Investing in the Classics

Machiavelli’s Discourses on Livy: On Conspiracies

Please note that for the purposes of this analysis, I use the Harvey C. Mansfield and Nathan Tarcov translation of Machiavelli’s Discourses on Livy.


Machiavelli, the most profound esoteric writer (in the Straussian, not the pejorative layman’s, understanding of the term) to have ever existed, wrote extensively of conspiracies in his magnum opus, the Discourses. Contained in the sixth chapter of the third and final book, Machiavelli’s discourse on conspiracies is by and large the longest chapter of the entire book, detailing intimately the proper mode of proceeding in a conspiracy for whoever wishes to take up such an enterprise. Machiavelli’s discourse is most surreptitious, for having been a victim of calumny in which he was accused of conspiracy, Machiavelli was arrested and tortured. Thus, he was prudent in being reticent in this discourse, so as to avoid suspicion of the party that ruled Florence at the time, which was the same party that suspected and tortured him.


How might this discourse be of use to the contemporary investor, one might ask? To answer this, one must look beyond the procrustean mores of the times. Human nature, being inveterate, has always yearned for power and has always been willing to usurp it for public good or private benefit. Today’s forms of financial conspiracy, though less macabre than that of our ancestors, nevertheless, adhere to the same modus operandi. Such examples can be seen in the activist conspiracies to usurp existing management, or in distressed investing to gain control of this or that fulcrum security, and the like. Further particular causes, being a source of ignominy and maintained by private reasons, would be a presumptuous and intrepid matter to speculate on further. Let this analysis be useful to whoever understands it.


Machiavelli opens his dialogue on conspiracies in his quintessential reticent manner; yet, the effectual truth of the matter demands assessment, however aberrant such a discourse is from the humanist denomination. By the law of large numbers and the constraints of opportunity, Machiavelli notes aptly that more princes are undone by conspiracy than by war, yet the uncouthness of the genus has caused its neglect. Machiavelli begins:

“It did not appear to me that reasoning about conspiracies should be omitted, since it is a thing so dangerous to princes and private individuals; for many more princes are seen to have lost their lives and states through these than by open war. For being able to make open war on a prince is granted to few; to be able to conspire against them is granted to everyone” (Book III.6).

Management, similarly, more often losses their entitlement by activist conspiracies than from removal by the war of competition. Having no levers to ouster opposition outside of conquest – that is, acquisition, competitors have few means for removal and even less desire to remove inept management of a rival prince. But to shareholders, who are many, the opportunity for conspiracy is abundant. Yet, as Machiavelli notes, conspiracy is precipitous for its progenitors. He states, “On the other side, private men enter upon no enterprise more dangerous or more bold than this, for it is difficult and very dangerous in every part of it. Hence it arises that many of them are attempted, and few have the desired end” (Book III.6). For private men today, these being the activist shareholders and creditors, it is likewise the case that many conspiracies are attempted and fewer succeed, nevertheless such enterprises remain difficult and dangerous, and are restricted to the bold and foolish.


For the prince, Machiavelli astutely articulates, the best defense against conspiracy is not to be hated by the generality of men. For when a prince is beloved, those who would conspire against him, turn craven at the thought of the danger of having the prince and a people against their cause. For a prince to gain the generality of people to his cause, he need only avoid those particular offenses against the people that incur the wrath of their hatred. Machiavelli writes:

“A prince, thus, should flee these private charges… for if he guards himself from this, simple particular offenses will make less trouble for him… because if there were even of spirit and had the power to do it, they are held back by the universal benevolence that they see the prince has” (Book III.6).

The best thing that management can do to obviate this risk is to make himself beloved. There is nothing more necessary to appear to have than this last quality, inasmuch as men judge generally more by the eye than by the hand, because it belongs to everybody to see you, but it is the privilege of the few to be able to touch who you really are. Everyone sees what you appear to be, few really know what you are, and those few dare not oppose themselves to the opinion of the many, who have the majesty of the herd to defend them; for in the world the few have no place to stand where the many have a voice, because the many are always taken by what a thing seems to be than by what comes of it.


For the imprudent prince, they sow the seeds of their own conspiracy. Through their offenses, they share more of the burden of responsibility of their demise than that of their conspirators. For such menaces, being unnecessary and immodest, provide for many enmities and press adversaries to dire straits. Thus, the most efficacious offense of a prince against conspiracies is their own measured restraint. Machiavelli writes:

“that menaces offend prices more and are the cause of more efficacious conspiracies than offense. From those a prince should guard himself, for they have either to caress men or secure themselves against them, and never reduce them to such straits that they have to think that they must either die or make someone else die” (Book III.6).

Egregious compensation, regal perks, licentious expenditures, and ostentatious and rarefied behavior, among other misdeeds, make a manager most hated by his shareholders; such blithe hedonism permeates in corporate culture… sometimes exsequor exequor.


The immodest prince to concern his security with regard to those closest to him, not those farther away. For the ‘great’ – the nobles, in Machiavelli’s caustic parlance – are those who are most disposed to conspire. It is not the plebs, for their nature is more decent and their opportunities fewer. As Machiavelli writes: “Therefore men… when they see themselves weak, guard themselves about doing it; and when they are fed up with a prince, they attend to cursing him and wait for those who have greater quality than they to avenge them” (Book III.6). Similarly, the malcontent retail shareholders may lament and lambaste management they perceive as menacing, but as sheep they will not act without a shepherd. As to the great, Machiavelli writes:

“I say it is to be found in the histories that all conspiracies are many by the great men or those very familiar to the prince. For others, if they are not quite mad, are unable to conspire, since weak men and those not familiar to the prince lack all those hopes and all those occasions that are required for the execution of a conspiracy” (Book III.6).

Conspiracies come from the ‘great’ – the activists and others of similar pomp – who have the reputation and the means for such endeavors; for this humor, being of an equally elite and immodest nature, easily identify the true disposition of a manager. For the immodest manager finding himself in such a scenario, in order to reprieve themselves ought to caress those capable of conspiring against themselves, if possible, to make the precautions necessary for one’s defense, if it is not, as Machiavelli advises. And, if it resorts to the latter, to present the opposition with alternatives sub rosa (e.g., poison pill, compromise, board seat, etc.), to divert him from any necessity that guides him on the path to your ruin and to conceal the knowledge from the public to prevent other potential conspirators, unless you are certain of your support.


Turning to the perspective of the conspirators, the focus of Machiavelli’s discussion, he enumerates the dangers born in conspiracies. He states, “The dangers borne in conspiracies, as I said above, are great, since they are borne at all times; for in such cases danger is encountered in managing them, in executing them, and after they are executed” (Book III.6). Machiavelli elaborates:

“As I said above, dangers are found within them at three times: before, in the deed, and after. Few are found that have a good outcome because it is impossible – almost – to pass through them all happily. And beginning to discourse of the dangers before, which are the most important, I say that one needs to be very prudent and to have great luck in managing a conspiracy for it not to be exposed. They are exposed either by report or conjecture. Report arises from finding lack of faith, or lack of prudence, in the men to whom you communicate it. Lack of faith is easily found because you cannot communicate it except to your trusted ones, who for your love will put themselves in the way of death, or to men who are discontented with the prince. Of the trusted one might be able to find one or two; but as you extend yourself to many, it is impossible for you to find them” (Book III.6).

For conspirators, the most danger and difficulty is incurred in the beginning, though the subsequent phases are not without these perils, for the word comes before the deed, one is exposed and one’s only advantage of surprise is spoiled. The root of this most common cause of condemned conspiracy is the inclusion of too many people. In order to insulate oneself from such mishaps and misfortune, one needs to be very prudent and to have great luck in managing a conspiracy for it not to be exposed. Prudence prevents mistake while good fortune prevents misfortune. The conspirator cannot rely on prudence alone, for many aspects of conspiracy are beyond the power of the individual to control and direct, hence the danger and difficulty.


It goes without saying that the more people a conspirator seeks to include, the higher the chance that the conspiracy will be exposed before its consummation. This phenomena arises from the credulity of men, who do not understand that past favor does not assure future patronage or that present discontent does not add to your armaments. As Machiavelli explains:

“men most often deceive themselves about the love that you judge a man bears to you, nor can you ever secure yourself of it unless you make an experiment of it; and to make experiment of it in this is very dangerous. Even if you have made experiment of it in some other dangerous thing in which they have been faithful to you, you cannot from that faith measure this one, since this surpasses every other kind of danger. If you measure faith by discontent that one individual has with the prince, you can easily deceive yourself in this; for as soon as you have manifested your intent to that discontented one, you give him matter with which to content himself, and to maintain faith it must indeed be either that the hatred is great or that your authority is very great” (Book III.6).

The dangers that lie in the beginning for political conspiracies are not commensurate with that of our pathologically softer milieu. Nevertheless, Machiavelli aptly indicates the epistemic limitations involved in conferring with another. Past performance is no guarantee of future favor. Biases and seemingly innocuous assumptions can undo you and your cause. One must recognize that conspiracies are dynamic events; the passage of information about your intent, even to another one discontented, gives him a means to improve his position. For example, a newly informed conspirator may use this knowledge privately to strong-arm management buyout his stake, which being to his benefit, is to your detriment for weakening your coalition and removing the advantage of surprise.


Machiavelli enumerates two other causes of error inflicted in the beginnings of conspiracies: lack of prudence and uncover by conjecture. To the former, Machiavelli states, “As to being exposed by lack of prudence, it arises when a conspirator speaks of it with little caution, so that a… third person hears you” (Book III.6). This, being relatively straightforward, merits no further elaboration beyond this: that those ruined for a lack of prudence are either fools or they desire more the glory of Brutus than the love of the liberty of their fatherland. As to the latter, conjecture, this arises when you’re actions give suspicion to your intent. For the modern activist, such actions include aggressively increasing your ownership or visible meetings with leading stakeholders. Conspiracies are not crafted in a vacuum; one must be cautious and cognizant of the signal that their actions provide, and to use these signals deceptively, to one’s advantage.


Because of man’s fickle and self-interested nature, the most efficacious means by which to ameliorate the difficulties incurred at the beginnings of conspiracies is to communicate your intent only when you want to do it, and not before. You must force your accomplices’ hands, unless they vehemently protest, for in imposing necessity upon your accomplices, you do not give them time to let their imagination of the consequences sap their courage. As Machiavelli explains:

“The first and most true – indeed, to say better, the only one – is not to give time to the conspirators to accuse you, and to communicate the thing to them when you want to do it, and not before. Those who have done thus escape for certain the dangers in practicing it, and most often the others; indeed they have all had a happy end, and any prudent individual would have occasion to govern himself in this mode” (Book III.6).

By holding yourself to this mode, you do not allow your conspirators gain private advantage from their knowledge of the conspiracy. Moreover, as was said above, it does not allow the accomplices’ imagination of the dangers interfere with their disposition. For delay brings tedium, and in tedium the imagination of the event often extends beyond the reality of the matter at hand. Thinking more of their imagination of the consequences than of the truth of the means, fear and greed take captive the minds of men, infecting the imagination, influencing their disposition. To this, Machiavelli surmises, “But because men ordinarily understand little of the actions of the world, they often make very grave errors, and so much the greater in those that have more of the extraordinary, as in this. Thus the thing should never be communicated unless necessary and in the deed” (Book III.6). Most men study books, and not the actions of men. Thus, armed only in theory, they make grave errors – indeed the same errors that their predecessors made, and so on.  


Having addressed the difficulties incurred and the remedies available to the beginning of conspiracies, Machiavelli concomitantly address the dangers that arise at the stage of execution. These dangers principally arise from varying the orders at the last minute, or from an error inflicted through lack or prudence or spirit. As Machiavelli writes:

“As to dangers that are incurred at the execution, these arise either from varying the order, or from spirit lacking in him who executes, or from an error that the executor makes through lack of prudence… I say, thus, that there is not anything that produces so much disturbance and hindrance to all actions of men as there is to have to vary an order in an instant, without having time, and to have to bend it from what had been ordered before” (Book III.6).

In the execution of a conspiracy, three things can undermine it. First, lack of spirit in carrying out the deed, which comes from an infirm disposition or lukewarm supporters. Secondly, lack of prudence that gives rise to an error, such as a failure in delivering one’s intended message in the right way. Thirdly and most importantly, varying the plan at the last minute, for such actions not having the time to consider its consequences, are more susceptible to rebuttal and rebuke. To this, Machiavelli concludes: “it is far better to execute a thing according to the order given, even though one sees some inconvenience in it, than to enter into a thousand inconveniences through wishing to suppress that. This happens when one has no time to reorder oneself, for if one has time, man can govern himself by his own mode” (Book III.6). Finally, a fourth and unlisted cause is that of misfortune or accident. To this, Machiavelli surmises best, “Because such accidents are rare, one cannot produce any remedy for them. It is necessary to examine all those that can arise and remedy them” (Book III.6).


Lastly, Machiavelli addresses the dangers incurred after the execution. According to his analysis of history, there is only one significant danger: that of leaving someone in a position who may avenge the late prince. Such a danger, to Machiavelli, is the product of imprudence or negligence, and as such, its victims merit no excuse. As Machiavelli concludes this section:

“At present it remains only to dispute about the dangers that are incurred after the execution. These are only one, and that is when someone is left who may avenge the dead prince… when someone who is left alive from it through lack of prudence or by their negligence, then it is that they merit no excuse” (Book III.6).

Notwithstanding the morbid nature of this discourse, the politic lesson is invaluable. In the exchange of one regime for another, one acquires partisans as well as enmities. As to these enmities, especially if they were partisans of the previous regime, one ought to assess whether their loyalties lie more with the fallen than with the fatherland. If this is to be the case, then they ought to be removed as well, for they can and will undermine the new modes and orders that one seeks to establish.


Finally, returning the perspective of the prince, Machiavelli reiterates that princes have no greater enemy than conspiracy, however dangerous and difficult an enterprise it may be for its actors. This conclusion relies on Machiavelli’s brilliant insight into the twofold nature of conspiracy: even when conspiracy fails, it still brings the prince infamy. As Machiavelli explains:

“Princes therefore have no greater enemy than conspiracy, for when a conspiracy is made against them, either it kills them or it brings them infamy. For if it succeeds, they are dead; if it is exposed and they kill the conspirators, it is always believed that it was the invention of that prince to vent his avarice and cruelty at the expense of the blood and property of those whom he has killed” (Book III.6).

Similarly, if today’s financial conspiracy succeeds, management (or whoever the target may be) loses their entitlement. Yet even if the conspiracy fails, it nevertheless brings the target infamy for being put in such a precarious position. For conspiracies, especially failed ones, when learned of by the public draw the attention of the hoi polloi as such events are extraordinary. Such attention brings scrutiny to the record of the prince to discover the cause that the culprits had to have recourse to such dramatic actions, and this examination undoes the appearance that a prince has cultivated and maintained for himself.


However, if and when a prince suspects or finds himself the target of a conspiracy, he must exercise the utmost prudence. For where delay brings tedium, haste brings danger. For just as conspirators ought not to let their accomplices be privy to their intent before they wish to execute the deed, neither should the prince allow his conspirators be privy to his knowledge of nor his intent toward the conspiracy in question. Machiavelli, concluding his discourse, details:

“Yet I do not wish to fail to warn that prince or republic that might be conspired against, so that they may have warning that when a conspiracy manifests itself to them, they should seek out and learn very well its quality, and measure well the conditions of the conspirators and of themselves, before they undertake an enterprise to avenge it. When they find it large and powerful, they should never expose it until they have prepared themselves with sufficient forces to crush it; if they do otherwise, they would expose their own ruin. So they ought to dissimulate it with all industry, for conspirators, seeing themselves exposed, are driven by necessity and work without hesitation” (Book III.6).

Management (or whoever the target of a conspiracy may be), if favored by fortune, catches wind of a conspiracy against them and their estate, ought above all else to exercise prudence and caution at first. He must measure carefully the conditions of the conspirators and that of himself, to judge and weigh the strength of each force. If the conspiracy is found to be powerful, he should not expose it. As Machiavelli explains:

“Nor can a prince or a republic that wishes to defer the exposure of a conspiracy to its advantage use better means than with art to offer opportunity soon to conspirators, so that in waiting for it – or since it appears to them that they have time – they give time to the former or the latter to punish them” (Book III.6).

By exposing the conspiracy, one accelerates their own ruin, for it gives necessity to the cause of the conspirators to turn from indolence to execution. Furthermore, it robs the prince of the time that needed to prepare sufficient forces and defenses for himself. Obversely, Machiavelli concludes, “when conspiracies are weak, they can and should be crushed without hesitation” (Book III.6).

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