Key Arguments

• If you join a stronger ally and he prevails, you are at his mercy; princes should avoid placing themselves at others’ mercy.
• The Venetians erred by allying with France against the Duke of Milan, leading to their ruin.
• When necessity compels alliance, a prince must still take a side (e.g., Florentines when Pope and Spain attacked Lombardy).
• There is no perfectly safe policy; every course carries risk, so wisdom lies in discriminating among harms and accepting a lesser evil.

Source Quotes

If he whom you help conquers, he remains in your power, and with your aid he cannot but conquer. And here let it be noted that a Prince should be careful never to join with one stronger than himself in attacking others, unless, as already said, he be driven to it by necessity. For if he whom you join prevails, you are at his mercy; and Princes, so far as in them lies, should avoid placing themselves at the mercy of others.

And here let it be noted that a Prince should be careful never to join with one stronger than himself in attacking others, unless, as already said, he be driven to it by necessity. For if he whom you join prevails, you are at his mercy; and Princes, so far as in them lies, should avoid placing themselves at the mercy of others. The Venetians, although they might have declined the alliance, joined with France against the Duke of Milan, which brought about their ruin.

For if he whom you join prevails, you are at his mercy; and Princes, so far as in them lies, should avoid placing themselves at the mercy of others. The Venetians, although they might have declined the alliance, joined with France against the Duke of Milan, which brought about their ruin. But when an alliance cannot be avoided, as was the case with the Florentines when the Pope and Spain together led their armies to attack Lombardy, a Prince, for the reasons given, must take a side.

But when an alliance cannot be avoided, as was the case with the Florentines when the Pope and Spain together led their armies to attack Lombardy, a Prince, for the reasons given, must take a side. Nor let it be supposed that any State can choose for itself a perfectly safe line of policy. On the contrary, it must reckon on every course which it may take being doubtful; for it happens in all human affairs that we never seek to escape one mischief without falling into another.

On the contrary, it must reckon on every course which it may take being doubtful; for it happens in all human affairs that we never seek to escape one mischief without falling into another. Prudence therefore consists in knowing how to distinguish degrees of disadvantage, and in accepting a less evil as a good. Again, a Prince should show himself a patron of merit, and should honour those who excel in every art.

Key Concepts

• a Prince should be careful never to join with one stronger than himself in attacking others, unless, as already said, he be driven to it by necessity.
• For if he whom you join prevails, you are at his mercy; and Princes, so far as in them lies, should avoid placing themselves at the mercy of others.
• The Venetians, although they might have declined the alliance, joined with France against the Duke of Milan, which brought about their ruin.
• Nor let it be supposed that any State can choose for itself a perfectly safe line of policy.
• Prudence therefore consists in knowing how to distinguish degrees of disadvantage, and in accepting a less evil as a good.

Context

Chapter 21, lines 1456-1523; strategic maxims on alliance formation, necessity, and prudential choice under unavoidable risk.