Thus to cause France to lose Milan the first time it was enough for the Duke Lodovico( *) to raise insurrections on the borders; but to cause him to lose it a second time it was necessary to bring the whole world against him, and that his armies should be defeated and driven out of Italy; which followed from the causes above mentioned.
(*) Duke Lodovico was Lodovico Moro, a son of Francesco Sforza, who married Beatrice d'Este.

He ruled over Milan from 1494 to 1500, and died in 1510.
Nevertheless Milan was taken from France both the first and the second time.

The general reasons for the first have been discussed; it remains to name those for the second, and to see what resources he had, and what any one in his situation would have had for maintaining himself more securely in his acquisition than did the King of France.
Now I say that those dominions which, when acquired, are added to an ancient state by him who acquires them, are either of the same country and language, or they are not.

When they are, it is easier to hold them, especially when they have not been accustomed to self-government; and to hold them securely it is enough to have destroyed the family of the prince who was ruling them; because the two peoples, preserving in other things the old conditions, and not being unlike in customs, will live quietly together, as one has seen in Brittany, Burgundy, Gascony, and Normandy, which have been bound to France for so long a time: and, although there may be some difference in language, nevertheless the customs are alike, and the people will easily be able to get on amongst themselves.

He who has annexed them, if he wishes to hold them, has only to bear in mind two considerations: the one, that the family of their former lord is extinguished; the other, that neither their laws nor their taxes are altered, so that in a very short time they will become entirely one body with the old principality.
But when states are acquired in a country differing in language, customs, or laws, there are difficulties, and good fortune and great energy are needed to hold them, and one of the greatest and most real helps would be that he who has acquired them should go and reside there.
This would make his position more secure and durable, as it has made that of the Turk in Greece, who, notwithstanding all the other measures taken by him for holding that state, if he had not settled there, would not have been able to keep it.