(Warning: some thinking out loud about some passages of Cicero and Machiavelli, in the course of doing some research for a work in progress. A footnote of interest to historians of political thought or political theorists with a historical bent, perhaps.)
Cicero, Philippics 1.33-34 (the Perseus text is unaccountably missing the last lines of 1.33; a full translation is found here):
What I am more afraid of is lest, being ignorant of the true path to glory, you should think it glorious for you to have more power by yourself than all the rest of the people put together, and lest you should prefer being feared by your fellow-citizens to being loved by them. And if you do think so, you are ignorant of the road to glory. For a citizen to be dear to his fellow-citizens, to deserve well of the republic, to be praised, to be respected, to be loved, is glorious; but to be feared, and to be an object of hatred, is odious, detestable; and moreover, pregnant with weakness and decay. And we see that, even in the play, the very man who said, "what care I though all men should hate my name, so long as fear accompanies their hate?" [The Latin is much more concise and lapidary: "oderint, dum metuant"] found that it was a mischievous principle to act upon.
I wish, O Antonius, that you could recollect your grandfather of whom, however, you have repeatedly heard me speak. Do you think that he would have been willing to deserve even immortality, at the price of being feared in consequence of his licentious use of arms? What he considered life, what he considered prosperity, was the being equal to the rest of the citizens in freedom, and chief of them all in worth.Machiavelli, The Prince, chapter XVII:
Upon this a question arises: whether it be better to be loved than feared or feared than loved? It may be answered that one should wish to be both, but, because it is difficult to unite them in one person, is much safer to be feared than loved, when, of the two, either must be dispensed with. Because this is to be asserted in general of men, that they are ungrateful, fickle, false, cowardly, covetous, and as long as you succeed they are yours entirely; they will offer you their blood, property, life and children, as is said above, when the need is far distant; but when it approaches they turn against you. And that prince who, relying entirely on their promises, has neglected other precautions, is ruined; because friendships that are obtained by payments, and not by greatness or nobility of mind, may indeed be earned, but they are not secured, and in time of need cannot be relied upon; and men have less scruple in offending one who is beloved than one who is feared, for love is preserved by the link of obligation which, owing to the baseness of men, is broken at every opportunity for their advantage; but fear preserves you by a dread of punishment which never fails.
Nevertheless a prince ought to inspire fear in such a way that, if he does not win love, he avoids hatred; because he can endure very well being feared whilst he is not hated, which will always be as long as he abstains from the property of his citizens and subjects and from their women. But when it is necessary for him to proceed against the life of someone, he must do it on proper justification and for manifest cause, but above all things he must keep his hands off the property of others, because men more quickly forget the death of their father than the loss of their patrimony. Besides, pretexts for taking away the property are never wanting; for he who has once begun to live by robbery will always find pretexts for seizing what belongs to others; but reasons for taking life, on the contrary, are more difficult to find and sooner lapse. But when a prince is with his army, and has under control a multitude of soldiers, then it is quite necessary for him to disregard the reputation of cruelty, for without it he would never hold his army united or disposed to its duties.At first glance, it looks as if Cicero and Machiavelli were presenting diametrically opposed positions: Cicero argues that a political leader should avoid being feared, and that it is better that he be loved, whereas Machiavelli suggests that it is fine if the prince is feared. This fits in with the "standard view" concerning Machiavelli's relationship to Cicero (see, e.g., Skinner; consider also, for example, the discussions in The Prince asserting that generosity or honesty are inessential to political leaders, which clearly reverse Cicero's discussion of the need for these virtues in On Duties). There are some (partial) dissents (e.g., Colish), but in general the consensus seems to be that Machiavelli and Cicero present fairly opposed views of the virtues of political leaders.
Yet it is clear from these passages that both Machiavelli and Cicero agree that being hated is fatal to a political leader. They differ mostly insofar as Cicero seems to think that becoming feared without incurring hatred is unlikely, whereas Machiavelli is more sanguine about this possibility. But even this difference can be attributed to the fact that Cicero is considering the kinds of actions that someone who used to be an equal (Antony) would have to do in order to become dominant; and in his view (perhaps exaggerated for rhetorical effect?) these actions are likely to incur hatred alongside fear, and are unlikely to bring real and durable fame. And that thought does not seem to be in conflict with Machiavelli's views at all.
Unrelated point: working through Cicero's Philippics after reading Boehm makes me think that the upper level of Roman society behaved very much like a tribe with a strong ethos of equality, despite the otherwise tremendous material and status inequalities in Roman society. Like tribesmen everywhere, Cicero and his contemporaries among the senatorial class seemed to be extremely sensitive to suggestions that this or that person aimed to become dominant over them, and expended great energy arguing over the symbols of such domination (the office of the dictator, crowns, funeral monuments, public thanksgivings), even as the real threats to their equality lay in the ability of the proconsuls to basically create private armies during their long periods of imperium away from Italy (by Marc Antony's time, they could sometimes spend 5 years on campaign away from Rome). Also, it is amazing how the Romans of the time, like many of the tribes described by Boehm, had few mechanisms to deal with persistent attempts at domination other than assassination. It's actually kind of astounding the sheer violence present in the background of politics at Rome in the waning days of the republic – people are being killed right and left, the senate is often surrounded by armed men, and prominent political figures, Cicero included, are always conscious of the very real threats to their physical safety. And yet they seemed to think that such extrajudicial killings were often quite legitimate, though they of course disagreed about which ones! Late republican Rome was really a Machiavellian jungle, and Cicero was very good at surviving in it; it would seem unlikely if Machiavelli's ideas about political survival were entirely alien to Cicero.