The Medici: "I hate democracy. 😊"

Explanation: The extremely influential and wealthy Medici family, having effectively run the Republic of Florence over the past ~100 years, finally and formally dealt the deathblow to the Republic of Florence, after having been briefly run out of town for incompetence (they returned two decades later at the head of a foreign army - very patriotic!).

Niccolo Machiavelli would be so upset by this that he wrote The Prince - either to attempt to preserve Florence’s power by advising the Medici rulers, or as an ‘apology’ of sorts in the hopes of being allowed to return to his native city after leading the republican defense, or as a veiled mockery of autocracy; depending on who you ask (I take the second option personally).

Explanation: The extremely influential and wealthy Medici family, having effectively run the Republic of Florence over the past ~100 years, finally and formally dealt the deathblow to the Republic of Florence, after having been briefly run out of town for incompetence (they returned two decades later at the head of a foreign army - very patriotic!).

Niccolo Machiavelli would be so upset by this that he wrote The Prince - either to attempt to preserve Florence’s power by advising the Medici rulers, or as an ‘apology’ of sorts in the hopes of being allowed to return to his native city after leading the republican defense, or as a veiled mockery of autocracy; depending on who you ask (I take the second option personally).