In The Prince, we could argue that Niccolò Machiavelli compares fortune to women for sexist reasons. In his comparison, Machiavelli brings in many toxic tropes about women, including the belief that they are unsteady or "changeful."

The purported unreliability of women is seen throughout history. We see the "changeful" notion in the 1690’s Salem witchcraft trials when women and young girls were accused of changing into witches. We also see this "changeful" notion in the tendency to not heed rape reports from women.

The purported inconstancy of fortune/woman contrasts with the purported reliability of mankind/man. Machiavelli calls mankind "steadfast in their ways." That idea plays into notions that men are somehow invariably reliable, firm, and dependable. Yet look at some of the most visible men in politics and culture -- do they seem steady to you? Would you characterize Donald Trump, Joseph Biden, Kanye West, or Tucker Carlson as stable and balanced?

The sexist parallel continues when Machiavelli declares,

if you wish to keep her [Fortune] under, it is necessary to beat and ill-use her....She allows herself to be mastered by the adventurous.

Here is another injurious stereotype about women: they like to be subjugated, dominated, and treated poorly. Women themselves have been accused of perpetuating this violent generalization. You might want to look into recent criticism concerning how Lana Del Rey's music might glamorize abuse.

However, by the end of Machiavelli's paragraph, we notice that fortune and man might not be so opposite. As it turns out, it's not the "steadfast" man that Machiavelli champions. Rather, it's the "less cautious" and "more violent" young man that Machiavelli supports. That's the kind of man that snares fortune.

If you are "less cautious" and "more violent," aren't you also "changeful"? It's interesting to think about how, in the end, Machiavelli's description of the ideal man who commands fortune is not so different from fortune itself.

Perhaps this is beyond the scope of your question, but you may want to consider employing queer theory. Maybe think through how Machiavelli’s young men could have more in common with fortune than his sexist binary acknowledges.

In the minds of most Renaissance writers, as well as the classical writers they emulated, Fortune, or "Fortuna," was gendered female. In fact, Fortuna was the Roman goddess of luck and chance, a fact of which Machiavelli, a classicist through and through, was keenly aware. So Machiavelli is by no means being original, nor notably sexist, by referring to Fortune with a feminine pronoun. Like most of his contemporaries, Machiavelli would have believed that women were more fickle, spiteful, and irrational than men. This belief, which of course is part and parcel of a patriarchal society, is probably why the Romans associated fortune with the feminine. Machiavelli, though, takes this gendered view of fortune much further:

Fortune is a woman, and if you wish to keep her under it is necessary to beat and ill-use her; and it is seen that she allows herself to be mastered by the adventurous rather than by those who go to work more coldly. She is, therefore, always, woman-like, a lover of young men, because they are less cautious, more violent, and with more audacity command her.

The misogynistic attitude expressed in this passage is a direct consequence of Machiavelli's understanding of fortune, which he views as a destructive, almost evil, force that can nevertheless be restrained through force. Elsewhere in this chapter, he compares fortune to a flood that destroys everything, and he points to examples of leaders who did not wait for fortune to bring them to their knees, but rather took bold action to assert their will. It reveals much about contemporary attitudes about gender that he drew parallels between this aggressive approach and a man's relationship with a woman.

To Machiavelli, fortune or luck, like a woman, is fickle: it is unreliable and changeable. You can't depend on it. It will betray you.

Machiavelli is leaning into some unfortunate Renaissance stereotypes about women—the same stereotypes that led Othello to kill Desdemona in Shakespeare's Othello. Women in that time period were often regarded by men as unfaithful, a stereotype that had more to do with men's projections and misunderstandings of women than with women themselves. Nevertheless, Machiavelli uses the comparison because he expects men to understand it in a personal way: the light bulb should turn on in their minds as they grasp fortune's likeness to women.

"Fortune," in this period, was often depicted as a wheel, hence the term "wheel of fortune." It was ever turning, so that even if a person was on the top today, eventually the wheel would crush him as it turned. Machiavelli, therefore, advises princes not to think their fortune will last forever, but to take precautions and work to hedge their bets as far as possible. Just as a man should try to control a woman rather than take chances with her unpredictable nature, so should a prince cautiously treat fortune.

In chapter 25 of The Prince Machiavelli infamously describes fortune as being like a woman. Fortune is a very important concept for Machiavelli; it's crucial for a successful ruler to learn how to master it. That's not to say that fortune can ever be controlled any more than you can control a river. But just as you can divert the course of a river or build a dam to prevent it from causing flooding, so too can the potentially damaging consequences of fortune be mitigated by taking wise precautions.

In doing so, it's always better to be bold rather than timid. After all, fortune favors the brave, as they say. Adopting such an approach does not guarantee success, of course, but it does increase one's chances. Fortune was often portrayed in Renaissance art as a female figure, forever spinning her wheel (the wheel of fortune, no less). At that time, the prevailing attitude towards women was completely at odds with what's considered acceptable today. Then, it was widely believed that women were physically and intellectually weaker than men and therefore needed to be kept firmly under the control of their husbands, brothers, and fathers. Fortune, according to Machiavelli, must be treated the exact same way.