alliances with despots are never safe for free states"

Demosthenes, one of Athens' most significant orators and statesmen, lived in a period defined by the struggle between the autonomy of Greek city-states and the rising power of Philip II of Macedon. His observation draws from keen political insight and the hard-won lessons of Athenian history. By warning against alliances with despots, he underscores the fundamental incompatibility between free, democratic societies and autocratic regimes.

Free states, built on laws, citizen participation, public discourse, and institutional checks, hold values in direct tension with those of despots, who rule through centralized, often unchecked, power, and cultivate obedience and fear. When a free state forms close partnerships with a despot, it exposes itself to external manipulation and internal erosion of its foundational values. Such alliances are fraught with risk, as the mutual interests binding a despot and a democracy are, almost by necessity, shallow and contingent. Despots may provide military or economic support, but always with an eye toward their own aggrandizement, often betraying their partners if it serves their power.

These partnerships can compromise the moral and civic integrity of a free state. The despot’s influence may extend to the political culture and institutions of the free state, subtly undermining liberties through imitation or through the introduction of autocratic practices under the pretext of security or necessity. Historical precedent abounds, whether in ancient Greece, Renaissance Italy, or the modern world, showing how republics that embraced tyrants as allies often found themselves endangered by those very relationships, confronting subversion, betrayal, or even outright conquest.

Ultimately, the warning is universal and timeless: democracies must carefully guard their alliances and maintain a vigilant skepticism towards entanglements with authoritarian regimes. The temporary advantages such relationships offer may come at the cost of long-term freedom and security, making them not only precarious but deeply perilous for the health and survival of free societies.