Michel de Montaigne mentioned Machiavelli only twice in his Essays, both in Book Two. This tells us he was aware of the latter, but not whether he was intimately familiar with his works. Nor does it tell us which of Machiavelli’s writings he is referring to (by this date, all of Machiavelli’s major works were in print). Machiavelli himself had died in 1527, some 50 or more years before Montaigne penned this part of his essays (first published in 1580).
The first mention is in Chapter XXXIV: OBSERVATION ON THE MEANS TO CARRY ON A WAR ACCORDING TO JULIUS CAESAR (emphasis added):
‘Tis related of many great leaders that they have had certain books in particular esteem, as Alexander the Great, Homer; Scipio Africanus, Xenophon; Marcus Brutus, Polybius; Charles V., Philip’de Comines; and ’tis said that, in our times, Machiavelli is elsewhere still in repute; but the late Marshal Strozzi, who had taken Caesar for his man, doubtless made the best choice, seeing that it indeed ought to be the breviary of every soldier, as being the true and sovereign pattern of the military art. And, moreover, God knows with that grace and beauty he has embellished that rich matter, with so pure, delicate, and perfect expression, that, in my opinion, there are no writings in the world comparable to his, as to that business.
It is unclear to me where Montaigne is referring to that Machiavelli is “still in repute.” It depends on the book in question: the reputation of The Prince was vastly different from that of The Art of War.
The second mention comes in Chapter XVII: OF PRESUMPTION (emphasis added):
Machiavelli’s writings, for example, were solid enough for the subject, yet were they easy enough to be controverted; and they who have done so, have left as great a facility of controverting theirs; there was never wanting in that kind of argument replies and replies upon replies, and as infinite a contexture of debates as our wrangling lawyers have extended in favour of long suits:
“Caedimur et totidem plagis consumimus hostem;”
["We are slain, and with as many blows kill the enemy" (or),
"It is a fight wherein we exhaust each other by mutual wounds."
—Horace, Epist., ii. 2, 97.]
The work here may well be The Prince – the main object of controversy in Machiavelli’s writings and the subject of several counterpoint books within its first century. Montaigne rather sardonically comments that in reputing Machiavelli. those authors open themselves up to the same sort of argumentative treatment; and those subsequent attacks in turn to other challenges – ad nauseum.
A little later in that chapter, Montaigne wrote what strikes me as a comment that parallel’s Machiavelli’s own political words (emphasis added):
Our manners are infinitely corrupt, and wonderfully incline to the worse; of our laws and customs there are many that are barbarous and monstrous nevertheless, by reason of the difficulty of reformation, and the danger of stirring things, if I could put something under to stop the wheel, and keep it where it is, I would do it with all my heart:
“Numquam adeo foedis, adeoque pudendis
Utimur exemplis, ut non pejora supersint.”
["The examples we use are not so shameful and foul
but that worse remain behind."—Juvenal, viii. 183.]
The worst thing I find in our state is instability, and that our laws, no more than our clothes, cannot settle in any certain form. It is very easy to accuse a government of imperfection, for all mortal things are full of it: it is very easy to beget in a people a contempt of ancient observances; never any man undertook it but he did it; but to establish a better regimen in the stead of that which a man has overthrown, many who have attempted it have foundered. I very little consult my prudence in my conduct; I am willing to let it be guided by the public rule. Happy the people who do what they are commanded, better than they who command, without tormenting themselves as to the causes; who suffer themselves gently to roll after the celestial revolution! Obedience is never pure nor calm in him who reasons and disputes.
I’ll need to do some more reading about the similarities between the two in the near future.